Methyl dimethyldithiocarbamate

Methyl dimethyldithiocarbamate
Names
	Preferred IUPAC name Methyl dimethylcarbamodithioate
	Other names Cystogon, DMDTM, Forbiat
Identifiers
CAS Number	3735-92-0;
ECHA InfoCard	100.021.005
PubChem CID	19526;
UNII	BKH76WPU8C ;
CompTox Dashboard (EPA)	DTXSID40190797 ;
Properties
Chemical formula	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). Infobox references

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

^ A. D. Ainley; W. H. Davies; H. Gudgeon; J. C. Harland; 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.
^ John R. Grunwell (1970). "Reaction of Grignard Reagents with Tetramethylthiuram Disulfide [yielding dithiocarbamates]". J. Org. Chem. 35 (5): 1500–1501. doi:10.1021/jo00830a052.

[1] A. D. Ainley; W. H. Davies; H. Gudgeon; J. C. Harland; 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.

[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.

[1]

[2]