Tetramethylthiuram sulfide
Tetramethylthiuram sulfide is an organosulfur compound with the formula ((CH3)2NCS)2S. It is a yellow solid that is soluble in organic solvents. It is the parent member of a large class of tetraalkylthiuram sulfides.[1] It is used as an activator in the sulfur vulcanization of natural and butyl rubbers.[2]
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| Names | |
|---|---|
| Preferred IUPAC name
N1,N1,N3,N3-Tetramethyl-1,2,3-trithiodicarbonic diamide | |
| Other names
N,N,N′,N′-Tetramethylthiuram monosulfide | |
| Identifiers | |
| ECHA InfoCard | 100.002.369 |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C6H12N2S3 | |
| Molar mass | 208.36 g·mol−1 |
| Density | 1.39 |
| Melting point | 107 °C (225 °F; 380 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references | |
Synthesis and structure
It is prepared by desulfuration of tetramethylthiuram disulfides with triphenylphosphine or cyanide:
- (Me2NCSS)2 + PPh3 → (Me2NCS)2S + SPPh3
According to X-ray crystallography, the molecule consists of two planar (CH3)2NCS subunits joined by a sulfide. The dihedral angle between the subunits is close to 90°.[3]
References
- Schubart, Rüdiger (2000). "Dithiocarbamic Acid and Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a09_001.
- "Patent information sheet: TMTM". ChemoTechnique. Chemotechnique Diagnostics. Retrieved 23 October 2018.
- Skelton, B. W.; White, A. H. (1977). "Crystal structures of N,N,N′,N′-tetramethylthiuram monosulphide and diiodo(N,N,N′,N′-tetramethylthiuram monosulphide)mercury(II)". Australian Journal of Chemistry. 30 (8): 1693. doi:10.1071/CH9771693.
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