| Identification | More | [Name]
Diphenyl chlorophosphate | [CAS]
2524-64-3 | [Synonyms]
1,1'-DIPHENYLPHOSPHORYL CHLORIDE
AURORA KA-1636
CHLORODIPHENYL PHOSPHATE
CHLOROPHOSPHORIC ACID DIPHENYL ESTER
DIPHENYL CHLOROPHOSPHATE
DIPHENYL PHOSPHOROCHLORIDATE
DIPHENYLPHOSPHORYL CHLORIDE
DPCP
PHOSPHORIC ACID DIPHENYL ESTER CHLORIDE
PHOSPHOROCHLORIDIC ACID DIPHENYL ESTER
Chlorodiphenoxyphosphine oxide
Diphenoxychlorophosphine oxide
Diphenyl chloridophosphate
Diphenyl phosphochloridate
Diphenylchlorophosphonate
Diphenylphosphoric acid monochloride
Diphenylphosphorus oxychloride
O,O-Diphenyl chlorophosphate
o,o-Diphenylphosphorochloridate
Phenyl phosphorochloridate ((PhO)2ClPO) | [EINECS(EC#)]
219-759-6 | [Molecular Formula]
C12H10ClO3P | [MDL Number]
MFCD00003030 | [Molecular Weight]
268.63 | [MOL File]
2524-64-3.mol |
| Chemical Properties | Back Directory | [Appearance]
CLEAR COLOURLESS TO LIGHT YELLOW LIQUID | [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 | [form ]
Liquid | [color ]
Clear colorless to light yellow | [Water Solubility ]
MAY DECOMPOSE | [Sensitive ]
Moisture Sensitive | [Detection Methods]
GC,NMR | [BRN ]
654130 | [CAS DataBase Reference]
2524-64-3(CAS DataBase Reference) | [NIST Chemistry Reference]
Diphenyl chlorophosphate(2524-64-3) | [Storage Precautions]
Moisture sensitive | [EPA Substance Registry System]
2524-64-3(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
C | [Risk Statements ]
R34:Causes burns.
R37:Irritating to the respiratory system. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S7:Keep container tightly closed .
S24/25:Avoid contact with skin and eyes .
S23:Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer) . | [RIDADR ]
UN 3265 8/PG 2
| [WGK Germany ]
3
| [TSCA ]
Yes | [HazardClass ]
8 | [PackingGroup ]
III | [HS Code ]
29209085 |
| Hazard Information | Back Directory | [General Description]
A 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. | [Reactivity Profile]
DIPHENYL CHLOROPHOSPHATE(2524-64-3) 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. | [Air & Water Reactions]
Insoluble in water. | [Health Hazard]
TOXIC; 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 Hazard]
Non-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. | [Preparation]
The 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%.
| [Purification Methods]
Fractionally 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.] |
| Questions And Answer | Back Directory | [Description]
Diphenyl 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. | [Uses]
Diphenyl 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]
- 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
- 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
- H. R. Allcock, M. A. Hofmann, C. M. Ambler, R. V. Morford, Phenylphosphonic Acid Functionalized Poly[aryloxyphosphazenes], 2002, vol. 35, pp. 3484-3489
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