28925-45-3

Basic information

• Product Name: S-methyl O-benzyl dithiocarbonate
• Synonyms: S-methyl O-benzyl dithiocarbonate
• CAS NO: 28925-45-3
• Molecular Weight: 198.31
• Mol File: 28925-45-3.mol
• Article Data: 12

Chemical Properties

• CAS DataBase Reference: S-methyl O-benzyl dithiocarbonate(CAS DataBase Reference)
• NIST Chemistry Reference: S-methyl O-benzyl dithiocarbonate(28925-45-3)
• EPA Substance Registry System: S-methyl O-benzyl dithiocarbonate(28925-45-3)

Safety Data

• Hazardous Substances Data: 28925-45-3(Hazardous Substances Data)

Upstream product

• 77-78-1 dimethyl sulfate 
• 74734-11-5 1H-imidazole-1-carbodithioic acid methyl ester 
• 100-51-6 benzyl alcohol 
• 75-15-0 carbon disulfide 
• 74-88-4 methyl iodide 

Downstream Products

• 103-30-0 (E)-1,2-diphenyl-ethene 
• 13049-99-5 S-Benzyl S-methyl dithiocarbonate 
• 60901-36-2 O-benzyl thiocarbamate 
• 108-88-3 toluene 
• 766-92-7 [(methylthio)methyl]-benzene 
• 624-92-0 Dimethyldisulphide 
• 100-39-0 benzyl bromide 
• 100-44-7 benzyl chloride 
• 588-59-0 stilbene 
• 478189-98-9 4-methyl-3-oxothiopentanoic acid O-benzyl ester 
• 10541-59-0 2,2-difluoro-1-phenylethane 
• 1215-52-7 N-benzoyl-N'-benzylhydrazine 
• 57260-70-5 4-benzyl-piperazine-1-carboxylic acid tert-butyl ester 
• 10316-00-4 4-benzyl-morpholine 

Relevant articles and documents

Aryl Radical Activation of C-O Bonds: Copper-Catalyzed Deoxygenative Difluoromethylation of Alcohols

Given their ubiquity in natural products and pharmaceuticals, alcohols represent one of the most attractive starting materials for the construction of C-C bonds. We report herein the first catalytic strategy to harness the reactivity of aryl radicals for the activation of C-O bonds in alcohol-derived xanthate esters, allowing for the discovery of the first catalytic deoxygenative difluoromethylation reaction. Under copper-catalyzed conditions, a wide variety of alkyl xanthate esters, readily synthesized from alcohol feedstocks, were activated by catalytically generated aryl radicals and were converted to the alkyl-difluoromethane products via alkyl radical intermediates. This scalable protocol exhibits a broad substrate scope and functional group tolerance, enabling late-stage modification of complex pharmaceutical agents. A one-pot protocol has been developed that allows for the direct use of free alcohols without purification of the xanthate esters. Mechanistic studies are consistent with the hypothesis of aryl radicals being formed and initiating the cleavage of the C-O bonds of xanthate esters, to generate alkyl radicals as the key intermediates. This aryl radical activation approach represents a new strategy for the activation of alcohols as cross-coupling partners.

Base-Induced Cyclization of Active Methylene Isocyanides with Xanthate Esters: An Efficient Method for the Synthesis of 5-Alkoxy-4-(tosyl/ethoxycarbonyl)-1,3-thiazoles

Sodium hydride-induced cyclization of 1-[(isocyanomethyl)sulfonyl]-4-methylbenzene or ethyl isocyanoacetate with various xanthate esters gave 5-alkoxy-4-tosylthiazoles or ethyl 5-alkoxythiazol-4-ylcarboxylates, respectively, in good to excellent yields. The xanthate ester S -methyl O -phenyl dithiocarbonate gave 5-(methylsulfanyl)-4-tosyl-1,3-thiazole when treated with 1-[(isocyanomethyl)sulfonyl]-4-methylbenzene under similar conditions.

An efficient, one-pot, Triton-B catalyzed synthesis of O-alkyl-S-methyl dithiocarbonates

A novel process for the one-step conversion of a variety of primary and secondary alcohols into their O-alkyl-S-methyl dithiocarbonates using methyl iodide catalyzed by the Triton-B/CS2 system was developed. Thus, O-alkyl-S-methyl dithiocarbonates were obtained in very good to excellent yields. This protocol is mild and efficient compared to other methods.