Dithiobiuret Explained

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

• Biuret

External links

• 6820683 . 1982 . Williams . KD . Porter . WR . Peterson . RE . Dithiobiuret metabolism in the rat . 3 . 4 . 221–31 . Neurotoxicology.
• Dithiobiuret at www.chemicalbook.com.

Notes and References

1. 10.1007/BF01275491. Crystal and molecular structure of dithiobiuret. Journal of Crystal and Molecular Structure. 2. 4. 151–158. 1972. Spofford. W. A.. Amma. E. L..
2. https://web.archive.org/web/20131103200840/http://www.emedco.info/NJ_RTK/2368.pdf Dithiobiuret Hazardous Substance Fact Sheet