4895-65-2

Usage

Uses

Used in Chemical Synthesis:
Phenyltetrachlorphosphorus serves as a fundamental building block in the creation of a variety of organophosphorus compounds. Its unique structure and reactivity make it indispensable for the development of new chemical entities with diverse applications across different industries.
Used in Catalyst Applications:
In the realm of catalysis, Phenyltetrachlorphosphorus is utilized to facilitate specific organic reactions, enhancing the efficiency and selectivity of these processes. Its catalytic properties are particularly valuable in the synthesis of complex organic molecules and pharmaceutical intermediates.
Used in Pharmaceutical Industry:
Phenyltetrachlorphosphorus is used as a precursor in the synthesis of certain pharmaceuticals, contributing to the development of life-saving drugs. Its role in creating organophosphorus compounds that possess biological activity is crucial for advancing medicinal chemistry.
Used in Agrochemical Industry:
Phenyltetrachlorphosphorus also finds application in the agrochemical sector, where it is employed in the synthesis of pesticides and other crop protection agents. The organophosphorus compounds derived from Phenyltetrachlorphosphorus can help in the development of more effective and targeted pest control solutions.
Used in Laboratory Research:
Phenyltetrachlorphosphorus is a valuable tool in academic and industrial research laboratories, where it is used to explore new chemical reactions and investigate the properties of organophosphorus chemistry. Its reactivity provides a platform for understanding and advancing the frontiers of chemical science.
Due to the toxic nature of Phenyltetrachlorphosphorus, it is imperative that it is handled with extreme care, using appropriate safety measures and equipment to mitigate any potential risks associated with its use.

InChI:InChI=1/C6H5Cl4P/c7-11(8,9,10)6-4-2-1-3-5-6/h1-5H

Synthetic route

Dichlorophenylphosphine (644-97-3) → phenyltetrachlorophosphorane (4895-65-2)

Conditions	Yield
With chlorine In tetrachloromethane at 20℃; for 5h;	86%
With chlorine
With chlorine In benzene octane was used as well (as solvent);
With chlorine In chloroform at 30℃; for 0.333333h;

Dichlorophenylphosphine (644-97-3) → phenyltetrachlorophosphorane (4895-65-2) + phenylthiophosphonic acid dichloride (3497-00-5)

Conditions	Yield
With sulphur monochloride

P,P-dichlorophenylphosphine oxide (824-72-6) → phenyltetrachlorophosphorane (4895-65-2)

Conditions	Yield
With chlorine

phenyltrichlorophosphonium hexachlorophosphorate (55045-25-5) → 3-chloro-cyclohexene (2441-97-6) + phenyltetrachlorophosphorane (4895-65-2) + trans-1,2-dichlorocyclohexane (822-86-6)

Conditions	Yield
With cyclohexene In 1,2-dichloro-ethane at 60℃; for 2h; Yields of byproduct given. Title compound not separated from byproducts;

phenyltrichlorophosphonium hexachlorophosphorate (55045-25-5) → phenyltetrachlorophosphorane (4895-65-2)

Conditions	Yield
With cyclohexene In 1,2-dichloro-ethane at 60℃; for 2h; Mechanism;

triphenylphosphine (603-35-0) → phenyltetrachlorophosphorane (4895-65-2)

Conditions	Yield
With chlorine In toluene

cyclohexene (110-83-8) → 3-chloro-cyclohexene (2441-97-6) + phenyltetrachlorophosphorane (4895-65-2) + trans-1,2-dichlorocyclohexane (822-86-6)

Conditions	Yield
With phenyltrichlorophosphonium hexachlorophosphorate In 1,2-dichloro-ethane at 60℃; for 2h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

chlorine (7782-50-5) + Dichlorophenylphosphine (644-97-3) → phenyltetrachlorophosphorane (4895-65-2)

Iodine monochloride (7790-99-0) + Dichlorophenylphosphine (644-97-3) → phenyltetrachlorophosphorane (4895-65-2)

diphenylmercury(II) (587-85-9) → phenyltetrachlorophosphorane (4895-65-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: phosphorus trichloride / 180 °C 2: chlorine View Scheme

benzene (71-43-2) → phenyltetrachlorophosphorane (4895-65-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: phosphorus trichloride 2: chlorine View Scheme

