Chloromethyl methyl sulfide

Chloromethyl methyl sulfide is the organosulfur compound with the formula ClCH2SCH3. In terms of functional groups, it is a thioether and an alkyl chloride. The compound is structurally related to sulfur mustards, i.e., it is a potentially hazardous alkylating agent. The compound finds some use in organic chemistry as a protecting group. In the presence of base, it converts carboxylic acids (RCO2H) to esters RCO2CH2SCH3. The compound is prepared by treatment of dimethylsulfide with sulfuryl chloride.

Chloromethyl methyl sulfide
Names
Other names
methylthiomethyl chloride; MTMCl
Identifiers
3D model (JSmol)
ChemSpider
EC Number
  • 219-148-4
PubChem CID
  • InChI=1S/C2H5ClS/c1-4-2-3/h2H2,1H3
    Key: JWMLCCRPDOIBAV-UHFFFAOYSA-N
SMILES
  • CSCCl
Properties
C2H5ClS
Molar mass 96.57 g·mol−1
Appearance colorless liquid
Density 1.1773 g cm−3
Boiling point 107 °C (225 °F; 380 K) 750 mmHg
Hazards
GHS labelling:
Danger
H225, H315, H319, H335
P210, P233, P240, P241, P242, P243, P261, P264, P264+P265, P271, P280, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P370+P378, P403+P233, P403+P235, P405, P501
Related compounds
Related compounds
Dimethyl sulfide; 2-Chloroethyl ethyl sulfide
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.