Chloromethyl_methyl_sulfide

Chloromethyl methyl sulfide

Chloromethyl methyl sulfide

Chemical compound

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]

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References

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