Dimethylthiocarbamoyl chloride


Dimethylthiocarbamoyl chloride is an organosulfur compound with the formula 2NCCl. A yellow solid, it is often encountered as a yellow syrup. It is a key reagent in the synthesis of arylthiols via the Newman-Kwart rearrangement.

Synthesis and reactions

Representative of other thiocarbamoyl chlorides, dimethylthiocarbamoyl chloride is electrophilic, serving as a source of R2NC+. It is analogous to dimethylcarbamoyl chloride.
Dimethylthiocarbamoyl chloride is prepared by chlorination of the related tetramethylthiuram disulfide:
Dimethylthiocarbamoyl chloride reacts with dithiocarbamates to give thiuram sulfides 2S. With methanethiolate, it gives methyl dimethyldithiocarbamate.