41320-26-7

Basic information

• Product Name: S-(n-Butyl)-S-methyl dithiocarbonate
• Synonyms: S-(n-Butyl)-S-methyl dithiocarbonate
• CAS NO: 41320-26-7
• Molecular Weight: 164.293
• Mol File: 41320-26-7.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: S-(n-Butyl)-S-methyl dithiocarbonate(CAS DataBase Reference)
• NIST Chemistry Reference: S-(n-Butyl)-S-methyl dithiocarbonate(41320-26-7)
• EPA Substance Registry System: S-(n-Butyl)-S-methyl dithiocarbonate(41320-26-7)

Safety Data

• Hazardous Substances Data: 41320-26-7(Hazardous Substances Data)

Upstream product

• 41320-38-1 O-n-butyl S-methyl xanthate 

Downstream Products

• 646-01-5 3-(methylsulfanyl)propionic acid 
• 22002-73-9 3-(butylthio)propionic acid 

Relevant articles and documents

Catalytic thione-thiol rearrangement of xanthates by 4- dialkylaminopyridine

Pyridines bearing electron-donating substituents are useful catalysts for the rearrangement of O,S-dialkyl xanthates (1) to S,S-dialkyl dithiocarbonates (2). The rearrangement was analyzed by semiempirical and ab initio molecular orbital methods. The transition-structure analyses indicate that the pyridine-ring nitrogen of dialkylaminopyridine rather than the dialkylamino nitrogen attacks the O-alkyl carbon of xanthates. The reaction proceeds through an S(N)2 mechanism to give the dithiolcarbonate anion (RSCOS-) which acts as an actual catalyst.

Thione-thiol rearrangement of xanthates catalyzed by pyridine N-oxides. Remarkably enhanced reactivity of 4-dialkylaminopyridine N-oxides

Pyridine N-oxides bearing electron-donating substituents (III) are efficient catalysts for rearrangement of O-alkyl S-methyl dithiocarbonates (xanthates) (I) to the corresponding S-alkyl S-methyl dithiocarbonates (dithiolcarbonates) (II). Of the catalysts tested, 4-piperidinopyridine N-oxide (IIIh) is the best from the viewpoints of catalytic activity and solubility in I. Heating of I in the presence of catalytic amounts (0.02-0.05 molar eq) of IIIh gave II together with the symmetric S,S-dialkyl and S,S-dimethyl dithiocarbonates in good yields. The catalytic behavior of donor-substituted pyridine N-oxides is discussed on the basis of kinetic and molecular orbital calculation data. The complete calculation of the perturbation equation on the initial stage of the reaction was consistent with the experimentally observed activity of the catalysts.

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.