Diphenyl chlorophosphate

Diphenyl chlorophosphate Basic information
Description Uses Reference
Product Name:Diphenyl chlorophosphate
Synonyms:Chlorodiphenoxyphosphine oxide;Diphenoxychlorophosphine oxide;Diphenyl chloridophosphate;Diphenyl phosphochloridate;Diphenylchlorophosphonate;Diphenylphosphoric acid monochloride;Diphenylphosphorus oxychloride;O,O-Diphenyl chlorophosphate
CAS:2524-64-3
MF:C12H10ClO3P
MW:268.63
EINECS:219-759-6
Product Categories:Synthetic Organic Chemistry;Pharmaceutical Intermediates;Phosphorus compounds;Biochemistry;Nucleosides, Nucleotides & Related Reagents;Phosphorylating and Phosphorothioating Agents;Phosphorylation;Protecting Agents, Phosphorylating Agents & Condensing Agents
Mol File:2524-64-3.mol
Diphenyl chlorophosphate Structure
Diphenyl chlorophosphate Chemical Properties
Boiling point 314-316 °C/272 mmHg (lit.)
density 1.296 g/mL at 25 °C (lit.)
vapor pressure 10 mm Hg ( 190 °C)
refractive index n20/D 1.55(lit.)
Fp >230 °F
storage temp. Inert atmosphere,2-8°C
solubility Chloroform (Slightly), DMSO (Slightly)
form Liquid
color Clear colorless to light yellow
Water Solubility MAY DECOMPOSE
Sensitive Moisture Sensitive
BRN 654130
Stability:Stable under recommended storage conditions., Stable Under Recommended Storage C
CAS DataBase Reference2524-64-3(CAS DataBase Reference)
NIST Chemistry ReferenceDiphenyl chlorophosphate(2524-64-3)
EPA Substance Registry SystemPhosphorochloridic acid, diphenyl ester (2524-64-3)
Safety Information
Hazard Codes C
Risk Statements 34-37
Safety Statements 26-36/37/39-45-7-24/25-23
RIDADR UN 3265 8/PG 2
WGK Germany 3
TSCA Yes
HazardClass 8
PackingGroup III
HS Code 29209085
MSDS Information
ProviderLanguage
Diphenyl chlorophosphate English
ACROS English
SigmaAldrich English
ALFA English
Diphenyl chlorophosphate Usage And Synthesis
DescriptionDiphenyl chlorophosphate is a viscous colorless liquid. It can be prepared in situ by the reaction between diphenyl hydrogen phosphonate and carbon tetrachloride. It is used to prepare aromatic polyesters by polycondensation reaction in pyridine and polyesteramide. Diphenyl chlorophosphate is used as a phosphonating agent, such as to prepare phenylphosphonic acid.
UsesDiphenyl chlorophosphate can be used to synthesize methadone, an opioid used for opioid maintenance therapy and for pain relief. It is used to control seedling grasses in turf. It undergoes anhydrous condensation with ethyl-4-bromo-butyrate and the hydrolysis product in alkaline medium of this condensation reaction is used in the quantitative determination of 3-cyano-3,3-diphenylpropionic acid.
Reference
  1. F. Higashi, A. Hoshio, J. Kiyoshige, Preparation of aromatic polyesters by the direct polycondensation reaction with diphenyl chlorophosphate in pyridine, Polymer Chemistry, 1983, vol. 21, pp. 3241-3247
  2. F. Higahi, M. Ozawa, A. Mochizuki, Synthesis of soluble aromatic polyesteramides by stepwise copolycondensation of bisphenols and aromatic diamines with diphenyl chlorophosphate in pyridine, 1986, vol. 24, pp.637-643
  3. H. R. Allcock, M. A. Hofmann, C. M. Ambler, R. V. Morford, Phenylphosphonic Acid Functionalized Poly[aryloxyphosphazenes], 2002, vol. 35, pp. 3484-3489
UsesDiphenyl chlorophosphate is used to prepare cyclohexyl-amidophosphoric acid diphenyl ester by reacting with cyclohexylamine. It is also used in the synthesis of alfa-substituted beta-lactams, anhydrides, esters and thioesters. It is also employed in the conversion of aldoximes to nitriles. Further, it is used in the preparation and reaction of enol phosphates, guanosine-adenosine-5',5'-triphosphate, guanosine-cytidine-5',5'-triphosphate, guanosine-uridine-5',5'-triphosphate, diguanosine-5',5'-diphosphate and diguanosine-5',5'-triphosphate. In addition to this, it serves as a phosphorylating agent for the preparation of 2-deoxy-D-galactose-3 and -6 phosphoric acids.
UsesDiphenyl chlorophosphate may be used:
  • in the preparation of guanosine-adenosine-5′,5′-triphosphate, guanosine-cytidine-5′,5′-triphosphate, guanosine-uridine-5′,5′-triphosphate, diguanosine-5′,5′-diphosphate and diguanosine-5′,5′-triphosphate
  • as phosphorylating agent for the synthesis of 2-deoxy-D-galactose-3 and -6 phosphoric acids
  • in the synthesis of diaryl phosphoryl derivatives of alkylene dithiophosphates
PreparationThe preparation of Diphenyl chlorophosphate is as follows:With a thermometer,Reflux condenser and mechanical agitation120 g of dichloromethane was placed in a 500 ml four-neck reaction flask.7.3 g of N,N-dimethylformamide,Stirring temperature control below 10 °C,Put 28g of bis(trichloromethyl) carbonate,A solution of 50 g of diphenyl phosphate and 120 g of dichloromethane was added.After the addition, the reaction was carried out for 3 hours. After the end of the reaction, the temperature was controlled below 10 ° C, 20 g of water was slowly added, and the mixture was stirred and the organic phase was dried over anhydrous sodium sulfate. The desiccant was removed by filtration, and the filtrate was evaporated under normal pressure. The temperature was lowered to 0 ° C, and the insoluble matter was removed by filtration to obtain 48.9 g of diphenyl chlorophosphate. The purity of GC was 99.2%, and the yield was 90.3%.

