Dimethylthiocarbamoyl chloride

Dimethylthiocarbamoyl chloride
Names
	Preferred IUPAC name Dimethylcarbamothioyl chloride
Identifiers
CAS Number	16420-13-6;
PubChem CID	24848243;
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).

References[]

^ Melvin S. Newman, Frederick W. Hetzel (1971). "Thiophenols from Phenols: 2-Naphthalenethiol". Org. Synth. 51: 139. doi:10.15227/orgsyn.051.0139.CS1 maint: uses authors parameter (link)
^ R. J. Cremlyn “An Introduction to Organosulfur Chemistry” John Wiley and Sons: Chichester (1996). ISBN 0 471 95512 4

[1] Melvin S. Newman, Frederick W. Hetzel (1971). "Thiophenols from Phenols: 2-Naphthalenethiol". Org. Synth. 51: 139. doi:10.15227/orgsyn.051.0139.CS1 maint: uses authors parameter (link)

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

[1]

[2]