Dithiobiuret

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Dithiobiuret
IUPAC name

Dicarbonodithioimidic diamide[citation needed]

Identifiers
CAS number 541-53-7 YesY
PubChem 2758725
ChemSpider 2039482 YesY
EC number 208-784-8
UN number 2811
MeSH 2,4-dithiobiuret
ChEMBL CHEMBL501562 YesY
RTECS number EC1575000
Jmol-3D images {{#if:[nH2]:c(:[s]):[nH]:c(:[nH2]):[s]NC(=S)NC(N)=S|Image 1
Image 2
Properties
Molecular formula C2H5N3S2
Molar mass 135.21 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 pictograms
GHS signal word DANGER
GHS hazard statements H300, H310, H330
GHS precautionary statements P260, P280, P284, P302+350, P310
EU classification T+
R-phrases R26/27/28
S-phrases S22, S36/37, S45
Related compounds
Related compounds
Except where noted otherwise, 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

  1. ↑ 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
  2. ↑ 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): 221–31. PMID 6820683. 
  • Dithiobiuret at www.chemicalbook.com.
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