588-72-7

Usage

Uses

Used in Pharmaceutical Industry:
[(Z)-2-bromoethenyl]benzene serves as an essential intermediate in the synthesis of pharmaceuticals, contributing to the development of new medications and therapeutic agents.
Used in Agrochemical Industry:
[(Z)-2-bromoethenyl]benzene is also utilized as an intermediate in the production of agrochemicals, playing a role in the creation of substances that help protect crops and enhance agricultural productivity.
Used in Specialty Chemicals Industry:
[(Z)-2-bromoethenyl]benzene is employed in the synthesis of specialty chemicals, which are tailored for specific applications and often have unique properties that differentiate them from commodity chemicals.
Used as a Reagent in Organic Synthesis:
Furthermore, it functions as a reagent in organic synthesis, facilitating various chemical reactions that are crucial for the production of complex organic compounds.
Safety Note:
Given its classification as a hazardous substance, [(Z)-2-bromoethenyl]benzene requires careful handling, with the use of appropriate protective equipment and adherence to safety procedures to ensure the well-being of those who work with this chemical.

Upstream product

• 64-17-5 ethanol 
• 6286-30-2 erythro-2,3-dibromo-3-phenylpropanoic acid 
• 127-09-3 sodium acetate 
• 6286-30-2 (+/-)-2r_F.3t_F-dibromo-3cat_F-phenyl-propionic acid 
• 127-08-2 potassium acetate 
• 623-11-0 1-methyl-4-nitrosobenzene 
• 67-56-1 methanol 
• 69967-70-0 3-benzyl-3-bromodiazirine 
• 99281-00-2 benzylbromocarbene 
• 563-79-1 2,3-Dimethyl-2-butene 
• 140-10-3 (E)-3-phenylacrylic acid 
• 7436-90-0 2,2-dibromostyrene 
• 65425-95-8 (E)-1-bromo-1-trimethylsilyl-2-phenylethene 
• 13084-50-9 cis-β-Styryl-diphenyl-arsin 

Downstream Products

• 886-65-7 trans,trans-1,4-Diphenyl-1,3-butadiene 
• 1522-13-0 1,1,3-triphenylprop-2-yn-1-ol 
• 52728-09-3 (E)-1-phenyl-2-<2-<(dimethylamino)methyl>phenyl>ethylene 
• 6111-82-6 (E)-1-phenyl-1-hexene 
• 2170-06-1 1-Phenyl-2-(trimethylsilyl)acetylene 
• 14374-45-9 1-heptynylbenzene 
• 37828-71-0 1-phenyl-3-isopropoxy-1-propyne 
• 62839-71-8 (E)-1-phenyl-1-decene 
• 42762-56-1 (E)-5-phenylpent-4-en-2-one 
• 39491-69-5 ((1E,3E)-octa-1,3-dien-1-yl)benzene 
• 29266-25-9 5r-bromo-2,6t-diphenyl-5,6-dihydro-4H-[1,3]oxazine 
• 13141-45-2 (Z)-1,4-diphenylbut-1-ene-3-yne 
• 13343-79-8 (E)-1,4-Diphenylbut-1-en-3-yne 
• 33236-96-3 1,1,2-tribromo-2-phenylethane 

Relevant academic research and scientific papers

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.

Iron(ii)-catalyzed intermolecular aziridination of alkenes employing hydroxylamine derivatives as clean nitrene sources

The iron-catalyzed intermolecular aziridination of alkenes with hydroxylamine derivatives is described. Using simple iron(ii) sources and readily available ligands, the formal (2 + 1) cycloaddition process proved to be efficient on both styrenes and aliphatic alkenes, providing access to a wide range of aziridines. In these particularly sustainable reaction conditions, yields up to 89% could be obtained, with a catalyst loading which could be lowered to 5 mol% when the reaction was performed on large scale. Preliminary mechanistic studies suggest that both concerted and stepwise pathways are operating in this transformation. This journal is

Iron-Catalyzed Regioselective Alkenylboration of Olefins

The first examples of an iron-catalyzed three-component synthesis of homoallylic boronates from regioselective union of bis(pinacolato)diboron, an alkenyl halide (bromide, chloride or fluoride), and an olefin are disclosed. Products that bear tertiary or quaternary carbon centers could be generated in up to 87 % yield as single regioisomers with complete retention of the olefin stereochemistry. With cyclopropylidene-containing substrates, ring cleavage leading to trisubstituted E-alkenylboronates were selectively obtained. Mechanistic studies revealed reaction attributes that are distinct from previously reported alkene carboboration pathways.

