16241-04-6

Basic information

• Product Name: Carbamothioic acid, dimethyl-, O-phenyl ester
• Synonyms: O-phenyl N,N-dimethylthiocarbamate;Monothiokohlensaeure-O-phenylester-dimethylamid;Dimethyl-thiocarbamidsaeure-O-phenylester;dimethylamino-methanethioic acid O-phenyl ester;Carbamothioic acid,dimethyl-,O-phenyl ester;dimethyl-thiocarbamic acid O-phenyl ester;O-phenyl dimethylthiocarbamate;O-phenyl thiocarbamate
• CAS NO: 16241-04-6
• Molecular Formula: C9H11NOS
• Molecular Weight: 181.258
• Mol File: 16241-04-6.mol
• Article Data: 15

Chemical Properties

• Melting Point: 30-30.4 °C
• Boiling Point: 234.0±23.0 °C(Predicted)
• Density: 1.142±0.06 g/cm3(Predicted)
• CAS DataBase Reference: Carbamothioic acid, dimethyl-, O-phenyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Carbamothioic acid, dimethyl-, O-phenyl ester(16241-04-6)
• EPA Substance Registry System: Carbamothioic acid, dimethyl-, O-phenyl ester(16241-04-6)

Safety Data

• Hazardous Substances Data: 16241-04-6(Hazardous Substances Data)

Upstream product

• 108-95-2 phenol 
• 139-02-6 sodium phenoxide 
• 16420-13-6 N,N-Dimethylthiocarbamoyl chloride 
• 137-26-8 Thiram 
• 42817-44-7 (E)-N,N-dimethyl-3-phenylprop-2-en-1-amine 
• 1005-56-7 phenylcarbonochloridothioate 
• 98-94-2 N,N-dimethyl-cyclohexanamine 
• 103-83-3 N,N'-dimethylbenzylamine 
• 918-02-5 N,N-dimethyl-tert-butylamine 
• 124-40-3 dimethyl amine 

Downstream Products

• 7304-68-9 phenyl N,N-dimethyl(thiocarbamate) 
• 6969-90-0 phenyl N,N-dimethylcarbamate 
• 71715-20-3 1,1-dimethyl-2-phenyl-3-p-toluenesulfonylisourea 
• 108-98-5 thiophenol 

Relevant articles and documents

Thiocarbamate-Directed Tandem Olefination-Intramolecular Sulfuration of Two Ortho C-H Bonds: Application to Synthesis of a COX-2 Inhibitor

A palladium-catalyzed dual ortho C-H bond activation of aryl thiocarbamates is developed. This tandem reaction initiates by thiocarbamate-directed ortho C-H palladation, which leads to favorable olefin insertion rather than reductive elimination. The oxid

Iron(II)/Persulfate Mediated Newman-Kwart Rearrangement

Herein, we report that iron(II)/ammonium persulfate in aqueous acetonitrile mediates the Newman-Kwart rearrangement of O-aryl carbamothioates. Electron-rich substrates react rapidly under moderate heating to afford the rearranged products in excellent yie

Electrochemically Catalyzed Newman-Kwart Rearrangement: Mechanism, Structure-Reactivity Relationship, and Parallels to Photoredox Catalysis

The facilitation of redox-neutral reactions by electrochemical injection of holes and electrons, also known as "electrochemical catalysis", is a little explored approach that has the potential to expand the scope of electrosynthesis immensely. To systematically improve existing protocols and to pave the way toward new developments, a better understanding of the underlying principles is crucial. In this context, we have studied the Newman-Kwart rearrangement of O-arylthiocarbamates to the corresponding S-aryl derivatives, the key step in the synthesis of thiophenols from the corresponding phenols. This transformation is a particularly useful example because the conventional method requires temperatures up to 300 °C, whereas electrochemical catalysis facilitates the reaction at room temperature. A combined experimental-quantum chemical approach revealed several reaction channels and rendered an explanation for the relationship between the structure and reactivity. Furthermore, it is shown how rapid cyclic voltammetry measurements can serve as a tool to predict the feasibility for specific substrates. The study also revealed distinct parallels to photoredox-catalyzed reactions, in which back-electron transfer and chain propagation are competing pathways.