2524-64-3 Usage
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
Different sources of media describe the Uses of 2524-64-3 differently. You can refer to the following data:
1. 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.
2. Diphenyl 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.
3. Diphenyl 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′-triphosphateas phosphorylating agent for the synthesis of 2-deoxy-D-galactose-3 and -6 phosphoric acidsin the synthesis of diaryl phosphoryl derivatives of alkylene dithiophosphates
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
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%.
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.
Air & Water Reactions
Insoluble in water.
Reactivity Profile
Diphenyl 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 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.
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.]
Check Digit Verification of cas no
The CAS Registry Mumber 2524-64-3 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,5,2 and 4 respectively; the second part has 2 digits, 6 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 2524-64:
(6*2)+(5*5)+(4*2)+(3*4)+(2*6)+(1*4)=73
73 % 10 = 3
So 2524-64-3 is a valid CAS Registry Number.
InChI:InChI=1/C12H10ClO2P/c13-16(14-11-7-3-1-4-8-11)15-12-9-5-2-6-10-12/h1-10H
2524-64-3Relevant articles and documents
Synthesis of flame-retardant phosphaphenanthrene derivatives with high phosphorus contents
Zheng, Jinyun,Yu, Yujian,Zhang, Lulu,Zhen, Xiaomin,Zhao, Yufen
, p. 1688 - 1692 (2014)
Two novel types of phosphate derivatives of phosphaphenanthrene with a high phosphorus content were prepared by phosphorylation reaction between either 2-(6-oxido-6H-dibenzc,e1,2oxaphosphorin-6-yl)-methanol (ODOPM) or 2-(6-oxido-6H-dibenzc,e1,2.oxaphosphorin-6-yl)-1,4-benzenediol (ODOPB) and dialkyl phosphoryl chloride. The structures of all compounds were characterised by 1H NMR, 13C NMR, 31P NMR, Fourier transform infrared spectroscopy, and high-resolution mass spectrometry. The thermal stability of representative compounds was determined by thermal gravimetric analysis and differential scanning calorimetry. The results showed that the compounds have excellent resistance to oxidation, high thermal stability with an onset decomposition temperature above 200°C, and a high char yield over 25 %, owing to the high P content. The representative compound was added to conventional electrolytes of lithium-ion batteries as flame retardant additive, and the self-extinguishing time and ionic conductivity were measured. The result showed that the compounds have effective flame retardant properties.
Preparation method of cresyl diphenyl phosphate
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Paragraph 0037; 0049-0050; 0054-0055; 0059-0064, (2019/11/21)
The invention relates to a preparation method of cresyl diphenyl phosphate. The method includes the steps of: 1) esterification reaction: mixing phosphorus oxychloride with a catalyst, then adding phenol dropwise, and at the end of the reaction, conducting reduced pressure distillation to obtain diphenoxy phosphoryl chloride; 2) reduced pressure reaction: reacting the intermediate diphenoxy phosphoryl chloride obtain in step 1) with m, p-cresol under a reduced pressure, and removing the reacted hydrogen chloride gas to obtain a cresyl diphenyl phosphate crude product; and 3) refining: carryingout alkali washing, washing and reduced pressure distillation on the cresyl diphenyl phosphate crude product obtained in step 2) to obtain cresyl diphenyl phosphate. Phosphorus oxychloride and phenolare employed for reaction to prepare the diphenoxy phosphoryl chloride intermediate, the generated intermediate reacts with m, p-cresol to prepare the product, the synthetic route reduces the impurities phenyl xylylphosphate, tricresyl phosphate and triphenyl phosphate, thus improving the purity.
Exploration of chiral Lewis acid Mg2+ catalysts in the synthesis of aryl organophosphate triesters from phosphorus oxychloride through a three-step, two-pot substitution sequence
Granger, Emily,Solomianko, Katarzyna,Young, Cori,Erb, Jeremy
, p. 1404 - 1408 (2018/03/13)
A variety of nucleophilic and Lewis acid catalysts were examined for use in promoting the synthesis of organophosphate triesters. Eight novel organophosphate triesters are reported here for the first time. MgSO4 was discovered as an inexpensive catalyst capable of improving the synthesis of a variety of aryl organophosphate triesters from the readily available and low cost precursor phosphorus oxychloride in a three-step, two-pot sequence. Yields for this method improve upon the uncatalyzed method by 8–36%. Several chiral catalysts were tested, but none were able to induce enantioselectivity in the reaction.
