Diphenyl chlorophosphate

Base Information

• Chemical Name: Diphenyl chlorophosphate
• CAS No.: 2524-64-3
• Deprecated CAS: 103137-47-9
• Molecular Formula: C12H10ClO3P
• Molecular Weight: 268.636
• Hs Code.: 29209085
• European Community (EC) Number: 219-759-6
• NSC Number: 43771
• UN Number: 1760
• UNII: 1KEE9757OT
• DSSTox Substance ID: DTXSID2044892
• Nikkaji Number: J7.599J
• Wikidata: Q10266258
• ChEMBL ID: CHEMBL3188224
• Mol file: 2524-64-3.mol

Synonyms:diphenylphosphorylchloridate

Chemical Property of Diphenyl chlorophosphate

Chemical Property:

• Appearance/Colour: clear colourless to light yellow liquid
• Vapor Pressure: 10 mm Hg ( 190 °C)
• Melting Point: 314-316oC
• Refractive Index: n20/D 1.55(lit.)
• Boiling Point: 363.5 °C at 760 mmHg
• Flash Point: 256.2 °C
• PSA: 45.34000
• Density: 1.337 g/cm³
• LogP: 4.49130
• Storage Temp.: Store below +30°C.
• Sensitive.: Moisture Sensitive
• Water Solubility.: MAY DECOMPOSE
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 268.0056089
• Heavy Atom Count: 17
• Complexity: 249
• Transport DOT Label: Corrosive

Purity/Quality:

99% ^*data from raw suppliers

DiphenylChlorophosphonate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 34-37
• Safety Statements: 26-36/37/39-45-7-24/25-23

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C=C1)OP(=O)(OC2=CC=CC=C2)Cl
• 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. 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. 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

Technology Process of Diphenyl chlorophosphate

There total 21 articles about Diphenyl chlorophosphate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

diphenyl hydrogen phosphite (4712-55-4) → chlorophosphoric acid diphenyl ester (2524-64-3)

Guidance literature:

With trichloroisocyanuric acid; In acetonitrile; at 20 ℃;

DOI:10.1016/j.tetlet.2005.06.024

Reference yield: 96.0%

phosphoryl chloride (POCl3) + N,N-dimethyl acetamide (127-19-5,116057-81-9) + phenol (108-95-2,27073-41-2) → chlorophosphoric acid diphenyl ester (2524-64-3)

Guidance literature:

With trichlorophosphate;

Reference yield: 90.3%

diphenyl hydrogen phosphate (838-85-7) → chlorophosphoric acid diphenyl ester (2524-64-3)

Guidance literature:

With bis(trichloromethyl) carbonate; In dichloromethane; N,N-dimethyl-formamide; at 10 ℃; for 3h;

upstream raw materials:

triphenyl phosphite

tetrachloromethane

diphenyl methyl phosphite

Diphenyl phosphorochloridite

Downstream raw materials:

2-chloroethyl diphenyl phosphate

morpholinodiphenylphosphine oxide

O³-diphenoxyphosphoryl-O¹,O²;O⁴,O⁵-diisopropylidene-β-D-fructopyranose

1-phenyl-2-phosphonooxy-ethanone

Refernces

• 1、 Ying, Jun,Gao, Qian,Wu, Xiao-Feng. "Zinc-catalyzed transformation of diarylphosphoryl azides to diarylphosphate esters and amides". supporting information. p. 1540 - 1543. Retrieved 2020/04/15.
• 2、 -. "Chemical synthesis method of diphenyl chlorophosphate". Paragraph 0019; 0020. . Retrieved 2019/10/01.