Phosphorus pentachloride [Phosphorus(V) chloride; PCl5]

Query Query

Results

Date

99 reactions in Reaxys

2017-10-13 06h:49m:11s (EST)

99 reactions in Reaxys

2017-10-13 06h:51m:36s (EST)

Cl

1. Query

Cl

PCl Cl Cl

Search as: As drawn, No salts, No mixtures, No charges, No radicals 2. Query

(1. Query) AND itemno in (1,2)

Copyright © 2017 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

1/33

2017-10-13 07:13:31

Cl

P

Cl

Cl Cl

Cl

PCl Cl Cl

Rx-ID: 26150637 View in Reaxys 1/99 Yield

Conditions & References With chlorine in tetrachloromethane, react. of PCl3 with Cl2 in CCl4; Downs, J.; Johnson, R. E.; Journal of Chemical Physics; vol. 22; (1954); p. 143 - 144 View in Reaxys vol. P: MVol.C; 183, page 421 - 424 ; (from Gmelin) View in Reaxys With chlorine in not given, react. with Cl2; Skaerblom, K. I.; Tek. Tidskr.; vol. 57; (1927); p. 87 - 90; C. II; (1927); p. 2033 View in Reaxys vol. P: MVol.C; 183, page 421 - 424 ; (from Gmelin) View in Reaxys 1 :97.1 g (0.706 mol) of phosphorus trichloride was added to a 200 ml glass container equipped with a reflux condenser, a thermometer and a stirrer.Thereafter, while stirring, the glass container was heated to 90 ° C. in an oil bath,Under reflux, 30.0 g (0.423 mol) of chlorine gas was fed over 9 hours. The produced phosphorus pentachloride is dissolved in phosphorus trichloride,There was no adhesion of solid phosphorus pentachloride to the wall surface of the glass container.

With chlorine, Time= 9h, Reflux Patent; DAIKIN INDUSTRIES LIMITED; MATSUDA, YUKI; SHIMADA, TOMO; HIRAI, MAI; (12 pag.); JP2017/31090; (2017); (A) Japanese View in Reaxys

Cl Cl

PCl Cl

O

Cl

Cl

Cl

Rx-ID: 23858052 View in Reaxys 2/99 Yield

Conditions & References 7-(3,4-Dichlorophenyl)-4,7-dihydro-5-methyl-6-(4-methyl-4H-imidazo[3,4-d][1,2,5]thiadiazol-5-yl)pyrazolo[1,5a]pyrimidine 7-(3,4-Dichlorophenyl)-4,7-dihydro-5-methyl-6-(4-methyl-4H-imidazo[3,4-d][1,2,5]thiadiazol-5-yl)pyrazolo[1,5-a]pyrimidine Preparation of compound 5: To a suspension of the acid (120 mg, 0.37 mmol) in 5 mL of anhydrou dichloromethane were added trichloroacetonitrile (55.9 mL, 0.56 mmol) and triphenylphosphine (146.2 mg, 0.56 mmol).

The mixture became clear and was allowed to stir at room temperature for 1 hour.

The reaction mixture was transferred into a solution of 3,4-diamino-1,2,5-thiadiazole (51.7 mg, 0.45 mmol, prepared according to J. Heterocycl. Chem. 1976, 13, 13) and triethylamine (103.6 μL, 0.74 mmol) in 5 mL of dichloromethane.

The reaction was monitored using TLC or LC/MS. Upon completion of the coupling, the reaction mixture was loaded directly onto silica gel and eluted with 50percent ethyl acetate/hexanes to yield the desired amide as a yellow solid (56.4 mg, 30percent).

Preparation of compound 6: A suspension of the resulting amide (80 mg, 0.19 mmol) and phosphorus pentachloride (79 mg, 0.38 mmol) in chloroform (10 mL) was stirred at room temperature under anhydrous argon for one hour and then heated to reflux for 2 hours.

The mixture was allowed to cool down to room temperature and solvent was removed under reduced pressure.

The residue was redissolved in ethyl acetate and briefly washed with saturated aqueous sodium bicarbonate solution.

Patent; Atwal, Karnail S.; Vaccaro, Wayne; Lloyd, John; Finlay, Heather; Yan, Lin; Bhandaru, Rao S.; US2003/22890; (2003); (A1) English View in Reaxys

Copyright © 2017 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

2/33

2017-10-13 07:13:31

Cl Cl

PCl Cl Cl

Rx-ID: 24294371 View in Reaxys 3/99 Yield 71%

Conditions & References 2 : EXAMPLE 2 EXAMPLE 2 By chlorination of the corresponding fluoral-semiacetal with phosphorus pentachloride in a manner analogous to that described in Example 1, (2,2,2-trifluoro-1-chloroethyl)-ethyl ether CF3 CHCl--O--C2 H5 was obtained.

Yield: 71percent of the theory.

Analysis: Calc.: C, 29.6 percent; H, 3.7 percent; F, 35.1 percent; Cl, 21.8 percent. Found: C, 29.6 percent; H, 3.9 percent; F, 35.4 percent; Cl, 21.5 percent.

Patent; Hoechst Aktiengesellschaft; US3980714; (1976); (A1) English View in Reaxys 7.C : N-[Cyclohexylimino-(2-methyl-piperidin-1-yl)-methyl]-N'-(4-fluoro-phenyl)-2,6-dimethyl-benzamidine Step C N-[Cyclohexylimino-(2-methyl-piperidin-1-yl)-methyl]-N'-(4-fluoro-phenyl)-2,6-dimethyl-benzamidine A neat mixture of the product from Step 8 (0.20 g, 0.544 mmol) and phosphorous pentachloride (0.113 g, 0.544 mmol) was heated to 125° C. and the melt obtained was stirred for 1 hour.

Toluene was added and the mixture was concentrated (twice).

Patent; Villalobos; Anabella; Yohannes; Daniel; Nowakowski; Jolanta; Liston; Dane R.; US6093733; (2000); (A1) English View in Reaxys 1 : EXAMPLE 1 52 g of a compound of the formula STR29 which can be further purified if necessary, by recrystallization from nitrobenzene with the addition of PCl5, are obtained.

IR data: 1535, 1292, 1240, 1183, 893 cm-1 UV VIS data: λ=452, 480 nm (19 300) 13 C-NMR data (solid): δ=117.6, 130.11, 132.3, 145.6, 155.3 ppm.

Patent; Bayer Aktiengesellschaft; US5095103; (1992); (A1) English View in Reaxys I : Preparation of N-(Diaminophosphinyl)-p-toluene-sulfonamide EXAMPLE I Preparation of N-(Diaminophosphinyl)-p-toluene-sulfonamide A mixture of 51.4 g (0.300 mol) of p-toluenes ulfonamide, 62.5 g (0.300 mol) of phosphorus pentachloride, and 500 mL of carbon tetrachloride was prepared under a nitrogen atmosphere in a dry 1000 mL, round bottom flask fitted with a mechanical stirrer and a condenser attached to a sodium hydroxide trap.

The stirred mixture was gradually heated to 75° C. During this process hydrogen chloride steadily began to evolve.

The mixture was heated for 60 h at 75° C. during which time gas evolution ceased and the solution became homogeneous.

Upon cooling, however, the reaction mixture gelled into a slightly pink solid.

The flask was rewarmed to 55° C. to redissolve the solid, the heating bath was removed, and 11.8 mL (14.4 g, 0.315 mol) of formic acid was added dropwise over a 20 min period.

Gases were vigorously evolved during this process and the color of the solution became yellow.

The solution was stirred for another 2 h without external heating and then for 1 h at 55° C. The mixture was cooled to ambient temperature causing two layers to form in the flask.

Analysis of each layer, however, showed them to be substantially the desired product, and, upon standing under nitrogen, each layer crystallized into a solid, mp 114°-118° C. and 118°-121° C. (upper and lower layers, respectively).

The solids, 64 g from the upper layer and 28 g from the lower layer, were combined and extracted with 1200 mL of hot carbon tetrachloride.

The mixture was filtered free from 5-10 g of residue, and 46.7 g (54percent) pure p-toluenesulfonylphosphoramidic dichloride, mp 115.5°-117.5° C. (lit. mp 115°-118° C.) was obtained by allowing the filtrate to crystallize.

1 H NMR (CDCl ): δ 8.82 (S, 1H, NH), 7.83 (d, J=8 Hz, 2H, ArH), 7.28 (d, J=8 Hz, 2H, ArH), and 2.43 ppm (s, 3H, 3 CH3).

Copyright © 2017 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

3/33

2017-10-13 07:13:31

Patent; Allied Corporation; US4629491; (1986); (A1) English View in Reaxys P.13 : Preparation of Benzylamine Derivative PREPARATION EXAMPLE 13 Preparation of Benzylamine Derivative A mixture of 49 grams (295 millimoles) of 3-methoxy-4-methylbenzoic acid, 53.9 grams (315 millimoles) of p-toluenesulfonamide, and 129 grams (619 millimoles) of phosphorus pentachloride was prepared and then heated at 200° C. while stirring.

Phosphorus oxychloride was distilled at 106°-112° C.; and the mixture was further heated at 200° C. while stirring until no distillated came out.

Patent; Idemitsu Kosan Company Limited; US4680054; (1987); (A1) English View in Reaxys EXPERIMENT EXPERIMENT A solution of chlorobenzene (150 ml) and phosphorus trichloride (73 g, 0.532 mole) was placed in a 500 ml fournecked flask under a nitrogen atmosphere.

The flask was fitted with an overhead stirrer, reflux condenser, thermometer, and gas inlet tube.

Chlorine gas (38 g, 0.535 mole) was blown onto the surface of the stirred solution at a rate of 1 g/min.

The reaction temperature increased to 70° C. as the chlorine reacted with the phosphorus trichloride to prepare phosphorus pentachloride.

The gas inlet tube was replaced with an addition funnel after the chlorine addition was completed.

Patent; Stauffer Chemical Company; US4727194; (1988); (A1) English View in Reaxys 1.a : (a) (a) Preparation of the Alpha-Monobromo Derivative 1 mole of dicarboxylic acid (for instance, azelaic acid) is introduced into a 3 liter flask placed on a magnetic agitator provided with a heating plate, and 500 g of phosphorous pentachloride are added.

After the reaction has taken place (complete melting), 60 ml of anhydrous bromine are added in small portions in the course of about 6 hours, with continuous agitation.

The reaction temperature is maintained at 60° to 70° C. After the reaction is complete, it is cooled and thereupon about 500 ml of distilled water are cautiously added; it is then warmed on the magnetic agitator for about 30 minutes and cooled.

The low organic phase, formed of an oily liquid of dark yellow color, constitutes the crude monobromo derivative which is distilled under vacuum.

Patent; Nazzaro-Porro; Marcella; US4292326; (1981); (A1) English View in Reaxys 3.5.4 : Step 4 Step 4 in 50 ml. of chloroform is added over a 30 minute period to 8.12 g. (39 mmoles) of phosphorus pentachloride in 100 ml. of chloroform stirred at -30° C., and the reaction mixture is allowed to warm to 20°-25° C., stirred at 20°-25° C. for 16 hours and cooled to 0° C., the reaction mixture being stirred under nitrogen throughout.

10 ml. of water is added, the mixture is stirred for 5 minutes, and 200 ml. of 2N. sodium hydroxide solution is added.

The organic phase is separated, and the aqueous phase is extracted with chloroform.

