82745-72-0

Basic information

• Product Name: 2-(4-methylphenyl)sulfonyloxybenzoic acid
• Synonyms: 2-(4-methylphenyl)sulfonyloxybenzoic acid;2-(p-Tolylsulfonyloxy)benzoic acid;2-(Tosyloxy)benzoic acid;2-Tosyloxybenzoic acid
• CAS NO: 82745-72-0
• Molecular Formula: C₁₄H₁₂O₅S
• Molecular Weight: 292.3071
• Mol File: 82745-72-0.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 488.4°Cat760mmHg
• Flash Point: 249.2°C
• Appearance: /
• Density: 1.379g/cm³
• Vapor Pressure: 2.37E-10mmHg at 25°C
• Refractive Index: 1.604
• CAS DataBase Reference: 2-(4-methylphenyl)sulfonyloxybenzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-methylphenyl)sulfonyloxybenzoic acid(82745-72-0)
• EPA Substance Registry System: 2-(4-methylphenyl)sulfonyloxybenzoic acid(82745-72-0)

Safety Data

• Hazardous Substances Data: 82745-72-0(Hazardous Substances Data)

Usage

General Description

2-(4-methylphenyl)sulfonyloxybenzoic acid is a compound with the chemical formula C14H12O5S. It is a sulfonate ester derivative of benzoic acid, meaning it contains a sulfonyloxy group attached to a benzene ring. 2-(4-methylphenyl)sulfonyloxybenzoic acid is often used as a reagent in organic synthesis and medicinal chemistry, as it can be utilized in the preparation of various pharmaceutical and agrochemical products. It has also been studied for its potential use as an anti-inflammatory and analgesic agent due to its structural similarity to non-steroidal anti-inflammatory drugs. The compound has a white crystalline appearance and is sparingly soluble in water.

InChI:InChI=1/C14H12O5S/c1-10-6-8-11(9-7-10)20(17,18)19-13-5-3-2-4-12(13)14(15)16/h2-9H,1H3,(H,15,16)

Upstream product

• 51207-44-4 methyl 2-{[(4-methylphenyl)sulfonyl]oxy}benzoate 
• 98-59-9 p-toluenesulfonyl chloride 
• 19820-56-5 2-formylphenyl tosylate 
• 90-02-8 salicylaldehyde 
• 127087-38-1 potassium 2-[[(4-methylphenyl)sulfonyl]oxy]benzoate 
• 69-72-7 salicylic acid 

Downstream Products

• 205989-12-4 luotonin A 
• 19434-30-1 2-hydroxy-4'-methylbenzophenone 
• 61153-72-8 2-(Tosyloxy)benzoylchlorid 
• 69-72-7 salicylic acid 
• 16106-44-8 potassium tosylate 
• 2948-14-3 furan-2-carboxylic acid phenyl ester 
• 751-38-2 1,2,3,4-tetraphenylnaphthalene 
• 60769-40-6 Sodium; 2-(toluene-4-sulfonyloxy)-benzoate 
• 127087-38-1 potassium 2-[[(4-methylphenyl)sulfonyl]oxy]benzoate 
• 640-60-8 toluene-4-sulfonic acid phenyl ester 

Relevant articles and documents

Cleavage of Carboxylic Esters by Aluminum and Iodine

A one-pot procedure for deprotecting carboxylic esters under nonhydrolytic conditions is described. Typical alkyl carboxylates are readily deblocked to the carboxylic acids by the action of aluminum powder and iodine in anhydrous acetonitrile. Cleavage of lactones affords the corresponding ω-iodoalkylcarboxylic acids. Aryl acetylates undergo deacetylation with the participation of the neighboring group. This method enables the selective cleavage of alkyl carboxylic esters in the presence of aryl esters.

Deoxygenative Arylation of Carboxylic Acids by Aryl Migration

An unprecedented deoxygenative arylation of aromatic carboxylic acids has been achieved, allowing the construction of an enhanced library of unsymmetrical diaryl ketones. The synergistic photoredox catalysis and phosphoranyl radical chemistry allows for precise cleavage of a stronger C?O bond and formation of a weaker C?C bond by 1,5-aryl migration under mild reaction conditions. This new protocol is independent of substrate redox-potential, electronic, and substituent effects. It affords a general and promising access to 60 examples of synthetically versatile o-amino and o-hydroxy diaryl ketones under redox-neutral conditions. Furthermore, it also brings one concise route to the total synthesis of quinolone alkaloid, (±)-yaequinolone A2, and a viridicatin derivative in satisfying yields.

A Predictive Model for the Decarboxylation of Silver Benzoate Complexes Relevant to Decarboxylative Coupling Reactions

Decarboxylative coupling reactions offer an attractive route to generate functionalized arenes from simple and readily available carboxylic acid coupling partners, yet they are underutilized due to limitations in the scope of carboxylic acid coupling partner. Here we report that the field effect parameter (F) has a substantial influence on the rate of decarboxylation of well-defined silver benzoate complexes. This finding provides the opportunity to surpass current substrate limitations associated with decarboxylation and to enable widespread utilization of decarboxylative coupling reactions.