55852-80-7

Basic information

• Product Name: S-methyl dipropylthiocarbamate
• Synonyms: Carbamothioic acid, dipropyl-, S-methyl ester; S-Methyl dipropylcarbamothioate
• CAS NO: 55852-80-7
• Molecular Formula: C₈H₁₇NOS
• Molecular Weight: 175.2917
• Mol File: 55852-80-7.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 235.4°C at 760 mmHg
• Flash Point: 96.2°C
• Density: 0.979g/cm³
• Vapor Pressure: 0.0501mmHg at 25°C
• Refractive Index: 1.48
• CAS DataBase Reference: S-methyl dipropylthiocarbamate(CAS DataBase Reference)
• NIST Chemistry Reference: S-methyl dipropylthiocarbamate(55852-80-7)
• EPA Substance Registry System: S-methyl dipropylthiocarbamate(55852-80-7)

Safety Data

• Hazardous Substances Data: 55852-80-7(Hazardous Substances Data)

Upstream product

• 19708-81-7 methyl O-methyldithiocarbonate 
• 142-84-7 di-n-propylamine 
• 74-88-4 methyl iodide 
• 27086-19-7 N,N-dipropylcarbamoyl chloride 
• 71280-90-5 Dipropyl-thiocarbamic acid; compound with dipropyl-amine 
• 201230-82-2 carbon monoxide 

Downstream Products

• 27086-19-7 N,N-dipropylcarbamoyl chloride 

Relevant articles and documents

O,S-Dimethyl carbonodithioate as a phosgene substitute for the preparation of S-methyl alkylcarbamothioates and dialkylcarbamothioates

O,S-Dimethyl carbonodithioate is proposed as a suitable and safely handled reagent that can be used as a replacement for phosgene in the synthesis of S-methyl alkyl- and dialkylcarbamothioates. The former were obtained by a two-step procedure, which can also be carried out in a one-pot fashion without isolating the intermediates O-methyl alkylcarbamothioates; the overall yields of the pure S-methyl alkylcarbamothioates were 94-98%. Optimal conditions for the synthesis of S-methyl dialkylcarbamothioates involved a one-step procedure in a solvent-free system in the presence of triethyl(methyl)ammonium methyl carbonate as a catalyst; yields of the pure products were 85-98%. A mechanism is proposed for the carbamothioate-formation reaction. Georg Thieme Verlag Stuttgart.

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).

Reaction of Thiolates with Carbon Monoxide

Thiolates generated from elemental sulfur with amines or lithium amides, easily reacted with carbon monoxide to form thiocarbamates in good yields.Furthermore, the reaction of diaminodisulfide with carbon monoxide in the presence of DBU proceeded similarl