80856-29-7

Basic information

• Product Name: phenyl (Z)-2-methyl-2-butenoate
• Synonyms: phenyl (Z)-2-methyl-2-butenoate
• CAS NO: 80856-29-7
• Molecular Weight: 176.215
• Mol File: 80856-29-7.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: phenyl (Z)-2-methyl-2-butenoate(CAS DataBase Reference)
• NIST Chemistry Reference: phenyl (Z)-2-methyl-2-butenoate(80856-29-7)
• EPA Substance Registry System: phenyl (Z)-2-methyl-2-butenoate(80856-29-7)

Safety Data

• Hazardous Substances Data: 80856-29-7(Hazardous Substances Data)

Upstream product

• 35660-94-7 (E)-2-methylbut-2-enoyl chloride 
• 108-95-2 phenol 
• 1529-17-5 phenyltrimethylsilyl ether 
• 55517-33-4 tiglic acid trimethylsilyl ester 
• 80-59-1 Tiglic acid 

Relevant articles and documents

Iridium(I)-catalyzed C-H borylation of α,β-unsaturated esters with bis(pinacolato)diboron

A new process has been developed for the iridium(I)-catalyzed vinylic C-H borylation of α,β-unsaturated esters with bis(pinacolato)diboron (B2pin2). These reactions proceeded in octane at temperatures in the range of 80-120 °C to afford the corresponding alkenylboronic compounds in high yields with excellent regio- and stereoselectivities. The presence of an aryl ester led to significant improvements in the yields of the acyclic alkenylboronates. Crossover experiments involving deuterated substrates as well as a mixture of stereoisomers confirmed that this reaction proceeds via a 1,4-addition/β-hydride elimination mechanism. Notably, this reaction was also used to develop a one-pot borylation/Suzuki-Miyaura cross-coupling procedure. A lucky strike with B2pin2: A new method has been developed for the vinylic C-H borylation of α,β-unsaturated esters with bis(pinacolato)diboron (B2pin2) using iridium(I) catalysts. These reactions proceeded in octane at 80-120 °C to afford the alkenylboronic compounds in high yields with excellent regio- and stereoselectivities.

13C-NMR. Spectral Differences between Corresponding Methyl Esters, Phenyl Esters and 2-Substituted Chromones

The 13C-NMR. spectra of 2-substituted chromones (3) are compared with the data of the analogous methyl and phenyl esters (1 and 2).The chemical shift differences found are most prominent for the C-atoms in β-position to the ester carbonyl and chromone C(2), respectively.These shift differences are discussed in terms of conformational differences between the esters 1 and 2 and the analogous chromones 3.