131061-15-9

Basic information

• Product Name: 2-Propenoic acid, 3-(4-nitrophenyl)-, butyl ester, (2E)-
• CAS NO: 131061-15-9
• Molecular Formula: C13H15NO4
• Molecular Weight: 249.266
• Mol File: 131061-15-9.mol
• Article Data: 242

Chemical Properties

• CAS DataBase Reference: 2-Propenoic acid, 3-(4-nitrophenyl)-, butyl ester, (2E)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Propenoic acid, 3-(4-nitrophenyl)-, butyl ester, (2E)-(131061-15-9)
• EPA Substance Registry System: 2-Propenoic acid, 3-(4-nitrophenyl)-, butyl ester, (2E)-(131061-15-9)

Safety Data

• Hazardous Substances Data: 131061-15-9(Hazardous Substances Data)

Upstream product

• 636-98-6 p-nitrobenzene iodide 
• 141-32-2 acrylic acid n-butyl ester 
• 98-74-8 4-Nitrobenzenesulfonyl chloride 
• 586-78-7 para-nitrophenyl bromide 
• 122-04-3 4-nitro-benzoyl chloride 
• 24067-17-2 4-nitrophenylboronic acid 
• 623-00-7 4-bromobenzenecarbonitrile 
• 1643-19-2 tetrabutylammomium bromide 
• 100-00-5 4-chlorobenzonitrile 
• 292638-85-8 acrylic acid methyl ester 
• 52707-93-4 N-(4-nitrobenzoyl)saccharin 
• 456-27-9 4-nitrobenzenediazonium tetrafluoroborate 
• 98-95-3 nitrobenzene 
• 15959-31-6 sodium 4-nitrobenzenesulfinate 

Downstream Products

• 62-23-7 4-nitro-benzoic acid 
• 86622-82-4 n-butyl 3-[4-(piperazin-1-yl)-phenyl]-propionate 

Relevant articles and documents

Palladium-grafted mesoporous MCM-41 material as heterogeneous catalyst for Heck reactions

Palladium grafted mesoporous MCM-41 materials, prepared by vapor grafting, show remarkable activity in Heck carbon-carbon coupling reactions.

Green synthesis of palladium nanoparticles using Pistacia atlantica kurdica gum and their catalytic performance in Mizoroki-Heck and Suzuki-Miyaura coupling reactions in aqueous solutions

A one-pot green method for the synthesis of palladium nanoparticles (Pd-NPs) supported on Pistacia atlantica kurdica (P. a. kurdica) gum is described. This natural gum is used as a reducing and stabilising agent. The formation of the Pd-NPs/P. a. kurdica gum catalyst was verified using several techniques, such as Fourier transform infrared spectroscopy, ultraviolet-visible spectrophotometry, scanning and transmission electron microscopies, X-ray diffraction, energy-dispersive X-ray spectroscopy, dynamic light scattering and wavelength-dispersive X-ray spectroscopy. The Pd-NPs stabilised by P. a. kurdica gum were employed as a heterogeneous catalyst in Mizoroki-Heck and Suzuki-Miyaura cross-coupling reactions at low palladium loading (0.1 mol%) under aerobic, phosphine-free and ligand-free conditions in water. Product yields of up to 98%, a facile work-up, no evidence of leached palladium from the catalyst surface and smooth recovery of the catalyst, which can be reused at least eight times, confirm the efficiency of the catalysts in the reactions investigated.

Palladium was supported on superparamagnetic nanoparticles: A magnetically recoverable catalyst for Heck reaction

A novel and high-performance palladium-based catalyst for Heck reaction was prepared easily by the co-precipitation method. The catalyst was characterized by transmission electron microscopy (TEM), X-ray powder diffraction (XRD), vibrating sample magnetometry (VSM), X-ray photoelectron spectroscopy (XPS) and atomic absorption spectrophotometry (AAS). The catalyst afforded a fast conversion of the 4-bromonitrobenzene to 4-nitrostilbene at a catalyst loading of 5 mol%, and the efficiency of the catalyst remains unaltered even after 6 repeated cycles. The excellent catalytic performance of the Pd/Fe 3O4 catalyst might be attributed to the enhanced synergistic effect between Pd nanoparticles and magnetite.

Anchored complexes of Ni, Pt, and Pd on Fe3O4 nanoparticles as new and eco-friendly nanocatalysts in Suzuki and Heck coupling reactions

