3371. 2,4-Dithiobiuret

Nomenclature

CAS number: 541-53-7
Thioimidodicarbonic diamide ([(H2N)C(S)]2NH).
C2H5N3S2; mol wt 135.21.
C 17.77%, H 3.73%, N 31.08%, S 47.43%.

Description and references

Prepd by the interaction of dicyandiamide and hydrogen sulfide in inert solvents under pressure: Sperry, US 2371112 (1945 to Am. Cyanamid). Review: Kurzer, Chem. Rev. 56, 138-144, 179-181 (1956).

Chemical structure

Properties

Monoclinic or triclinic crystals. Poisonous. Apparent bulk density 1.522 g/ml at 30°. Dec 181°. uv max: 225, 280 nm (log ε 2.0, 2.2). Solubility at 27° = 0.27 g/100 ml water; 2.2 g/100 g ethanol; 16 g/100 g acetone; about 34 g/100 g Cellosolve. Solubility in boiling water about 8.0%. pH of satd aq soln at 30° = 5.8. Soluble in alkalies with formation of water-soluble salts. Solubility in 1% NaOH = 3.6 g/100 g soln; in 5% NaOH = 16 g/100 g; in 10% NaOH = 29 g/100 g.

Caution

Limited animal expts suggest high toxicity due to respiratory paralysis.

Use

Plasticizer, rubber accelerator, intermediate in resin manuf, in making insecticides and rodenticides. Can be used to delay the wilting of flowers.