Aminium cation-radical catalysed selective hydration of (E)-aryl enynes

The hydration of carbon-carbon triple bonds is an important and atom economic synthetic transformation. Herein, we report a mild and selective method for the catalytic Markovnikov hydration of (E)-aryl enynes to the corresponding enones, mediated through the bench-stable aminium salt, tris(4-bromophenyl)ammoniumyl hexachloroantimonate (TBPA). The chemoselective and diastereoselective method proceeds under neutral metal-free conditions, delivering excellent product yields from terminal and internal alkyne units. The synthesis of biologically important (E)-3-styrylisocoumarins, including a formal synthesis of the natural product achlisocoumarin III, demonstrates the utility of this novel transformation.

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.

Visible light-mediated metal-free double bond deuteration of substituted phenylalkenes

Various bromophenylalkenes were reductively photodebrominated by using 1,3-dimethyl-2-phenyl-1H-benzo-[d]imidazoline (DMBI) and 9,10-dicyanoanthracene. With deuterated DMBI analogs (the most effective was DMBI-d11), satisfactory to excellent isotopic yields were obtained. DMBI-d11 could also be regenerated from the reaction mixtures with a recovery rate of up to 50%. The combination of the photodebromination reaction with conventional methods for bromoalkene synthesis enables sequential monodeuteration of a double bond without the necessity of a metal catalyst. This journal is

Electrochemical Nozaki-Hiyama-Kishi Coupling: Scope, Applications, and Mechanism

One of the most oft-employed methods for C-C bond formation involving the coupling of vinyl-halides with aldehydes catalyzed by Ni and Cr (Nozaki-Hiyama-Kishi, NHK) has been rendered more practical using an electroreductive manifold. Although early studies pointed to the feasibility of such a process, those precedents were never applied by others due to cumbersome setups and limited scope. Here we show that a carefully optimized electroreductive procedure can enable a more sustainable approach to NHK, even in an asymmetric fashion on highly complex medicinally relevant systems. The e-NHK can even enable non-canonical substrate classes, such as redox-active esters, to participate with low loadings of Cr when conventional chemical techniques fail. A combination of detailed kinetics, cyclic voltammetry, and in situ UV-vis spectroelectrochemistry of these processes illuminates the subtle features of this mechanistically intricate process.

Illuminatinganti-hydrozirconation: controlled geometric isomerization of an organometallic species

A general strategy to enable the formalanti-hydrozirconation of arylacetylenes is reported that mergescis-hydrometallation using the Schwartz Reagent (Cp2ZrHCl) with a subsequent light-mediated geometric isomerization atλ= 400 nm. Mechanistic delineation of thecontra-thermodynamic isomerization step indicates that a minor reaction product functions as an efficientin situgenerated photocatalyst. Coupling of theE-vinyl zirconium species with an alkyne unit generates a conjugated diene: this has been leveraged as a selective energy transfer catalyst to enableE→Zisomerization of an organometallic species. Through anUmpolungmetal-halogen exchange process (Cl, Br, I), synthetically useful vinyl halides can be generated (up toZ?:?E= 90?:?10). This enabling platform provides a strategy to access nucleophilic and electrophilic alkene fragments in both geometric forms from simple arylacetylenes.

Manganese-catalysed divergent silylation of alkenes

Transition-metal-catalysed, redox-neutral dehydrosilylation of alkenes is a long-standing challenge in organic synthesis, with current methods suffering from low selectivity and narrow scope. In this study, we report a general and simple method for the manganese-catalysed dehydrosilylation and hydrosilylation of alkenes, with Mn2(CO)10 as a catalyst precursor, by using a ligand-tuned metalloradical reactivity strategy. This enables versatility and controllable selectivity with a 1:1 ratio of alkenes and silanes, and the synthetic robustness and practicality of this method are demonstrated using complex alkenes and light olefins. The selectivity of the reaction has been studied using density functional theory calculations, showing the use of an iPrPNP ligand to favour dehydrosilylation, while a JackiePhos ligand favours hydrosilylation. The reaction is redox-neutral and atom-economical, exhibits a broad substrate scope and excellent functional group tolerance, and is suitable for various synthetic applications on a gram scale. [Figure not available: see fulltext.].

Electrochemical intramolecular C-H/N-H functionalization for the synthesis of isoxazolidine-fused isoquinolin-1(2: H)-ones

A general and practical protocol for the construction of isoxazolidine-fused isoquinolin-1(2H)-ones has been described by electrochemical-oxidation-induced intramolecular annulation via amidyl radicals. In an undivided cell, isoquinolinones could be easily generated from various available amides bearing CONHOR groups under metal-free, additive-free and external oxidant-free conditions. Moreover, this transformation proceeded smoothly by using cheap 95% ethanol as the green solvent and could be extended to the gram scale.