Chloromethyl methyl sulfide explained

Chloromethyl methyl sulfide is the organosulfur compound with the formula . 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 .[1] The compound is prepared by treatment of dimethylsulfide with sulfuryl chloride.[2]

References

  1. Book: 10.1002/047084289X.rc119. Chloromethyl Methyl Sulfide . Encyclopedia of Reagents for Organic Synthesis . 2001 . Tsai . Yeun-Min . 0471936235 .
  2. 10.1021/ja01608a016. The Formation of α-Chloro Sulfides from Sulfides and from Sulfoxides . 1955 . Bordwell . F. G. . Pitt . Burnett M. . Journal of the American Chemical Society . 77 . 3 . 572–577 .