Methyl dimethyldithiocarbamate

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Methyl dimethyldithiocarbamate
Me2NCS2Me.svg
Names
Preferred IUPAC name
Methyl dimethylcarbamodithioate
Other names
Cystogon, DMDTM, Forbiat
Identifiers
ECHA InfoCard 100.021.005 Edit this at Wikidata
UNII
Properties
C4H9NS2
Molar mass 135.24 g·mol−1
Appearance colorless or white solid
Melting point 45–47 °C (113–117 °F; 318–320 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Methyl dimethyldithiocarbamate is the organosulfur compound with the formula (CH3)2NC(S)SCH3. It is the one of simplest dithiocarbamic esters. It is a white volatile solid that is poorly soluble in water but soluble in many organic solvents. It was once used as a pesticide.

Methyl dimethyldithiocarbamate can be prepared by methylation of salts of dimethyldithiocarbamate:[1]

(CH3)2NCS2Na + (CH3O)2SO2 → (CH3)2NC(S)SCH3 + Na[CH3OSO3]

It can also be prepared by the reaction of a tetramethylthiuram disulfide with methyl Grignard reagents:[2]

[(CH3)2NC(S)S]2 + CH3MgBr → (CH3)2NC(S)SCH3 + (CH3)2NCS2MgBr

References[edit]

  1. ^ A. D. Ainley, W. H. Davies, H. Gudgeon, J. C. Harland and W. A. Sexton (1944). "The Constitution of the So-Called Carbothialdines and the Preparation of Some Homologous Compounds". J. Chem. Soc.: 147–152. doi:10.1039/JR9440000147.{{cite journal}}: CS1 maint: uses authors parameter (link)
  2. ^ John R. Grunwell (1970). "Reaction of Grignard Reagents with Tetramethylthiuram Disulfide [yielding dithiocarbamates]". J. Org. Chem. 35 (5): 1500–1501. doi:10.1021/jo00830a052.