51804-15-0

Basic information

• Product Name: 4-carboxyphenyl 4-methylbenzenesulfonate
• Synonyms: 4-carboxyphenyl 4-methylbenzenesulfonate
• CAS NO: 51804-15-0
• Molecular Weight: 292.312
• Mol File: 51804-15-0.mol

Chemical Properties

• CAS DataBase Reference: 4-carboxyphenyl 4-methylbenzenesulfonate(CAS DataBase Reference)
• NIST Chemistry Reference: 4-carboxyphenyl 4-methylbenzenesulfonate(51804-15-0)
• EPA Substance Registry System: 4-carboxyphenyl 4-methylbenzenesulfonate(51804-15-0)

Safety Data

• Hazardous Substances Data: 51804-15-0(Hazardous Substances Data)

Upstream product

• 6324-15-8 toluene-4-sulfonic acid 4-bromo-phenyl ester 
• 4124-41-8 p-toluenesulfonylanhydride 
• 99-96-7 4-hydroxy-benzoic acid 
• 24962-55-8 4-hydroxybenzaldehyde 4-methylbenzenesulfonate ester 
• 590-29-4 potassium formate 
• 18414-58-9 diphenylmethylsilanecarboxylic acid 
• 84672-48-0 2-bromophenyl 4-methylbenzenesulfonate 
• 51207-43-3 methyl 4-(tosyloxy)benzoate 

Downstream Products

• 64675-83-8 4-(toluene-4-sulfonyloxy)-benzoyl chloride 
• 1293362-53-4 toluenesulfonic acid-4-[6-methoxy-2-(4-methoxy-phenyl)-benzo[b]thiophene-3-carbonyl]-phenyl ester 
• 51207-43-3 methyl 4-(tosyloxy)benzoate 
• 640-60-8 toluene-4-sulfonic acid phenyl ester 
• 1345403-81-7 cyclohex-2-enyl 4-(tosyloxy)benzoate 
• 1284251-49-5 C₁₈H₁₈O₇S 
• 103281-39-6 4-(toluene-4-sulfonyloxy)-benzoic acid-[4-(toluene-4-sulfonyloxy)-benzyl ester] 
• 106473-33-0 4-carbamoylphenyl-4-methylbenzenesulfonate 

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.

Nickel-catalyzed carboxylation of aryl iodides with lithium formate through catalytic CO recycling

A protocol for the Ni-catalyzed carboxylation of aryl iodides with formate has been developed with good functional group compatibility for the synthesis of a variety of aromatic carboxylic acids under mild conditions. The reaction tolerates other functionalities for cross-coupling, such as aryl bromide, aryl chloride, aryl tosylate, and aryl pinacol boronate. The reaction proceeds through a carbonylation process with in situ generated carbon monoxide in the presence of a catalytic amount of acetic anhydride and lithium formate, avoiding the use of gaseous CO. The strategy of CO recycling in catalytic amounts is critical for the success of the reaction.

Palladium-catalyzed synthesis of aromatic carboxylic acids with silacarboxylic acids

Aryl iodides and bromides were easily converted to their corresponding aromatic carboxylic acids via a Pd-catalyzed carbonylation reaction using silacarboxylic acids as an in situ source of carbon monoxide. The reaction conditions were compatible with a wide range of functional groups, and with the aryl iodides, the carbonylation was complete within minutes. The method was adapted to the double and selective isotope labeling of tamibarotene.

Effective palladium-catalyzed hydroxycarbonylation of aryl halides with substoichiometric carbon monoxide

A protocol for the Pd-catalyzed hydroxycarbonylation of aryl iodides, bromides, and chlorides has been developed using only 1-5 mol % of CO, corresponding to a pCO as low as 0.1 bar. Potassium formate is the only stoichiometric reagent, acting as a mildly basic nucleophile and a reservoir of CO. The substoichiometric CO could be delivered to the reaction from an acyl-Pd(II) precatalyst, which provides both the CO and an active catalyst, and thereby obviates the need for handling a toxic gas.