Chloromethyl methyl sulfide

Chloromethyl methyl sulfide
Names
	Other names methylthiomethyl chloride; MTMCl
Identifiers
CAS Number	2373-51-5 ;
3D model (JSmol)	Interactive image;
ChemSpider	16027;
EC Number	219-148-4;
PubChem CID	16916;
	InChI InChI=1S/C2H5ClS/c1-4-2-3/h2H2,1H3 Key: JWMLCCRPDOIBAV-UHFFFAOYSA-N;
	SMILES CSCCl;
Properties
Chemical formula	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:
Pictograms
Signal word	Danger
Hazard statements	H225, H315, H319, H335
Precautionary statements	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

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.^[2] The compound is prepared by treatment of dimethylsulfide with sulfuryl chloride.^[3]

^ "Chloromethyl methyl sulfide". pubchem.ncbi.nlm.nih.gov.
^ Tsai, Yeun-Min (2001). "Chloromethyl Methyl Sulfide". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rc119. ISBN 0471936235.
^ Bordwell, F. G.; Pitt, Burnett M. (1955). "The Formation of α-Chloro Sulfides from Sulfides and from Sulfoxides". Journal of the American Chemical Society. 77 (3): 572–577. doi:10.1021/ja01608a016.