76557-95-4

Usage

Uses

Used in Pharmaceutical Industry:
(E)-1-(2-bromovinyl)-3-chlorobenzene is used as a building block for the synthesis of various organic compounds, particularly in the pharmaceutical industry.
Used in Agrochemicals:
(E)-1-(2-bromovinyl)-3-chlorobenzene is used as an intermediate in the manufacturing of pesticides and other agrochemicals.
Used in Materials Science:
(E)-1-(2-bromovinyl)-3-chlorobenzene has potential applications in the field of materials science.
Used in Chemical Research and Development:
(E)-1-(2-bromovinyl)-3-chlorobenzene is used as a reagent in chemical research and development.
It is important to handle (E)-1-(2-bromovinyl)-3-chlorobenzene with caution, as it is a hazardous chemical that can cause irritation to the skin, eyes, and respiratory system.

Upstream product

• 24654-07-7 (2RS,3SR)-2,3-dibromo-3-(2-chlorophenyl)propanoic acid 
• 587-04-2 m-Chlorobenzaldehyde 
• 2039-85-2 3-Chlorostyrene 
• 117538-45-1 2-bromo-1-(3-chlorophenyl)ethanol 
• 704-96-1 trans-2-chlorocinnamic acid 
• 1866-38-2 m-Chlorocinnamic acid 
• 5431-97-0 2,3-dibromo-3-(3-chloro-phenyl)-propionic acid 
• 1866-38-2 3-chlorocinnamic acid 

Downstream Products

• 1607020-77-8 N-(4-methylphenyl)-3-exo-(4-chlorobenzylidene)tricyclo[3.2.1.0^2,4]octane-6,7-endo-dicarboximide 
• 1607020-84-7 N-isobutyl-3-exo-(3-chlorobenzylidene)tricyclo[3.2.1.02,4]octane-6,7-endo-dicarboximide 
• 1607020-88-1 3-exo-(3-chlorobenzylidene)tricyclo[3.2.1.02,4]octane 

Relevant academic research and scientific papers

Method for synthesizing beta-bromostyrene through metal-free catalysis

The invention discloses a method for synthesizing beta-bromostyrene through metal-free catalysis, and belongs to the technical field of organic chemistry. Substituted styrene 1 is used as a raw material and is reacted in the presence of a bromination reagent, sodium persulfate and dichloroethane, and the beta-bromostyrene compound 2 can be obtained in one step. The method is capable of solving thetechnical problem that in the traditional synthesis method, conversion into alkenyl boron, alkenyl silicon and other intermediates under the catalysis of noble metals and then further halogenation are needed; the defects of expensive reaction reagent, high catalytic cost, complex operation, incapability of large-scale preparation and the like in the traditional preparation method are avoided; byadopting the method, a series of beta-bromostyrene compounds can be obtained, and the method has a potential application prospect.

Facile Synthesis of β-Bromostyrenes by Direct Bromination of Styrenes with N -Bromosuccinimide and Sodium Persulfate

A new, direct, efficient, and transition-metal-free method is reported for the synthesis of β-bromostyrenes from styrenes by using N -bromosuccinimide as the brominating reagent and sodium persulfate (Na 2S 2O 8) as the oxidant. This convenient and concise reaction is practical, operationally simple, and can be adapted for large-scale syntheses.

Photocatalytic Isomerization of Styrenyl Halides: Stereodivergent Synthesis of Functionalized Alkenes

An efficient and general method for the isomerization of styrenyl halides under different photocatalytic conditions (fac-Ir(ppy)3 in methanol for E to Z isomerization and fluorescein in 1,4-dioxane for Z to E isomerization, respectively) is disclosed. A series of stereospecific transformations constitute preliminary validation of this strategy in the synthesis of functionalized alkenes, including two diaryl alkenes, a styrenyl boronic ester and an enyne. The photocatalytic isomerization and subsequent cross coupling reaction can be run in a one-pot manner. The stereodivergent synthesis of all four isomers of a conjugated diene, as well as the antitumor agent DMU-212 and its (Z)-isomer highlights the synthetic applicability of this method.

