89330-93-8

Basic information

• Product Name: 2-Butenedioic acid, 2-phenyl-, dimethyl ester
• Synonyms: 2-Butenedioic acid, 2-phenyl-, dimethyl ester
• CAS NO: 89330-93-8
• Molecular Formula: C12H12O4
• Molecular Weight: 220.225
• Mol File: 89330-93-8.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 2-Butenedioic acid, 2-phenyl-, dimethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Butenedioic acid, 2-phenyl-, dimethyl ester(89330-93-8)
• EPA Substance Registry System: 2-Butenedioic acid, 2-phenyl-, dimethyl ester(89330-93-8)

Safety Data

• Hazardous Substances Data: 89330-93-8(Hazardous Substances Data)

Upstream product

• 582-25-2 Potassium benzoate 
• 762-42-5 dimethyl acetylenedicarboxylate 
• 67-56-1 methanol 
• 201230-82-2 carbon monoxide 
• 536-74-3 phenylacetylene 

Relevant articles and documents

Decarboxylative olefination of potassium benzoates via bimetallic catalysis strategy

Abstract: A novel synthesis of styrene derivatives through decaroxylative olefination of potassium benzoates with alkynes using Pd2dba3/CuBr as catalyst system has been developed. The protocol proceeded smoothly and in most cases Z-alkene was the main product. Electron-rich potassium benzoates reacted more efficiently than those of electron-deficient substrates. Heteroaromatic and electron-deficient aryl alkynes were not consistent with this transformation. Graphical abstract: [Figure not available: see fulltext.].

Mechanisms by which alkynes react with CpCr(CO)3H. Application to radical cyclization

The reaction of CpCr(CO)3H with activated alkynes in benzene has been examined. The kinetics of these reactions have been studied with various alkynes, along with the stereochemistry with which the alkynes are hydrogenated. The hydrogenation of phenyl acetylene and diphenyl acetylene with CpCr(CO) 3H has been shown to occur by a hydrogen atom transfer (HAT) mechanism. The reaction of CpCr(CO)3H with dimethyl acetylenedicarboxylate (DMAD) produced hydrogenated products as well as phenyl substitution from reaction with solvent. On the basis of kinetic data, it is thought that the reaction of DMAD may proceed via a single electron transfer (SET) as the rate-determining step. The radical anion of dimethylfumarate was observed by EPR spectroscopy during the course of the reaction, supporting this claim. The aromatic 1,6 eneyne (8) gave cyclized products in 78% yield under catalytic conditions (35 psi H2), presumably by the 5-exo-trig cyclization of the vinyl radical arising from H? transfer. Using a cobaloxime catalyst (12) hydrogenation was completely eliminated to yield 100% cyclized products.

A novel stereoselective synthesis of maleate derivatives via palladium- catalyzed dicarboalkoxylation of terminal alkynes

Alkynes were dicarboalkoxylated efficiently and stereoselectively in high yields reacting for about 2h under atmospheric pressure of carbon monoxide at room temperature using a catalytic amount of PdCl2 and a stoichiometric amount of CuCl2