P,P-dichlorophenylphosphine oxide (824-72-6) + nicotinic acid (59-67-6) + Dichlorophenylphosphine (644-97-3) → phenyltetrachlorophosphorane (4895-65-2)

Conditions	Yield
With chlorine

phenyltetrachlorophosphorane (4895-65-2) → P,P-dichlorophenylphosphine oxide (824-72-6)

Conditions	Yield
With sodium dithionite In tetrachloromethane at 20℃; Substitution;	96%
With water
With sulfur dioxide
Multi-step reaction with 2 steps 1: NEt3 / CH2Cl2 / 13 h / 40 °C 2: 38 percent Spectr. / NEt3 / toluene; CH2Cl2 / 4 h / 0 °C View Scheme
With amino acid at 20 - 25℃;

2,6-diimino-3,3,4,4,5,5-hexafluoropiperidine (376-67-0) + phenyltetrachlorophosphorane (4895-65-2) → 2,2,6-trichloro-3,3,4,4,5,5-hexafluoro-2,3,4,5-tetrahydropyridine (714-36-3)

Conditions	Yield
reflux, 15 h;; byproducts are easy to remove;;	95%
reflux, 15 h;; byproducts are easy to remove;;	95%

phenyltetrachlorophosphorane (4895-65-2) → phenyltetraiodophosphorane (26852-27-7)

Conditions	Yield
With trimethylsilyl iodide In benzene at 20℃; for 1h;	91%

phenyltetrachlorophosphorane (4895-65-2) + ethyl vinyl ether (109-92-2) → trichloro(2-ethoxyvinyl)phenylphosphorane (90876-60-1)

Conditions	Yield
In tetrachloromethane at 60℃; for 0.5h;	87%

phenyltetrachlorophosphorane (4895-65-2) → Dichlorophenylphosphine (644-97-3)

Conditions	Yield
With tetraethylammonium iodide In benzene for 1h;	79%
With phosphorous acid trimethyl ester; triethyl phosphite

phenyltetrachlorophosphorane (4895-65-2) + 3-trifluoromethylaniline (98-16-8) → C13H9Cl2F3NP (76616-13-2)

Conditions	Yield
In 1,2-dichloro-ethane Heating;	78%

phenyltetrachlorophosphorane (4895-65-2) + 3-amino-4-chlorobenzotrifluoride (121-50-6) → C13H8Cl3F3NP (76616-20-1)

Conditions	Yield
In 1,2-dichloro-ethane Heating;	71%

trimethylsilyl cyanide (7677-24-9) + phenyltetrachlorophosphorane (4895-65-2) → ethanedinitrile (460-19-5) + dicyano(phenyl)phosphine (2946-59-0)

Conditions	Yield
In tetrachloromethane for 0.25h;	A n/a B 70%

2-(1,1,2,2-tetrafluoroethoxy)aniline (35295-34-2) + phenyltetrachlorophosphorane (4895-65-2) → C14H10Cl2F4NOP (76616-14-3)

Conditions	Yield
In 1,2-dichloro-ethane Heating;	63%

4-chloro-2-(trifluoromethyl)aniline (445-03-4) + phenyltetrachlorophosphorane (4895-65-2) → C13H8Cl3F3NP (76616-18-7)

Conditions	Yield
In 1,2-dichloro-ethane Heating;	63%

3-(1,1,2,2-tetrafluoroethoxy)aniline (831-75-4) + phenyltetrachlorophosphorane (4895-65-2) → C14H10Cl2F4NOP (76616-15-4)

Conditions	Yield
In 1,2-dichloro-ethane Heating;	62%

phenyltetrachlorophosphorane (4895-65-2) + ethyl vinyl ether (109-92-2) → P,P-dichlorophenylphosphine oxide (824-72-6) + phenyl-β-ethoxyvinylphosphinic chloride (90876-11-2)

Conditions	Yield
With acetone In benzene 2.) 5 deg C;	A 20% B 58%

-butyl vinyl ether (111-34-2) + phenyltetrachlorophosphorane (4895-65-2) → phenyl-β-chlorovinylphosphinic chloride (3135-58-8)

