Dithiobiuret

Dithiobiuret
Names
IUPAC name
Dicarbonodithioimidic diamide
Identifiers
541-53-7 YesY
ChEMBL ChEMBL501562 YesY
ChemSpider 2039482 YesY
EC Number 208-784-8
Jmol interactive 3D Image
Image
MeSH 2,4-dithiobiuret
PubChem 2758725
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
GHS signal word DANGER
H300, H310, H330
P260, P280, P284, P302+350, P310
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

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


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