89982-11-6

Basic information

• Product Name: Phosphonic acid, (chloromethyl)-, ethyl methyl ester, (S)-
• CAS NO: 89982-11-6
• Molecular Formula: C4H10ClO3P
• Mol File: 89982-11-6.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: Phosphonic acid, (chloromethyl)-, ethyl methyl ester, (S)-(CAS DataBase Reference)
• NIST Chemistry Reference: Phosphonic acid, (chloromethyl)-, ethyl methyl ester, (S)-(89982-11-6)
• EPA Substance Registry System: Phosphonic acid, (chloromethyl)-, ethyl methyl ester, (S)-(89982-11-6)

Safety Data

• Hazardous Substances Data: 89982-11-6(Hazardous Substances Data)

Upstream product

• 67-56-1 methanol 
• 89982-10-5 (+)-(R)-ethyl S-methyl chloromethylphosphonothioate 

Relevant articles and documents

Chiral Mono-, Di, and Tri-chloromethylphosphonates and Phosphonothioates: Preparation, Absolute Configuration, and the Stereochemical Course of Their Reaction with Methoxide

Enantiomerically pure (+)-(R)-O-ethyl S-methyl dichloromethylphosphonothioate, prepared using (-)-ephedrine as a chiral template, is futher chlorinated to the trichloro analogue using BunLi-CCl4 and dechlorinated by hydrogenolysis via the monochloro analogue to the corresponding methyl-phosphonothioate of known configuration.With methoxide, the trichloro derivatives gives P-C bond cleavage with inversion and the dichloro derivatives gives P-S bond cleavages with retention of configuration.In the monochloroderivative P-S and P-O bond cleavages are competitive, P-S bond cleavage occuring with 70percent inversion.Under similar reaction conditions P-S bond cleavage occurs stereospecifically with inversion of configuration in methylphosphonothioates.Methoxide treatment of (+)-(R)-ethyl isopropyl trichloromethylphosphonate results in P-C bond cleavage with inversion while (-)-(S)-ethyl phenyl dichloromethylphosphonate loses the OPh group also with inversion.Possible reaction mechanisms are discussed.