Dithiobiuret

Dithiobiuret
Names
IUPAC name
Dicarbonodithioimidic diamide
Identifiers
541-53-7 Yes
ChEMBL ChEMBL501562 Yes
ChemSpider 2039482 Yes
EC number 208-784-8
Jmol-3D images Image
Image
MeSH 2,4-dithiobiuret
PubChem 2758725
RTECS number EC1575000
UN number 2811
Properties
Molecular formula
C2H5N3S2
Molar mass 135.21 gยทmolโˆ’1
Appearance White crystals
Density 1.54 g/cm3
log P โˆ’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
EU classification T+
R-phrases R26/27/28
S-phrases S22, S36/37, S45
Related compounds
Related compounds
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

  1. 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
  2. โ†‘ Dithiobiuret Hazardous Substance Fact Sheet, New Jersey Department of Health and Senior Services

External links