Sodium dimethyldithiocarbamate is the organosulfur compound with the formula NaS2NN(CH3)2. It is one of the simplest organic dithiocarbamates. It is a white or pale yellow, water soluble solid. The compound is a precursor to fungicides and rubber chemicals.
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| Identifiers | |
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| ECHA InfoCard | 100.004.434 |
CompTox Dashboard (EPA)
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| Properties | |
| C3H6NNaS2 | |
| Molar mass | 143.20 g·mol−1 |
| Appearance | white solid |
| Density | 1.18 g/cm3 |
| Melting point | 106–108 °C (223–226 °F; 379–381 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Preparation
editSodium dimethyldithiocarbamate typically crystallizes from water as the diihydrate NaS2CN(CH3)2.2H2O. The anhydrous salt and the trihydrate are often used interchangeably.[1]
Sodium dimethyldithiocarbamate is obtained by treating carbon disulfide with dimethylamine in the presence of sodium hydroxide:
- CS2 + HN(CH3)2 + NaOH → NaS2CN(CH3)2 + H2O
Other dithiocarbamates can be prepared similarly from secondary amines and carbon disulfide. They are used as chelating agents for transition metal ions and as precursors to herbicides and vulcanization reagents.
Uses
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It is a component of various pesticides and rubber chemicals in the form of its salts. Well established derivatives include potassium dimethyldithiocarbamate) as well as its complexes zinc dimethyldithiocarbamate, ferric dimethyldithiocarbamate, and nickel bis(dimethyldithiocarbamate). Oxidation gives thiram.[3][4]
References
edit- ^ Mereiter, K.; Preisinger, A.; Mikenda, W.; Steidl, H. (1985). "Hydrogen bonds in sodium dialkylthiocarbamate hydrates. X-ray diffraction and vibrational spectroscopic study". Inorganica Chimica Acta. 98 (2): 71–78. doi:10.1016/s0020-1693(00)84914-2.
- ^ D. Coucouvanis (2007). "The Chemistry of the Dithioacid and 1,1-Dithiolate Complexes". Progress in Inorganic Chemistry. 11: 233–371. doi:10.1002/9780470166123.ch4. ISBN 9780470166123.
- ^ "Dimethyldithiocarbamate salts". Environmental Protection Agency. Retrieved July 26, 2016.
- ^ Rüdiger Schubart (2000). "Dithiocarbamic Acid and Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a09_001. ISBN 3527306730.