Methyl benzenesulfonate

Base Information

• Chemical Name: Methyl benzenesulfonate
• CAS No.: 80-18-2
• Molecular Formula: C7H8O3S
• Molecular Weight: 172.205
• Hs Code.: 29051990
• European Community (EC) Number: 201-256-8,690-039-5
• NSC Number: 3214
• UNII: 69X50842RM
• DSSTox Substance ID: DTXSID5052549
• Nikkaji Number: J32.713A
• Wikidata: Q18500364
• Mol file: 80-18-2.mol

Synonyms:METHYL BENZENESULFONATE;80-18-2;Benzenesulfonic acid, methyl ester;Methyl benzenesulphonate;Methyl besylate;Benzenesulfonic Acid Methyl Ester;methylbenzenesulfonate;20ND3-5;CCRIS 9156;NSC 3214;EINECS 201-256-8;NSC 06624;BRN 0908448;AI3-06624;NSC-3214;Methyl ester of benzenesulphonic acid;69X50842RM;4-11-00-00029 (Beilstein Handbook Reference);METHYL BENZENE SULFONATE;methylbenzensulfonat-;methylbenzene sulfonate;methyl benzene-sulfonate;Benzolsulfonsauremethylester;Benzenesulfonic acid methyl;SCHEMBL94530;DTXSID5052549;UNII-69X50842RM;NSC3214;BCP22900;MFCD00014737;AKOS000120218;LS-32007;PS-10679;B0033;CS-0020960;FT-0622649;EN300-15725;E76340;A839862;J-522589;Q18500364;Z45457929

Chemical Property of Methyl benzenesulfonate

Chemical Property:

• Appearance/Colour: clear colourless to slightly brown liquid
• Vapor Pressure: 0.0122mmHg at 25°C
• Melting Point: -4 °C
• Refractive Index: 1.514-1.516
• Boiling Point: 269.1 °C at 760 mmHg
• Flash Point: 116.6 °C
• PSA: 51.75000
• Density: 1.251 g/cm³
• LogP: 2.10250
• Storage Temp.: Refrigerator
• Water Solubility.: Miscible with chloroform, methanol, ethanol and ether. Immiscible with water.
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 172.01941529
• Heavy Atom Count: 11
• Complexity: 196

Purity/Quality:

99%min ^*data from raw suppliers

Methyl Benzenesulfonate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C,Xi
• Hazard Codes: C,Xi
• Statements: 34-22-43
• Safety Statements: 28A-26-45-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Benzenesulfonic Acid Derivatives
• Canonical SMILES: COS(=O)(=O)C1=CC=CC=C1
• Description: Methyl benzenesulfonate is used as a raw material for the dye and pharmaceutical industries, used as an alkylating agent in organic synthesis for the production of some synthetic dye. It can also be used for the manufacturing the thin-cation exchanger film.
• Uses: Methyl benzenesulfonate is a sulfonate ester which acts as a potential genotoxic impurity in drug substances. Further, it exerts genotoxic effects in bacterial and mammalian cell systems.

Technology Process of Methyl benzenesulfonate

There total 37 articles about Methyl benzenesulfonate 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: 92.0%

methanol (67-56-1) + benzenesulfonyl chloride (98-09-9) → Methyl benzenesulfonate (80-18-2)

Guidance literature:

With cesium fluoride supported on Celite; at 50 ℃; for 1.5h; chemoselective reaction;

DOI:10.1016/j.catcom.2011.04.005

Reference yield: 91.0%

diphenylmethyl phenyl sulfone (5433-76-1) + methyl iodide (74-88-4) → benzophenone (119-61-9) + Methyl benzenesulfonate (80-18-2)

Guidance literature:

With oxygen; Product distribution; multistep reaction: 1.) electrolysis, DMF;

Reference yield: 82.0%

Trimethylmethoxysilane (1825-61-2) + phenylsulfonyl fluoride (368-43-4) → trimethylsilyl fluoride (420-56-4) + Methyl benzenesulfonate (80-18-2)

Guidance literature:

With tin(IV) chloride; at 80 - 100 ℃;

upstream raw materials:

tetrachloromethane

acetone oxime-o-benzenesulfonic ester

methanol

benzenesulfonyl chloride

Downstream raw materials:

3-ethoxycarbonyl-1-methyl-pyridinium; benzenesulfonate

6-benzoyl-1-methyl-1H-benzo[cd]indol-2-one

2-chloro-1,1'-biphenyl

2-bromo-N-methylaniline

Refernces

• 1、 He, Yang,Zhang, Jinli,Xu, Liang,Wei, Yu. "Electrochemical synthesis of sulfinic esters from alcohols and thiophenols". supporting information. . Retrieved 2020/01/31.
• 2、 Wang, Yang,Deng, Lingling,Deng, Yu,Han, Jianlin. "Copper-Catalyzed Multicomponent Reaction of DABCO·(SO2)2, Alcohols, and Aryl Diazoniums for the Synthesis of Sulfonic Esters". . p. 4674 - 4680. Retrieved 2018/04/26.