65594-65-2

Basic information

• Product Name: Benzoic acid, 2,2'-carbonylbis-, dimethyl ester
• CAS NO: 65594-65-2
• Molecular Formula: C17H14O5
• Molecular Weight: 298.295
• Mol File: 65594-65-2.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: Benzoic acid, 2,2'-carbonylbis-, dimethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Benzoic acid, 2,2'-carbonylbis-, dimethyl ester(65594-65-2)
• EPA Substance Registry System: Benzoic acid, 2,2'-carbonylbis-, dimethyl ester(65594-65-2)

Safety Data

• Hazardous Substances Data: 65594-65-2(Hazardous Substances Data)

Upstream product

• 610-94-6 2-bromobenzoic acid methyl ester 
• 201230-82-2 carbon monoxide 
• 374538-03-1 2-methoxycarbonylphenylboronic acid 
• 38487-11-5 diphenylmethane-2,2'-dicarboxylic acid 
• 67-56-1 methanol 
• 573-32-0 benzophenone-2,2'-dicarboxylic acid 

Relevant articles and documents

Carbonylative Suzuki-Miyaura couplings of sterically hindered aryl halides: Synthesis of 2-aroylbenzoate derivatives

We have developed a carbonylative approach to the synthesis of diversely substituted 2-aroylbenzoate esters featuring a new protocol for the carbonylative coupling of aryl bromides with boronic acids and a new strategy to favour carbonylative over non-carbonylative reactions. Two different synthetic pathways-(i) the alkoxycarbonylation of 2-bromo benzophenones and (ii) the carbonylative Suzuki-Miyaura coupling of 2-bromobenzoate esters-were evaluated. The latter approach provided a broader substrate tolerance, and thus was the preferred pathway. We observed that 2-substituted aryl bromides were challenging substrates for carbonylative chemistry favouring the non-carbonylative pathway. However, we found that carbonylative Suzuki-Miyaura couplings can be improved by slow addition of the boronic acid, suppressing the unwanted direct Suzuki coupling and, thus increasing the yield of the carbonylative reaction.