80-18-2

Usage

Uses

Used in Dye Industry:
Methyl benzenesulfonate is used as a raw material for the production of synthetic dyes. Its alkylating properties make it a valuable component in the synthesis of various dye compounds.
Used in Pharmaceutical Industry:
Methyl benzenesulfonate is used as a raw material in the pharmaceutical industry, where it can be utilized in the synthesis of certain drugs.
Used in Organic Synthesis:
Methyl benzenesulfonate is used as an alkylating agent in organic synthesis, enabling the production of various chemical compounds.
Used in Manufacturing Thin-Cation Exchanger Films:
Methyl benzenesulfonate is utilized in the manufacturing process of thin-cation exchanger films, which have applications in various industries, including water treatment and ion exchange processes.

Preparation

Methyl benzenesulfonate is the effective methylating reagent of synthetic multiple organic intermediate, and industry is at present gone up and mainly adopted Phenylsulfonic acid and methyl alcohol to carry out after the esterification essence to steam, this technology starting material costliness, and reaction time is long, and product yield is low. How to get Methyl benzenesulfonate with high yield, scientists have lots of researcher.

Genotoxicity

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. Incompatible with strong oxidizing agents, strong acids and strong bases.

Reaction

V. M. Nesterov and I. E. Chubova prepared theobromine from 3-methylxanthine, methyl benzenesulfonate, which has been used as the methylating agent. To obtain theobromine, 3-methylxanthine is generally methylated with dimethyl sulfate in an aqueous ethanolic solution of caustic potash. However, if in the reaction the pH exceeds 8.0, the methylation of 3-methylxanthine leads to caffeine, which forms a by-product.

InChI:InChI=1/C7H8O3S/c1-10-11(8,9)7-5-3-2-4-6-7/h2-6H,1H3

Upstream product

• 56-23-5 tetrachloromethane 
• 39083-10-8 acetone oxime-o-benzenesulfonic ester 
• 67-56-1 methanol 
• 98-09-9 benzenesulfonyl chloride 
• 124-41-4 sodium methylate 
• 108-88-3 toluene 
• 515-42-4 sodium phenylsulfonate 
• 77-78-1 dimethyl sulfate 
• 98-11-3 benzenesulfonic acid 
• 812-01-1 methyl chlorosulfate 
• 71-43-2 benzene 
• 108-98-5 thiophenol 
• 1825-61-2 Trimethylmethoxysilane 
• 75620-67-6 neopentyl benzenesulfonate 

Downstream Products

• 6473-98-9 5-imino-1,4-dimethyl-1,4-dihydro-5H-tetrazole 
• 109510-52-3 3-ethoxycarbonyl-1-methyl-pyridinium; benzenesulfonate 
• 57913-64-1 1-methyl-4-phenyl-1,4-dihydro-tetrazol-5-ylideneamine 
• 65610-86-8 2-(2-aminophenyl)-1-methyl-1H-indole 
• 3481-26-3 furfuryl-trimethyl-ammonium; benzenesulfonate 
• 66739-87-5 4-methylpiperazin-1-ylbenzenesulfonamide 
• 55441-71-9 9-methyluric acid 
• 19031-27-7 6-benzoyl-1-methyl-1H-benzo[cd]indol-2-one 
• 2051-60-7 2-chloro-1,1'-biphenyl 
• 6832-87-7 2-bromo-N-methylaniline 
• 22056-67-3 benzenesulfonic acid ; (2-acetoxy-ethyl)-trimethyl-ammonium salt 
• 101084-96-2 2-methoxy-4-nitrobenzonitrile 
• 39106-79-1 methyl 2-methoxy-4-nitrobenzoate 

Relevant academic research and scientific papers

A simple method for the synthesis of sulfonic esters

An efficient and simple approach for the direct synthesis of aryl and heteroaryl sulfonic esters was developed using DMS and DES as alkoxysulfonylation reagents. The reaction is operationally simple and scalable. This protocol does not require solvent, expensive catalysts, base, ligand additives or other reagents. A wide range of sulfonic esters were synthesized in moderate to good chemical yields. This method has the advantage of low cost, facile and tolerated a wide range of substrates.

Electrochemical synthesis of sulfinic esters from alcohols and thiophenols

Electrochemical oxidative couplings between S[sbnd]H and O[sbnd]H bonds are achieved herein directly from readily-available alcohols and thiophenols, affording a series of diverse sulfinic esters. This strategy can take advantage of 6 equivalents of alcohol, relative to thiophenol, to achieve moderate to good yields, without the assistance of any metallic catalysts, bases, and additional oxidants.

Copper-Catalyzed Multicomponent Reaction of DABCO·(SO2)2, Alcohols, and Aryl Diazoniums for the Synthesis of Sulfonic Esters

A Cu-catalyzed multicomponent cascade reaction of DABCO·(SO2)2 (DABSO), alcohol, and aryl diazonium tetrafluoroborate was developed which afforded sulfonic esters in moderate to good chemical yields. In this reaction, the SO2 surrogate DABSO was used for the first time in the synthesis of sulfonic aliphatic esters. This multicomponent reaction was carried out under mild conditions and tolerated a wide range of substrates, which provides a new and efficient strategy for the synthesis of sulfonic esters.

