Trisha Shetty (Editor)

Dithiobiuret

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Density
  
1.54 g/cm³

Appearance
  
White crystals

Dithiobiuret

Related compounds
  
DimethylamineTrimethylamineUnsymmetrical dimethylhydrazineN-NitrosodimethylamineBiguanideDiethylamineTriethylamineDiisopropylamineDimethylaminopropylamineDiethylenetriamineN,N-DiisopropylethylamineTriisopropylamineTris(2-aminoethyl)amineMechlorethamineHN1 (nitrogen mustard)HN3 (nitrogen mustard)

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.

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. It is extremely toxic; exposure can result in respiratory failure.

References

Dithiobiuret Wikipedia
(Text) CC BY-SA


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