The chloroform extract and the organic phase are combined, washed twice with saturated sodium chloride solution, dried over anhydrous magnesium sulfate, filtered and evaporated at reduced pressure to a tan solid.

The tan solid is recrystallized from benzene to obtain the product as a white solid (2.33 g.).

A second crop is obtained from the mother liquor (200 mg.).

An analytical sample is recrystallized from aqueous ethanol. M.p. 161°-162° C. Patent; Sandoz Pharm. Corp.; US4808607; (1989); (A1) English View in Reaxys 7.C : N-[Cyclohexylimino-(2-methyl-piperidin-1-yl)-methy)l-N'-(4-fluoro-phenyl)-2,6-dimethyl-benzamidine Step C N-[Cyclohexylimino-(2-methyl-piperidin-1-yl)-methy)l-N'-(4-fluoro-phenyl)-2,6-dimethyl-benzamidine

Copyright © 2017 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

4/33

2017-10-13 07:13:31

A neat mixture of the product from Step B (0.20 g, 0.544 mmol) and phosphorous pentachloride (0.113 g, 0.544 mmol) was heated to 125°C and the melt obtained was stirred for 1 hour.

Toluene was added and the mixture was concentrated (twice).

Patent; PFIZER INC.; EP805153; (1997); (A1) English View in Reaxys 12.b : (b) (b) Preparation of (3-Phthalimido)propionyl chloride 87.6 g (0.4 mol) of N-phthalylalanine was added to a stirring suspension of 83.2 g (0.4 mol) of phosphorus pentachloride in toluene at 60° C. under nitrogen.

After the mixture was stirred for 2 hours, the solvent and excess phosphorus pentachloride were removed to give a white solid Recrystallization in benzene/petroleum ether yielded 76.0 g of a hygroscopic white powder: mp 94°-99° C.; NMR (CDCl3) 7.7 (4H,m), 3.9 (2H,t), 3.2 (2H,t).

Patent; Nelson Research and Development Co.; US4849436; (1989); (A1) English View in Reaxys 12 : 3-Bromo-2-chloropyridine-5-sulphonyl Chloride The residue was dried under vacuum at 70° C. for 72 hours, then a mixture of the resulting solid, phosphorus pentachloride (30 g, 144 mmol) and phosphorus oxychloride (1 ml) was heated at 125° C. for 3 hours and then allowed to cool.

Patent; Pfizer Inc.; US6251904; (2001); (B1) English View in Reaxys

Cl

Cl

Cl Re (v5)

Cl

Cl

Cl

P

Cl

Cl

Cl

Cl

Cl 9Re 3

PCl Cl Cl

Rx-ID: 26455658 View in Reaxys 4/99 Yield

Conditions & References Baranov; Khvorykh; Troyanov; Zeitschrift fur Anorganische und Allgemeine Chemie; vol. 625; nb. 8; (1999); p.

1240 - 1242 ; (from Gmelin) View in Reaxys Cl N

Cl P Cl Cl

Cl P+ Cl Cl P–Cl Cl Cl Cl Cl Cl

O

Cl O P

Cl

P N H

Cl

Cl Cl

Cl

Cl

PCl Cl

P

Cl

N

Cl

O

P

O

Cl

Cl P

Cl

Cl

Cl

Rx-ID: 26381377 View in Reaxys 5/99 Yield

Conditions & References in 1,4-dioxane, Kinetics, byproducts: HCl; addn. of suspn. of (Cl3PNPCl3)PCl6 in dioxane to HN(POCl2)2 in dioxane (molar ratio 1:1) dropwise during 1 h at ambient temp., standing (several days); various product ratio for various conditions; (31)P-NMR spectroscopic monitoring Heubel, Joseph; Hammoutou, Yahia; Jaeger, Roger De; Phosphorus, Sulfur, and Silicon and the Related Elements; vol. 63; (1991); p. 19 - 32 ; (from Gmelin) View in Reaxys

N Cl P Cl Cl

Cl

Cl P+ Cl Cl P–Cl Cl Cl Cl Cl Cl

(v5)

Cl MoCl Cl Cl

Cl – Cl MoCl Cl Cl P Cl (v6) Cl Cl Cl

Cl

N P+ Cl Cl Cl

Cl

PCl Cl Cl

Rx-ID: 26381375 View in Reaxys 6/99 Yield 89 %

Conditions & References in not given, exclusion of moisture, stirred for 12 h at room temp.; filtered, dissolved in CH2Cl2, pptd. with CCl4, filtered, washed with CCl4, dried in vac.; elem. anal.

Mueller, Ulrich; Conradi, Elke; Patt-Siebel, Ute; Kersting, Meinolf; Schmidt, Inge; et al.; Zeitschrift fuer Anorganische und Allgemeine Chemie; vol. 560; (1988); p. 93 - 104 ; (from Gmelin) View in Reaxys

Copyright © 2017 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

5/33

2017-10-13 07:13:31

Cl

N

Cl

Cl Cl

Cl

PCl Cl Cl

Rx-ID: 26453063 View in Reaxys 7/99 Yield

Conditions & References With phosphorus trichoride in chloroform Kren, Robert M.; Sisler, Harry H.; Inorganica Chimica Acta; vol. 111; (1986); p. 31 - 34 ; (from Gmelin) View in Reaxys

HO

O

NH 2

Cl

O N

O

Cl

O

PCl Cl Cl

H 2N

H

S

Rx-ID: 25283265 View in Reaxys 8/99 Yield

Conditions & References

40 %

5 : Preparation of 7-Amino-3-Carbamoyloxymethyl-3-Cephem-4-Carboxylic Acid by Phosphorus Pentachloride Cleavage of 7-(5-Phthalimido-5-Carboxyvaleramido)-3-Carbamoyloxymethyl-3-Cephem-4-Carboxylic Acid EXAMPLE 5 Preparation of 7-Amino-3-Carbamoyloxymethyl-3-Cephem-4-Carboxylic Acid by Phosphorus Pentachloride Cleavage of 7-(5-Phthalimido-5-Carboxyvaleramido)-3-Carbamoyloxymethyl-3-Cephem-4-Carboxylic Acid To a stirred slurry of 3.0 grams of 7-(5-phthalimido-5-carboxyvaleramido)-3-carbamoyloxymethyl-3-cephem-4-carboxylic acid in 50 milliliters of absolute methylene chloride were added 2.9 milliliters of absolute pyridine and 4.5 milliliters of trimethylchlorosilane, to protect both of the carboxyl groups.

The resulting reaction mixture was stirred for two and one-half hours, then cooled to -12° C. in a carbon tetrachloride: dry ice bath.

To this were added 5.6 milliliters of absolute pyridine in one lot, and then 36.2 milliliters of a 10 percent solution of phosphorus pentachloride in absolute methylene chloride, dropwise, maintaining the temperature at -12° C. The reaction mixture was stirred for two and one-half hours, 40 milliliters of absolute methanol was added dropwise at -12° C. and stirred for thirty minutes, and for another thirty minutes at room temperature.

Then 10 milliliters of 50 percent formic acid was added dropwise, the pH adjusted to 2 by addition of triethylamine, and the reaction mixture stirred for forty-five minutes.

The solution became cloudy.

Then the pH was adjusted to 3.4, and the reaction mixture was refrigerated overnight and filtered, yielding 600 milligrams of 7-amino-3-carbamoyloxymethyl-3-cephem-4-carboxylic acid, 40 percent yield.

This was taken up in 5 milliliters of water, stirred and filtered.

The solid was washed with about 2 milliliters of water and 10 milliliters of acetone, yielding 450 milligrams of purified 7-amino-3-carbamoyloxymethyl-3-cephem-4-carboxylic acid, 30 percent yield.

Calc., for C9 H11 N3 O5 S: C, 39.56; H, 4.06; N, 15.38; S, 11.73. Found: C, 39.70; H, 4.12; N, 15.34; S, 11.98.

Patent; Eli Lilly and Company; US4145538; (1979); (A1) English View in Reaxys

Cl Cl

B

N

N

B

Cl

(v5)

Cl

Cl

B– ClCl

Cl

Cl

Cl

(v5)

N

P+ Cl Cl

Cl

PCl Cl Cl

Rx-ID: 26437760 View in Reaxys 9/99 Yield

Conditions & References Binder, H.; Fluck, E.; Zeitschrift fuer Anorganische und Allgemeine Chemie; vol. 381; (1971); p. 123 - 128 ; (from Gmelin) View in Reaxys vol. B: B-Verb.4; 4.4.2.3.1, page 120 - 124 ; (from Gmelin) View in Reaxys

Copyright © 2017 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

6/33

2017-10-13 07:13:31

Cl

F

Cl TB-5 PCl Cl F

F

Cl

F

F

Cl

F

F

F

P

F

Cl Cl

PCl Cl Cl

Cl

Rx-ID: 26386548 View in Reaxys 10/99 Yield

Conditions & References byproducts: PCl3; Irradiation (UV/VIS); UV; 6h vol. F: PerFHalOrg.3; 1.9, page 70 - 123 ; (from Gmelin) View in Reaxys byproducts: PCl3; Irradiation (UV/VIS); UV; 6h Griffiths, J. E.; Journal of Chemical Physics; vol. 41; (1964); p. 3510 - 3516 ; (from Gmelin) View in Reaxys

F F

F

Cl

(v6)F

Mo F

F

P

Cl

Cl Cl

Cl

Cl

F

(v5)

PCl Cl

Cl MoCl Cl

Cl

F

Cl

P F

Rx-ID: 26150705 View in Reaxys 11/99 Yield

Conditions & References in not given, react. of an excess of PCl3 with MoF6 forming PF3, MoCl5, Cl2; further react. of an excess of PCl3 with Cl2 forming PCl5; O'Donnell, T. A.; Stewart, D. F.; Journal of Inorganic and Nuclear Chemistry; vol. 24; (1962); p. 309 - 314 ; (from Gmelin) View in Reaxys in not given, react. of an excess of PCl3 with MoF6 forming PF3, MoCl5, Cl2; further react. of an excess of PCl3 with Cl2 forming PCl5; vol. P: MVol.C; 186, page 429 - 431 ; (from Gmelin) View in Reaxys 1

Cl –

Cl Cl

Cl

Cl P

Cl

P N

Cl

Cl(x)N(x)P(x)

Cl

PCl Cl Cl

(v4)

Cl

Rx-ID: 26540290 View in Reaxys 12/99 Yield

Conditions & References in neat (no solvent), decompn. on heating at 140 °C in vac.; Glemser, O.; Wyszomirski, E.; Naturwissenschaften; vol. 48; (1961); p. 25 - 25 View in Reaxys vol. P: MVol.C; 233, page 533 - 535 ; (from Gmelin) View in Reaxys

F

Cl

Cl

F

P

Cl

F

P+ ClCl

Cl

F

F –F FP F F

F Cl

PF Cl TB-5 F

F

Cl Cl

PCl Cl Cl

F

P FF F

Rx-ID: 26435511 View in Reaxys 13/99 Yield

Conditions & References in not given, fast react. of PF3 with Cl2 forming PF3Cl2; slow react. of PF3Cl2 forming (PCl4)(PF6) and slow react. forming PCl5 and PF5;; solid (PCl4)(PF6) contains small amounts of PCl5 or PFCl4; Muetterties, E. L.; Bither, T. A.; Farlow, M. W.; Coffman, D. D.; Journal of Inorganic and Nuclear Chemistry; vol.

