18755-36-7

Basic information

• Product Name: ethyl methyl methylphosphonate
• Synonyms: phosphonic acid, P-methyl-, ethyl methyl ester
• CAS NO: 18755-36-7
• Molecular Formula: C₄H₁₁O₃P
• Molecular Weight: 138.1021
• Mol File: 18755-36-7.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 162.9°C at 760 mmHg
• Flash Point: 66.7°C
• Density: 1.05g/cm³
• Vapor Pressure: 2.77mmHg at 25°C
• Refractive Index: 1.387
• CAS DataBase Reference: ethyl methyl methylphosphonate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl methyl methylphosphonate(18755-36-7)
• EPA Substance Registry System: ethyl methyl methylphosphonate(18755-36-7)

Safety Data

• Hazardous Substances Data: 18755-36-7(Hazardous Substances Data)

Upstream product

• 22946-83-4 O-Ethyl-S-phenyl-methylphosphonothioat 
• 124-41-4 sodium methylate 
• 67-56-1 methanol 
• 65143-05-7 O-ethyl S-(2-diisopropylaminoethyl) methylphosphonothiolate 
• 886227-40-3 O-ethyl S-3,5-dichlorophenyl methylphosphonothioate 
• 886227-42-5 methyl-phosphonothioic acid O-ethyl ester S-(4-methoxy-phenyl) ester 
• 93115-94-7 methyl-phosphonothioic acid S-(4-chloro-phenyl) ester O-ethyl ester 
• 886227-41-4 methyl-phosphonothioic acid O-ethyl ester S-(4-fluoro-phenyl) ester 
• 141-78-6 ethyl acetate 
• 756-79-6 dimethyl methane phosphonate 
• 141-52-6 sodium ethanolate 
• 58259-60-2 methylphosphonothioic acid O,S-dimethyl ester 
• 4987-37-5 ethyl N-chloroethanimidate 
• 20278-51-7 dimethyl methylphosphonite 

Relevant articles and documents

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Catalytic decomposition of simulants for chemical warfare V agents: Highly efficient catalysis of the methanolysis of phosphonothioate esters

(Chemical Equation Presented) As good as the original: Extremely effective methanolysis of phosphonothioates using metal-containing systems (e.g., 1) was achieved. The catalytic methanolysis of a SCH2CH2NEt 2 derivative, an analogue of the organophosphorus chemical warfare material VX, was predicted, and the catalyzed methanolysis of S-(3,5-dichlorophenyl) O-ethyl methylphosphonothioate was shown to involve a concerted displacement of the aryl thioate (transition state 2)

A MECHANISTIC STUDY OF THE REACTION OF PHOSPHONITE ESTERS WITH ETHYL AND METHYL N-CHLOROACETIMIDE

The reaction of a dialkyl methylphosphonite with an alkyl N-chloroacetimide leads to the formation of the expected Arbusov reaction product (3) plus a dialkyl methylphosphonate and acetonitrile.For dissimilarly substituted reagents, a mixture of symmetrical (4) and unsymmetrical (5) dialkyl methylphosphonates are produced.We have shown that the latter (4 and 5) result from a phosphonium intermediate (6), formed from an initial attack by phosphorus on the chlorine atom of the acetimide, followed by ligand exchange with alkoxide, and not from a simple air oxidation of the dialkyl methylphosphonite starting material.However, it is uncertain whether the Arbusov product is also formed via the same initial phosphonium intermediate (6), or whether competing paths of attack by tervalent phosphorus on the halogen vs. the nitrogen atom of the N-chloroacetimide are operative in this system.