50363-84-3

Usage

Uses

Used in Fragrance and Flavoring Industry:
(Z)-methyl 3-(4-methylphenyl)propenoate is used as a key ingredient in the fragrance and flavoring industry for its sweet, fruity, and slightly balsamic aroma. This characteristic makes it a valuable addition to various products, such as perfumes, colognes, and flavorings for the food and beverage industry.
Used in Pharmaceutical Research:
(Z)-methyl 3-(4-methylphenyl)propenoate is used as a subject of pharmaceutical research due to its potential antioxidant, anti-inflammatory, and anti-cancer properties. These pharmacological activities suggest that the compound may have therapeutic applications in the treatment of various diseases and conditions, making it a promising candidate for further investigation and development.
Used in Cosmetics Industry:
In the cosmetics industry, (Z)-methyl 3-(4-methylphenyl)propenoate is used as an additive for its pleasant aroma and potential skin care benefits. Its antioxidant and anti-inflammatory properties may contribute to the development of products that promote skin health and well-being.
Used in the Agricultural Industry:
(Z)-methyl 3-(4-methylphenyl)propenoate may also find applications in the agricultural industry, particularly as a natural pesticide or repellent due to its strong aroma and potential biological activities. Further research and development in this area could lead to the creation of environmentally friendly and effective pest control solutions.

Upstream product

• 67-56-1 methanol 
• 1866-39-3 4-methylcinnamic acid 
• 79-20-9 acetic acid methyl ester 
• 104-87-0 4-methyl-benzaldehyde 
• 96-32-2 bromoacetic acid methyl ester 
• 13565-07-6 4-methylcinnamoyl chloride 
• 459-44-9 4-methylbenzenediazonium tetrafluoroborate 
• 292638-85-8 acrylic acid methyl ester 
• 624-31-7 4-tolyl iodide 
• 1005421-77-1 tris(para-tolyl)antimony diacetate 
• 111873-48-4 (carbomethoxymethyl)dibutyltelluronium bromide 
• 74-88-4 methyl iodide 
• 21204-67-1 methyl (triphenylphosphoranylidene)acetate 
• 1070879-04-7 C₂₁H₁₉O₅PS 

Downstream Products

• 946-99-6 methyl 3-(4-bromomethyl)cinnamate 
• 59339-61-6 (trans)-methyl 2,3-dibromo-3-(p-tolyl)propanoate 
• 34966-53-5 methyl 4-methylphenylglyoxylate 
• 157087-14-4 (2R,3R)-3-p-Tolyl-oxirane-2-carboxylic acid methyl ester 
• 84009-57-4 5-Oxo-2,3-di-p-tolyl-cyclopentanecarboxylic acid methyl ester 
• 188524-66-5 4-p-Tolyl-1H-pyrrole-3-carboxylic acid methyl ester 
• 1393880-66-4 (S)-methyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(p-tolyl)propanoate 
• 96000-21-4 1-(3-chloro-1-propenyl)-4-methylbenzene 

Relevant academic research and scientific papers

Z-Selective phosphine promoted 1,4-reduction of ynoates and propynoic amides in the presence of water

Phosphine-mediated reductions of substituted propynoic esters and amides in the presence of water yield the partially reduced α,β-unsaturated esters and amides with highZ-selectivity. The competitivein situ ZtoE-isomerization of the product in some cases lowers theZtoEratios of the isolated α,β-unsaturated carbonyl products. Reaction time and the amounts of phosphine and water in the reaction mixture are the key experimental factors which control the selectivity by preventing or reducing the rates ofZ- toE-product isomerization. Close reaction monitoring enables isolation of theZ-alkenes with high selectivities. The computational results suggest that the reactions could be highlyZ-selective owing to the stereoselective formation of theE-P-hydroxyphosphorane intermediate.

Triazine-hyperbranched polymer-modified magnetic nanoparticles-supported nano-cobalt for C–C cross-coupling reactions

