1340-14-3

Usage

Uses

Used in Pharmaceutical Synthesis:
[(E)-2-bromoethenyl]benzene is used as a reagent for the synthesis of various pharmaceuticals. Its chemical structure allows for the creation of a diverse range of medicinal compounds, contributing to the development of new treatments and therapies.
Used in Agrochemical Production:
In the agrochemical industry, [(E)-2-bromoethenyl]benzene is utilized as a reagent for synthesizing different compounds used in agriculture. These compounds can include pesticides, herbicides, and other chemicals that help protect crops and enhance agricultural productivity.
Used in Polymer and Plastics Manufacturing:
[(E)-2-bromoethenyl]benzene also serves as a precursor in the production of polymers and plastics. Its role in this process is crucial for the development of new materials with specific properties, such as durability, flexibility, or heat resistance, which can be tailored for various applications in different industries.
Used in Chemical Research:
Due to its unique chemical properties, [(E)-2-bromoethenyl]benzene is employed in research settings to study various chemical reactions and mechanisms. It can be used to explore new methods of synthesis or to understand the behavior of similar compounds, furthering scientific knowledge in the field of chemistry.

Upstream product

• 64-17-5 ethanol 
• 6286-30-2 erythro-2,3-dibromo-3-phenylpropanoic acid 
• 127-09-3 sodium acetate 
• 513-35-9 2-methyl-but-2-ene 
• 69967-70-0 3-benzyl-3-bromodiazirine 
• 563-79-1 2,3-Dimethyl-2-butene 
• 691-38-3 (Z)-4-methyl-2-pentene 
• 7436-90-0 2,2-dibromostyrene 
• 81501-26-0 (E)-β-(trifluorosilyl)styrene 
• 536-74-3 phenylacetylene 
• 67-64-1 acetone 
• 7732-18-5 water 
• 588-72-7 [(E)-2-bromoethenyl]benzene 
• 100-52-7 benzaldehyde 

Downstream Products

• 62839-72-9 (Z)-1-(dec-1-enyl)benzene 
• 62839-71-8 (E)-1-phenyl-1-decene 
• 52921-98-9 (Z)-5-phenyl-4-pentene-2-one 
• 56949-84-9 1-(1Z)-1-hexen-1-yl-4-methylbenzene 
• 63860-10-6 ethyl 2,2-dimethyl-4-phenylbut-3-enoate 
• 81060-60-8 C₂₀H₂₄ 
• 6111-82-6 1-phenylhex-1-ene 
• 22139-13-5 (E,Z)-[β-D₁]styrene 
• 57194-69-1 cinnamaldehyde 
• 130654-88-5 ((Z)-5,5,6,6,7,7,8,8,8-Nonafluoro-oct-1-en-3-ynyl)-benzene 
• 152554-98-8 1-phenyl-1-benzarsole 
• 40596-14-3 (±)-(2R,3S)-3-phenylpent-4-en-2-ol 
• 937-53-1 (Z)-4-phenylbut-3-en-2-one 
• 74104-16-8 ((Z)-3-Methoxy-buta-1,3-dienyl)-benzene 

Relevant academic research and scientific papers

CHEMICAL EVIDENCE FOR STABILIZATION OF ELECTRICALLY NEUTRAL DIVALENT CARBON BY POLAR SOLVENTS

Benzylhalocarbene generated in non-polar solvent is trapped readily by alkene, but the intermolecular process comes to compete poorly with the intramolecular process as the solvent polarity is increased.

Regio- and stereoselective synthesis of bromoalkenes by homolytic hydrobromination of alkynes with hydrogen bromide

Homolytic hydrobromination of terminal and internal alkynes with a commercially available solution of hydrogen bromide in acetic acid has been investigated for regio- and stereoselective synthesis of bromoalkenes. Under an aerobic atmosphere at room temperature, the reaction of ethynylarenes with a small excess of HBr efficiently gave (2-bromoethenyl)arenes with good to high E-selectivity. (Alk-1-ynyl)arenes, or internal alkynes bearing both phenyl and alkyl groups at the sp-carbons also underwent the air-initiated hydrobromination to exhibit high Z-selectivity under kinetic conditions using a half equivalent of HBr.