16; (1960); p. 52 - 59 ; (from Gmelin) View in Reaxys in not given, fast react. of PF3 with Cl2 forming PF3Cl2; slow react. of PF3Cl2 forming (PCl4)(PF6) and slow react. forming PCl5 and PF5;; solid (PCl4)(PF6) contains small amounts of PCl5 or PFCl4;

Copyright © 2017 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

7/33

2017-10-13 07:13:31

vol. P: MVol.C; 211, page 484 - 487 ; (from Gmelin) View in Reaxys

Cl P Cl

F

F

S

F

Cl

F

Cl

Cl

Cl

F Cl

S

F

Cl

PCl Cl

P

Cl

Cl

Cl

Rx-ID: 26453930 View in Reaxys 14/99 Yield

Conditions & References -78°C Emeleus,H.J.; Pugh,H.; Journal of the Chemical Society; (1960); p. 1108 - 1112 View in Reaxys vol. F: PerFHalOrg.2; 1.1.6.10, page 27 - 31 ; (from Gmelin) View in Reaxys

P+ ClCl

Cl

F

F

Cl

– Cl PCl Cl Cl

Cl

Cl Cl P Cl

Cl

Cl

Cl

PCl Cl Cl

Rx-ID: 26587116 View in Reaxys 15/99 Yield

Conditions & References in neat (no solvent), dissociation above 110 °C; Kennedy, T.; Payne, D. S.; Journal of the Chemical Society; (1960); p. 4126 - 4130 View in Reaxys vol. P: MVol.C; 211, page 484 - 487 ; (from Gmelin) View in Reaxys

Cl (v1)

O

Cl

O

P

Cl

Cl Cl

Cl

O

PCl Cl

Cl P

Cl

Cl

Cl

Rx-ID: 26089281 View in Reaxys 16/99 Yield

Conditions & References in tetrachloromethane, addn. of a soln. of ClO2 in CCl4 to PCl3 dissolved in CCl4 below 20 °C; Perotti, A.; Gazzetta Chimica Italiana; vol. 89; (1959); p. 2046 - 2052 ; (from Gmelin) View in Reaxys in tetrachloromethane, addn. of a soln. of ClO2 in CCl4 to PCl3 dissolved in CCl4 below 20 °C; vol. P: MVol.C; 184, page 424 - 427 ; (from Gmelin) View in Reaxys Cl

S Cl

P Cl

Cl Cl

O

Cl

Cl

PCl Cl

O

S

O

Cl

O

Cl P

Cl

Cl

Rx-ID: 26391123 View in Reaxys 17/99 Yield

Conditions & References in tetrachloromethane, dropping PSCl3 to a soln. of ClO2 in CCl4; Perotti, A.; Gazzetta Chimica Italiana; vol. 89; (1959); p. 2046 - 2052 ; (from Gmelin) View in Reaxys in tetrachloromethane, dropping PSCl3 to a soln. of ClO2 in CCl4; vol. P: MVol.C; 260, page 594 - 596 ; (from Gmelin) View in Reaxys

Copyright © 2017 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

8/33

2017-10-13 07:13:31

Cl S

S

Cl

P

Cl

H

Cl

Cl

P Cl

Cl

OH

Cl

HO

Cl

P OH O

PCl Cl Cl

Rx-ID: 26448773 View in Reaxys 18/99 Yield

Conditions & References With aluminium trichloride in neat (no solvent), heating PCl3 with S and AlCl3 (catalyst) under exclusion of H2O; react. with the intermediate AlCl3*PCl3; addn. of AlCl3 in small portions to the boiling mixt. of PCl3 and S, react. on boiling completed after 10 min;; extraction of the cold crude product with H2O and separation with a separatory funnel; drying over CaCl2 and distn. at 125-126 °C at ambient pressure; Knotz, F.; Oesterr. Chem. - Ztg.; vol. 50; (1949); p. 128 - 129 View in Reaxys vol. P: MVol.C; 258, page 590 - 592 View in Reaxys Patent; Knotz, F.; US2915361; (1959); C. A.; (1960); p. 13579 ; (from Gmelin) View in Reaxys

Cl

Br – Cl Cl P Cl Cl

Cl

Cl Cl

P+ ClCl

Cl

PCl Cl Cl

Br

Br

Br

P

Br

Br

Br PBr Br

Br

Br

Rx-ID: 26456918 View in Reaxys 19/99 Yield

Conditions & References in tetrachloromethane, decomposition with deep red color in CCl4 soln., formed PBr5 partially decomposes into Br2 and PBr3; Kolditz, L.; Feltz, A.; Z. Anorg. Chem.; vol. 293; (1958); p. 286 - 293 View in Reaxys vol. P: MVol.C; 224, page 513 - 516 ; (from Gmelin) View in Reaxys

Cl

Br – Cl Cl P Cl Cl

Cl

Cl Cl

P+ ClCl

Cl

PCl Cl Cl

Rx-ID: 26456919 View in Reaxys 20/99 Yield

Conditions & References in neat (no solvent), decomposition in open tube at 120°C and in sealed tube at 145°C with formation of PCl5 as residue; Kolditz, L.; Feltz, A.; Z. Anorg. Chem.; vol. 293; (1958); p. 286 - 293 View in Reaxys vol. P: MVol.C; 224, page 513 - 516 ; (from Gmelin) View in Reaxys 1

Cl –

Cl Cl

Cl

P N

Cl P

(v4)

Cl

Cl

Cl

Cl

PCl Cl Cl

Rx-ID: 26540291 View in Reaxys 21/99 Yield

Conditions & References in neat (no solvent), sublimation of PCl5 at 150 °C in vac.; Groeneveld, W. L.; Visser, J. H.; Seuter, A. M. J. H.; Journal of Inorganic and Nuclear Chemistry; vol. 8; (1958); p.

245 - 248 View in Reaxys vol. P: MVol.C; 233, page 533 - 535 ; (from Gmelin) View in Reaxys

Copyright © 2017 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

9/33

2017-10-13 07:13:31

O

Cl

Cl

Cl

Cl Cl

P Cl

Cl

PCl Cl Cl

Rx-ID: 26161293 View in Reaxys 22/99 Yield

Conditions & References With carbon in neat (no solvent), passing a mixture of POCl3 vapor and an excess of Cl2 through a porous C mass above 162°C; Patent; Lind, R.; Broadley, J. S.; United Kingdom Atomic Energy Authority; GB786760; (1957); C.; (1958); p.

12800 View in Reaxys Patent; Lind, R.; Broadley, J. S.; United Kingdom Atomic Energy Authority; GB788241; (1957); C. A.; (1958); p.

11374 ; (from Gmelin) View in Reaxys With C in neat (no solvent), passing a mixture of POCl3 vapor and an excess of Cl2 through a porous C mass above 162°C; vol. P: MVol.C; 189, page 434 - 437 ; (from Gmelin) View in Reaxys

F

Cl

Cl Cl P Cl

Cl

Cl

P+

ClCl

Cl

F F

–F FP F

F

Cl

PCl Cl Cl

Rx-ID: 26453731 View in Reaxys 23/99 Yield

Conditions & References in neat (no solvent), decompn. above 60 °C; further react. with PF5 forming (PCl4)(PF6); Kolditz, L.; Z. Anorg. Chem.; vol. 286; (1956); p. 307 - 316 View in Reaxys Kolditz, L.; Z. Anorg. Chem.; vol. 289; (1957); p. 128 - 140 View in Reaxys Kolditz, L.; Z. Anorg. Chem.; vol. 293; (1957); p. 147 - 154 View in Reaxys vol. P: MVol.C; 211, page 484 - 487 ; (from Gmelin) View in Reaxys in neat (no solvent), react. by liquefaction and solidification; Kolditz, L.; Z. Anorg. Chem.; vol. 286; (1956); p. 307 - 316 View in Reaxys vol. P: MVol.C; 210, page 482 - 484 ; (from Gmelin) View in Reaxys

Cl

Cl

Cl

P Cl

Cl

Cl Cl

PCl Cl Cl

Rx-ID: 26150736 View in Reaxys 24/99 Yield

Conditions & References in not given, prepn. in laboratory; react. of Cl2 with PCl3; apparatus described; Lisowski, W.; Roczniki Chemii; vol. 30; (1956); p. 973 - 976; C. A.; (1957); p. 7061 ; (from Gmelin) View in Reaxys in trichlorophosphate, passing Cl2 in a soln. of PCl3 in POCl3; Patent; Wirth, W. V.; E. I. du Pont de Nemours & Co.; US1906440; (1933); C. II; (1933); p. 426 ; (from Gmelin) View in Reaxys in tetrachloromethane, passing Cl2 in soln. of PCl3 in CCl4 (ratio 1:1) in a vessel cooled with water;; filtration; Wazer, J. R. van; Encyclopedia of Chemical Technology, herausgegeben von Kirk, R. E., Othmer, D. F., The Interscience Encyclopedia, Inc., New York, Bd. 10, 1953, S. 479 ; (from Gmelin)

Copyright © 2017 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

10/33

2017-10-13 07:13:31

View in Reaxys in neat (no solvent), continous process in a column; passing PCl3 and Cl2 through the column in counterflow; use of Pb tubes and leaded steel; Wazer, J. R. van; Encyclopedia of Chemical Technology, herausgegeben von Kirk, R. E., Othmer, D. F., The Interscience Encyclopedia, Inc., New York, Bd. 10, 1953, S. 479 ; (from Gmelin) View in Reaxys in neat (no solvent), dropping PCl3 in an atmosphere of Cl2 in iron vessels;; product contains 0.07 percent Fe; Manoev, D.; Mazel', V.; SSSR nauchno-tekhn. Otdel VSNKH Nr. 214 (1927) 39/45; C. II; (1930); p. 1511 ; (from Gmelin) View in Reaxys in neat (no solvent), prepn. in laboratory; dropping PCl3 and passing HCl in the reaction vessel; apparatus described; Maxson, R. N.; Booth, H. S.; Hermann, C. V.; Booth, H. S., Inorganic syntheses, Bd. 1, Nw York-London 1939, S. 99/100 ; (from Gmelin) View in Reaxys in neat (no solvent), react. of liquid Cl2 with PCl3 without sublimation of PCl5; Patent; Marsh, W. J.; Hooker Electrochemical Co.; US1914750; (1933); C. II; (1933); p. 1912 ; (from Gmelin) View in Reaxys in not given, react. of Cl2 with PCl3 under exclusion of air;; sublimation in a Cl2 stream; Fischer, W.; Juebermann, O.; Z. anorg. allg. Chem.; vol. 235; (1938); p. 337 - 351 ; (from Gmelin) View in Reaxys in not given, react. of PCl3 with Cl2 in sealed vessel; anonymous; Ind. Chem.; vol. 25; (1949); p. 517 - 520 ; (from Gmelin) View in Reaxys in not given, react. of PCl3 with excess Cl2; Sorel, J.; Chim. et Ind.; vol. 60; (1948); p. 541 - 549 ; (from Gmelin) View in Reaxys in not given, react. of PCl3 with Cl2 in sealed vessel; vol. P: MVol.C; 189, page 434 - 437 ; (from Gmelin) View in Reaxys in neat (no solvent), continous process in a column; passing PCl3 and Cl2 through the column in counterflow; use of Pb tubes and leaded steel; vol. P: MVol.C; 189, page 434 - 437 ; (from Gmelin) View in Reaxys in neat (no solvent), dropping PCl3 in an atmosphere of Cl2 in iron vessels;; product contains 0.07 percent Fe; vol. P: MVol.C; 189, page 434 - 437 ; (from Gmelin) View in Reaxys in neat (no solvent), prepn. in laboratory; dropping PCl3 and passing HCl in the reaction vessel; apparatus described; vol. P: MVol.C; 189, page 434 - 437 ; (from Gmelin) View in Reaxys in neat (no solvent), react. of liquid Cl2 with PCl3 without sublimation of PCl5; vol. P: MVol.C; 189, page 434 - 437 ; (from Gmelin) View in Reaxys