Design of hyperbranched polymers (HBPs) and crafting them in catalytic systems especially in organic chemistry are a relatively unexplored domain. This paper reports the utilization of triazine-hyperbranched polymer (THBP)-coated magnetic chitosan nanoparticles (MCs) as stabilizing matrix for cobalt nanoparticles. Cobalt nanoparticles were fabricated by coordination cobalt(II) ions with amine-terminated triazine polymer and then reduced into Co(0) using sodium borohydride in aqueous medium. The Co(0)-THBP@MCs were fully characterized by FT-IR, SEM–EDX, TEM, and TGA analyses. The presence of metallic cobalt was determined by ICP and XRD techniques. This novel hyperbranched polyaromatic polymer-encapsulated cobalt nanoparticles showed high catalytic activity in Mizoroki–Heck and Suzuki–Miyaura cross-coupling reactions. Heck and Suzuki reactions were carried out using 0.35 and 0.4?mol% of cobalt nanoparticles in which the turnover number (TON) values were calculated as 271 and 225, respectively. In addition, the produced heterogeneous catalyst could be recovered and reused without considerable loss of activity. Oxygen stability and high reusability over 7 runs with trace leaching of the cobalt into the reaction media as well as moisture stability of the immobilized cobalt nanoparticles are their considerable worthwhile advantages.

Palladium and silk fibroin-containing magnetic nano-biocomposite: a highly efficient heterogeneous nanocatalyst in Heck coupling reactions

Supported metal catalysts, for instance, palladium, are one of the foundations of chemical reactions, especially in C–C bond formation. The present study reports preparation of a magnetically separable palladium-supported nano-biocomposite with a low cost and easy immobilization technique. Fibroin, a natural biodegradable polymer, was used through an in situ method to cover the Fe3O4 nanoparticles to make a nano-biocomposite followed by anchoring palladium on the fibroin surface. The morphology and the structure of palladium-supported nano-biocomposite Fe3O4@fibroin-Pd were characterized by FT-IR, XRD, TGA, SEM, EDX, and TEM techniques. Consequently, the nanocatalyst activity was evaluated in the Heck coupling reactions. Only a very small amount of the nanocatalyst was employed in the reaction, and it showed excellent catalytic activity; in most cases more than 90% efficiency. The significant advantages of employing this nanocatalyst include high catalytic activity, short reaction times, easy separation of the nanocatalyst with an external magnet and great reusability. The results demonstrated that the used nanocatalysts were very active for four consecutive reaction rounds.

A Practice of Reticular Chemistry: Construction of a Robust Mesoporous Palladium Metal-Organic Framework via Metal Metathesis

Constructing stable palladium(II)-based metal-organic frameworks (MOFs) would unlock more opportunities for MOF chemistry, particularly toward applications in catalysis. However, their availability is limited by synthetic challenges due to the inertness of the Pd-ligand coordination bond, as well as the strong tendency of the Pd(II) source to be reduced under typical solvothermal conditions. Under the guidance of reticular chemistry, herein, we present the first example of an azolate Pd-MOF, BUT-33(Pd), obtained via a deuterated solvent-assisted metal metathesis. BUT-33(Pd) retains the underlying sodalite network and mesoporosity of the template BUT-33(Ni) and shows excellent chemical stability (resistance to an 8 M NaOH aqueous solution). With rich Pd(II) sites in the atomically precise distribution, it also demonstrates good performances as a heterogeneous Pd(II) catalyst in a wide application scope, including Suzuki/Heck coupling reactions and photocatalytic CO2 reduction to CH4. This work highlights a feasible approach to reticularly construct noble metal based MOFs via metal metathesis, in which various merits, including high chemical stability, large pores, and tunable functions, have been integrated for addressing challenging tasks.

Highly Regio- A nd Enantioselective Hydrogenation of Conjugated α-Substituted Dienoic Acids

Highly regio- A nd enantioselective hydrogenation of conjugated α-substituted dienoic acids was realized for the first time using Trifer-Rh complex, providing a straightforward method for the synthesis of chiral α-substituted ?,?′-unsaturated acids. DFT calculations revealed N+H-O hydrogen bonding interaction is formed to stabilize the transition state and the coordination of 4,5-double bond to Rh(III) center would facilitate the reductive elimination process. This hydrogenation provided a gram-scale synthesis of the precursor of sacubitril.

Palladium Ion Catalysed Oxidative C–C Bond Formation Reactions in Arylboronic Acid: Application of Cordierite Monolith Coated Catalyst

Abstract: Catalytic efficiency of palladium ion substituted in TiO2, Ti0.97Pd0.03O1.97 is successfully exploited for the oxidative homocoupling of arylboronic acid and oxidative Heck coupling reactions between arylboronic acid and olefins. The reaction protocol provides direct approach to synthesize biphenyls and cinnamates from moderate to good yield with good functional group tolerance. As a result, 11 symmetrical biaryls and 14 cinnamates were synthesized from readily available arylboronic acids. Ti0.97Pd0.03O1.97 powder catalyst is synthesized by solution combustion method and characterized by powder X-ray diffraction. The C–C bond formation reactions were carried out by catalyst cartridge method using Ti0.97Pd0.03O1.97 catalyst coated cordierite monolith. Coating of the catalyst on a cordierite monolith enhanced the applicability of the catalyst and made handling and recycling of the catalyst very easy. Catalyst was recovered and recycled for eight times in both homocoupling and oxidative Heck coupling reactions. The turnover number for both the reactions found to be 443 and 424, respectively. Graphic Abstract: [Figure not available: see fulltext.].

