Thiocarbamoyl chloride

General chemical structure of a thiocarbamoyl chloride

A thiocarbamoyl chloride is an organosulfur compound with the formula R₂NC(S)Cl (R = alkyl, aryl, etc.).^[1] These compounds are electrophiles, serving as a source of R₂NC(S)⁺. They are analogous to carbamoyl chlorides, which have the formula R₂NC(O)Cl. A common example of this class of compound is dimethylthiocarbamoyl chloride, Me₂NC(S)Cl (CAS#16420-13-6), which is a pale yellow, volatile solid.

Synthesis and reactions

Thiocarbamoyl chlorides are prepared by chlorination of the related thiuram disulfides:

[R₂NC(S)]₂S₂ + 3 Cl₂ → 2 R₂NC(S)Cl + 2 SCl₂

Thiocarbamoyl chlorides react with dithiocarbamates (R₂NCS₂^-) to give thiuram sulfides [R₂NC(S)]₂S.

References

1. R. J. Cremlyn “An Introduction to Organosulfur Chemistry” John Wiley and Sons: Chichester (1996). ISBN 0 471 95512 4.