Dithiobiuret
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Names | |
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Preferred IUPAC name
2-Imido-1,3-dithiodicarbonic diamide | |
Identifiers | |
3D model (JSmol)
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ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.007.987 ![]() |
EC Number |
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MeSH | 2,4-dithiobiuret |
PubChem CID
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RTECS number |
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UNII | |
UN number | 2811 |
CompTox Dashboard (EPA)
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Properties | |
C2H5N3S2 | |
Molar mass | 135.20 g·mol−1 |
Appearance | White crystals |
Density | 1.54 g/cm3 |
log P | −0.415 |
Acidity (pKa) | 11.152 |
Basicity (pKb) | 2.845 |
Hazards | |
GHS labelling: | |
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Signal word
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Danger |
H300, H310, H330 | |
P260, P280, P284, P302+P350, P310 | |
Related compounds | |
Related compounds
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
Infobox references | |
Dithiobiuret is an organosulfur compound with the formula HN(C(S)NH2)2. It is a colourless solid that is soluble in warm water and polar organic solvents. It is a planar molecule with short C-S and C-N distances (1.69, 1.38 Å, resp.) indicative of multiple C-S and C-N bonding.[1]
The compound can be viewed as the product from the condensation of two molecules of thiourea, but it is prepared by treatment of 2-cyanoguanidine with hydrogen sulfide. The conversion proceeds via guanylthiourea:
- NCNC(NH2) + H2S → HN(C(S)NH2)(C(NH)NH2)
- HN(C(S)NH2)(C(NH)NH2) + H2S → HN(C(S)NH2)2
It is used as a plasticizer, a rubber accelerator, and as an intermediate in pesticide manufacturing.[2] It is extremely toxic; exposure can result in respiratory failure.
See also[]
References[]
- ^ Spofford, W. A.; Amma, E. L. (1972). "Crystal and molecular structure of dithiobiuret". Journal of Crystal and Molecular Structure. 2 (4): 151–158. doi:10.1007/BF01275491.
- ^ Dithiobiuret Hazardous Substance Fact Sheet[permanent dead link], New Jersey Department of Health and Senior Services
External links[]
- Williams, KD; Porter, WR; Peterson, RE (1982). "Dithiobiuret metabolism in the rat". Neurotoxicology. 3 (4): 221–31. PMID 6820683.
- Dithiobiuret at www.chemicalbook.com.
Categories:
- Thioureas