Copyright © 2017 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

11/33

2017-10-13 07:13:31

in not given, prepn. in laboratory; react. of Cl2 with PCl3; apparatus described; vol. P: MVol.C; 189, page 434 - 437 ; (from Gmelin) View in Reaxys in not given, react. of Cl2 with PCl3 under exclusion of air;; sublimation in a Cl2 stream; vol. P: MVol.C; 189, page 434 - 437 ; (from Gmelin) View in Reaxys in not given, react. of PCl3 with excess Cl2; vol. P: MVol.C; 189, page 434 - 437 ; (from Gmelin) View in Reaxys in trichlorophosphate, passing Cl2 in a soln. of PCl3 in POCl3; vol. P: MVol.C; 189, page 434 - 437 ; (from Gmelin) View in Reaxys in tetrachloromethane, passing Cl2 in soln. of PCl3 in CCl4 (ratio 1:1) in a vessel cooled with water;; filtration; vol. P: MVol.C; 189, page 434 - 437 ; (from Gmelin) View in Reaxys Cl Cl

Br4Cl 56P12

PCl Cl Cl

Rx-ID: 26153574 View in Reaxys 25/99 Yield

Conditions & References in neat (no solvent), sublimation at 80°C;; compound has nearly composition of PCl5, but x-ray diagram shows some differences to that of tetragonal PCl5; Popov, I. A.; Geske, D. H.; Baenziger, N. C.; Journal of the American Chemical Society; vol. 78; (1956); p. 1793 1796 View in Reaxys vol. P: MVol.C; 223, page 511 - 513 ; (from Gmelin) View in Reaxys Cl

P

red

Cl

Cl

Cl

PCl Cl Cl

O

Cl P

Cl

Cl

Cl

P

Cl

Cl

Rx-ID: 26182465 View in Reaxys 26/99 Yield <1

Conditions & References in tetrachloromethane, pouring red P with dry CCl4, cooling at 5°C and passing in Cl2; keeping temp. below 70 °C; stirring; standing for 2-3 h and repeating the process;; decanting pptd. PCl5; passing Cl2 through the soln. for 20 min; filtration in vacuum; product contains a small amount of PCl3, traces of POCl3 and 25-40 percent CCl4; distn. in vacuum; Bulashevich, E. A.; Zh. prikl. Khim.; vol. 28; (1955); p. 431 - 433; C. A.; (1955); p. 13811 ; (from Gmelin) View in Reaxys

<1

in tetrachloromethane, pouring red P with dry CCl4, cooling at 5°C and passing in Cl2; keeping temp. below 70 °C; stirring; standing for 2-3 h and repeating the process;; decanting pptd. PCl5; passing Cl2 through the soln. for 20 min; filtration in vacuum; product contains a small amount of PCl3, traces of POCl3 and 25-40 percent CCl4; distn. in vacuum; vol. P: MVol.C; 189, page 434 - 437 ; (from Gmelin) View in Reaxys

Copyright © 2017 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

12/33

2017-10-13 07:13:31

Cl PCl Cl

Cl

Cl Cl

Cl

PCl Cl

Cl 2Hg

Cl

Cl 2Hg

Rx-ID: 26144058 View in Reaxys 27/99 Yield

Conditions & References heating; decompn.

Groeneveld, W. L.; Diss. Leiden 1953, p. 32, 47 View in Reaxys Groeneveld, W. L.; Rec. Trav. Chim.; vol. 71; (1952); p. 1152 - 1156 ; (from Gmelin) View in Reaxys heating; decompn. vol. Hg: MVol.B4; 3, page 1357 - 1369 ; (from Gmelin) View in Reaxys

O

Cl

O N

P

Cl

Cl

Cl

Cl

PCl Cl

Cl

Cl

O

O N O

O

O

N

N O

Cl P

Cl

Cl

Cl

Rx-ID: 26144143 View in Reaxys 28/99 Yield

Conditions & References in neat (no solvent), distilling NO2Cl to an excess of PCl3 at -75 °C; exothermic react.; Batey, H. H.; Sisler, H. H.; Journal of the American Chemical Society; vol. 74; (1952); p. 3408 - 3410 ; (from Gmelin) View in Reaxys in neat (no solvent), reaction of NO2Cl and excess of PCl3 at -75°C; Batey, H. H.; Sisler,, H. H.; J. Am. Chem. soc.; vol. 74; (1952); p. 3408 - 3410 View in Reaxys vol. Cl: SVol.B2; 99, page 529 - 531 ; (from Gmelin) View in Reaxys in neat (no solvent), distilling NO2Cl to an excess of PCl3 at -75 °C; exothermic react.; vol. P: MVol.C; 184, page 424 - 427 ; (from Gmelin) View in Reaxys

Cl Bi

Cl

Cl

Cl

Cl 3

Cl

Cl

PCl Cl

PCl Cl Cl

Cl

Rx-ID: 26171602 View in Reaxys 29/99 Yield

Conditions & References in neat (no solvent), decomposition on heating; Groeneveld, W. L.; REcueil Trav. chim. Pays-Bas; vol. 71; (1952); p. 1152 - 1156 View in Reaxys Groeneveld, W. L.; Diss. Leiden 1953, S. 55 ; (from Gmelin) View in Reaxys in neat (no solvent), decomposition on heating; vol. Bi: SVol.; 167, page 681 - 683 ; (from Gmelin) View in Reaxys

Copyright © 2017 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

13/33

2017-10-13 07:13:31

(v2)

Cl

Cl

I– Cl

Cl

Cl

Cl

P+ ClCl

PCl Cl

I

Cl

Cl

Rx-ID: 26588683 View in Reaxys 30/99 Yield

Conditions & References in tetrachloromethane, dissociation in CCl4;; detected by spectroscopy; Popov; Schmorr; Journal of the American Chemical Society; vol. 74; (1952); p. 4672 ; (from Gmelin) View in Reaxys in tetrachloromethane, dissociation in CCl4;; detected by spectroscopy; vol. P: MVol.C; 232, page 531 - 533 ; (from Gmelin) View in Reaxys Cl

P P

P

P

I

Cl

Cl

PCl Cl Cl

Rx-ID: 26090333 View in Reaxys 31/99 Yield

Conditions & References in neat (no solvent), react. of P4 with molten ICl under explosion; Gutmann, V.; Z. anorg. allg. Chem.; vol. 264; (1951); p. 169 - 173 ; (from Gmelin) View in Reaxys in neat (no solvent), react. of P4 with molten ICl under explosion; vol. P: MVol.C; 189, page 434 - 437 ; (from Gmelin) View in Reaxys Cl

P

red

I

Cl

Cl

PCl Cl Cl

Rx-ID: 26090355 View in Reaxys 32/99 Yield

Conditions & References

>99

byproducts: J2; with explosion vol. P: MVol.B; 3.4.2.2, page 307 - 310 View in Reaxys Gutmann, V.; Z. Anorg. Chem.; vol. 264; (1951); p. 169 - 173 ; (from Gmelin) View in Reaxys in neat (no solvent), react. of red P with molten ICl under explosion; Gutmann, V.; Z. anorg. allg. Chem.; vol. 264; (1951); p. 169 - 173 ; (from Gmelin) View in Reaxys in neat (no solvent), react. of red P with molten ICl under explosion; vol. P: MVol.C; 189, page 434 - 437 ; (from Gmelin) View in Reaxys

P P PP white

Cl I

Cl

Cl

PCl Cl Cl

Rx-ID: 26382320 View in Reaxys 33/99 Yield

Conditions & References byproducts: I2 vol. P: MVol.B; 3.4.2.2, page 307 - 310 View in Reaxys Gutmann, V.; Z. Anorg. Chem.; vol. 264; (1951); p. 169 - 173 ; (from Gmelin)

Copyright © 2017 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

14/33

2017-10-13 07:13:31

View in Reaxys Cl N

Cl

Cl

N 5P3

Cl

Cl

P Cl

P

Cl

cyclic polyphosphorus nitride dichloride

N N

Cl

P Cl Cl

PCl Cl

N

N

Cl

Rx-ID: 26364443 View in Reaxys 34/99 Yield

Conditions & References in neat (no solvent), formation of a mixt. of phosphorus nitride dichlorides with a large amount of (NPCl2)3 and a small amount of PCl5 by react. of P3N5 with Cl2 at 700 °C; Wetroff, G.; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 208; (1939); p. 580 583 ; (from Gmelin) View in Reaxys vol. P: MVol.C; 240, page 549 - 551 ; (from Gmelin) View in Reaxys Cl N

Cl

Cl

N 6P4

Cl

Cl

P Cl

P

Cl

cyclic polyphosphorus nitride dichloride

N N

P Cl Cl

Cl

PCl Cl

N

N

Cl

Rx-ID: 26441544 View in Reaxys 35/99 Yield

Conditions & References in neat (no solvent), formation of a mixt. of phosphorus nitride dichlorides with a large amount of (NPCl2)3 and a small amount of PCl5 by react. of P4N6 with Cl2 at 700 °C; Wetroff, G.; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 208; (1939); p. 580 583 ; (from Gmelin) View in Reaxys vol. P: MVol.C; 240, page 549 - 551 ; (from Gmelin) View in Reaxys F

F Cl Cl P Cl

F

Cl

Cl

P FF TB-5

Cl

PCl Cl Cl

F

Rx-ID: 26453732 View in Reaxys 36/99 Yield

Conditions & References in neat (no solvent), decompn. at 25 °C after 30 h; Booth, H. S.; Bozarth, A. R.; Journal of the American Chemical Society; vol. 61; (1939); p. 2927 - 2934 View in Reaxys vol. P: MVol.C; 211, page 484 - 487 ; (from Gmelin) View in Reaxys Cl

Cl

P

S Cl

O

O

white

Cl

PCl Cl Cl

Cl

P

Cl

Cl

Rx-ID: 26402938 View in Reaxys 37/99 Yield

Conditions & References in neat (no solvent), excess of SO2Cl2; sealed tube (180°C); Danneel, H.; Schlottmann, F.; Z. Anorg. Chem.; vol. 212; (1933); p. 225 - 232 View in Reaxys Koechlin, P.; Heumann, K.; Ber.; vol. 15; (1882); p. 1736 - 1738 View in Reaxys vol. S: MVol.B3; 135, page 1815 - 1817 ; (from Gmelin) View in Reaxys

