2404-05-9

Basic information

• Product Name: O,O-diethyl S-methyl phosphorothioate
• Synonyms: O,O-Diethyl S-methyl phosphorothioate; phosphorothioic acid, O,O-diethyl S-methyl ester
• CAS NO: 2404-05-9
• Molecular Formula: C₅H₁₃O₃PS
• Molecular Weight: 184.1937
• Mol File: 2404-05-9.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 211.6°C at 760 mmHg
• Flash Point: 81.8°C
• Density: 1.137g/cm³
• Vapor Pressure: 0.262mmHg at 25°C
• Refractive Index: 1.45
• CAS DataBase Reference: O,O-diethyl S-methyl phosphorothioate(CAS DataBase Reference)
• NIST Chemistry Reference: O,O-diethyl S-methyl phosphorothioate(2404-05-9)
• EPA Substance Registry System: O,O-diethyl S-methyl phosphorothioate(2404-05-9)

Safety Data

• Hazardous Substances Data: 2404-05-9(Hazardous Substances Data)

Upstream product

• 556-64-9 methyl thiocyanate 
• 2303-76-6 sodium diethyl phosphite 
• 5813-48-9 Methanesulfenyl chloride 
• 108-88-3 toluene 
• 122-52-1 triethyl phosphite 
• 64-17-5 ethanol 
• 18281-76-0 S-methyl dichlorothiophosphate 
• 4020-99-9 diphenylphosphinous acid methyl ester 
• 4403-51-4 bis(diethylphosphoryl)disulfide 
• 186581-53-3 diazomethane 
• 7732-18-5 water 
• 2465-65-8 O,O'-diethyl thiophosphoric acid 
• 71-43-2 benzene 
• 67-56-1 methanol 

Downstream Products

• 75-75-2 methanesulfonic acid 
• 814-22-2 diethyl n-propyl phosphate 
• 78-40-0 triethyl phosphate 
• 598-02-7 Diethyl phosphate 
• 2736-99-4 diethyl 2-propyl phosphate 
• 926-06-7 isopropyl methanesulfonate 
• 16156-54-0 sec-butyl methanesulfonate 
• 31774-59-1 diethyl sec-butyl phosphate 
• 13232-08-1 (2-methyl-2-propyl) diethyl phosphate 
• 16427-41-1 tert-butyl mesylate 
• 867-17-4 diethyl methyl phosphate 

Relevant articles and documents

A Robust Methodology for the Synthesis of Phosphorothioates, Phosphinothioates and Phosphonothioates

A robust methodology for the synthesis of phosphorothioates, phosphinothioates and phosphonothioates, including those bearing low molecular weight S-alkyl side-chains, is presented. Application of the “caesium effect” in conjunction with the disulfide 3,3’-dithiobis(propionitrile), which acts as a shelf-stable sulfur source, avoids recourse to malodorous alkanethiols and toxic P?Cl precursors. A diverse range of sulfur-containing organophosphorus targets, including phosphorus-based heterocycles, may be prepared in consistently high yields. This chemistry also provides ready access to the corresponding DBU salts which are potential substrates for Pd-catalysed coupling reactions. (Figure presented.).

A new method of introducing SCH3 and SCD3 groups to phosphorothioates

A new synthesis of phosphorothioates starting from phosphites and cyanuric chloride (TCT)-activated DMSO is reported herein. This method enables the incorporation of SCH3 and SCD3 groups into phosphorothioates in good yields. The labeling purities of the products are excellent.

Fluorinated phosphorus compounds part 8. The reactions of bis(fluoroalkyl) phosphorochloridates with sulfur nucleophiles

The reactivity of bis (fluoroalkyl)phosphorochloridates to nucleophiles is summarised. Previous data and the results described here indicate that reactivities decrease in the order: amines > alcohols > thiols. The synthesis of CF3CH2OP(O)(SEt)2 in 30% yield was accomplished by treating CF3CHOP(O)Cl2 with two molar equivalents of EtSH and Et3N in ether. The chloridates (CF3CH2O)2P(O)Cl and (C2F5CH2O)2-P(O)Cl did not react with MeSH in ether at -78 °C or when heated with Pb(SMe)2 in benzene. Ethanethiol and propanethiol reacted with fluorinated chloridates in the presence of triethylamine to give thiolates (RFO)2P(O)SR in 13-41% yield where RF was CF3CH2, C2F5CH2, C3F7CH2 or (CF3)2CH and R was Et or n-Pr. Similarly, reaction of phosphorobromidates (RFCH2O)2P(O)Br, made by brominating the corresponding bis(fluoroalkyl) H-phosphonates, with benzenethiol gave derivatives (RFCH2O)2P(O)SPh in 43 and 46% yield where RF was CF3 and C2F5, respectively. Treatment of the chloridothiolate Cl(EtO)P(O)SMe, prepared in two steps from triethyl phosphite, with flouroalcohols and triethylamine in ether gave species RFO(EtO)P(O)SMe in 62-74% yield where RF was CF3CH2, C2F5CH2, C3F7CH2 or (CF3)2CH. The reactions of bis(trifluoroethyl) phosphorochloridate with 2-mercaptoethanol, 3-mercaptopropanol and ethane-1,2-dithiol gave several unexpected products whose structures were tentatively assigned.