Estoy de acuerdo utilizamos cookies para mejorar la experiencia de navegación del usuario y para estudiar cómo se utiliza nuestro sitio web. si navega por nuestro sitio web, estará aceptando el uso de las cookies en las condiciones establecidas en la presente política de cookies. esta política puede ser actualizada, por lo que le invitamos a revisarla de forma regular
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).
Indicaciones de peligro (UE): H225-H315-H319-H335
Highly flammable liquid and vapour. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.
Indicaciones de precaución: 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.