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

• 4987-37-5 ethyl N-chloroethanimidate 
• 20278-51-7 dimethyl methylphosphonite 
• 67-56-1 methanol 
• 65143-05-7 O-ethyl S-(2-diisopropylaminoethyl) methylphosphonothiolate 
• 886227-40-3 O-ethyl S-3,5-dichlorophenyl methylphosphonothioate 
• 124-41-4 sodium methylate 
• 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 
• 22946-83-4 O-Ethyl-S-phenyl-methylphosphonothioat 
• 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 

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)

STEREOCHEMISTRY OF SOME REACTIONS BETWEEN ALKYL S-METHYL METHYLPHOSPHONOTHIOATES AND CHIRAL ALKOXIDES

With R-(+) ethyl (or methyl) S-methyl methylphosphonothioate and (+)-pinacolyl alkoxide competitive and highly stereoselective displacements of O-alkyl and S-methyl occur, both reactions being with inversion of configuration.With the enantiomeric S-(-) ethyl (and methyl) S-methyl methylphosphonothioates and (+)-pinacolyl alkoxide the reactions, although still competitive, are no longer stereoselective.In contrast similar reactions with the sodium salt of (-)-menthol, (which might be considered to be the mirror image of (+)-pinacolyl alkoxide) occur highly stereoselectively with the S-(-) but not with R-(+) enantiomers.The displacement of O-alkyl from alkyl S-methyl methylphosphonothioates by ethoxide, pinacolyl alkoxide and menthyl alkoxide is not observed when methoxide is the nucleophile; in this case only displacement of S-alkyl group occurs.