Chloromethyl methyl sulfide
Names
Other names
methylthiomethyl chloride; MTMCl
Identifiers
3D model (JSmol)
ChemSpider
EC Number
  • 219-148-4
  • InChI=1S/C2H5ClS/c1-4-2-3/h2H2,1H3
    Key: JWMLCCRPDOIBAV-UHFFFAOYSA-N
  • 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:[1]
GHS02: FlammableGHS07: Exclamation mark
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

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]

References

  1. ↑ "Chloromethyl methyl sulfide". pubchem.ncbi.nlm.nih.gov.
  2. ↑ Tsai, Yeun-Min (2001). "Chloromethyl Methyl Sulfide". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rc119. ISBN 0471936235.
  3. ↑ 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.


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