Generation of VBr? VBi? VO?? defect clusters for 1O2 production for molecular oxygen activation in photocatalysis

Defect engineering on a semiconductor surface can provide coordinatively unsaturated sites for molecular oxygen activation in photocatalysis. In this work, we demonstrated that the vacancy type was key to modulate the molecular oxygen activation process on BiOBr nanosheets. By regulating the reaction time, an oxygen vacancy (VO??), a double atom defect cluster (VBi? VO??) and triple atom clusters (VBi? VO?? VBi? and VBr? VBi? VO??) were accordingly generated on the surface, subsurface and bulk of BiOBr. More importantly, the newly-discovered VBr? VBi? VO?? defect cluster was highly related to the singlet oxygen (1O2) production ability of BiOBr. Meanwhile, the excellent photocatalytic selective oxidation reactions were successfully realized over BiOBr with the VBr? VBi? VO?? defect cluster. In addition, time-dependent defect cluster generation and the associated molecular oxygen activation were discussed.

HIGHLY PURE SALTS OF CLOPIDOGREL FREE OF GENOTOXIC IMPURITIES

The present invention relates to substantially pure salts of clopidogrel of Formula (I) substantially free from genotoxic impurities. (I) wherein (S) represents a suitable organic or inorganic acid, which forms a salt with clopidogrel having less acidity.

CsF-Celite as an efficient heterogeneous catalyst for sulfonylation and desulfonylation of heteroatoms

CsF-Celite is found to be as an efficient reusable catalyst for sulfonylation and desulfonylation of heteroatoms. Sulfonamides and N-acylsulfonamides deprotect efficiently in the presence of CsF-Celite under solvent free conditions to give the free amines or amides in good to excellent yields.

The SN3-SN2 spectrum. Rate constants and product selectivities for solvolyses of benzenesulfonyl chlorides in aqueous alcohols

Rate constants for a wide range of binary aqueous mixtures and product selectivities (S) in ethanol - Water (EW) and methanol-water (MW) mixtures, are reported at 25 °C for solvolyses of benzenesulfonyl chloride and the 4-chloro - Derivative. S is defined as follows using molar concentrations: S =([ester product]/[acid product]) × ([water solvent]/[alcohol solvent]). Additional selectivity data are reported for solvolyses of 4-Z-substituted sulfonyl chlorides (Z - OMe, Me, H, Cl and NO2) in 2, 2, 2-trifluoroethanol-water. To explain these results and previously published data on kinetic solvent isotope effects (KSIEs) and on other solvolyses of 4-nitro and 4-methoxybenzenesulfonyl chloride, a mechanistic spectrum involving a change from third order to second order is proposed. The molecularity of these reactions is discussed, along with new term 'SN3-SN2 spectrum' and its connection with the better established term 'S N2-SN1 spectrum'. Copyright

The Hammett equation and micellar effects on SN2 reactions of methyl benzenesulfonates - The role of micellar polarity

Substituent effects on the reaction of H2O, OH-, and Br- with p-substituted methyl benzenesulfonates in cationic micelles of cetyl trialkylammonium ion surfactants (n-C16H33NR3X, X = OH, Br, R = Me, Et, nPr, nBu) and in water were analyzed by using the Hammett equation. Values of p in the various media confirm that micellar interfacial regions are less polar than water and polarities decrease with increasing bulk of the surfactant head-group. Wiley-VCH Verlag GmbH, 2000.

Process for preparation of oxyglutaric acid ester derivatives

A process for preparing an oxyglutaric acid ester derivative of the formula: STR1 in which each of R1 and R2 is C1-5 alkoxy, C1-7 aralkyloxy, C7-9 halogenated aralkyloxy or phenyl, R4 is a hydroxyl-protecting group, and R5 is C1-10 alkyl which may have a substituent, comprises the steps of reacting a methyl phosphonate derivative or methyl phosphine oxide derivative with an oxyglutaric acid mono-ester to give a reaction product which comprises an oxyglutaric acid derivative having a phosphorus-containing group and a pentenedioic acid mono-ester (by-product), removing the pendenedioic acid mono-ester from the reaction product to isolate the oxyglutaric acid derivative, and converting the isolated oxyglutaric acid derivative into the oxyglutaric acid ester derivative. A process for obtaining an optically active oxyglutaric acid ester derivative is also disclosed.

Solvolysis of benzenesulfonyl chloride. Base and nucleophilic catalysis mechanisms with tertiary amines

Competing pathways in the phenolysis and methanolysis of benzenesulfonyl chloride in acetonitrile, catalyzed by tertiary amines, have been distinguished. The rate of the reaction pathway, where nucleophilic catalysis is operative, is strongly sensitive to inductive and steric effects of substituents in the tertiary amine and almost insensitive to the nature of the nucleophile. The rate of the general base catalysis pathway is very sensitive to nucleophilic power of the amine and nucleophile and almost insensitive to steric accessibility of the catalyst. 1996 MAEe Cyrillic signΚ Hayκa/Interperiodica Publishing.