Chemistry:Chloromethyl methyl sulfide

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Chloromethyl methyl sulfide
ClCH2SCH3.svg
Names
Other names
methylthiomethyl chloride; MTMCl
Identifiers
3D model (JSmol)
ChemSpider
EC Number
  • 219-148-4
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 pictograms GHS02: FlammableGHS07: Harmful
GHS Signal word Danger
H225, H315, H319, H335
P210, P233, P240, P241, P242, P243, P261, P264, P264+265Script error: No such module "Preview warning".Category:GHS errors, P271, P280, P302+352, P303+361+353, P304+340, P305+351+338, P319Script error: No such module "Preview warning".Category:GHS errors, P321, P332+317Script error: No such module "Preview warning".Category:GHS errors, P337+317Script error: No such module "Preview warning".Category:GHS errors, P362+364Script error: No such module "Preview warning".Category:GHS errors, P370+378, P403+233, P403+235, 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 ClCH
2
SCH
3
. 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 RCO
2
CH
2
SCH
3
.[2] The compound is prepared by treatment of dimethylsulfide with sulfuryl chloride.[3]

References

  1. "Chloromethyl methyl sulfide" (in en). https://pubchem.ncbi.nlm.nih.gov/compound/16916#section=Safety-and-Hazards. 
  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.