71205-17-9

Usage

Uses

Used in Pharmaceutical Industry:
(E)-Methyl 3-(4-bromophenyl)acrylate is used as a key intermediate in the manufacturing of pharmaceuticals for its ability to contribute to the synthesis of various medicinal compounds.
Used in Agrochemical Industry:
In the agrochemical sector, (E)-Methyl 3-(4-bromophenyl)acrylate is utilized as a precursor in the production of agrochemicals, playing a role in the development of compounds for crop protection and enhancement.
Used in Organic Synthesis:
(E)-Methyl 3-(4-bromophenyl)acrylate is employed as a building block in organic synthesis for its capacity to form various organic compounds with potential applications in different fields.
Used in Asymmetric Catalysis:
(E)-Methyl 3-(4-bromophenyl)acrylate is also used as a reagent in the production of enantioenriched compounds through asymmetric catalysis, a technique crucial for creating chiral molecules with specific three-dimensional orientations, which are vital in pharmaceuticals and other industries.
Safety Considerations:
It is important to handle (E)-Methyl 3-(4-bromophenyl)acrylate with care, as it may pose health risks if ingested, inhaled, or comes into contact with the skin, highlighting the need for proper safety measures during its use in laboratories and industrial settings.

Upstream product

• 96-32-2 bromoacetic acid methyl ester 
• 1122-91-4 4-bromo-benzaldehyde 
• 67-56-1 methanol 
• 1200-07-3 3-(4-bromophenyl)acrylic acid 
• 589-87-7 1,4-bromoiodobenzene 
• 292638-85-8 acrylic acid methyl ester 
• 106-40-1 4-bromo-aniline 
• 105515-33-1 3-(4-bromophenyl)prop-2-en-1-ol 
• 106-37-6 1.4-dibromobenzene 
• 92846-10-1 tert-butyl 2-(4-bromophenyl)diazene-1-carboxylate 
• 79-20-9 acetic acid methyl ester 
• 186581-53-3 diazomethane 
• 1200-07-3 trans-4-bromocinnamic acid 
• 38788-38-4 dibutyl telluride 

Downstream Products

• 91329-32-7 3-(4-bromo-phenyl)-3-hydrazino-propionic acid hydrazide 
• 540481-48-9 methyl 3-(4-bromophenyl)-4-nitrobutyrate 
• 1155662-82-0 methyl (E)-3-(4'-thiophen-2-yl-phenyl)-acrylate 
• 1155662-80-8 methyl (E)-3-(4-pyridin-4-yl-phenyl)-acrylate 
• 1155662-85-3 methyl (E)-3-[4-(1H-indol-5-yl)-phenyl]-acrylate 
• 1160615-46-2 (1R,2R,3R)-1-methoxycarbonyl-trans-2-(4-bromophenyl)-cis-3-[(E)-2-(trimethylsilyl)vinyl]cyclopropane 
• 1196972-75-4 4-(4-bromophenyl)-3,4-dihydro-1H-quinolin-2-one 
• 1176888-27-9 (1E,3E)-1,4-bis(4-bromophenyl)buta-1,3-diene 
• 1097691-82-1 C₁₃H₁₈BrO₃P 
• 105515-33-1 3-(4-bromophenyl)prop-2-en-1-ol 
• 49678-04-8 4-bromocinnamaldeyde 
• 1264276-52-9 methyl (Z)-3-(4-bromophenyl)-3-(4-methoxyphenyl)acrylate 
• 1298117-18-6 C₂₄H₂₉NO₂ 
• 1422445-95-1 C₂₅H₃₁NO₂ 

Relevant academic research and scientific papers

Pd-Catalyzed desulfitative arylation of olefins by: N -methoxysulfonamide

A novel Pd-catalyzed protocol for the desulfitative Heck-type reaction of N-methoxy aryl sulfonamides with alkenes was reported. The cross-coupling reaction was performed successfully with a variety of olefins to obtain aryl alkenes. Different substituents on the aromatic ring of N-methoxysulfonamides were also found to be compatible with the reaction conditions. Expectedly, the reaction proceeds through CuCl2-promoted generation of the nitrogen radical and subsequent desulfonylation under thermal conditions to afford the aryl radical for the Pd-catalyzed coupling reaction. N-Methoxysulfonamide was further exploited for the synthesis of symmetrical biaryls in the presence of CuCl2. This journal is

Multiple-Functional Diphosphines: Synthesis, Characterization, and Application to Pd-Catalyzed Alkoxycarbonylation of Alkynes

