22013-97-4

Basic information

• Product Name: S-methyl methylcarbamothioate
• Synonyms: Carbamothioic acid, methyl-, S-methyl ester
• CAS NO: 22013-97-4
• Molecular Formula: C₃H₇NOS
• Molecular Weight: 105.1588
• Mol File: 22013-97-4.mol
• Article Data: 4

Chemical Properties

• Density: 1.073g/cm³
• Refractive Index: 1.474
• CAS DataBase Reference: S-methyl methylcarbamothioate(CAS DataBase Reference)
• NIST Chemistry Reference: S-methyl methylcarbamothioate(22013-97-4)
• EPA Substance Registry System: S-methyl methylcarbamothioate(22013-97-4)

Safety Data

• Hazardous Substances Data: 22013-97-4(Hazardous Substances Data)

Upstream product

• 67-56-1 methanol 
• 18805-25-9 methyl carbonimidodithioic acid dimethyl ester 
• 868-84-8 S,S-dimethyl dithiocarbonate 
• 74-89-5 methylamine 

Downstream Products

• 39804-96-1 1-cyclohexyl-3-methylurea 
• 39499-81-5 N,n-diethyl-N'-methylurea 
• 6957-05-7 N-methyl-N'-benzylurea 
• 38126-73-7 S-(N-methylcarbamoyl)glutathione 
• 2655-14-3 3,5-xylyl-N-methylcarbamate 
• 13538-50-6 4-bromophenyl methylcarbamate 
• 6452-47-7 methylcarbamoyl chloride 
• 598-50-5 N-Methylurea 
• 6642-30-4 methyl N-methylcarbamate 
• 74-93-1 methylthiol 
• 21260-54-8 N,N-dibutyl-N'-methyl urea 
• 30379-59-0 benzyl N-methylcarbamate 
• 10047-90-2 isopropyl N-methylcarbamate 
• 63-25-2 1-naphthalenol methylcarbamate 

Relevant articles and documents

Alcoholysis of naturally occurring imides: Misleading interpretation of antifungal activities

The frequent presence of the sulfur-containing amide penangin (10) in leaf extracts of Glycosmis species turned out to be the result of decomposition of imides generated by extraction and storage in MeOH. Reinvestigation of Glycosmis mauritiana and G. cf. puberula with acetone revealed the presence of six imides. In addition to penimides A (1) and B (2) and ritigalin (6), three new derivatives, krabin (4), isokrabin (5), and methoxypenimide B (3), were isolated and identified by spectroscopic methods. All six imides were shown to be susceptible to different rates of methanolic cleavage, leading to their corresponding methyl esters and sulfur-containing amides. Whereas the decomposition products penangin (10), isopenangin (11), and sinharin (14) are known, the corresponding cleavage of methyl N-methylthiocarbamate (7) from ritigalin (6), monitored in situ by 1H NMR spectroscopy, is described here for the first time. Its structure was further confirmed by GC-MS coupling. HPLC-UV comparison of many different samples of G. mauritiana, extracted with MeOH, revealed considerable chemical variations in sulfur-containing amides, strongly correlated with different antifungal potency. The lack of activity of many methanolic crude extracts can be explained by a preponderance of the inactive decomposition product penangin (10), whereas the corresponding naturally occurring imides penimides A (1) and B (2) and methoxypenimide B (3), extracted with acetone, showed high fungitoxic properties.

Process for making alkyl N-alkyl or N-aryl-thiocarbamates

A process for the preparation of alkyl esters of N-alkyl or N-aryl thiocarbamic acid having the formula: STR1 wherein R is alkyl or aryl, R2 is alkyl and R1 is hydrogen or alkyl which comprises reacting the S-alkyl ester of N-alkyl or aryl dithiocarbamic acid having the formula: STR2 wherein R, R1, R2 have the meanings stated above with an appropriate alkali metal alkoxide in the presence of one or more alcoholic solvents.