Three recoverable nanocatalysts were developed by immobilizing Ni, Pt, and Pd Schiff-base complexes on the magnetite nanoparticles. Successful preparation of the nanocatalysts was evidenced by Fourier transform infrared (FT-IR) and energy dispersive X-ray (EDX) spectroscopy. Nano-sized spherical structure of the nanocatalysts was indicated by scanning electron microscopy (SEM). X-ray powder diffraction (XRD) determined that the crystalline cubic spinel structure of Fe3O4 remained constant through the synthesis of three complexes on Fe3O4 nanoparticles. Magnetic properties of the nanocatalysts were analyzed by the vibration sample magnetometer (VSM). Thermostability of the nanocatalysts was studied by thermogravimetric analysis (TGA). Metal loading of these nanocatalysts was evidenced by inductively coupled plasma atomic emission (ICP-AES). Investigating the catalytic activity of these nanocatalysts in Suzuki and Heck reactions implicated that in the presence of Pd nanocatalyst coupling reactions proceeded efficiently. For Pt nanocatalyst, Suzuki reaction took place in longer time with moderate to good yield. For the Heck reaction, the desired products were achieved only for aryl iodide and some aryl bromides. The Ni nanocatalyst could just catalyze the Suzuki reaction. Relying on the magnetic characteristic, these nanocatalysts could be simply recovered and reused several cycles without significant loss in catalytic activity.

Palladium-S-propyl-2-aminobenzothioate immobilized on Fe3O4 magnetic nanoparticles as catalyst for Suzuki and Heck reactions in water or poly(ethylene glycol)

A moisture- and air-stable heterogenized palladium catalyst was synthesized by coordination of palladium with S-propyl-2-aminothiobenzamide supported on Fe3O4 magnetic nanoparticles. The prepared nanocatalyst was characterized using Fourier transform infrared, energy-dispersive X-ray and inductively coupled plasma atomic emission spectroscopies, X-ray diffraction, vibrating sample magnetometry, transmission and scanning electron microscopies, dynamic laser scattering and thermogravimetric analysis. This catalyst could be dispersed homogeneously in water or poly(ethylene glycol) and further applied as an excellent nano-organometal catalyst for Suzuki and Heck reactions. The catalyst was easily separated with the assistance of an external magnet from the reaction mixture and reused for several consecutive runs without significant loss of its catalytic efficiency or palladium leaching. The leaching of catalyst was examined using hot filtration and inductively coupled plasma atomic emission spectroscopy. Also, the effects of various reaction parameters on the Suzuki and Heck reactions are discussed.

Palladium(II) complexes bearing the 1,2,3-triazole based organosulfur/ selenium ligand: Synthesis, structure and applications in Heck and Suzuki-Miyaura coupling as a catalyst via palladium nanoparticles

Air and moisture insensitive palladium complexes, [Pd(L)Cl2] (1/2), in which L = 1-benzyl-4-phenylthiomethyl or 1-benzyl-4-phenylselenomethyl-1H-1,2,3-triazole (L1 or L2) catalyze Heck (HC) and Suzuki-Miyaura coupling (SMC) reactions between a series of aryl bromides including deactivated bromides and n-butyl acrylate and phenylboronic acid, respectively. The optimal catalytic loading was found to be in the order of 0.01 mol%. HRTEM, TGA and EDX data indicated that 3-11 nm nanoparticles (NPs) composed of palladium and sulfur or selenium and protected with L or its fragment, were formed during the catalyzed reaction. The isolated NPs displayed catalytic activity and appeared to have a role in the catalysis. A two-phase test indicated that both homogeneous and heterogeneous catalysis took place. The complexes 1 and 2 were synthesized by the reactions of L1 and L2 respectively with [(MeCN)2PdCl2]. Their single crystal X-ray diffraction indicated that the geometry adopted by ligands around Pd in both complexes is distorted square planar with Pd-S and Pd-Se bond lengths of 2.2727(14) and 2.3693(8) A, respectively. DFT calculation gave bond lengths and angles in keeping with the experimental values. The DFT calculated HOMO-LUMO energy difference is lower for 1 than for 2 in accordance with the observed higher catalytic activity of 1.

New monodispersed palladium nanoparticles stabilized by poly-(N-vinyl-2-pyrrolidone): Preparation, structural study and catalytic properties

Mesitylene/1-hexene solvated palladium nanoparticles, obtained by metal vapour synthesis (MVS) technique, were stabilized in solution at room temperature with poly-(N-vinyl-2-pyrrolidone) (PVP) and isolated by precipitation with a diethyl ether or THF as brown powder. HRTEM and FT-IR analyses on samples with different Pd/PVP ratio (1%, 5%, 10%, 15%, 20 w/w%) showed palladium nanoparticles with mean diameters limited in the range 1.5-2.5 nm and the presence of competitive intermolecular interactions between CO groups and palladium atoms on nanoparticle surface. The Pd-PVP systems, dissolved in EtOH solvent, showed excellent catalytic activity and selectivity in the hydrogenation of aliphatic alkynes (1-hexyne, 2-hexyne, 3-hexyne, 3-hexyne-1-ol) to the corresponding (Z)-alkenes. The catalytic activity of Pd-PVP samples, dissolved in 1-methyl-2-pyrrolidinone (NMP), has been also evaluated in the Mizoroki-Heck C-C coupling reaction of iodobenzene and bromo-arenes with butyl acrylate showing high efficiency. Moreover, the catalyst can be quantitatively recovered at the end of the reaction by precipitation with diethyl ether and reused without significant loss of catalytic activity.