Nickel-Catalyzed, Regio- and Enantioselective Benzylic Alkenylation of Olefins with Alkenyl Bromide

A NiH-catalyzed migratory hydroalkenylation reaction of olefins with alkenyl bromides has been developed, affording benzylic alkenylation products with high yields and excellent chemoselectivity. The mild conditions of the reaction preclude olefinic products from undergoing further isomerization or subsequent alkenylation. Catalytic enantioselective hydroalkenylation of styrenes was achieved by using a chiral bisoxazoline ligand.

Selective Rhodium-Catalyzed Hydroformylation of Terminal Arylalkynes and Conjugated Enynes to (Poly)enals Enabled by a π-Acceptor Biphosphoramidite Ligand

The hydroformylation of terminal arylalkynes and enynes offers a straightforward synthetic route to the valuable (poly)enals. However, the hydroformylation of terminal alkynes has remained a long-standing challenge. Herein, an efficient and selective Rh-catalyzed hydroformylation of terminal arylalkynes and conjugated enynes has been achieved by using a new stable biphosphoramidite ligand with strong π-acceptor capacity, which affords various important E-(poly)enals in good yields with excellent chemo- and regioselectivity at low temperatures and low syngas pressures.

The hydrodebromination of 1,1-dibromoalkenes via visible light catalysis

Vinyl bromides are versatile synthetic intermediates and widely applied in organic synthesis and pharmaceuticals. Herein, a hydrodebromination reaction of 1,1-dibromoalkenes was established via visible light catalysis. A variety of structurally different vinyl bromides were obtained in moderate to excellent yields.

Dual nickel- and photoredox-catalyzed reductive cross-coupling of aryl vinyl halides and unactivated tertiary alkyl bromides

A novel reductive cross-coupling of aryl vinyl halides and unactivated tertiary alkyl bromides has been realized via photoredox/nickel dual catalysis to produce vinyl arene derivatives bearing all-carbon quaternary centers with excellent E-selectivity. A stoichiometric metal reductant could be avoided by employing commercially available N,N,N′,N′-tetramethylethylenediamine (TMEDA) as the terminal reductant.

Construction of Phenanthrenes and Chrysenes from β-Bromovinylarenes via Aryne Diels-Alder Reaction/Aromatization

A highly efficient transition-metal-free general method for the synthesis of polycyclic aromatic hydrocarbons like phenanthrenes and chrysenes (and tetraphene) from β-bromovinylarenes and arynes has been developed. The reactions proceed via an aryne Diels-Alder (ADA) reaction, followed by a facile aromatization. This is the first report on direct construction of chrysenes (and tetraphene) using the ADA approach. Unlike the literature method which is limited to only 9/10-substituted derivatives, this method gives access to a wide variety of functionalized phenanthrenes.

Transition metal free large-scale synthesis of aromatic vinyl chlorides from aromatic vinyl carboxylic acids using bleach

While continuing our research on Hunsdiecker reaction, we came across an interesting application of bleach, sodium hypochlorite (NaOCl) for decarboxylative chlorination reaction. The reaction is easily scaled up to 10 mmol. The reaction has good tolerance towards wide variety of functional groups. The reaction has mild conditions and gave relatively high chemical yield of the desired product.

Organic electroluminescent material and organic light emitting device

The invention provides an organic electroluminescent material and an organic light emitting device and belongs to the technical field of organic photoelectric materials. The structure of the organic electroluminescent material contains a structure similar to carbazole; and by linking more conjugated groups, a glass transition temperature of the organic electroluminescent material can be effectively raised, the possible crystallization in use is reduced, and the ability of transporting holes is stronger. Compared with the prior art, the organic electroluminescent material is applied to the organic light emitting device and has relatively high light emitting efficiency and longer service life when being particularly used as a light emitting material.

Nickel-Catalyzed Reductive Cross-Coupling of Vinyl Bromides with Unactivated Alkyl Halides

The use of pyridine as the sole ligand for the reductive vinylation of unactivated secondary alkyl halides under Ni-catalyzed conditions has been developed. Both alkyl- and aryl-substituted vinyl bromides are suitable, in which alkyl-decorated α-alkenyl bromides resulted in the α-products in good results.