Copyright © 2017 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

15/33

2017-10-13 07:13:31

3 Ca 2+ – O 2 O

Cl

O– P

Cl O–

Cl

Cl

PCl Cl Cl

Rx-ID: 26112960 View in Reaxys 38/99 Yield

Conditions & References With silicate, carbon in neat (no solvent), heating a mixture of phosphate and silicate with coal in a stream of Cl2 at 1300 °C; Patent; Miner, C. G.; US1730521; (1929); C. II; (1929); p. 3174 ; (from Gmelin) View in Reaxys With silicate, carbon, copper dichloride in neat (no solvent), heating a mixture of phosphate and silicate with coal in a stream of Cl2 at 1300 °C in presence of a catalyst (CuCl2); Patent; Gelissen, H.; N. V. Electrochemische Industrie; DE522270; (1931); C. I; (1931); p. 3496 View in Reaxys Patent; Gelissen, H.; N. V. Electrochemische Industrie; GB302927; (1929); C. I; (1929); p. 1851 View in Reaxys Patent; Gelissen, H.; N. V. Electrochemische Industrie; GB356238; (1932); C. A.; (1932); p. 4422 View in Reaxys Patent; Gelissen, H.; N. V. Electrochemische Industrie; FR664850; (1929); C. A.; (1930); p. 926 ; (from Gmelin) View in Reaxys With silicate, carbon, copper dichloride in neat (no solvent), heating a mixture of phosphate and silicate with coal in a stream of Cl2 at 1300 °C under pressure in vessels lined with insoluble halogenides; Patent; Gelissen, H.; N. V. Electrochemische Industrie; GB304694; (1929); C. I; (1929); p. 2564 ; (from Gmelin) View in Reaxys With silicate, carbon in neat (no solvent), heating a mixture of phosphate and silicate with coal in a stream of Cl2 at 1300 °C in presence of a dispersion agent (ZnCl2); Patent; Gelissen, H.; N. V. Electrochemische Industrie; DE522270; (1931); C. I; (1931); p. 3496 View in Reaxys Patent; Gelissen, H.; N. V. Electrochemische Industrie; GB302927; (1929); C. I; (1929); p. 1851 View in Reaxys Patent; Gelissen, H.; N. V. Electrochemische Industrie; GB356238; (1932); C. A.; (1932); p. 4422 View in Reaxys Patent; Gelissen, H.; N. V. Electrochemische Industrie; FR664850; (1929); C. A.; (1930); p. 926 ; (from Gmelin) View in Reaxys With silicate, carbon in not given, heating a mixture of phosphate and silicate with coal in a stream of Cl2 at 1300 °C in presence of a solvent; Patent; Gelissen, H.; N. V. Electrochemische Industrie; DE522270; (1931); C. I; (1931); p. 3496 View in Reaxys Patent; Gelissen, H.; N. V. Electrochemische Industrie; GB302927; (1929); C. I; (1929); p. 1851 View in Reaxys Patent; Gelissen, H.; N. V. Electrochemische Industrie; GB356238; (1932); C. A.; (1932); p. 4422 View in Reaxys Patent; Gelissen, H.; N. V. Electrochemische Industrie; FR664850; (1929); C. A.; (1930); p. 926 ; (from Gmelin) View in Reaxys With coal, silicate, copper dichloride in neat (no solvent), heating a mixture of phosphate and silicate with coal in a stream of Cl2 at 1300 °C under pressure in vessels lined with insoluble halogenides; vol. P: MVol.C; 189, page 434 - 437 ; (from Gmelin) View in Reaxys With coal, silicate, copper dichloride in neat (no solvent), heating a mixture of phosphate and silicate with coal in a stream of Cl2 at 1300 °C in presence of a catalyst (CuCl2); vol. P: MVol.C; 189, page 434 - 437 ; (from Gmelin) View in Reaxys

Copyright © 2017 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

16/33

2017-10-13 07:13:31

With coal, silicate in neat (no solvent), heating a mixture of phosphate and silicate with coal in a stream of Cl2 at 1300 °C in presence of a dispersion agent (ZnCl2); vol. P: MVol.C; 189, page 434 - 437 ; (from Gmelin) View in Reaxys With coal, silicate in neat (no solvent), heating a mixture of phosphate and silicate with coal in a stream of Cl2 at 1300 °C; vol. P: MVol.C; 189, page 434 - 437 ; (from Gmelin) View in Reaxys With coal, silicate in not given, heating a mixture of phosphate and silicate with coal in a stream of Cl2 at 1300 °C in presence of a solvent; vol. P: MVol.C; 189, page 434 - 437 ; (from Gmelin) View in Reaxys

Cl

Cl

O

Cl

Cl Cl

P Cl

O

Cl

PCl Cl Cl

Rx-ID: 26146644 View in Reaxys 39/99 Yield

Conditions & References With charcoal or active carbon in neat (no solvent), react. of POCl3 with COCl2 and charcoal or active carbon above 400 °C; Patent; Klebert, L.; I. G. Farbenindustrie A.-G.; DE492061; (1930); C. I; (1930); p. 2292 ; (from Gmelin) View in Reaxys With charcoal or active carbon in neat (no solvent), react. of POCl3 with COCl2 and charcoal or active carbon above 400 °C; vol. P: MVol.C; 189, page 434 - 437 ; (from Gmelin) View in Reaxys

O

Cl

Cl

O

P Cl

O

Cl

Cl

PCl Cl Cl

Rx-ID: 26161239 View in Reaxys 40/99 Yield

Conditions & References With carbon monoxide, chlorine, above 400°C vol. C: MVol.C2; 1.10.5, page 150 - 151 View in Reaxys Patent; Kleber, L.; I. G. Farbenindustrie; DE492061; (1930) ; (from Gmelin) View in Reaxys

O C

O

Cl

Cl Cl

Cl

Cl Cl

P Cl

PCl Cl Cl

Rx-ID: 26161273 View in Reaxys 41/99 Yield

Conditions & References With charcoal or active carbon in neat (no solvent), react. of POCl3 with CO, Cl2 and charcoal or active carbon above 400 °C; Patent; Klebert, L.; I. G. Farbenindustrie A.-G.; DE492061; (1930); C. I; (1930); p. 2292 ; (from Gmelin) View in Reaxys With charcoal or active carbon in neat (no solvent), react. of POCl3 with CO, Cl2 and charcoal or active carbon above 400 °C; vol. P: MVol.C; 189, page 434 - 437 ; (from Gmelin)

Copyright © 2017 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

17/33

2017-10-13 07:13:31

View in Reaxys

3 Ca 2+ – O 2

Cl

O– P

O

ClNa

O2Si

O–

Cl

CaNa 10O18Si6

PCl Cl Cl

Rx-ID: 26099668 View in Reaxys 42/99 Yield

Conditions & References in neat (no solvent), heating phosphate with NaCl and SiO2 at 1100-1400 °C; Patent; Miner, C. G.; US1688503; (1928); C. I; (1929); p. 126 ; (from Gmelin) View in Reaxys in neat (no solvent), heating phosphate with NaCl and SiO2 at 1100-1400 °C; vol. P: MVol.C; 189, page 434 - 437 ; (from Gmelin) View in Reaxys Cl

Cl

Cl

Cl

PCl Cl Cl

Rx-ID: 26182420 View in Reaxys 43/99 Yield

Conditions & References in neat (no solvent), pptn. by react. of PCl3 with Cl2; Biltz, W.; Jeep, K.; Z. anorg. allg. Chem.; vol. 162; (1927); p. 32 - 48 View in Reaxys vol. P: MVol.C; 188, page 433 - 434 ; (from Gmelin) View in Reaxys

O

2 Cl

P ClCl

O (v6)

O

O

O

Cl

O

Cl

S

2+Cr (v4)

Cr O Cl

O–

O –O

Cl

S OO

PCl Cl Cl

O

Cl P

Cl

Cl

Rx-ID: 26391755 View in Reaxys 44/99 Yield

Conditions & References in neat (no solvent), react. with CrO2Cl2; Oddo, G.; Casalino, A.; Gazzetta Chimica Italiana; vol. 57; (1927); p. 60 - 74 ; (from Gmelin) View in Reaxys in neat (no solvent), react. with CrO2Cl2; vol. P: MVol.C; 261, page 596 - 599 ; (from Gmelin) View in Reaxys Cl Cl SbCl Cl

Cl Cl SbCl Cl Cl

Cl Cl

Cl

PCl Cl

Cl Cl

I

PCl Cl Cl

Sb

I

I

Cl

Rx-ID: 26167037 View in Reaxys 45/99 Yield

Conditions & References With Pl3, byproducts: I2; heating (water bath), evolution of heat and I2 vapor Karantassis; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 182; (1926); p.

1392 - 1392 ; (from Gmelin) View in Reaxys vol. Sb: MVol.B2; 9.6, page 443 - 447 ; (from Gmelin) View in Reaxys

Copyright © 2017 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

18/33

2017-10-13 07:13:31

Cl

Cl

P

Cl

Cl

PCl Cl Cl

Rx-ID: 26125236 View in Reaxys 46/99 Yield

Conditions & References in neat (no solvent), react. of P distd. under N2 with Cl2 in a stream of N2; Holroyd, G. W. F.; Chadwick, H.; Mitchell, J. E. H.; Journal of the Chemical Society; vol. 127; (1925); p. 2492 2493 ; (from Gmelin) View in Reaxys in neat (no solvent), react. of P distd. under N2 with Cl2 in a stream of N2; vol. P: MVol.C; 189, page 434 - 437 ; (from Gmelin) View in Reaxys

Cl

Cl

Cl

P

Cl

Cl

PCl Cl TB-5 Cl

Rx-ID: 26150638 View in Reaxys 47/99 Yield

Conditions & References With chlorine in neat (no solvent), react. of PCl3 with Cl2 under exclusion of H2O at ambient temp.; formation of an white oversaturated vapor; Taylor, H. A.; Journal of Physical Chemistry; vol. 28; (1924); p. 510 - 513 View in Reaxys vol. P: MVol.C; 183, page 421 - 424 ; (from Gmelin) View in Reaxys Cl

H P

H

Cl

H

PCl Cl Cl

Rx-ID: 26170032 View in Reaxys 48/99 Yield

Conditions & References With chlorine in neat (no solvent), igniting in Cl2-atmosphere; formation of PCl5; Thomson, T.; Philosophical Magazine (1798-1977); vol. 8; (1816); p. 87 - 93 View in Reaxys vol. P: MVol.C; 20, page 39 - 40 ; (from Gmelin) View in Reaxys With chlorine in neat (no solvent), vigorous react. of PH3 with Cl2 even at -100°C; Stock, A.; Ber. Dtsch. Chem. Ges.; vol. 53; (1920); p. 837 - 842 View in Reaxys vol. P: MVol.C; 20, page 39 - 40 ; (from Gmelin) View in Reaxys Cl

Cl –

H

Cl

+

H

P HH

PCl Cl Cl

Rx-ID: 26391202 View in Reaxys 49/99 Yield

Conditions & References With chlorine in further solvent(s), react. of a suspension of PH4Cl in liquid HCl with an excess of Cl2 at -100 °C Stock, A.; Ber. dtsch. chem. Ges.; vol. 53; (1920); p. 837 - 842 ; (from Gmelin) View in Reaxys With Cl2 vol. P: MVol.C; 197, page 451 - 452 ; (from Gmelin)

Copyright © 2017 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

19/33

2017-10-13 07:13:31

View in Reaxys

Cl

S

Cl

S

Cl

P

Cl

white

S

S

Cl

Cl

O

P Cl

Cl

PCl Cl

Cl

O

S

O

Cl

P

Cl

Cl

Cl

Rx-ID: 26105601 View in Reaxys 50/99 Yield

Conditions & References in neat (no solvent), excess of SOCl2; 180°C; North, H. B.; Thomson, J. C.; Journal of the American Chemical Society; vol. 40; (1918); p. 774 - 777 ; (from Gmelin) View in Reaxys in neat (no solvent), excess of SOCl2; 180°C; vol. S: MVol.B3; 124, page 1796 - 1798 ; (from Gmelin) View in Reaxys Cl

