39076-43-2

Basic information

• Product Name: S-methyl ethylcarbamothioate
• CAS NO: 39076-43-2
• Molecular Formula: C₄H₉NOS
• Molecular Weight: 119.1854
• Mol File: 39076-43-2.mol
• Article Data: 7

Chemical Properties

• Density: 1.041g/cm³
• Refractive Index: 1.474
• CAS DataBase Reference: S-methyl ethylcarbamothioate(CAS DataBase Reference)
• NIST Chemistry Reference: S-methyl ethylcarbamothioate(39076-43-2)
• EPA Substance Registry System: S-methyl ethylcarbamothioate(39076-43-2)

Safety Data

• Hazardous Substances Data: 39076-43-2(Hazardous Substances Data)

Upstream product

• 65351-53-3 N-ethyl O-methyl thiocarbamate 
• 77-78-1 dimethyl sulfate 
• 868-84-8 S,S-dimethyl dithiocarbonate 
• 75-04-7 ethylamine 

Downstream Products

• 74-93-1 methylthiol 
• 623-76-7 N,N'-diethylurea 
• 41891-13-8 ethyl carbamoyl chloride 
• 625-52-5 N-Ethylurea 
• 5188-07-8 sodium thiomethoxide 
• 28145-10-0 1-ethyl-3-methylurea 

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.

Preparation of mono-, di-, and trisubstituted ureas by carbonylation of aliphatic amines with S,S-dimethyl dithiocarbonate

General procedures are reported to prepare N-alkylureas, N,N′-dialkylureas (both symmetrical and unsymmetrical), and N,N,N′-trialkylureas by carbonylation of aliphatic amines, employing S,S-dimethyl dithiocarbonate (DMDTC) as a phosgene substitute. All reactions were carried out in water. Symmetrical disubstituted ureas were prepared directly working at 60°C with a molar ratio of DMDTC:amine = 1:2, preferably under nitrogen. Unsymmetrical ureas were prepared in two steps via S-methyl N-alkyl-thiocarbamate intermediates, which are formed selectively in the first step at room temperature. These intermediates react in the second step with ammonia or various aliphatic amines, both primary and secondary, at temperatures varying between 50 and 70°C. All the target ureas were obtained in high yields (28 examples, average yield 94%) and with very high purity (generally >99.2%). Also to be noted is the recovery of a co-product of industrial interest, methanethiol, in an amount of two moles for each mole of DMDTC, with complete exploitation of the reagent. Georg Thieme Verlag Stuttgart.

Process to prepare alkyl-ureas from O,S-dimethyl dithiocarbonate

The present invention relates to the preparation of alkyl-ureas, starting from O,S-dimethyl dithiocarbonate, which provides the following steps: A) causing the O,S-dimethyl dithiocarbonate to react with a primary amine of general formula R1NH2in order to obtain an O-methyl thiocarbamate; B) isomerising the O-methyl thiocarbamate in order to obtain an S-methyl thiocarbamate; C) causing the S-methyl thiocarbamate with a compound of general formula R′R″NH, wherein R′ and R″ may be equal or different one in respect of the other and of R1and may be H, R2or R3, in order to obtain one of the alkyl-ureas of formula (4), (5) or (6).