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

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.

Recyclable Pd ionic catalyst coated on cordierite monolith for high TOF Heck coupling reaction

Abstract : Pd 2 + ionic catalyst, Ti 0.97Pd 0.03O 1.97 was coated over cordierite monolith by solution combustion method. The catalyst coated on the cordierite is nano-crystalline as seen from XRD studies. Coated catalyst was used for Heck coupling reactions with different substrates of aryl halides and olefins. Thus handling nano-crystalline catalyst powder is avoided by fixing it on a solid catalyst cartridge. Heck coupled products were characterized using 1H NMR, 13C NMR, Mass and FTIR spectroscopy. This catalyst showed high selectivity towards Heck coupling reaction. Turnover frequencies (TOF) for each of the reactions were found to be very high. The catalyst was recycled up to 7 times with total TOF 3017 h - 1, which is found to be a new green technique in the Heck coupling reaction. Graphical abstract: Ti 0.97Pd 0.03O 1.97 catalyst is coated on cordierite monolith honeycomb (HC) by solution combustion method and it is used in the Heck coupling reaction. Reactions are done in a specially designed flask. Catalyst is recycled for 7 times. The total turnover frequency (TOF) after 7 cycles was 3017 h - 1. [Figure not available: see fulltext.].

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.

"nok": A phytosterol-based amphiphile enabling transition-metal-catalyzed couplings in water at room temperature

The third-generation designer amphiphile/surfactant, "Nok" (i.e., SPGS-550-M; β-sitosterol methoxypolyethyleneglycol succinate), soon to be commercially available from Aldrich, can be prepared in two steps using an abundant plant feedstock and β-sitosterol, together with succinic anhydride and PEG-550-M. Upon dissolution in water, it forms nanomicelles that serve as nanoreactors, which can be characterized by both cryo-TEM and dynamic light scattering analyses. Several transition-metal-catalyzed reactions have been run under micellar conditions to evaluate this surfactant relative to results obtained in nanoparticles composed of TPGS-750-M (i.e., a second-generation surfactant). It is shown that Nok usually affords yields that are, in general, as good or better than those typically obtained with TPGS-750-M, and yet is far less costly.

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.

Mechanistic insights into palladium leaching in novel Pd/C-catalyzed boron-heck reaction of arylboronic acid

For the first time, Pd/C has been used for the Boron-Heck reaction, and the detailed mechanistic aspects of the reaction have been proven experimentally by a leaching test as well as by cyclic voltammetry studies. The results indicate that palladium leaching as a Pd(II) species, by oxidative addition of the arylboronic acid, is responsible for the reaction. Georg Thieme Verlag Stuttgart - New York.

Interfacially cross-linked reverse micelles as soluble support for palladium nanoparticle catalysts

Reverse micelles (RM) were formed in heptane/CHCl3 with a surfactant carrying the triallylammonium (=triprop-2-en-1-ylammonium) head group (Scheme). Photo-cross-linking with dithiothreitol (=rel-(2R,3R)-1,4- dimercaptobutane-2,3-diol; DTT) captured the RMs and afforded organic, soluble nanoparticles in a one-step reaction. Similar to dendrimers, the cross-linked reverse micelles could encapsulate palladium nanoparticles within their hydrophilic cores and protect them in catalytic reactions. Good to excellent yields were obtained in the Heck coupling of a range of alkyl acrylates (=alkyl prop-2-enoates) and iodobenzenes (Tables 1 and 2). The catalytic activity of the palladium nanoparticles was maintained in several repeated runs.

Microwave-assisted ligand-free, base-free Heck reactions in a task-specific imidazolium ionic liquid

1-(2-cyanoethyl)-3-(2-hydroxyethyl)-1H-imidazol-3-ium tetrafluoroborate (IL-2) in presence of PdCl2 was found to be an efficient and reusable, ligand-free, base-free catalytic system for Heckcoupling of activated and deactivated iodo-and bromoarenes with different olefins. Under microwave irradiation, it exhibited good efficiency in terms of activity, selectivity and recyclability for six consecutive runs without significant loss of activity. ARKAT-USA, Inc.

Study on the Heck reaction promoted by carbene adduct of cyclopalladated ferrocenylimine and the related reaction mechanism

Carbene adduct of cyclopalladated ferrocenylimine has been successfully applied to Heck reaction of various aryl bromides with olefins. On the basis of kinetic studies, in situ 13C NMR spectra investigations and Hg poisoning experiments, it was proposed that the Heck reaction catalyzed by carbene adduct of cyclopalladated ferrocenylimine proceeded through a classical Pd(0)/Pd(II) cycle and such palladacycle was only a reservoir of the catalytically active Pd(0) species.