Methyl dimethyldithiocarbamate

Last updated
Methyl dimethyldithiocarbamate
Me2NCS2Me.svg
Names
Preferred IUPAC name
Methyl dimethylcarbamodithioate
Other names
Cystogon, DMDTM, Forbiat
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.021.005 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 223-105-5
PubChem CID
UNII
  • InChI=1S/C4H9NS2/c1-5(2)4(6)7-3/h1-3H3
    Key: NBBZMDUHKWRYSZ-UHFFFAOYSA-N
  • CN(C)C(=S)SC
Properties
C4H9NS2
Molar mass 135.24 g·mol−1
Appearancecolorless or white solid
Melting point 45–47 °C (113–117 °F; 318–320 K)
Hazards
GHS labelling: [1]
GHS-pictogram-exclam.svg
Warning
H302, H312, H315, H319, H332, H335
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).

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)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: [3]

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

References

  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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