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General DescriptionA clear colorless to light yellow liquid with a pungent odor. Insoluble in water and denser than water. Hence sinks in water. Contact may severely irritate skin, eyes and mucous membranes. Flash point above 235°F.
Air & Water ReactionsInsoluble in water.
Reactivity ProfileDiphenyl chlorophosphate is incompatible with bases (including amines) strong oxidizing agents, and alcohols. May react vigorously or explosively if mixed with diisopropyl ether or other ethers in the presence of trace amounts of metal salts [J. Haz. Mat., 1981, 4, 291]. May form highly toxic and flammable phosphine gas in the presence of strong reducing agents such as hydrides. Partial oxidation by oxidizing agents may result in the release of toxic phosphorus oxides.
Health HazardTOXIC; inhalation, ingestion or skin contact with material may cause severe injury or death. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.
Fire HazardNon-combustible, substance itself does not burn but may decompose upon heating to produce corrosive and/or toxic fumes. Some are oxidizers and may ignite combustibles (wood, paper, oil, clothing, etc.). Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated.
Purification MethodsFractionally distil it in 30 351.5490. a good vacuum; better use a spinning band column. [Walsh J Am Chem Soc 81 3023 1959, IR: Bellamy & Beecher J Chem Soc 475 1952, Beilstein 6 IV 737.]
Diphenyl chlorophosphate Preparation Products And Raw materials
Preparation Products(TRIMETHYLSILYL)DIAZOMETHANE-->N-ACRYLOXYSUCCINIMIDE-->DIPHENYL PHOSPHORAMIDATE-->4,4'-DIPYRIDYL SULFIDE-->PHENYL PHOSPHORODICHLORIDITE-->Triphenyl phosphate-->GB-1-->DIPHENYL CYANOPHOSPHONATE-->Phosphoric acid, diphenyl tetradecyl ester-->Phosphoric acid, ethenyl diphenyl ester-->1,2,3,4-TETRA-O-ACETYL-6-DIPHENYLPHOSPHORYL-BETA-D-MANNOPYRANOSE
DIPHENYL PHOSPHITE Methylene Chloride Clodronate disodium Benzyl chloride Biphenyl Diphenylphosphoryl azide Calcium chloride Starch, hydrogen phosphate, 2-hydroxypropyl ether Diphenyl phosphate Triphenyl phosphite Choline chloride 4-Nitrophenyl phosphate bis(cyclohexylammonium) salt Ammonium chloride Diphenyl chlorophosphate Mepiquat chloride Polyvinyl chloride Triphenyl phosphate 2-​[[(2-​ethylphenyl)​(2-​hydroxyethyl)​amino]​methyl]​-​3,​3-​difluoro-Propanenitrile

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