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Chloromethyl methyl sulfide, 94%, Thermo Scientific Chemicals
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Catalog number L10858.09
also known as L10858-09
Price (USD)/ Each
65.20
-
Quantity:
10 g
Price (USD)/ Each
65.20
Chloromethyl methyl sulfide, 94%, Thermo Scientific Chemicals
Catalog numberL10858.09
Price (USD)/ Each
65.20
-
Chemical Identifiers
CAS2373-51-5
IUPAC Namechloro(methylsulfanyl)methane
Molecular FormulaC2H5ClS
InChI KeyJWMLCCRPDOIBAV-UHFFFAOYSA-N
SMILESCSCCl
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Specifications
Specification Sheet
Specification SheetAppearance (Color)Clear colorless to yellow
Assay (GC)≥92.0%
FormLiquid
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.
This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.
Applications
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.
Solubility
Soluble in acetonitrile, ether and dichloromethane. Insoluble in water.
Notes
Store in cool place. Keep container tightly closed in a dry and well-ventilated place. Containers which are opened must be carefully resealed and kept upright to prevent leakage. Recommended storage temperature: 2 - 8°C. Incompatible with strong oxidizing agents.
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.
Solubility
Soluble in acetonitrile, ether and dichloromethane. Insoluble in water.
Notes
Store in cool place. Keep container tightly closed in a dry and well-ventilated place. Containers which are opened must be carefully resealed and kept upright to prevent leakage. Recommended storage temperature: 2 - 8°C. Incompatible with strong oxidizing agents.
RUO – Research Use Only
General References:
- 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 NaHaI 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).