3096-08-0

Basic information

• Product Name: O-methyl diphenylphosphinothioate
• Synonyms: O-methyl diphenylphosphinothioate
• CAS NO: 3096-08-0
• Molecular Weight: 248.285
• Mol File: 3096-08-0.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: O-methyl diphenylphosphinothioate(CAS DataBase Reference)
• NIST Chemistry Reference: O-methyl diphenylphosphinothioate(3096-08-0)
• EPA Substance Registry System: O-methyl diphenylphosphinothioate(3096-08-0)

Safety Data

• Hazardous Substances Data: 3096-08-0(Hazardous Substances Data)

Upstream product

• 67-56-1 methanol 
• 100-47-0 benzonitrile 
• 107-56-2 O,O-diisopropyl hydrogen phosphorodithioate 
• 19172-47-5 Lawessons reagent 
• 1706-90-7 methyl diphenylphosphinate 
• 4020-99-9 diphenylphosphinous acid methyl ester 
• 7139-34-6 5-phenyl-3(3H)-thioxo-1,2,4-dithiazole 
• 1015-37-8 diphenylthiophosphinoyl chloride 
• 124-41-4 sodium methylate 
• 1144028-84-1 N-methyl-N-diphenylphosphinothioyloxy-4-chlorobenzamide 
• 6079-77-2 bis(diphenylphosphinothioyl)disulfide 
• 957799-24-5 C₂₃H₂₂NO₂PS 
• 957799-23-4 C₂₃H₂₂NOPS 

Downstream Products

• 1707-03-5 diphenyl-phosphinic acid 
• 1135-98-4 diphenylphosphinic fluoride 
• 66004-03-3 1-methylbutyldiphenylphosphine sulfide 
• 67-56-1 methanol 
• 4020-99-9 diphenylphosphinous acid methyl ester 
• 71-43-2 benzene 
• 1706-90-7 methyl diphenylphosphinate 

Relevant articles and documents

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1,2,4-Dithiazole-5-ones and 5-thiones as efficient sulfurizing agents of phosphorus(iii) compounds - A kinetic comparative study

The sulfurization efficiency of 25 3-substituted-1,2,4-dithiazole-5-ones and 5-thiones towards triphenyl phosphite in acetonitrile, DCM, THF and toluene at 25 °C was evaluated. All the 1,2,4-dithiazoles are much better sulfurizing reagents than commercially available agents (PADS, TETD, Beaucage's reagent). The most efficient sulfurizing agents in all solvents are 3-phenoxy (4), 3-phenylthio (5) and 3-ethoxy-1,2,4-dithiazole-5-one (1) whose reactivity is at least two orders of magnitude higher than that of other 1,2,4-dithiazoles. Contrary to a previous report, the sulfurization with 1 does not yield carbonylsulfide and ethyl cyanate as the additional reaction products but unstable ethoxythiocarbonyl isocyanate which has been trapped with 4-methoxyaniline. Similar trapping experiments have proven that the site of attack is at the sulfur adjacent to the CO group for compounds 4 and 5. The reaction pathway involves rate-limiting initial nucleophilic attack of the phosphorus at sulfur followed by decomposition of the phosphonium intermediate to the corresponding phosphorothioate and isocyanate/isothiocyanate species. The existence of the phosphonium intermediate during sulfurization of triphenyl phosphine with 3-phenyl-1,2,4-dithiazole-5-thione (7a) was proven using kinetic studies. From the Hammett and Bronsted correlations and from other kinetic measurements it was concluded that the transition-state structure is almost apolar for the most reactive 1,2,4-dithiazoles whereas a polar structure resembling a zwitter-ionic intermediate may be more appropriate for the least reactive 1,2,4-dithiazoles. The extent of P-S bond formation and S-S bond cleavage is very similar in all reaction series but it gradually decreases with the reactivity of the 1,2,4-dithiazole derivatives.

The study of the reaction between thiophosphoryl esters and boron tribromide. The synthesis of oxathiaphosphaboretanes

Reactions between three thiophosphoryl esters and boron tribromide are reported. O,O,O-triethyl phosphorothionate (1) and O,O-diethyl methanephosphonothionate (5) gave substituted oxathiaphosphaboretanes 4 and 7 respectively. O-methyl diphenyl-phosphinothionate (9) led to the complex 11 and the corresponding oxathiaphosphaboretane 12. In order to establish the mechanism, reactions were monitored by the multinuclear NMR spectroscopy.