Cl P

S Cl

O

Cl

O

O

PCl Cl

S

O

Cl

Rx-ID: 26125200 View in Reaxys 51/99 Yield

Conditions & References in not given, react. of P with SO2Cl2 under evolution of SO2; intermediate PCl3; North, H. B.; Thomson, J. C.; Journal of the American Chemical Society; vol. 40; (1918); p. 774 - 777 ; (from Gmelin) View in Reaxys in not given, react. of P with SO2Cl2 under evolution of SO2; intermediate PCl3; vol. P: MVol.C; 189, page 434 - 437 ; (from Gmelin) View in Reaxys

Cl

S

Cl

Cl

O

P

Cl

S

Cl

P

Cl

Cl

Cl

Cl

Cl

O

PCl Cl

Cl P

Cl

Cl

Cl

Rx-ID: 26144249 View in Reaxys 52/99 Yield

Conditions & References in neat (no solvent), slowly at 80-160°C;; POCl3 only supposed; North, H. B.; Thomson, J. C.; Journal of the American Chemical Society; vol. 40; (1918); p. 774 - 777 View in Reaxys Michaelis, A.; Jena. Z. Med. Naturwiss.; vol. 6; (1870); p. 239 - 241 ; (from Gmelin) View in Reaxys vol. S: MVol.B3; 126, page 1800 - 1801 ; (from Gmelin) View in Reaxys

Cl

S

Cl

Cl

S

P

red

Cl

S

S

Cl

O

Cl

P Cl

Cl

Cl

PCl Cl Cl

O

S

O

Cl

P

Cl

Cl

Rx-ID: 26144308 View in Reaxys 53/99 Yield

Conditions & References in neat (no solvent), excess of SOCl2; 180°C; North, H. B.; Thomson, J. C.; Journal of the American Chemical Society; vol. 40; (1918); p. 774 - 777 ; (from Gmelin) View in Reaxys in neat (no solvent), excess of SOCl2; 180°C;

Copyright © 2017 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

20/33

2017-10-13 07:13:31

vol. S: MVol.B3; 124, page 1796 - 1798 ; (from Gmelin) View in Reaxys

Cl

Cl

S

Cl

P

Cl

red

S

S

Cl

Cl

O

O

PCl Cl

S

O

Cl

P

Cl

Cl

Cl

Rx-ID: 26144309 View in Reaxys 54/99 Yield

Conditions & References at 180°C vol. P: MVol.B; 3.4.2.2, page 307 - 310 View in Reaxys North, H. B.; Thomson, J. C.; Journal of the American Chemical Society; vol. 40; (1918); p. 774 - 777 ; (from Gmelin) View in Reaxys

Cl

Cl

S Cl

O

O

P

Cl

Cl

O

PCl Cl

Cl

Cl

S

O

Cl

Rx-ID: 26150688 View in Reaxys 55/99 Yield

Conditions & References in not given, react. with SO2Cl2; North, H. B.; Thomson, J. C.; Journal of the American Chemical Society; vol. 40; (1918); p. 774 - 777 ; (from Gmelin) View in Reaxys in not given, react. with SO2Cl2; vol. P: MVol.C; 184, page 424 - 427 ; (from Gmelin) View in Reaxys

Cl

S

Cl

O

Cl

P P PP

Cl

S

S

Cl

white

Cl

O

PCl Cl

S

O

Cl

Cl

P

Cl

Cl

Rx-ID: 26441676 View in Reaxys 56/99 Yield

Conditions & References at 180°C vol. P: MVol.B; 3.4.2.2, page 307 - 310 View in Reaxys North, H. B.; Thomson, J. C.; Journal of the American Chemical Society; vol. 40; (1918); p. 774 - 777 ; (from Gmelin) View in Reaxys O

Cl (v6)

O

Cr O Cl

Cl

P

Cl

Cl

P ClCl

Cl ClCrO

Cl Cl

PCl Cl Cl

Rx-ID: 26150681 View in Reaxys 57/99 Yield

Conditions & References in tetrachloromethane, react. of equimolar amount of PCl3 and CrO2Cl2 in CCl4; pptn. of CrOCl*POCl3; Fry, H. S.; Donelly, J. L.; Journal of the American Chemical Society; vol. 38; (1916); p. 1923 - 1928 ; (from Gmelin) View in Reaxys in tetrachloromethane, react. of equimolar amount of PCl3 and CrO2Cl2 in CCl4; pptn. of CrOCl*POCl3; vol. P: MVol.C; 186, page 429 - 431 ; (from Gmelin) View in Reaxys

Copyright © 2017 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

21/33

2017-10-13 07:13:31

3 Ca 2+ – O 2

Cl

O– P

O

Cl

O–

PCl Cl Cl

Rx-ID: 26112931 View in Reaxys 58/99 Yield

Conditions & References With alkali chloride in neat (no solvent), heating Ca-phosphate and alkali chloride in a sealed vessel under exclusion of air; fast react. at 1100 °C;; sucking off the gaseous products; Patent; Paecock, S.; Agricultural Research Corp.; US1147183; (1915); C. A.; (1915); p. 2433 View in Reaxys Patent; Paecock, S.; Agricultural Research Corp.; DE276024; (1914); C. II; (1914); p. 364 View in Reaxys Patent; Paecock, S.; Agricultural Research Corp.; GB23023; (1913) View in Reaxys Patent; Paecock, S.; Agricultural Research Corp.; FR463497; (1913); C. A.; (1914); p. 2785 ; (from Gmelin) View in Reaxys With alkali chloride in neat (no solvent), heating Ca-phosphate and alkali chloride in a sealed vessel under exclusion of air; fast react. at 1100 °C;; sucking off the gaseous products; vol. P: MVol.C; 189, page 434 - 437 ; (from Gmelin) View in Reaxys Cl

Cl

P

Cl

P

PCl Cl

Cl

Cl

Cl

Cl

Cl

Rx-ID: 26125235 View in Reaxys 59/99 Yield

Conditions & References in neat (no solvent), react. of a small excess of Cl2 with P in vac. under exclusion of H2O;; removal of formed PCl5 by fractional distn..; Baxter, G. P.; Moore, C. J.; Journal of the American Chemical Society; vol. 34; (1912); p. 1644 - 1657 View in Reaxys Baxter, G. P.; Moore, C. J.; Z. anorg. allg. Chem.; vol. 80; (1913); p. 185 - 200 View in Reaxys vol. P: MVol.C; 179, page 412 - 414 ; (from Gmelin) View in Reaxys

Cl

P

Cl

Cl

Cl

S

H

Cl

HS

Cl

S

PCl Cl Cl

Rx-ID: 5809426 View in Reaxys 60/99 Yield

Conditions & References T= -15 - -10 °C Autenrieth; Geyer; Chemische Berichte; vol. 41; (1908); p. 4254 View in Reaxys H 2N

O N

N

N

OH

N

N

N

Cl

O Cl

PCl Cl Cl

Rx-ID: 7046945 View in Reaxys 61/99 Yield

Conditions & References Einw. von NH3 Bamberger; Demuth; Chemische Berichte; vol. 35; (1902); p. 1895 View in Reaxys

Copyright © 2017 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

22/33

2017-10-13 07:13:31

Cl

Cl

OP4

Cl

Cl

O

PCl Cl

Cl P

Cl

Cl

Cl

Rx-ID: 26147000 View in Reaxys 62/99 Yield

Conditions & References in neat (no solvent), react. of Cl2 with dry P4O; Michaelis, A.; Pitsch, M.; Liebigs. Ann. Chem.; vol. 310; (1900); p. 45 - 74 ; (from Gmelin) View in Reaxys

0%

in tetrachloromethane, react. of an excess of Cl2 with P4O in CCl4; no formation of POCl3; Besson, A.; C. r. Acad. Sci. (Paris); vol. 124; (1897); p. 763 - 765 ; (from Gmelin) View in Reaxys

0%

in neat (no solvent), react. of an excess of Cl2 with P4O under inflammation; no formation of POCl3; Besson, A.; C. r. Acad. Sci. (Paris); vol. 124; (1897); p. 763 - 765 ; (from Gmelin) View in Reaxys in neat (no solvent), reaction of Cl2 with dry P4O; vol. P: MVol.C; 200, page 458 - 460 ; (from Gmelin) View in Reaxys in neat (no solvent), reaction of Cl2 with dry P4O; Michaelis, A.; Pitsch, M.; Liebigs Annalen der Chemie; vol. 310; (1900); p. 45 - 74 ; (from Gmelin) View in Reaxys in neat (no solvent), react. of Cl2 with dry P4O; vol. P: MVol.C; 189, page 434 - 437 ; (from Gmelin) View in Reaxys

0%

in neat (no solvent), react. of an excess of Cl2 with P4O under inflammation; no formation of POCl3; vol. P: MVol.C; 189, page 434 - 437 ; (from Gmelin) View in Reaxys

0%

in tetrachloromethane, react. of an excess of Cl2 with P4O in CCl4; no formation of POCl3; vol. P: MVol.C; 189, page 434 - 437 ; (from Gmelin) View in Reaxys Cl Cl

OP4

O

PCl Cl

Cl P

Cl

Cl

Cl

Rx-ID: 26446445 View in Reaxys 63/99 Yield

Conditions & References With Cl2 in neat (no solvent), reaction of Cl2 with dry P4O; Michaelis, A.; Pitsch, M.; Liebigs Annalen der Chemie; vol. 310; (1900); p. 45 - 74 View in Reaxys vol. P: MVol.C; 31, page 60 - 62 ; (from Gmelin) View in Reaxys

O P

O

P O P

O

O P

O

Cl

P

Cl

Cl P

Cl

Cl

PCl Cl

O5P2

Cl

Rx-ID: 26150706 View in Reaxys 64/99 Yield

Conditions & References in neat (no solvent), heating PCl3 with P4O6 in a melting tube at 180 °C;

Copyright © 2017 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

23/33

2017-10-13 07:13:31

Thorpe, T. E.; Tutton, A. E.; Journal of the Chemical Society; vol. 59; (1891); p. 1019 - 1029 ; (from Gmelin) View in Reaxys in neat (no solvent), heating PCl3 with P4O6 in a sealing tube at 180 °C; Thorpe, T. E.; Tutton, A. E.; Journal of the Chemical Society; vol. 59; (1891); p. 1019 - 1029 ; (from Gmelin) View in Reaxys in neat (no solvent), heating PCl3 with P4O6 in a melting tube at 180 °C; vol. P: MVol.C; 184, page 424 - 427 ; (from Gmelin) View in Reaxys in neat (no solvent), heating PCl3 with P4O6 in a sealing tube at 180 °C; vol. P: MVol.C; 189, page 434 - 437 ; (from Gmelin) View in Reaxys F

F Cl

PF Cl TB-5

F

F

Cl

P FF TB-5

Cl

PCl Cl Cl

F

Rx-ID: 26168118 View in Reaxys 65/99 Yield

Conditions & References in neat (no solvent), heating at 200-250 °C; Pulenc, C.; C. r. Acad. Sci. (Paris); vol. 113; (1891); p. 75 - 78 ; (from Gmelin) View in Reaxys in neat (no solvent), heating at 200-250 °C; vol. P: MVol.C; 189, page 434 - 437 ; (from Gmelin) View in Reaxys

Cl Cl

Cl

Cl Ir

(v3)

Cl3

P

Cl

Cl

Cl

Cl

PCl Cl

P

Cl

Cl

Cl

Rx-ID: 26284121 View in Reaxys 66/99 Yield

Conditions & References under reduced pressure Geisenheimer, G.; Ann. Chim. Phys.; vol. 23; (1891); p. 246 - 282 View in Reaxys vol. Ir: MVol.; 5.12, page 83 - 86 ; (from Gmelin) View in Reaxys

2

Cl Ir Cl

(v3)

Cl

Cl 3

Cl PCl Cl

3

Cl P

Cl

Cl

Cl Cl

PCl Cl Cl

Cl

Rx-ID: 26390651 View in Reaxys 67/99 Yield

Conditions & References byproducts: PCl3; heating fast up to 150°C Geisenheimer, G.; Ann. Chim. Phys.; vol. 23; (1891); p. 246 - 282 View in Reaxys Geisenheimer, G.; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 110; (1890); p.

