Methanesulfonyl chloride

Base Information

• Chemical Name: Methanesulfonyl chloride
• CAS No.: 124-63-0
• Deprecated CAS: 2101638-66-6
• Molecular Formula: CH3ClO2S
• Molecular Weight: 114.553
• Hs Code.: HYSICAL AND CHEMICAL PROPERTIES PHYSICAL STATE Colourless To Pale Yellow Fuming Liquid
• European Community (EC) Number: 204-706-1
• ICSC Number: 1163
• NSC Number: 15039
• UN Number: 3246
• UNII: B17EWY1R7Q
• DSSTox Substance ID: DTXSID1021615
• Nikkaji Number: J2.507K
• Wikipedia: Methanesulfonyl_chloride
• Wikidata: Q417706
• Mol file: 124-63-0.mol

Synonyms:methanesulfonyl chloride;methanesulfonyl chloride, 35Cl-labeled;methanesulfonyl chloride, 35S-labeled;methanesulfonyl chloride, 37Cl-labeled

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Chemical Property of Methanesulfonyl chloride

Chemical Property:

• Appearance/Colour: Colorless to yellow liquid
• Vapor Pressure: 3.07mmHg at 25°C
• Melting Point: -33 °C
• Refractive Index: 1.45
• Boiling Point: 160.7 °C at 760 mmHg
• Flash Point: 42.2 °C
• PSA: 42.52000
• Density: 1.478 g/cm³
• LogP: 1.26560
• Storage Temp.: Store at R.T.
• Sensitive.: Moisture Sensitive
• Solubility.: Chloroform, Hexanes
• Water Solubility.: Miscible with alcohol, ether and organic solvents. Immiscible with water.
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 113.9542282
• Heavy Atom Count: 5
• Complexity: 95.3
• Transport DOT Label: Poison Inhalation Hazard Corrosive

Purity/Quality:

Safty Information:

• Pictogram(s): T+,T,C
• Hazard Codes: T+,T,C
• Statements: 24/25-26-34-37-35-22-41
• Safety Statements: 26-28-36/37/39-45-25-28A

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Toxic Gases & Vapors -> Acid Halides
• Canonical SMILES: CS(=O)(=O)Cl
• Inhalation Risk: No indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.
• Effects of Short Term Exposure: The substance is corrosive to the eyes, skin and respiratory tract. Corrosive on ingestion.
• Effects of Long Term Exposure: Repeated or prolonged contact may cause skin sensitization.
• Uses: In the synthesis of photographic and agricultural chemicals, pharmaceutical intermediates. As a stabilizer; catalyst; curing and chlorinating agent; precursor to methanesulfonic acid. Methanesulfonyl chloride is used as a reagent for conversion of alcohols to mesylate esters such as methanesulfonate, which is an intermediate in substitution reactions, elimination reactions, reductions, and rearrangement reactions viz. Beckmann rearrangement. It is an electrophile and acts as a source of CH3SO2+ group. It is also used to prepare beta-chloro sulfones, methanesulfonamide and heterocyclic compounds containing five membered sultones. Methanesulfonyl chloride can be used for the mesylation of primary alcohols to synthesize the corresponding methanesulfonates. It may also be used for the conversion of amines to the corresponding sulfonamides.

Technology Process of Methanesulfonyl chloride

There total 51 articles about Methanesulfonyl chloride 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: 99.81%

Dimethyldisulphide (624-92-0) → methanesulfonyl chloride (124-63-0)

Guidance literature:

With hydrogenchloride; manganese(IV) oxide; potassium sulfate; water; at 60 - 90 ℃; for 22h; Reagent/catalyst; Temperature; Large scale;

Reference yield: 95.0%

S,S-dimethyl dithiocarbonate (868-84-8) → methanesulfonyl chloride (124-63-0)

Guidance literature:

With water; chlorine; at 5 - 10 ℃; for 0.25h;

DOI:10.1055/s-1989-27445

Reference yield: 92.0%

Chloromethyltrimethylsilane (2344-80-1) → Chloro(chloromethyl)dimethylsilane (1719-57-9) + sulfate de bis-(dimethylchloromethylsilyle) (20991-92-8) + methanesulfonyl chloride (124-63-0)

Guidance literature:

With chlorosulfonic acid; at 50 - 80 ℃;

upstream raw materials:

methyl thiocyanate

methyl magnesium iodide

methanesulfonic acid

dimethylsulfide

Downstream raw materials:

2-chloroethyl mesylate

N-(2-chloroethyl)-methanesulfonamide

4-chlorobutyl methanesulfonate

1-(methanesulfonyl)piperidine

Refernces

• 1、 Field,Settlage. "-". . p. 170. Retrieved 1955.
• 2、 Mukhopadhyay, Sudip,Zerella, Mark,Bell, Alexis T.,Srinivas, R. Vijay,Smith, Gary S.. "Synthesis of methanesulfonyl chloride (MSC) from methane and sulfuryl chloride". . p. 472 - 473. Retrieved 2004.
• 3、 Sohmiya, Hajime,Kimura, Takahide,Fujita, Mitsue,Ando, Takashi. "Novel One-Step Synthesis of Sulfonyl Chlorides from Sulfides with Iodosobenzene and Hydrogen Chloride-Treated Silica Gel". . p. 891 - 892. Retrieved 1992.
• 4、 Hanai,Okuda. "Preparation of methanesulfonyl chloride d3 from dimethyl sulfoxide d6". . p. 815 - 816. Retrieved 1977.
• 5、 Bennett et al.. "-". . p. 2485. Retrieved 1963.
• 6、 Ye, Lianbao,Wu, Jie,Chen, Weiqiang,Feng, Yu,Shen, Zhibing. "Novel anti-cancer agents based on germacrone: design, synthesis, biological activity, docking studies and MD simulations". . p. 3760 - 3767. Retrieved 2017.
• 7、 -. "METHOD FOR PRODUCING TRIAZOLE COMPOUND". . . Retrieved 2020/02/05.
• 8、 Gómez-Palomino, Alejandro,Cornella, Josep. "Selective Late-Stage Sulfonyl Chloride Formation from Sulfonamides Enabled by Pyry-BF4". supporting information. p. 18235 - 18239. Retrieved 2019/11/13.