10596-54-0

Basic information

• Product Name: S-methyl S-(n-propyl) dithiocarbonate
• Synonyms: S-methyl S-(n-propyl) dithiocarbonate
• CAS NO: 10596-54-0
• Molecular Weight: 150.266
• Mol File: 10596-54-0.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: S-methyl S-(n-propyl) dithiocarbonate(CAS DataBase Reference)
• NIST Chemistry Reference: S-methyl S-(n-propyl) dithiocarbonate(10596-54-0)
• EPA Substance Registry System: S-methyl S-(n-propyl) dithiocarbonate(10596-54-0)

Safety Data

• Hazardous Substances Data: 10596-54-0(Hazardous Substances Data)

Upstream product

• 25954-88-5 methyl O-n-propyl dithiocarbonate 

Relevant articles and documents

4-DIMETHYLAMINOPYRIDINE N-OXIDE AS AN EXCELLENT CATALYST FOR THIONE TO THIOL REARRANGEMENT OF XANTHATES

4-Dimethylaminopyridine N-oxide effectively catalyzes the thione to hiol rearrangement of O,S-dialkyl dithiocarbonates (xanthates) to provide S,S-dialkyl dithiocarbonates.

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