1004 View in Reaxys vol. Ir: MVol.; 5.12, page 83 - 86 ; (from Gmelin) View in Reaxys

Copyright © 2017 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

24/33

2017-10-13 07:13:31

2

Cl Ir Cl

(v3)

Cl

3

Cl P

Cl

Cl

Cl

Cl 3

P

Cl

Cl

Cl

Cl PCl Cl

Cl

Cl

Cl Ir

(v3)

Cl3

P

Cl

Cl

Cl

PCl Cl Cl

Cl

Rx-ID: 26390654 View in Reaxys 68/99 Yield

Conditions & References Geisenheimer, G.; Ann. Chim. Phys.; vol. 23; (1891); p. 246 - 282 View in Reaxys Geisenheimer, G.; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 110; (1890); p.

1004 View in Reaxys vol. Ir: MVol.; 5.12, page 83 - 86 ; (from Gmelin) View in Reaxys

Cl

O3P2

P

Cl

Cl

P

Cl

red

Cl

PCl Cl

O5P2

Cl

Rx-ID: 26441561 View in Reaxys 69/99 Yield

Conditions & References in neat (no solvent), reaction after heating over period of several hours to 180°C in closed tube there is formation of solid mixture; Thorpe, T. E.; Tutton, A. E.; Journal of the Chemical Society; vol. 59; (1891); p. 1019 - 1029 View in Reaxys vol. P: MVol.C; 37, page 74 - 75 ; (from Gmelin) View in Reaxys

F Cl

F

Cl

PF Cl TB-5

Cl

F

PCl Cl

F

Cl

P FF F

Rx-ID: 26486764 View in Reaxys 70/99 Yield

Conditions & References in neat (no solvent), decompon. starting at 200 °C under inluence of an electric spark; Poulenc, C.; Ann. Chim. Phys.; vol. 24; (1891); p. 548 - 570 View in Reaxys Poulenc, C.; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 113; (1891); p. 75 78 View in Reaxys vol. P: MVol.C; 211, page 484 - 487 ; (from Gmelin) View in Reaxys Cl

BP

Cl

Cl

PCl Cl Cl

B

Cl

Cl

Rx-ID: 26506182 View in Reaxys 71/99 Yield

Conditions & References With chlorine in not given, react. with Cl2; Moissan, H.; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 113; (1891); p. 726 729 ; (from Gmelin) View in Reaxys With Cl2 in not given, react. with Cl2; vol. P: MVol.C; 265, page 608 - 611 ; (from Gmelin) View in Reaxys

Copyright © 2017 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

25/33

2017-10-13 07:13:31

F F

P F

F

Cl

F

Cl

Cl

P FF TB-5

PCl Cl

Cl

Cl

F

Rx-ID: 26535673 View in Reaxys 72/99 Yield

Conditions & References in neat (no solvent), decompn. of PF3Cl on heating up to 250°C or by electric sparks; Poulenc, C.; C. r. Acad. Sci. (Paris); vol. 113; (1891); p. 75 - 78 View in Reaxys vol. P: MVol.C; 172, page 395 - 397 ; (from Gmelin) View in Reaxys

Cl

3 Ca 2+ – O 2

Cl

Cl

Cl

Cl

O– P

O

PCl Cl

Cl

O–

Cl

Rx-ID: 26112951 View in Reaxys 73/99 Yield

Conditions & References in neat (no solvent), react. of CCl4 vapor with Ca3(PO4)2 at red heat; Quantin, H.; C. r. Acad. Sci. (Paris); vol. 106; (1888); p. 1074 - 1076 ; (from Gmelin) View in Reaxys in neat (no solvent), react. of CCl4 vapor with Ca3(PO4)2 at red heat; vol. P: MVol.C; 189, page 434 - 437 ; (from Gmelin) View in Reaxys

Cl

O–

Cl

Cl

Fe 3+ O

Cl

P

Cl

O–

Cl

O–

Cl

PCl Cl

Fe Cl

Cl

(v3)

Cl

Rx-ID: 26061712 View in Reaxys 74/99 Yield

Conditions & References in neat (no solvent), passing CCl4 over FePO4 below red heat; Quantin, H.; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 104; (1887); p. 223 223 View in Reaxys vol. Cl: MVol.; 65, page 183 - 186 ; (from Gmelin) View in Reaxys in neat (no solvent), react. of CCl4 vapor with FePO4 below the decompn. temp. of CCl4;; removal of FeCl3 with a layer of KCl heated at 200 °C; Quantin, H.; C. r. Acad. (Paris); vol. 104; (1887); p. 223 - 224 ; (from Gmelin) View in Reaxys in neat (no solvent), react. of CCl4 vapor with FePO4 below the decompn. temp. of CCl4;; removal of FeCl3 with a layer of KCl heated at 200 °C; vol. P: MVol.C; 189, page 434 - 437 ; (from Gmelin) View in Reaxys Cl

Cl Au Cl Cl

(v3)

Cl

Cl

PCl Cl Cl

Cl

Cl

PCl Cl Cl

Au Cl Cl

(v3)

Rx-ID: 26440965 View in Reaxys 75/99 Yield

Conditions & References 120°C; reaction started at ambient temp. (PCl5 gas developed) Lindet, L.; Ann. Chim. Phys.; vol. 11; (1887); p. 177 - 220 View in Reaxys Lindet, L.; Bulletin de la Societe Chimique de France; vol. 42; (1884); p. 70 - 74

Copyright © 2017 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

26/33

2017-10-13 07:13:31

View in Reaxys Lindet, L.; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 98; (1884); p. 1382 1384 ; (from Gmelin) View in Reaxys 120°C; reaction started at ambient temp. (PCl5 gas developed) vol. Au: MVol.3; 8.4, page 693 - 702 ; (from Gmelin) View in Reaxys

O

Cl

Cl Cl

P Cl

Cl

PCl Cl

O5P2

Cl

Rx-ID: 26161238 View in Reaxys 76/99 Yield

Conditions & References in neat (no solvent), decompn.; Divers, E.; Shimidzu, T.; Journal of the Chemical Society; vol. 49; (1886); p. 533 - 590 View in Reaxys vol. S: MVol.B3; 122, page 1791 - 1793 ; (from Gmelin) View in Reaxys

O

O O S

Cl

O S

O

Cl

Cl

P

Cl

Cl Cl

Cl

O

PCl Cl

S

O

Cl

O

Cl P

Cl

Cl

Rx-ID: 26062838 View in Reaxys 77/99 Yield

Conditions & References in not given, react. with S2O5Cl2 in coldness; Michaelis, A.; Jena. Z. Med. Naturwiss.; vol. 7; (1873); p. 110 - 117 View in Reaxys Michaelis, A.; J. prakt. Chem. (2); vol. 4; (1871); p. 449 - 457 ; (from Gmelin) View in Reaxys in neat (no solvent) Michaelis, A.; Jena. Z. Med. Naturwiss.; vol. 7; (1871); p. 110 - 117 View in Reaxys vol. S: MVol.B3; 141, page 1826 - 1828 ; (from Gmelin) View in Reaxys in not given, react. with S2O5Cl2 in coldness; vol. P: MVol.C; 184, page 424 - 427 ; (from Gmelin) View in Reaxys Cl (v5)

Cl U Cl Cl Cl Cl

PCl Cl

Cl

Cl Cl

PCl Cl Cl

Cl (v4)

U Cl ClCl

Cl

Rx-ID: 26588381 View in Reaxys 78/99 Yield

Conditions & References With potassium chloride, byproducts: Cl; react. with KCl on heating; Cronander, A. W.; Bulletin de la Societe Chimique de France; vol. 19; (1873); p. 500 View in Reaxys Cronander, A. W.; Uppsala Univ. Arsskr.; (1873); p. 1 ; (from Gmelin) View in Reaxys With KCl, byproducts: Cl; react. with KCl on heating;

Copyright © 2017 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

27/33

2017-10-13 07:13:31

vol. U: MVol.; 42, page 130 - 132 ; (from Gmelin) View in Reaxys Cl

Cl As

Cl

Cl

Cl

Cl

PCl Cl

Cl

Cl

PCl Cl

As

Cl

Cl

Cl

Cl

Rx-ID: 26729328 View in Reaxys 79/99 Yield

Conditions & References in not given, very instable; Cronander, A. W.; Uppsala Univ. Arsskr.; (1873); p. 1 - 36 View in Reaxys Cronander, A. W.; Bulletin de la Societe Chimique de France; vol. 19; (1873); p. 499 - 501 ; (from Gmelin) View in Reaxys in not given, very instable; vol. As: MVol.; 148, page 388 - 390 ; (from Gmelin) View in Reaxys

Cl Cl

S

S

Cl

P

Cl

S

Cl Cl

Cl

P Cl

Cl

Cl

PCl Cl Cl

Rx-ID: 26150650 View in Reaxys 80/99 Yield >99, >99

Conditions & References in neat (no solvent), 6h, 160°C; Michaelis, A.; Jena. Z. Med. Naturwiss.; vol. 6; (1870); p. 239 - 241 ; (from Gmelin) View in Reaxys

>99, >99

in neat (no solvent), 6h, 160°C; vol. S: MVol.B3; 115, page 1776 - 1778 ; (from Gmelin) View in Reaxys

Cl

Cl

Cl

H

Cl SbCl Cl

P

H

Cl

H

Cl

PCl Cl

Sb Cl Cl

Cl

Rx-ID: 26167068 View in Reaxys 81/99 Yield

Conditions & References byproducts: HCl Mahn, R.; Jena. Z. Med. Naturwiss.; vol. 5; (1870); p. 159 - 164 ; (from Gmelin) View in Reaxys vol. Sb: MVol.B2; 9.6, page 443 - 447 ; (from Gmelin) View in Reaxys

Cl Cl SbCl Cl TB-5 Cl

Cl

H P

H

Cl

H

H

Cl

Cl

PCl Cl Cl

Sb Cl Cl

Rx-ID: 26168204 View in Reaxys 82/99 Yield

Conditions & References in not given, react. under evolution of HCl; Rose, H.; Ann. Physik (2); vol. 24; (1832); p. 109 - 165 View in Reaxys vol. P: MVol.C; 23, page 44 - 46 ; (from Gmelin) View in Reaxys in neat (no solvent), passing PH3 in SbCl5;