Conditions	Yield
In benzene for 24h;	57%

phenyltetrachlorophosphorane (4895-65-2) + 2,2,2-trifluoro-N,N'-dimethylacetamidine (86650-37-5) → 1,3-dimethyl-2,2-dichloro-2-phenyl-4-chloro-4-(trifluoromethyl)-1,3,2-diazaphosphetidine

Conditions	Yield
In benzene at 0℃; for 12h;	56%

2,4-difluorophenylamine (367-25-9) + phenyltetrachlorophosphorane (4895-65-2) → C12H8Cl2F2NP (76616-16-5)

Conditions	Yield
In 1,2-dichloro-ethane Heating;	54%

phenyltetrachlorophosphorane (4895-65-2) + 2-(trifluoromethyl)benzenamine (88-17-5) → C13H9Cl2F3NP (76616-12-1)

Conditions	Yield
In 1,2-dichloro-ethane Heating;	46%

phenyltetrachlorophosphorane (4895-65-2) + sodium 1-trifluoromethyl-2-cyano-2-trifluoromethylthiovinyl oxide → 1-cyano-1-trifluoromethylthio-2-chloro-2-trifluoromethylethylene (77429-05-1)

Conditions	Yield
In dichloromethane	42.3%
In dichloromethane	42.3%

phenyltetrachlorophosphorane (4895-65-2) + 3,3,3-trichloro-2-<(trimethylsilyl)imino>propionitrile (71985-40-5) → P-phenyl-N-(1,2,2,2-tetrachloro-1-cyanoethyl)phosphonimidic dichloride (76486-56-1)

Conditions	Yield
In tetrachloromethane for 16h; Heating;	40%

3-chloro-4-fluorophenylamine (367-21-5) + phenyltetrachlorophosphorane (4895-65-2) → C12H8Cl3FNP (76616-17-6)

Conditions	Yield
In 1,2-dichloro-ethane Heating;	38%

phenyltetrachlorophosphorane (4895-65-2) + 4-chloro-3-trifluoromethyl-aniline (320-51-4) → C13H8Cl3F3NP (76616-19-8)

Conditions	Yield
In 1,2-dichloro-ethane Heating;	31%

diazomethane (186581-53-3, 908094-01-9) + phenyltetrachlorophosphorane (4895-65-2) → phenylbis(chloromethyl)phosphine oxide (18788-46-0)

Conditions	Yield
beim Behandeln anschliessend mit H2O;
bei nachfolgenden Umsetzung mit H2O;

benzenesulfonamide (98-10-2) + phenyltetrachlorophosphorane (4895-65-2) → P-phenyl-N-(phenylsulfonyl)phosphonimidic dichloride (52315-49-8)

phenylphosphonate (1571-33-1) + phenyltetrachlorophosphorane (4895-65-2) → P,P-dichlorophenylphosphine oxide (824-72-6)

phenyltetrachlorophosphorane (4895-65-2) → phenylphosphonate (1571-33-1)

Conditions	Yield
With water

phenyltetrachlorophosphorane (4895-65-2) → phenyltetrafluorophosphorane (666-23-9)

Conditions	Yield
With antimony(III) fluoride

phenyltetrachlorophosphorane (4895-65-2) → ethyl hydrogen phenylphosphonate (4546-19-4)

Conditions	Yield
With ethanol

phenyltetrachlorophosphorane (4895-65-2) → 6-chloro-2,4,6-triphenyl-2λ5,4λ5,6λ5-cyclotriphosphazene-2,4-diol

Conditions	Yield
With ammonium chloride; 1,1,2,2-tetrachloroethane at 140℃; und Erhitzen des Reaktionsprodukts mit Essigsaeure;

phenyltetrachlorophosphorane (4895-65-2) + acetic acid (64-19-7) → P,P-dichlorophenylphosphine oxide (824-72-6) + acetyl chloride (75-36-5)

phenyltetrachlorophosphorane (4895-65-2) + 4-chloro-phenol (106-48-9) → phenyl-phosphonic acid bis-(4-chloro-phenyl ester) (20858-29-1)

