217324-58-8

Basic information

• Product Name: 2-Propenoic acid, 3-phenyl-, 2-ethylhexyl ester, (2E)-
• Synonyms: 2-Propenoic acid, 3-phenyl-, 2-ethylhexyl ester, (2E)-
• CAS NO: 217324-58-8
• Molecular Formula: C17H24O2
• Molecular Weight: 260.37126
• Mol File: 217324-58-8.mol
• Article Data: 16

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-Propenoic acid, 3-phenyl-, 2-ethylhexyl ester, (2E)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Propenoic acid, 3-phenyl-, 2-ethylhexyl ester, (2E)-(217324-58-8)
• EPA Substance Registry System: 2-Propenoic acid, 3-phenyl-, 2-ethylhexyl ester, (2E)-(217324-58-8)

Safety Data

• Hazardous Substances Data: 217324-58-8(Hazardous Substances Data)

Upstream product

• 108-86-1 bromobenzene 
• 103-11-7 2-Ethylhexyl acrylate 
• 108-90-7 chlorobenzene 
• 591-50-4 iodobenzene 
• 98-80-6 phenylboronic acid 
• 873-66-5 1-propenylbenzene 

Relevant articles and documents

Olefin Metathesis, p-Cresol, and the Second Generation Grubbs Catalyst: Fitting the Pieces

p-Cresol as additive to the Grubbs second generation catalyst (GII) allows the cross-metathesis of acrylates with prop-1-en-1-ylbenzenes under conditions that only give the prop-1-en-1-ylbenzene self-metathesis product in the absence of cresol. NMR and IR spectroscopy, MALDI-TOF MS and XPS supported the formation of a ruthenium benzylidene with hydrogen bonds between p-cresol and the chloride ligands of GII. XPS furthermore confirmed p-cresol to increase the binding energies of the GII Ru 3d5/2, 3d3/2, 3p3/2 and 3p1/2 photoelectron lines, whereas 1H NMR spectroscopy indicated the carbene carbon and hydrogen to be shielded. It is thus postulated that p-cresol allows for more facile interaction between electron-deficient compounds and the ruthenium benzylidene by decreasing the electron density on the metal center and increasing the electron density on the carbene.

Palladium-catalyzed Mizoroki-Heck reactions in water using thermoresponsive polymer micelles

Palladium-catalyzed Mizoroki-Heck reactions were carried out in water using thermoresponsive polymer micelles. The micelles were generated from thermoresponsive block copolymers consisting of a poly(N-isopropylacrylamide) (PNIPAAm) segment and a hydrophilic segment such as nonionic poly(ethylene glycol) (PEG) (2) and anionic poly(sodium p-styrenesulfonate) (PSSNa) (9). These copolymers exhibited lower critical solution temperature (LCST) behavior at ca. 40–50 °C and showed thermal stimuli-induced formation and dissociation of micelles. The copolymers formed micelles in aqueous solution at higher temperature, where catalytic reactions proceeded. At lower temperature, the micelles dissociated to form a clear solution, enabling efficient extraction of the products from aqueous reaction mixture. In the presence of these copolymers, palladium complexes catalyzed the coupling reactions between aryl iodides and alkene compounds inside the hydrophobic micelle cores in water under relatively milder conditions. Extraction of the products from the aqueous solution of 2 or 9 was found to be efficient enough in comparison with conventional surfactants.

Investigation of sol-gel supported palladium catalysts for Heck coupling reactions in o/w-microemulsions

Sol-gel supported palladium catalysts are investigated for the Heck coupling reaction between styrene and iodo-/bromobenzene to trans-stilbenes in o/w-microemulsions as alternative reaction medium. High conversions and selectivities are obtained with these catalysts and they show better catalytic performance than their commercial analogs Pd@SiO2 or Pd/C. The influence of the catalyst structure on the activity is investigated in detail showing mass transport limitations that can be optimized by the palladium loading. The catalyst is recyclable >6 times with negligible palladium leaching into the solution. Because of the good recyclability under retention of activity and selectivity, the influence of transport limitations is suppressed and the total catalyst efficiency is increased to more than 2.