Dithiobiuret
Names | |
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IUPAC name
Dicarbonodithioimidic diamide | |
Identifiers | |
541-53-7 | |
ChEMBL | ChEMBL501562 |
ChemSpider | 2039482 |
EC number | 208-784-8 |
| |
Jmol-3D images | Image Image |
MeSH | 2,4-dithiobiuret |
PubChem | 2758725 |
RTECS number | EC1575000 |
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UN number | 2811 |
Properties | |
Molecular formula |
C2H5N3S2 |
Molar mass | 135.21 gยทmolโ1 |
Appearance | White crystals |
Density | 1.54 g/cm3 |
log P | โ0.415 |
Acidity (pKa) | 11.152 |
Basicity (pKb) | 2.845 |
Hazards | |
GHS pictograms | |
GHS signal word | DANGER |
H300, H310, H330 | |
P260, P280, P284, P302+350, P310 | |
EU classification | T+ |
R-phrases | R26/27/28 |
S-phrases | S22, S36/37, S45 |
Related compounds | |
Related compounds |
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Except where noted otherwise, data is given for materials in their standard state (at 25 ยฐC (77 ยฐF), 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 ร , 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 โ HN(C(S)NH2)(C(NH)NH2)
- HN(C(S)NH2)(C(NH)NH2) + H2S โ 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
- โ Spofford, W. A., III; Amma, E. L. "Crystal and molecular structure of dithiobiuret" Journal of Crystal and Molecular Structure 1972, vol. 2, 151-8. doi:10.1007/BF01275491
- โ Dithiobiuret Hazardous Substance Fact Sheet, 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): 221โ31. PMID 6820683.
- Dithiobiuret at www.chemicalbook.com.