Chloromethyl methyl sulfide

Base Information

• Chemical Name: Chloromethyl methyl sulfide
• CAS No.: 2373-51-5
• Molecular Formula: C2H5ClS
• Molecular Weight: 96.5807
• Hs Code.: 2930909090
• European Community (EC) Number: 219-148-4
• NSC Number: 63205
• DSSTox Substance ID: DTXSID10178406
• Nikkaji Number: J149.595J
• Wikipedia: Chloromethyl_methyl_sulfide
• Wikidata: Q72454322
• Mol file: 2373-51-5.mol

Synonyms:chlorodimethyl sulfide

Chemical Property of Chloromethyl methyl sulfide

Chemical Property:

• Appearance/Colour: clear yellow to brown liquid
• Vapor Pressure: 35mmHg at 25°C
• Refractive Index: n20/D 1.498(lit.)
• Boiling Point: 105 °C at 760 mmHg
• Flash Point: 17.2 °C
• PSA: 25.30000
• Density: 1.111 g/cm³
• LogP: 1.54570
• Storage Temp.: 2-8°C
• Sensitive.: Moisture Sensitive
• Water Solubility.: Soluble in acetonitrile, ether and dichloromethane. Insoluble in water.
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 95.9800490
• Heavy Atom Count: 4
• Complexity: 10

Purity/Quality:

99.5% ^*data from raw suppliers

Chloromethyl Methyl Sulfide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,Xi
• Hazard Codes: F,Xi
• Statements: 11-37
• Safety Statements: 9-16-33

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CSCCl
• Uses: 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. Methylthiomethylating reagent for carbonyl and aromatic compounds. Methylene transfer reagent for iron(II) mediated cyclopropanation.

Technology Process of Chloromethyl methyl sulfide

There total 57 articles about Chloromethyl methyl sulfide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

dimethyl sulfoxide (67-68-5,8070-53-9) → chloro-methylsulfanyl-methane (2373-51-5)

Guidance literature:

With tetrachlorosilane; In dichloromethane; for 0.166667h; Ambient temperature;

DOI:10.1016/0040-4039(94)88094-8

Reference yield: 79.0%

dimethyl sulfoxide (67-68-5,8070-53-9) + dimethylsilicon dichloride (75-78-5,30107-43-8) → chloro-methylsulfanyl-methane (2373-51-5) + Hexamethylcyclotrisiloxane (541-05-9) + octamethylcyclotetrasiloxane (556-67-2) + decamethylcyclopentasiloxane (541-02-6) + dodecamethyl-cyclohexasiloxane (540-97-6)

Guidance literature:

at 0 ℃; Mechanism; other diorganyldichlorosilanes; reactions in the presence of hexamethyldisiloxane, trimethylchlorosilane, tetramethoxysilane, tetraethoxysilane;

Reference yield: 74.0%

dimethyl sulfoxide (67-68-5,8070-53-9) → chloro-methylsulfanyl-methane (2373-51-5) + methyltrimethicone (17928-28-8) + methylbis(trimethylsilyloxy)vinylsilane (5356-85-4) + C24H54O7Si8

Guidance literature:

With Hexamethyldisiloxane; Dichloromethylvinylsilane; Further byproducts given;

DOI:10.1007/BF02495612

upstream raw materials:

formaldehyd

methylthiol

dimethylsulfide

2,4-dithiapentane

Downstream raw materials:

diethyl 2-benzyl-2-(methylthiomethyl)malonate

[(methylthio)methyl]-benzene

{[(methylsulfanyl)methyl]sulfanyl}benzene

formaldehyde methyldithiohemiacetal

Refernces

• 1、 Dyke,Ghosh,Kinnison,Levita,Morris,Shallcross. "A kinetics and mechanistic study of the atmospherically relevant reaction between molecular chlorine and dimethyl sulfide (DMS)". . p. 866 - 873. Retrieved 2005.
• 2、 Voronkov,Gavrilova,Basenko. "Complex of tetrachlorogermane with dimethyl sulfoxide and its IR spectral study". . p. 210 - 212. Retrieved 2001.
• 3、 Fragis, Meghan,Deobald, Jackson L.,Dharavath, Srinivas,Scott, Jeffrey,Magolan, Jakob. "Aldehyde to Ketone Homologation Enabled by Improved Access to Thioalkyl Phosphonium Salts". supporting information. p. 4548 - 4552. Retrieved 2021/06/28.
• 4、 Ielo, Laura,Pillari, Veronica,Miele, Margherita,Holzer, Wolfgang,Pace, Vittorio. "Consecutive C1-Homologation / Displacement Strategy for Converting Thiosulfonates into O,S-Oxothioacetals". supporting information. p. 5444 - 5449. Retrieved 2020/10/12.