Sodium pyruvate as a peroxide scavenger in aerobic oxidation under carbene catalysis

NHC-Catalyzed aerobic oxidative reactions of imines and aldehydes have been developed by using sodium pyruvate as a novel and efficient peroxide scavenger. A structurally diverse set of imidates and amidines has been prepared from imines using this strategy. This general and efficient strategy features the use of sodium pyruvate as a novel and efficient peroxide scavenger and ambient air as the sole oxidant to efficiently control the NHC-catalyzed aerobic reaction pathway (selective realization of the oxidative pathway) under mild and green conditions. This journal is

Synthesis and characterization of mesoporous organosilica supported palladium (SBA-Pr-NCQ-Pd) as an efficient nanocatalyst in the Mizoroki–Heck coupling reaction

In the present study, the modification of a mesoporous organosilica nanocomposite SBA-15 (Santa Barbara Amorphous 15) was carried out in two steps, first through the surface functionalization of SBA-Pr-NH2 with 2-chloroquinoline-3-carbaldehyde to form SBA-Pr-NCQ, and then through a post-modification process with palladium ions. The target nanocompound structure of SBA-Pr-NCQ-Pd was characterized by different techniques (thermogravimetric analysis, X-ray diffraction, scanning electron microscopy, Energy-dispersive X-ray spectroscopy (EDX), and Fourier transform infrared spectroscopy). The catalytic performance of the porous inorganic–organic hybrid nanocomposite (SBA-Pr-NCQ-Pd) in one of the most important carbon–carbon bond-forming processes, the Mizoroki–Heck coupling reaction of aryl halides and methacrylate in water/ethanol media, was examined. Compared to previous reports, this protocol afforded some advantages, such as high yields of products, short reaction times, catalyst stability without leaching, simple methodology, easy workup, and greener conditions. Also, the nanocatalyst can be easily separated from the reaction mixture and reused several times without a significant decrease in activity and promises economic as well as environmental benefits.

Highly effective cellulose supported 2-aminopyridine palladium complex (Pd(II)-AMP-Cell?Al2O3) for Suzuki-Miyaura and Mizoroki–Heck cross-coupling

In the present work, a novel, highly efficient, retrievable organo–inorganic hybrid heterogeneous catalyst (Pd(II)-AMP-Cell?Al2O3) has been prepared by covalent grafting of 2-aminopyridine on chloropropyl modified cellulose-alumina composite followed by complexation with palladium acetate. The catalyst was characterized by techniques such as scanning electron microscopy (SEM), transmission electron microscopy (TEM), energy dispersive X-ray spectroscopy (EDX), X-ray diffraction (XRD), inductive coupled plasma-atomic emission spectroscopy (ICP-AES) and thermo gravimetric analysis (TGA). The catalyst has been successfully employed in Suzuki-Miyaura as well as Mizoroki–Heck cross-coupling reactions. The reactions proceed smoothly resulting in the high yields of cross-coupling products (81 to 95%) within short reaction times. The catalyst can be efficiently recovered by simple filtration and reused for multiple cycles without considerable loss in the catalytic activity. The key-features of the present protocol include mild reaction conditions, simple work-up procedure, high stability of the catalyst, high turnover number (TON) and frequency (TOF), ease recovery and reusability of the catalyst.

Biogenic synthesis of palladium nanoparticles using Boswellia sarrata and their applications in cross-coupling reactions

A facile and green route for biogenic synthesis of palladium nanoparticles (PdNPs) using aqueous extract of nontoxic and renewable Boswellia sarrata leaves is reported. The as-synthesized PdNPs were systematically characterized by using ultraviolet (UV)–visible spectroscopy, X-ray diffraction analysis, scanning electron microscopy, transmission electron microscopy, energy-dispersive X-ray spectroscopy, and X-ray photoelectron spectroscopy. The PdNPs were crystalline and cubic in nature with average particle size of ~6 nm and successfully employed as heterogeneous catalyst in the Suzuki–Miyaura and Mizoroki–Heck cross-coupling reactions. The PdNPs could be recycled up to five times with modest change in the catalytic activity.