Polymer-supported palladium complexes with C,N-ligands as efficient recoverable catalysts for the Heck reaction

A series of new polymer-supported palladium complexes with C,N-ligands (1a-e and 2a-c) were easily synthesized. The synthesized catalysts could be applied as efficient heterogeneous catalysts for the Heck coupling reaction (turnover frequency up to 12 600 h-1). Additionally, the catalysts could be recovered by a simple filtration progress and could be reused for at least five times with a slow progressive decrease in activity. Copyright

A highly efficient palladium complex supported on MCM-41 nanocatalyst for Mizoroki–Heck and Suzuki–Miyaura cross-coupling reaction

Palladium-3,4-dihydroxybenzaldehyde complex supported on MCM-41 was synthesized by a post-grafting method as selective complex a and shows remarkable properties such as thermal and chemical stability, reusable, easily prepared from very cheap materials and can be used as an efficient and versatile catalyst for Mizoroki–Heck and Suzuki–Miyaura cross-coupling reaction. This catalyst was characterized by SEM, TEM, EDX, XRD, FT-IR, TGA, BET and ICP techniques. The synthesized Pd-BS-MCM-41 heterogeneous catalyst could be recovered easily and reused several times without significant loss of its catalytic activity. Further investigations showed that among different aryl halides that used for the synthesis of biaryls and butyl cinnamate derivatives, the reactivity of aryl iodides is higher than aryl bromides, and aryl chlorides. The heterogeneity manner of this nanocatalyst was confirmed via a hot filtration test.

A colorimetric high-throughput screening method for palladium-catalyzed coupling reactions of aryl iodides using a gold nanoparticle-based iodide-selective probe

Catching the couplings: A general and simple screening method for palladium-catalyzed coupling reactions of aryl iodides utilizes gold nanoparticles. This assay was successfully employed in several aminations, α-arylation of ketones, and decarboxylative couplings. 96 samples were screened in a few minutes. Copyright

Pd supported on clicked cellulose-modified magnetite-graphene oxide nanocomposite for C-C coupling reactions in deep eutectic solvent

Cellulose-modified magnetite-graphene oxide nanocomposite was prepared via click reaction and utilized for immobilization of palladium (Pd) nanoparticles without using additional reducing agent. The abundant OH groups of cellulose provided the uniform dispersion and high stability of Pd nanoparticles, while magnetite-graphene oxide as a supporting material offered high specific surface area and easy magnetic separation. The as-prepared nanocomposite served as a heterogeneous catalyst for the Heck and Sonogashira coupling reactions in various hydrophilic and hydrophobic deep eutectic solvents (DESs) as sustainable and environmentally benign reaction media. Among the fifteen DESs evaluated for coupling reactions, the hydrophilic DES composed of dimethyl ammonium chloride and glycerol exhibited the best results. Due to the low miscibility of catalyst and DES in organic solvents, the separated aqueous phase containing both of the catalyst and DES can be readily recovered by evaporating water and retrieved eight times with negligible loss of catalytic performance.

Reusable, magnetic Raney nickel based palladium catalysts for the Heck coupling in aqueous media

Hybrid materials based on Pd- and Cu-doped Raney nickel appeared to be highly efficient catalysts for the Heck reaction in aqueous media in the absence of organic cosolvents. The catalysts can be easily removed by an external magnet and reused without losing catalytic activity.

Palladium supported aminobenzamide modified silica coated superparamagnetic iron oxide as an applicable nanocatalyst for Heck cross-coupling reaction

An applicable palladium-based nanocatalyst was constructed through the immobilization of palladium onto 2-aminobenzamide functionalized silica coated superparamagnetic iron oxide magnetic nanoparticles. The nanocatalyst (named as Pd@ABA@SPIONs@SiO2) was characterized by several characterization methods, including scanning electron microscope (SEM), transmission electron microscopy (TEM), vibrating-sample magnetometry (VSM), energy-dispersive X-ray spectroscopy (EDS), dynamic light scattering (DLS), X-ray powder diffraction (XRD), Fourier transform infrared spectroscopy (FT-IR), inductively coupled plasma (ICP), and X-ray photoelectron spectroscopy (XPS) analyses. Microscopy results showed that the nanoparticles are spherical in shape with 20–25 nm size. The size of the nanoparticles was confirmed by the DLS method. The superparamagnetic nature of the catalyst was confirmed by the VSM method. The successful functionalization of SPIONs@SiO2 was confirmed by FT-IR spectroscopy. The presence of palladium in the structure of the nanocatalyst was illustrated by XRD and EDS analysis. Also using XPS technique, the oxidation state of palladium in Pd@ABA@SPIONs@SiO2 was determined zero before and after the catalyst was applied in Mizoroki-Heck reaction. Several aryl halides and alkenes were reacted in the presence of the nanocatalyst and formed the corresponding products in high isolated yields. The nanocatalyst showed very good reusability and did not decrease its activity after 10 sequential runs. Density functional theory (DFT) calculation was performed to provide a mechanism for the reaction and confirmed the role of the palladium catalyst in the reaction function.