Methyl dimethyldithiocarbamate

Methyl dimethyldithiocarbamate
Names
	Preferred IUPAC name Methyl dimethylcarbamodithioate
	Other names Cystogon, DMDTM, Forbiat
Identifiers
CAS Number	3735-92-0 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL504894;
ChemSpider	18397;
ECHA InfoCard	100.021.005
EC Number	223-105-5;
PubChem CID	19526;
UNII	BKH76WPU8C ;
CompTox Dashboard (EPA)	DTXSID40190797 ;
	InChI InChI=1S/C4H9NS2/c1-5(2)4(6)7-3/h1-3H3 Key: NBBZMDUHKWRYSZ-UHFFFAOYSA-N;
	SMILES CN(C)C(=S)SC;
Properties
Chemical formula	(CH3)2NC(S)SCH3
Molar mass	135.24 g·mol−1
Appearance	colorless or white solid
Melting point	45–47 °C (113–117 °F; 318–320 K)
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H302, H312, H315, H319, H332, H335
Precautionary statements	P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, P501
	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:^[2]

(CH₃)₂NCS−2Na⁺ + (CH₃O)₂SO₂ → (CH₃)₂NC(S)SCH₃ + CH₃OSO−3Na⁺

It can also be prepared by the reaction of a tetramethylthiuram disulfide with methyl Grignard reagents:^[3]

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

References

^ "Methyl dimethyldithiocarbamate". pubchem.ncbi.nlm.nih.gov.
^ 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] "Methyl dimethyldithiocarbamate". pubchem.ncbi.nlm.nih.gov.

[2] 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.

[3] John R. Grunwell (1970). "Reaction of Grignard Reagents with Tetramethylthiuram Disulfide [yielding dithiocarbamates]". J. Org. Chem. 35 (5): 1500–1501. doi:10.1021/jo00830a052.

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