Dithiobiuret
# Dithiobiuret

Dithiobiuret is an organosulfur compound with the formula $HN(C(S)NH_2)_2.$ 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:

    $NCNC(NH_2)$ + $H_2S$ → $HN(C(S)NH_2)(C(NH)NH_2)$
    $HN(C(S)NH_2)(C(NH)NH_2)$ + $H_2S$ → $HN(C(S)NH_2)_2$

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.