Upstream product

• 644-97-3 Dichlorophenylphosphine 
• 824-72-6 P,P-dichlorophenylphosphine oxide 
• 55045-25-5 phenyltrichlorophosphonium hexachlorophosphorate 
• 603-35-0 triphenylphosphine 
• 110-83-8 cyclohexene 
• 7782-50-5 chlorine 
• 7790-99-0 Iodine monochloride 
• 587-85-9 diphenylmercury(II) 
• 71-43-2 benzene 
• 59-67-6 nicotinic acid 

Downstream Products

• 18788-46-0 phenylbis(chloromethyl)phosphine oxide 
• 52315-49-8 P-phenyl-N-(phenylsulfonyl)phosphonimidic dichloride 
• 824-72-6 P,P-dichlorophenylphosphine oxide 
• 1571-33-1 phenylphosphonate 
• 666-23-9 phenyltetrafluorophosphorane 
• 4546-19-4 ethyl hydrogen phenylphosphonate 
• 75-36-5 acetyl chloride 
• 3049-24-9 diphenyl phenylphosphonate 
• 67247-92-1 2,4-dichloro-2-phenyl-2λ⁵-[1,3,2]diazaphosphinine-5-carbonitrile 
• 91983-99-2 Dichloressigsaeure-<(dichlor-phenyl-phosphoranyliden)-amid> 
• 17538-07-7 Trichloressigsaeure-<(dichlor-phenyl-phosphoranyliden)-amid> 
• 24604-09-9 C₁₅H₁₅Cl₅NO₄P 
• 67247-93-2 2,4-dichloro-6-ethyl-5-methyl-2-phenyl-2λ⁵-[1,3,2]diazaphosphinine 
• 67247-94-3 2,4-dichloro-5-ethyl-2-phenyl-6-propyl-2λ⁵-[1,3,2]diazaphosphinine 

Relevant academic research and scientific papers

METHOD FOR PRODUCING BIS(FLUORALKYL)PHOSPHINIC ACID CHLORIDES OR FLUORALKYLPHOSPHONIC ACID CHLORIDES

The invention relates to a process for the preparation of bis(fluoroalkyl)phosphinyl chlorides or fluoroalkylphosphonyl dichlorides by reaction of the corresponding bis(fluoroalkyl)phosphinic acid or fluoroalkylphosphonic acid with aryltetrachlorophosphorane as chlorinating agent

Ionic-Molecular Isomerism in Chlorophenylphosphoranes PhnPCl5-n (1n3)

Both ionic and molecular modifications of the three chlorophenylphosphoranes PhnPCl5-n (1n3) have been isolated for the first time as solids and all have been characterised by elemental analysis, Raman spectroscopy and 31P magic angle spinning (MAS) NMR spectroscopy.

Process of converting a carboxylic acid or carboxylic acid halide group to a trihalomethyl group

Carboxylic acid or carboxylic acid halide groups on aryl or heterocyclic aryl rings are directly converted to trihalomethyl groups by using a phenylhalophosphorane, optionally generated in situ by reaction of a phenylphosphonous halide and chlorine.

Preparation of aryl halides

A process for selectively substituting an aromatic nitro group with a halo group which comprises contacting the nitroaromatic compound with a phosphorushalide of formula: Rn PX5-n wherein n is selected from 0, 1, 2 and 3; R is selected from the group consisting of C-6 to C-10 aryl and substituted aryl wherein the substituents are selected from the group consisting of: straight and branched chain alkyl, alkoxy, and haloalkyl; halogen, sulfonate and mixtures thereof; and X is a halogen in the presence of an arylphosphorusoxydihalide solvent. The use of an arylphosphorustetrahalide and particularly phenylphosphorustetrachloride is preferred. The arylphosphorustetrahalide can be prepared in situ by contacting a solution of the corresponding arylphosphorusdihalide in an arylphosphorusoxydihalide solvent with a halogen. The process can further comprise the step of heating the reaction mixture to maintain a temperature of from about 100° C. to about 175° C. for from about 1 hour to about 24 hours.