Dimethylthiocarbamoyl chloride is an

organosulfur compound Organosulfur chemistry is the study of the properties and synthesis of organosulfur compounds, which are organic compounds that contain sulfur. They are often associated with foul odors, but many of the sweetest compounds known are organosulfur der ...

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.

Synthesis and reactions

Representative of other thiocarbamoyl chlorides, dimethylthiocarbamoyl chloride is electrophilic, serving as a source of R₂NC(S)⁺.R. J. Cremlyn "An Introduction to Organosulfur Chemistry" John Wiley and Sons: Chichester (1996). It is analogous to dimethyl

carbamoyl chloride A carbamoyl chloride is the functional group with the formula R2NC(O)Cl. The parent carbamoyl chloride, H2NCOCl, is unstable, but many N-substituted analogues are known. Most examples are moisture sensitive, colourless, and soluble in nonpolar org ...

(R₂NC(O)Cl). Dimethylthiocarbamoyl chloride is prepared by chlorination of the related tetramethylthiuram disulfide: : e₂NC(S)sub>2S₂ + 3 Cl₂ → 2 Me₂NC(S)Cl + 2 SCl₂ Dimethylthiocarbamoyl chloride reacts with

dithiocarbamate In organic chemistry, a dithiocarbamate is a chemical compound with the general formula . It contains the functional group with the Chemical structure, structure . It is the analog of a carbamate in which both oxygen atoms are replaced by sulfur ...

s (R₂NCS{{su, b=2, p=−) to give thiuram sulfides ₂NC(S)sub>2S. With methanethiolate, it gives

methyl dimethyldithiocarbamate Methyl dimethyldithiocarbamate is the organosulfur compound with the formula . It is the one of simplest dithiocarbamic esters. It is a white volatile solid that is poorly soluble in water but soluble in many organic solvents. It was once used as ...

(Me₂NC(S)SMe).

References

Thioacyl chlorides Dimethylamino compounds