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Chloromethyl methyl sulfide is used as a methylene transfer reagent for iron(II) mediated cyclopropanation and for carbonyl and aromatic compounds. It protects alcohols as their methylthiomethyl (MTM) ethers by reaction, e.g. with NaH/NaI in DME. It is also used for the preparation of MTM esters of carboxylic acids, e.g. by treatment of the K salt of the acid in the presence of NaI and 18-crown-6 and for reaction with cyclopentadienyl iron dicarbonyl dimer in the formation of an iron-containing methylene transfer agent.
Lucas C. Ducati.; Matheus P. Freitas.; Cláudio F. Tormena, Roberto Rittner. Conformational and stereoelectronic investigation of chloromethyl methyl sulfide and its sulfinyl and sulfonyl analogs. Journal of Molecular Structure. 2006, 800 (1-3), 45-50.
Akira Hosomi.; Shinji Hayashi.; Koichiro Hoashi.; Shinya Kohra.; Yoshinori Tominaga. Intramolecular cyclization via onium salts: a novel synthesis of 1,3-thiazolidines from chloromethyl (trimethylsilyl)methyl sulfide and nitrogen-containing heteroaromatic compounds. J. Org. Chem. 1987, 52 (19), 4423-4424.
Protects alcohols as their methylthiomethyl (MTM) ethers by reaction, e.g. with NaH/NaI in DME: Tetrahedron Lett., 3269 (1975), or with AgNO3/Et3N: Chem. Lett., 1277 (1979). MTM ethers are relatively stable to acid but can be cleaved selectively with HgCl2 in aqueous acetonitrile or AgNO3/ 2,6-lutidine: Tetrahedron Lett., 3269 (1975), by methylation (MeI) and hydrolysis: Austral. J. Chem., 31, 1031 (1978); Chem. Lett., 715 (1984), or with TMS chloride and Ac2O: Chem. Ind. (London), 223 (1984). For protection of phenols, see: Tetrahedron Lett., 533 (1977); 24, 1189 (1984).
Can also be used for the preparation of MTM esters of carboxylic acids, e.g. by treatment of the K salt of the acid in the presence of NaI and 18-crown-6: Tetrahedron Lett., 731 (1978) which also describes cleavage with HgCl2. The ester can also be cleaved with TFA: J. Chem. Soc., Chem. Commun., 224 (1973); or by methylation-hydrolysis: Tetrahedron Lett., 689 (1979).
For reaction with cyclopentadienyl iron dicarbonyl dimer in the formation of an iron-containing methylene transfer agent, see: Org. Synth. Coll., 9, 372 (1998).
Hazard Statements: H225-H315-H319-H335
Highly flammable liquid and vapour. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.
Precautionary Statements: P210-P261-P303+P361+P353-P305+P351+P338-P405-P501a
Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Avoid breathing dust/fume/gas/mist/vapours/spray. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.