Dithiobiuret

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]

Dithiobiuret
Skeletal formula of dithiobiuret
Names
Preferred IUPAC name
2-Imido-1,3-dithiodicarbonic diamide
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.007.987
EC Number
  • 208-784-8
MeSH 2,4-dithiobiuret
RTECS number
  • EC1575000
UNII
UN number 2811
  • InChI=1S/C2H5N3S2/c3-1(6)5-2(4)7/h(H5,3,4,5,6,7) checkY
    Key: JIRRNZWTWJGJCT-UHFFFAOYSA-N checkY
  • NC(=S)NC(N)=S
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:
GHS06: Toxic
Danger
H300, H310, H330
P260, P280, P284, P302+P350, P310
Related compounds
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

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.; Amma, E. L. (1972). "Crystal and molecular structure of dithiobiuret". Journal of Crystal and Molecular Structure. 2 (4): 151–158. doi:10.1007/BF01275491.
  2. Dithiobiuret Hazardous Substance Fact Sheet, New Jersey Department of Health and Senior Services
  • 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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