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A thiocarbamoyl chloride is an organosulfur compound with the formula R2NC(S)Cl (R = alkyl, aryl, etc.). 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 SCl2Thiocarbamoyl chlorides react with dithiocarbamates (R2NCS−
2) to give thiuram sulfides [R2NC(S)]2S.
References
Thiocarbamoyl chloride Wikipedia(Text) CC BY-SA