55716-09-1

Basic information

• Product Name: S,S-Di(n-butyl) dithiocarbonate
• Synonyms: S,S-Di(n-butyl) dithiocarbonate
• CAS NO: 55716-09-1
• Molecular Weight: 206.373
• Mol File: 55716-09-1.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: S,S-Di(n-butyl) dithiocarbonate(CAS DataBase Reference)
• NIST Chemistry Reference: S,S-Di(n-butyl) dithiocarbonate(55716-09-1)
• EPA Substance Registry System: S,S-Di(n-butyl) dithiocarbonate(55716-09-1)

Safety Data

• Hazardous Substances Data: 55716-09-1(Hazardous Substances Data)

Upstream product

• 41320-38-1 O-n-butyl S-methyl xanthate 
• 10226-07-0 S-butyl O-butyl dithiocarbonate 
• 67038-53-3 O-Methyl S-octyl dithiocarbonate 
• 74728-43-1 S-Butyl O-trideuteriomethyl dithiocarbonate 
• 77570-35-5 O-butyl S-octyl dithiocarbonate 
• 13889-94-6 butyl chlorothioformate 

Downstream Products

• 2386-60-9 perfluoro-1-butanesulfonyl fluoride 
• 3972-46-1 n-Butylthiobernsteinsaeureanhydrid 
• 109480-90-2 (E)-3-Butylsulfanyl-3-phenyl-acrylic acid 
• 629-45-8 dibutyl disulfide 

Relevant articles and documents

The thermal and mass spectral fragmentation of N-butyl thiolo-, thiono-, and dithio-chloroformate

Thermal decomposition of n-butyl thiolochloroformate at 150C follows a similar pattern to that reported previously for n-butyl chloroformate, to give butyl chloride which is largely rearranged to the s-butyl isomer. An ion-pair mechanism, involving 1,2-and 1,3-hydride shifts, is proposed. The less stable thiono-and dithio-chloroformates decompose to give lower yields of butyl chlorides (mainly without rearrangement) together with numerous other byproducts, indicating the operation of a more complex combination of reaction pathways. The mass spectra of all three thio compounds exhibit molecular ions; the most prominent fragment ions in their spectra are the n-butyl cation, and the radical cations COS+ and CS2+. Numerous chlorine-containing ions of low intensity are also observed, and their mode of formation is discussed. Copyright Taylor &Francis Group, LLC.

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