30085-50-8

Basic information

• Product Name: DIETHYL-THIOCARBAMIC ACID S-BENZYL ESTER
• Synonyms: DIETHYL-THIOCARBAMIC ACID S-BENZYL ESTER
• CAS NO: 30085-50-8
• Molecular Formula: C₁₂H₁₇NOS
• Molecular Weight: 223.33448
• Mol File: 30085-50-8.mol
• Article Data: 15

Chemical Properties

• Boiling Point: 321.8±35.0 °C(Predicted)
• Appearance: /
• Density: 1.080±0.06 g/cm3(Predicted)
• PKA: -1.22±0.70(Predicted)
• CAS DataBase Reference: DIETHYL-THIOCARBAMIC ACID S-BENZYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: DIETHYL-THIOCARBAMIC ACID S-BENZYL ESTER(30085-50-8)
• EPA Substance Registry System: DIETHYL-THIOCARBAMIC ACID S-BENZYL ESTER(30085-50-8)

Safety Data

• Hazardous Substances Data: 30085-50-8(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Tetrahedron Letters, 32, p. 6867, 1991 DOI: 10.1016/0040-4039(91)80428-9

Upstream product

• 100-39-0 benzyl bromide 
• 22318-01-0 diethylamonium N,N'-dimethylmonothiocarbamate 
• 201230-82-2 carbon monoxide 
• 109-89-7 diethylamine 
• 463-58-1 carbon oxide sulfide 
• 100-44-7 benzyl chloride 
• 88-10-8 N,N-diethylcarbamyl chloride 
• 100-53-8 phenylmethanethiol 
• 21055-93-6 sodium salt of diethylthiocarbamic acid 
• 34879-74-8 1-diethylaminyl benzyl sulfide 
• 150-60-7 dibenzyl disulphide 
• 3052-61-7 N,N-diethylaminodithiocarboxylic acid benzyl ester 
• 2430-00-4 2,2,2-trichloro-N,N-diethylacetamide 
• 6258-66-8 (4-chlorophenyl)methanethiol 

Relevant articles and documents

Visible-light-promoted synthesis of secondary and tertiary thiocarbamates from thiosulfonates andN-substituted formamides

A general visible-light-promoted metal-free synthesis of secondary and tertiary thiocarbamates starting from thiosulfonates andN-substituted formamides is developed. By employing rhodamine B as a photocatalyst andtert-butyl hydroperoxide (TBHP) as an oxidant, a wide scope of thiocarbamates can be obtained through direct thiolation of acyl C-H bonds under irradiation of blue light at room temperature for 12 h.

Solvent-assisted thiocarboxylation of amines and alcohols with carbon monoxide and sulfur under mild conditions

DMSO or DMF as a solvent strongly accelerated the thiocarboxylation of amines and alcohols with carbon monoxide and sulfur. Under mild conditions (1 atm, 20°C), this thiocarboxylation of amines assisted by DMSO with carbon monoxide and sulfur has been developed into a practical and convenient synthetic method for S-alkyl thiocarbamates in good to excellent yields, including EPTC, thiobencarb, orbencarb, and molinate (herbicides). DMF also showed the similar solvent effect. NMP slightly decreased the effect for the thiocarboxylation of amines, and the yield of S-alkyl thiocarbamate was lowered in DMAc. Surprisingly, no formation of S-alkyl thiocarbamate was observed at the use of the other solvents, such as THF, hexane, toluene, AcOEt, MeCN, MeOH, and H 2O. The present solvent-assisted thiocarboxylation with carbon monoxide and sulfur could be also applied to a new synthesis of S-alkyl O-alkyl carbonothioates from alcohols under mild conditions (1 atm, 20°C) in DMF using DBU (1,8-diazabicyclo[5.4.0]undec-7-ene).

Palladium-catalyzed azathiolation of carbon monoxide

A novel palladium-catalyzed azathiolation of carbon monoxide using sulfenamide (RSNR'2) (1) is described to provide thiocarbamate 2 in good yields. The mechanistic proposal includes the following: (1) insertion of CO into Pd-S bond of Pd(SR)2(PPh3)(n) 4 to provide Pd[C(O)SR](SR)(PPh3)(n) 5 and (2) σ-bond metathesis between S-N and Pd-C(O) bonds to afford 2 with the regeneration of 4.