10596-55-1

Basic information

• Product Name: S-Ethyl S'-methyl dithiocarbonate
• Synonyms: S-Ethyl S'-methyl dithiocarbonate
• CAS NO: 10596-55-1
• Molecular Weight: 136.239
• Mol File: 10596-55-1.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: S-Ethyl S'-methyl dithiocarbonate(CAS DataBase Reference)
• NIST Chemistry Reference: S-Ethyl S'-methyl dithiocarbonate(10596-55-1)
• EPA Substance Registry System: S-Ethyl S'-methyl dithiocarbonate(10596-55-1)

Safety Data

• Hazardous Substances Data: 10596-55-1(Hazardous Substances Data)

Upstream product

• 97-94-9 triethyl borane 
• 4373-12-0 O-cyclododecyl-S-methyl dithiocarbonate 
• 688-73-3 tri-n-butyl-tin hydride 
• 26404-95-5 O-Methyl S-Ethyl Dithiocarbonate 
• 623-54-1 O-ethyl S-methyl dithiocarbonate 
• 1005-31-8 4-(dimethylamino)pyridine N-oxide 

Relevant articles and documents

On the mechanism of deoxygenation of secondary alcohols by tin hydride reduction of methyl xanthates and other thiocarbonyl derivatives

The room temperature deoxygenation of xanthates and thionocarbonates using (n - Bu) 3Sn-H - Et3B - air has been studied, especially with 119Sn N.M.R. spectroscopy. The orignal conception of tin radical attack on thiocarbonyl is confirmed.

4-PIPERIDINOPYRIDINE AS AN EFFECTIVE CATALYST FOR THIONE-THIOL REARRANGEMENT OF XANTHATES

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Catalytic Rearrangement of O,S-Dialkyl Dithiocarbonates to S,S-Dialkyl Dithiocarbonates by Pyridine N-Oxides. The Reaction Mechanism

The reaction of O-alkyl S-methyl dithiocarbonates (xanthates) (I) with pyridine N-oxides (II) gave the corresponding S-alkyl S-methyl dithiocarbonates (dithiolcarbonate) (III) together with the symmetric S,S-dialkyl and S,S-dimethyl dithiocarbonates in good yields.Pyridine N-oxides bearing electron-donating substituents are efficient catalysts for rearrangement of I to III.The reaction is pseudo-first-order and the apparent first-order rate constant is proportional to the concentration of II.The role of pyridine N-oxides and the reaction behavior of O,S-dialkyldithiocarbonates are discussed on the basis of kinetic and molecular orbital calculation data.The rearrangement may proceed by nucleophilic attack of -SCOSR derived from a complex of I and II on the O-alkyl group of xanthates.The reaction provides a useful preparation method for alkanethiols by aminolysis of the products with ethanolamine.Keywords O,S-dialkyl dithiocarbonate; S,S-dialkyl dithiocarbonate; pyridine N-oxide; thiol; charge transfer; catalytic rearrangement; kinetics; ethanolamine; frontier molecular orbital