A series of diphosphine ligands (L1-L5) containing bis-phosphino fragments and bis-amido groups as well as intensive electron-withdrawing F atoms were synthesized and fully characterized. The structures of the prepared complex of Pd-L5 demonstrate that as for L5, the incorporated two phosphino fragments participate in the chelation to the Pd center inversely along with two Cl-ligands to present a typical square-planar configuration, whereas the two amido groups simultaneously develop a hydrogen-bond interaction with Cl-ligands to facilitate the timely dissociation of Cl-ligands from the Pd center. It was found that L5 enabled the Pd complex to be more active in the alkoxycarbonylation of alkynes with MeOH for the synthesis of branched/linear α,β-unsaturated carboxylic esters with general yields of 60-89%. In L5, the incorporated diphosphino fragments, diamino groups, and F atoms conferred a catalytic effect to the Pd complex synergetic toward the reaction.

Crystallization-Based Synthetic Route to Antimalarial Agent BRD5018: Diazocene Ring Formation via a Staudinger-aza-Wittig Reaction on an Azetidine-Ribose Template

The development of an entirely crystallization-based synthetic route to the antimalarial BRD5018 is described, which assembles a structurally complex bicyclic azetidine scaffold adorned with five stereogenic centers without the need for any chromatographic separations. A diastereoselective glycine ester Claisen rearrangement, diastereomeric salt resolution, and diastereoselective iodo-lactonization are utilized to provide an efficient access to three contiguous stereogenic centers on an acyclic template with the desired relative and absolute configurations. A tandem aziridine ring-opening/azetidine ring-closure on the derived 2-amino-1,4-diol template was developed to efficiently establish the all-cis trisubstituted azetidine scaffold with the proper ancillary functionality for end-game maneuvers. d-Ribose-2,3-acetonide provided a conveniently differentiated vicinal syn-diol suitable for the planned reductive amination/periodate cleavage/Staudinger-aza-Wittig sequence to form the eight-membered diazocene ring. An early quantitative installation of the diaryl acetylene moiety via a Sonogashira coupling on an electronically matched methyl 4-bromocinnamate circumvented a low-yielding, late-stage reaction in the first-generation synthesis. Multiple crystalline intermediates enabled the complete removal of chromatography from the synthesis resulting in a substantially reduced cost and waste generation with enhanced throughput and quality control.

Chiral sulfoxide containing styrene monomer and preparation method thereof

The present invention relates to a chiral sulfoxide containing a styrene monomer and a preparation method thereof. The chiral sulfoxide containing a styrene monomer comprises chiral sulfoxide, a styrene monomer and an extended chain located between the ch

Aryl alkylamine compound, preparation method thereof and application of aryl alkylamine compound in medicines

The invention relates to an aryl alkylamine compound, a preparation method thereof and application of the aryl alkylamine compound in medicines. Particularly, the compound disclosed by the invention is suitable for being used as a calcium-sensitive recept

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.

Hydrogen peroxide based oxidation of hydrazines using HBr catalyst

Azo compounds (RN = NR′) are an important class of organic molecules that find wide application in organic synthesis. Herein, we report an efficient, practical and metal-free oxidation of hydrazines (RNH-NHR’) to azo compounds using 5 mol% HBr and hydrogen peroxide as terminal oxidant. This new method has been demonstrated by 40 examples with excellent yields. In addition, we showcased two examples of the one-pot sequential reactions involving our hydrazine oxidation/hydrolysis/Heck reaction or Cu-catalyzed N-arylation with aryl boronic acid. The distinct advantages of this protocol include metal-free catalysis, waste prevention, and easy operation.

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.

Oxoammonium-Mediated Allylsilane–Ether Coupling Reaction

A new C(sp3)?H functionalization reaction consisting of the oxidative α-allylation of allyl- and benzyl- methyl ethers has been developed. The C?C coupling could be carried out under mild conditions thanks to the use of cheap and green oxoammonium salts. The scope of the reaction was studied over 27 examples, considering the nature of the substituents on the two coupling partners.

METHOD FOR SYNTHESIS OF DIAZABICYCLO[6.2.0]DECANE RELATED COMPOUNDS

A method for the synthesis of diazabicyclo[6.2.0]decane compounds is provided. The synthesis proceeds by stereoselective synthesis of a chiral lactone followed by azetidine formation via a series of chemoselective reactions. Bicyclization results with the