Copyright © 2017 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

28/33

2017-10-13 07:13:31

Mahn, R.; Zeitschrift fuer Chemie (Stuttgart, Germany); vol. 12; (1869); p. 729 - 731 View in Reaxys Mahn, r.; Jena. Z. Med. Naturwiss.; vol. 5; (1870); p. 158 - 166 ; (from Gmelin) View in Reaxys in neat (no solvent), passing PH3 in SbCl5; vol. P: MVol.C; 189, page 434 - 437 ; (from Gmelin) View in Reaxys Cl

S Cl

P Cl

Cl

Cl

Cl

Cl

Cl

PCl Cl

S

Cl

Cl

Rx-ID: 26162932 View in Reaxys 83/99 Yield

Conditions & References in not given, react. of PSCl3 with Cl2; Chevrier; C. r. Acad. Sci. (Paris); vol. 68; (1869); p. 1174 - 1176 ; (from Gmelin) View in Reaxys in not given, react. of PSCl3 with Cl2; vol. P: MVol.C; 189, page 434 - 437 ; (from Gmelin) View in Reaxys Cl

S Cl

P Cl

Cl

Cl

S

S

Cl

Cl

PCl Cl Cl

Rx-ID: 26475678 View in Reaxys 84/99 Yield

Conditions & References With chlorine in not given, react. with Cl2; Baudrimont, E.; Ann. Chim. Phys.; vol. 2; (1864); p. 5 - 67 View in Reaxys Chevrier; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 68; (1869); p. 1174 1176 ; (from Gmelin) View in Reaxys With Cl2 in not given, react. with Cl2; vol. P: MVol.C; 260, page 594 - 596 ; (from Gmelin) View in Reaxys

I

Cl

Cl Cl

PCl Cl Cl

Cl

P

Cl

Cl Cl

Cl

PCl Cl

I

I

Cl

Rx-ID: 26150666 View in Reaxys 85/99 Yield

Conditions & References in not given, react. with PCl5*ICl; Baudrimont, E.; Ann. Chim. Phys.; vol. 2; (1864); p. 5 - 67 ; (from Gmelin) View in Reaxys in not given, react. with PCl5*ICl; vol. P: MVol.C; 184, page 424 - 427 ; (from Gmelin) View in Reaxys

Copyright © 2017 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

29/33

2017-10-13 07:13:31

S

P Br

Cl

S

Br Br

Cl

P Cl

Cl

Cl

PCl Cl

Br

Br

Br

Cl

Cl

Rx-ID: 26486986 View in Reaxys 86/99 Yield

Conditions & References With chlorine in not given, react. with an excess of Cl2; Baudrimont, E.; Ann. Chim. Phys.; vol. 2; (1864); p. 5 - 67 ; (from Gmelin) View in Reaxys With Cl2 in not given, react. with an excess of Cl2; vol. P: MVol.C; 262, page 599 - 602 ; (from Gmelin) View in Reaxys Cl

P

Cl

red

Cl

Cl

PCl Cl Cl

Rx-ID: 26182466 View in Reaxys 87/99 Yield

Conditions & References in neat (no solvent), inflammation of red P in Cl2 at ambient temp.; Personne, J.; C. r. Acad. Sci. (Paris); vol. 45; (1857); p. 113 - 117 ; (from Gmelin) View in Reaxys in neat (no solvent), react. of red P with Cl2 at ambient temp.; Schroetter, A.; Sitz.-Ber. Akad. Wiss. (wien); vol. 1; (1848); p. 130 - 137 ; (from Gmelin) View in Reaxys in not given, at first prepn. of PCl3; passing Cl2 in PCl3; Mueller, H.; Dinglers politechn. J.; vol. 164; (1862); p. 385 - 386 View in Reaxys Mueller, H.; Zeitschrift fuer Chemie (Stuttgart, Germany); vol. 5; (1862); p. 295 - 297 ; (from Gmelin) View in Reaxys in neat (no solvent), react. of red P with Cl2 at ambient temp.; vol. P: MVol.C; 159, page 363 - 366 ; (from Gmelin) View in Reaxys in neat (no solvent), inflammation of red P in Cl2 at ambient temp.; vol. P: MVol.C; 189, page 434 - 437 ; (from Gmelin) View in Reaxys in not given, at first prepn. of PCl3; passing Cl2 in PCl3; vol. P: MVol.C; 189, page 434 - 437 ; (from Gmelin) View in Reaxys

O

O S Cl

Cl

S

Cl

O

Cl Cl

Cl

PCl Cl Cl

O

Cl P

Cl

Cl

Rx-ID: 6207653 View in Reaxys 88/99 Yield

Conditions & References Carius; Justus Liebigs Annalen der Chemie; vol. 114; (1860); p. 145 View in Reaxys

Copyright © 2017 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

30/33

2017-10-13 07:13:31

Cl

P

PCl Cl

Cl

red

Cl

Rx-ID: 26184764 View in Reaxys 89/99 Yield

Conditions & References With chlorine in water, byproducts: HCl Personne, J.; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 45; (1857); p. 113 117 View in Reaxys vol. P: MVol.B; 3.4.1.6, page 282 - 285 ; (from Gmelin) View in Reaxys

Cl

P

Cl

Cl P

Cl

Cl

PCl Cl Cl

Rx-ID: 26150622 View in Reaxys 90/99 Yield

Conditions & References in neat (no solvent), disproportionation on storing for a longer period of time; vol. P: MVol.C; 183, page 421 - 424 View in Reaxys Casselmann, W.; Liebigs Annalen der Chemie; vol. 83; (1852); p. 257 - 275 ; (from Gmelin) View in Reaxys in neat (no solvent), disproportionation on storing for a longer period of time; Casselmann, W.; Liebigs Annalen der Chemie; vol. 83; (1852); p. 257 - 275 ; (from Gmelin) View in Reaxys in neat (no solvent), disproportionation on storing for a longer period of time; vol. P: MVol.C; 189, page 434 - 437 ; (from Gmelin) View in Reaxys Cl Cl

2 Cl

Cl

S ClCl

Sn Cl ClCl

Cl

P

Cl Cl

S

S

Cl

Cl

Cl

Sn ClCl

Cl Cl

Cl

PCl Cl

Cl

PCl Cl Cl

Cl

Rx-ID: 26582829 View in Reaxys 91/99 Yield

Conditions & References With hydrogenchloride in neat (no solvent), reaction on warming of SnCl4*2SCl4 with PCl3 in a HCl stream; Casselmann, W.; Liebigs Annalen der Chemie; vol. 83; (1852); p. 257 - 275 View in Reaxys vol. Sn: MVol.C2; 9.27.2, page 75 - 75 ; (from Gmelin) View in Reaxys Cl

P

Cl

PCl Cl Cl

Rx-ID: 26124862 View in Reaxys 92/99 Yield

Conditions & References With chlorine in carbon disulfide Corenwinder, B.; Ann. Chim. Phys.; vol. 30; (1850); p. 242 - 243 View in Reaxys Corenwinder, B.; Justus Liebigs Annalen der Chemie; vol. 78; (1851); p. 76 - 84 View in Reaxys vol. P: MVol.B; 3.4.1.6, page 282 - 285 ; (from Gmelin)

Copyright © 2017 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

31/33

2017-10-13 07:13:31

View in Reaxys Cl

P

Cl

red

Cl

PCl Cl

P

Cl

Cl

Cl

Rx-ID: 26184757 View in Reaxys 93/99 Yield

Conditions & References With chlorine, at room temp.

Schroetter, A.; Annalen der Physik (Weinheim, Germany); vol. 81; (1850); p. 276 - 298 View in Reaxys vol. P: MVol.B; 3.4.1.6, page 282 - 285 ; (from Gmelin) View in Reaxys Cl

Co 3P2

Cl

Cl

Cl

PCl Cl

Cl 2Co

Cl

Rx-ID: 26456731 View in Reaxys 94/99 Yield

Conditions & References at light warming of Co3P2 in a chlorine stream formation of PCl5 and CoCl2 under fire phenomenon; Rose, H.; Annalen der Physik (Weinheim, Germany); vol. 24; (1832); p. 331 - 331 ; (from Gmelin) View in Reaxys at light warming of Co3P2 in a chlorine stream formation of PCl5 and CoCl2 under fire phenomenon; vol. Co: MVol.A2; 75, page 388 - 389 ; (from Gmelin) View in Reaxys Cl

Br–

Br Br

Cl

P+

Cl

Cl

BrBr

PCl Cl Cl

Rx-ID: 26150366 View in Reaxys 95/99 Yield

Conditions & References in not given, react. of Cl2 with PBr5; Balard, A.-J.; Ann. Chim. Phys.; vol. 32; (1826); p. 337 - 381 ; (from Gmelin) View in Reaxys in not given, react. of Cl2 with PBr5; vol. P: MVol.C; 189, page 434 - 437 ; (from Gmelin) View in Reaxys

Br Br Br TB-5 P Br Br

Cl Cl

PCl Cl TB-5

Br

Br

Cl

Rx-ID: 26535844 View in Reaxys 96/99 Yield

Conditions & References With chlorine in neat (no solvent) Balard, A.-J.; Ann. Chim. Phys.; vol. 32; (1826); p. 337 - 381 View in Reaxys Loewig, C.; Das Brom und seine chemischen Verhaeltnisse, Heidelberg 1829, 1/74 ; (from Gmelin) View in Reaxys With Cl2 in neat (no solvent) vol. P: MVol.C; 218, page 501 - 503 ; (from Gmelin) View in Reaxys

Copyright © 2017 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

32/33

2017-10-13 07:13:31

Cl

H P

H

Cl

Cl

Cl

Cl

H

H

PCl Cl Cl

Rx-ID: 26170082 View in Reaxys 97/99 Yield

Conditions & References in neat (no solvent), oxidation of PH3 in Cl2; Thomson, T.; Schweiggers J. Chem. Phys.; vol. 18; (1816); p. 357 - 364 ; (from Gmelin) View in Reaxys in neat (no solvent), oxidation of PH3 in Cl2; vol. P: MVol.C; 189, page 434 - 437 ; (from Gmelin) View in Reaxys Cl

P P

P

Cl

P

PCl Cl Cl

Cl

P

Cl

Cl

Rx-ID: 26454674 View in Reaxys 98/99 Yield

Conditions & References With chlorine, depending on Cl2 volume vol. P: MVol.B; 3.4.1.6, page 282 - 285 View in Reaxys Berzelius, J. J.; Lehrbuch der Chemie, 5.Ed., Vol. 1, Dresden-Leipzig 1843, p. 235 View in Reaxys Berzelius, J. J.; Lehrbuch der Chemie, 5.Ed., Vol. 1, Dresden-Leipzig 1843, p. 236 View in Reaxys Berzelius, J. J.; Lehrbuch der Chemie, 5.Ed., Vol. 1, Dresden-Leipzig 1843, p. 239 ; (from Gmelin) View in Reaxys Cl Cl

PCl Cl Cl

Cl Cl

PCl Cl Cl

Cl(x)N(x)P(x)

Rx-ID: 26585292 View in Reaxys 99/99 Yield

Conditions & References in not given, easy cleavage of PCl5 even in weakly polar solvents; vol. P: MVol.C; 233, page 533 - 535 View in Reaxys Paddock, N. L.; Searle, H. T.; Emeleus, H. J., Sharpe, A. G., Advances in inorganic chemistry and radiochemistry, Bd. 1, New York 1959, S. 347/83 ; (from Gmelin) View in Reaxys

Copyright © 2017 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

33/33

2017-10-13 07:13:31