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Dimethylthiocarbamoyl chloride

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Dimethylthiocarbamoyl chloride
Names
Preferred IUPAC name Dimethylcarbamothioyl chloride
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
EC Number
  • 240-468-5
PubChem CID
UNII
InChI
  • InChI=1S/C3H6ClNS/c1-5(2)3(4)6/h1-2H3Key: PHWISQNXPLXQRU-UHFFFAOYSA-N
SMILES
  • CN(C)C(=S)Cl
Properties
Chemical formula C3H6ClNS
Molar mass 123.60 g·mol
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)
Hazards
GHS labelling:
Pictograms GHS05: CorrosiveGHS07: Exclamation mark
Signal word Warning
Hazard statements H290, H302, H314, H317
Precautionary statements P234, P260, P261, P264, P264+P265, P270, P272, P280, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P321, P330, P333+P317, P362+P364, P363, P390, P405, P406, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

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.

Synthesis and reactions

Representative of other thiocarbamoyl chlorides, dimethylthiocarbamoyl chloride is electrophilic, serving as a source of R2NC(S). It is analogous to dimethylcarbamoyl chloride (R2NC(O)Cl).

Dimethylthiocarbamoyl chloride is prepared by chlorination of the related tetramethylthiuram disulfide:

2S2 + 3 Cl2 → 2 Me2NC(S)Cl + 2 SCl2

Dimethylthiocarbamoyl chloride reacts with dithiocarbamates (R2NCS
2) to give thiuram sulfides 2S. With methanethiolate, it gives methyl dimethyldithiocarbamate (Me2NC(S)SMe).

References

  1. Melvin S. Newman; Frederick W. Hetzel (1971). "Thiophenols from Phenols: 2-Naphthalenethiol". Org. Synth. 51: 139. doi:10.15227/orgsyn.051.0139.
  2. R. J. Cremlyn "An Introduction to Organosulfur Chemistry" John Wiley and Sons: Chichester (1996). ISBN 0 471 95512 4
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