10265-93-7

Basic information

• Product Name: Phosphoramidothioic acid O-ethyl S-methyl ester
• Synonyms: BAY-65258;Bayer-65258;ENT-27398;Phosphoramidothioic acid O-ethyl S-methyl ester
• CAS NO: 10265-93-7
• Molecular Formula: C₃H₁₀NO₂PS
• Molecular Weight: 155.1558
• Mol File: 10265-93-7.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 226.1°Cat760mmHg
• Flash Point: 90.5°C
• Appearance: /
• Density: 1.229g/cm³
• Vapor Pressure: 0.0834mmHg at 25°C
• Refractive Index: 1.483
• CAS DataBase Reference: Phosphoramidothioic acid O-ethyl S-methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Phosphoramidothioic acid O-ethyl S-methyl ester(10265-93-7)
• EPA Substance Registry System: Phosphoramidothioic acid O-ethyl S-methyl ester(10265-93-7)

Safety Data

• Hazardous Substances Data: 10265-93-7(Hazardous Substances Data)

Usage

General Description

Phosphoramidothioic acid O-ethyl S-methyl ester, also known as S-ethyl O-methyl ethyl phosphoramidothioate, is a chemical compound used as a pesticide and insecticide. It is a member of the organophosphate class of chemicals and is commonly used to control a wide range of pests, including insects and mites. It works by inhibiting the activity of acetylcholinesterase, an enzyme necessary for the proper functioning of the nervous system in pests. However, it is also highly toxic to humans and other non-target organisms, and can cause a range of negative health effects if not handled and used carefully. Therefore, it is important to exercise caution and follow safety guidelines when using products containing this chemical.

InChI:InChI=1/C3H10NO2PS/c1-3-6-7(4,5)8-2/h3H2,1-2H3,(H2,4,5)

Upstream product

• 64-17-5 ethanol 
• 65960-97-6 (+)-(R)-O,S-dimethyl phosphoramidothioate 
• 65960-90-9 (2R)-3,4c-dimethyl-5c-phenyl-2-thioxo-2λ⁵-[1,3,2]oxazaphospholidin-2r-ylamine 
• 74-88-4 methyl iodide 
• 17321-48-1 O,O-diethyl phosphoramidothioate 

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.