58259-60-2

Usage

InChI:InChI=1/C3H9O2PS/c1-5-6(2,4)7-3/h1-3H3

Upstream product

• 79236-70-7 C₁₄H₂₂NO₃PS 
• 1066-52-0 methyl methylphosphonochloridate 
• 5188-07-8 sodium thiomethoxide 
• 186581-53-3 diazomethane 
• 5994-73-0 methylphosphonothioic acid 

Downstream Products

• 7040-58-6 dipinacolyl methylphosphonate 
• 103687-40-7 S-methyl methylphosphonate 
• 103687-39-4 R-(+) methyl methylphosphonate 
• 103687-43-0 S-(-) S-methyl methylphosphonothioate 
• 103687-44-1 R-(+) S-methyl methylphosphonothioate 
• 756-79-6 dimethyl methane phosphonate 
• 103687-41-8 R-(-) <(-)-menthyl> methyl methylphosphonate 
• 103687-41-8 S-(-) <(-)-menthyl> methyl methylphosphonate 
• 25257-18-5 <(-)-O-menthyl> S-methyl methylphosphonothioate 
• 18755-36-7 O-ethyl O-methyl methylphosphonate 
• 683-08-9 Diethyl methylphosphonate 
• 57578-88-8 (R)-(+)-O-ethyl S-methyl methylphosphonothioate 
• 51865-09-9 (S)-(-)-O-ethyl S-methyl methylphosphonothioate 

Relevant academic research and scientific papers

Detoxification of O, S-diethyl methyl phosphonothiolate (OSDEMP), a simulant of VX, by N, N-dichlorourethane as an effective decontaminating agent

N, N-Dichlorourethane has been synthesized and characterized by FT-IR, NMR. Efficiency of this compound as decontaminant has been evaluated by the reaction of O, S-diethyl methyl phosphonothiolate (OSDEMP), a simulant of VX at RT. The decontamination reaction has been monitored by gas chromatography (GC) and the products have been identified by GC-MS.

Ion-molecule reactions of O,S-dimethyl methylphosphonothioate: Evidence for intramolecular sulfur oxidation during VX perhydrolysis

(Chemical Equation Presented) The alkaline perhydrolysis of the nerve agent O-ethyl S-[2-(diisopropylamino)ethyl] methylphosphonothioate (VX) was investigated by studying the ion-molecule reactions of HOO- with O,S-dimethyl methylphosphonothioate in a modified linear ion-trap mass spectrometer. In addition to simple proton transfer, two other abundant product ions are observed at m/z 125 and 109 corresponding to the S-methyl methylphosphonothioate and methyl methylphosphonate anions, respectively. The structure of these product ions is demonstrated by a combination of collision-induced dissociation and isotope-labeling experiments that also provide evidence for their formation by nucleophilic reaction pathways, namely, (i) SN2 at carbon to yield the S-methyl methylphosphonothioate anion and (ii) nucleophilic addition at phosphorus affording a reactive pentavalent intermediate that readily undergoes internal sulfur oxidation and concomitant elimination of CH3SOH to yield the methyl methylphosphonate anion. Consistent with previous solution phase observations of VX perhydrolysis, the toxic P-O cleavage product is not observed in this VX model system and theoretical calculations identify P-O cleavage to be energetically uncompetitive. Conversely, intramolecular sulfur oxidation is calculated to be extremely exothermic and kinetically accessible explaining its competitiveness with the facile gas phase proton transfer process. Elimination of a sulfur moiety deactivates the nerve agent VX and thus the intramolecular sulfur oxidation process reported here is also able to explain the selective perhydrolysis of the nerve agent to relatively nontoxic products.

Stereochemictry of Alkaline Hydrolyses of 1,3,2-Oxazaphospholidine-2-thiones and Related Reactions

Essentially exclusive cleavage, with retention of configuration, of the endocyclic P-O bond occurs during basic hydrolysis of 2-alkoxy-1,3,2-oxazaphospholidine-2-thiones.In the 2-methyl analogues, P-O bond cleavage occurs with both inversion and retention