Dithiobiuret

From Wikipedia, the free encyclopedia
Jump to: navigation, search
Dithiobiuret
Skeletal formula of dithiobiuret
Names
IUPAC name
Dicarbonodithioimidic diamide[citation needed]
Identifiers
3D model (Jmol)
ChemSpider
ECHA InfoCard 100.007.987
EC Number 208-784-8
MeSH 2,4-dithiobiuret
RTECS number EC1575000
UN number 2811
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 pictograms The skull-and-crossbones pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
GHS signal word DANGER
H300, H310, H330
P260, P280, P284, P302+350, P310
Very Toxic T+
R-phrases R26/27/28
S-phrases S22, S36/37, S45
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

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[edit]

References[edit]

  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[permanent dead link], New Jersey Department of Health and Senior Services

External links[edit]

  • Williams, KD; Porter, WR; Peterson, RE (1982). "Dithiobiuret metabolism in the rat". Neurotoxicology. 3 (4): 221–31. PMID 6820683. 
  • Dithiobiuret at www.chemicalbook.com.