Dimethylthiocarbamoyl chloride
Names | |
---|---|
Preferred IUPAC name Dimethylcarbamothioyl chloride | |
Identifiers | |
CAS Number |
|
PubChem CID |
|
UNII |
|
Properties | |
Chemical formula | C3H6ClNS |
Molar mass | 123.60 g·mol−1 |
Appearance | yellow solid |
Melting point | 39–43 °C (102–109 °F; 312–316 K) |
Boiling point | 90–95 °C (194–203 °F; 363–368 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references |
Dimethylthiocarbamoyl chloride is an organosulfur compound with the formula (CH3)2NC(S)Cl. 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.[1]
Synthesis and reactions
Representative of other thiocarbamoyl chlorides, dimethylthiocarbamoyl chloride is electrophilic, serving as a source of R2NC(S)+.[2] It is analogous to dimethylcarbamoyl chloride (R2NC(O)Cl).
Dimethylthiocarbamoyl chloride is prepared by chlorination of the related tetramethylthiuram disulfide:
- [Me2NC(S)]2S2 + 3 Cl2 → 2 Me2NC(S)Cl + 2 SCl2
Dimethylthiocarbamoyl chloride reacts with dithiocarbamates (R2NCS−
2) to give thiuram sulfides [R2NC(S)]2S. With methanethiolate, it gives methyl dimethyldithiocarbamate (Me2NC(S)SMe).