16118-33-5

Basic information

• Product Name: Dithiocarbonic acid S,S-diisopropyl ester
• Synonyms: Dithiocarbonic acid S,S-diisopropyl ester
• CAS NO: 16118-33-5
• Molecular Formula: C₇H₁₄OS₂
• Molecular Weight: 178.32
• Mol File: 16118-33-5.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Dithiocarbonic acid S,S-diisopropyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Dithiocarbonic acid S,S-diisopropyl ester(16118-33-5)
• EPA Substance Registry System: Dithiocarbonic acid S,S-diisopropyl ester(16118-33-5)

Safety Data

• Hazardous Substances Data: 16118-33-5(Hazardous Substances Data)

Upstream product

• 16754-59-9 tris-isopropylsulfanyl-methane 
• 17241-10-0 tris(p-tolylthio)methane 
• 35200-02-3 O-isopropyl S-methyl xanthate 

Relevant articles and documents

Trithioorthoester Exchange and Metathesis: New Tools for Dynamic Covalent Chemistry

To expand the toolbox of dynamic covalent and systems chemistry, we investigated the acid-catalyzed exchange reaction of trithioorthoesters with thiols. We found that trithioorthoester exchange occurs readily in various solvents in the presence of stoichiometric amounts of strong Bronsted acids or catalytic amounts of certain Lewis acids. The scope of the exchange reaction was explored with various substrates, and conditions were identified that permit clean metathesis reactions between two different trithioorthoesters. One distinct advantage of S, S, S-orthoester exchange over O, O, O-orthoester exchange is that the exchange reaction can kinetically outcompete hydrolysis, thereby making the process less sensitive to residual moisture. We expect that the relatively high stability of the products might be beneficial in future supramolecular receptors or porous materials.

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