Decarboxylative bromination of α,β-unsaturated carboxylic acids via an anodic oxidation

A novel bromination of α,β-unsaturated carboxylic acids was developed via a decarboxylation by virtue of a direct anodic electro-oxidation. In this method, ammonium bromide was employed as a bromine source and the reaction features transition-metal-free, short time, and no additional supporting electrolyte.

Palladium-Catalyzed Two-Component Domino Coupling Reaction of (Z)-β-Bromostyrenes with Norbornenes: Synthesis of 1,5-Enynes

Polyfunctional molecules, 1,5-enynes, have been achieved via a palladium(0)-catalyzed domino coupling reaction of (Z)-β-bromostyrenes with norbornenes in the presence of cesium carbonate and N,N-dimethylformamide. The process involves a double Heck-type procedure, two-fold C(sp2) H activation and formation of two carbon-carbon bonds. There are possibilities of diversified transformation for the domino coupling of (Z)-β-bromostyrenes with norbornenes, the procedure is successfully driven to 1,5-enynes via accurate adjustment of the reaction conditions. (Figure presented.) .

Palladium(0)-Catalyzed Methylcyclopropanation of Norbornenes with Vinyl Bromides and Mechanism Study

An unusual methylcyclopropanation from [2 + 1] cycloadditions of vinyl bromides to norbornenes catalyzed by Pd(OAc)2/PPh3 in the presence of CH3ONa and CH3OH has been established. A methylcyclopropane subunit was installed by a 3-fold domino procedure involving a key protonation course. Preliminary deuterium-labeling studies revealed that the proton came from methyl of CH3OH and also exposed an additional hydrogen/deuterium exchange process. These two proton-concerned reactions were fully chemoselective.

Palladium(0)-catalyzed methylenecyclopropanation of norbornenes with vinyl bromides

Highly strained methylenecyclopropane derivatives have been achieved via a novel and efficient Pd(0)-catalyzed domino reaction. The formal [2 + 1] cycloaddition reaction of vinyl bromides to norbornenes involves a Heck-type coupling and a C(sp2)-H bond activation.

Palladium-catalyzed [2+1+1] annulation of norbornenes with (z)-bromostyrenes: Synthesis of bismethylenecyclobutanes via twofold C(sp2)-H bond activation

The first Pd-catalyzed intermolecular [2+1+1] annulation reaction of (Z)-bromostyrene derivatives and norbornenes has been realized. Bismethylenecyclobutane derivatives were obtained with high yields. The domino coupling reaction involves a double Heck-type coupling process, twofold C(sp2)-H bond activation and formation of three carbon-carbon bonds.

H-β-zeolite catalyzed synthesis of β-bromostyrenes from styrene bromohydrins

Synthesis of β-bromostyrenes from styrene bromohydrins using H-β-zeolite as catalyst under moderate conditions is reported. The catalyst could be regenerated and reused up to three consecutive cycles.

Synthesis and biological evaluation of polyenylpyrrole derivatives as anticancer agents acting through caspases-dependent apoptosis

A class of polyenylpyrroles and their analogues were designed from a hit compound identified in a fungus. The compounds synthesized were evaluated for their cell cytotoxicity against human non-small-cell lung carcinoma cell lines A549. Two compounds were found to exhibit high cytotoxicity against A549 cells with IC50 of 0.6 and 0.01 μM, respectively. The underlying mechanisms for the anticancer activity were demonstrated as caspases activation dependent apoptosis induction through loss of mitochondrial membrane potential, release of cytochrome c, increase in B-cell lymphoma-2-associated X protein (Bax) level, and decrease in B-cell lymphoma-2 (Bcl-2) level. The two compounds were nontoxic to normal human lung Beas-2b cells (IC50 > 80 μM), indicating that they are highly selective in their cytotoxicity activities. Furthermore, one compound showed in vivo anticancer activity in human-lung-cancer-cell-bearing mice. These results open promising insights on how these conjugated polyenes mediate cytotoxicity and may provide a molecular rationale for future therapeutic interventions in carcinogenesis.