115665-77-5

Basic information

• Product Name: Benzene, 1-bromo-4-[(1E)-2-bromoethenyl]-
• CAS NO: 115665-77-5
• Molecular Formula: C8H6Br2
• Molecular Weight: 261.944
• Mol File: 115665-77-5.mol

Chemical Properties

• CAS DataBase Reference: Benzene, 1-bromo-4-[(1E)-2-bromoethenyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, 1-bromo-4-[(1E)-2-bromoethenyl]-(115665-77-5)
• EPA Substance Registry System: Benzene, 1-bromo-4-[(1E)-2-bromoethenyl]-(115665-77-5)

Safety Data

• Hazardous Substances Data: 115665-77-5(Hazardous Substances Data)

Upstream product

• 1200-07-3 trans-4-bromocinnamic acid 
• 136350-66-8 1-bromo-4-(2,2-dibromovinyl)benzene 
• 1122-91-4 4-bromo-benzaldehyde 
• 7567-22-8 bromocyclooctatetraene 
• 1200-07-3 3-(4-bromophenyl)acrylic acid 
• 766-96-1 4-bromo-1-ethynylbenzene 
• 778641-02-4 1-bromo-4-(2-bromovinyl)benzene 
• 1242770-51-9 (E)-1-(4’,4’,5’,5’-tetramethyl)-1’,3’,2’-dioxaboronalyl-2-(4’’-bromophenyl)ethene 
• 2039-82-9 1-bromo-4-ethenyl-benzene 
• 117465-34-6 2-bromo-1-(4-bromophenyl)ethanol 
• 75-25-2 Bromoform 
• 57477-93-7 hydrazone of p-bromobenzaldehyde 
• 112595-55-8 (2RS,3SR)-2,3-dibromo-3-(4-bromophenyl)propanoic acid 
• 112595-55-8 2,3-Dibromo-3-(4-bromophenyl)propionic acid 

Downstream Products

• 27549-93-5 (E)-3-(4-bromophenyl)acrylonitrile 
• 58177-59-6 (2Z)-3-(4-bromophenyl)prop-2-enenitrile 
• 1438389-05-9 (Z)-1-bromo-4-(3,3-difluoroprop-1-en-1-yl)benzene 
• 1243726-49-9 (R,Z)-(+)-tert-butyl 2-(3-phenylallyl)pyrrolidine-1-carboxylate 
• 766-96-1 4-bromo-1-ethynylbenzene 
• 33277-15-5 ethyl 5-(4-bromo-phenyl)-isoxazole-3-carboxylate 
• 1201224-41-0 2-[(E)-2-(4-bromophenyl)ethenyl]tetrahydrofuran 

Relevant articles and documents

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.

Cyclic Diaryl λ3-Bromanes: A Rapid Access to Molecular Complexity via Cycloaddition Reactions

Biaryls have widespread applications in organic synthesis. However, sequentially polysubstituted biaryls are underdeveloped due to their challenging preparation. Herein, we report the synthesis of dissymetric 2,3,2′,3′,4-substituted biaryls via pericyclic reactions of cyclic diaryl λ3-bromanes. The functional groups tolerance and atom economy allow access to molecular complexity in a single reaction step. Continuous flow protocol has been designed for the scale-up of the reaction, while postfunctionalizations have been developed taking advantage of the residual Br-atom.

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.

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.

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.

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.

Understanding the regioselectivity in the oxidative condensation of catechins using pyrogallol-type model compounds

Catechins are found in many foods, including tea. These compounds are bioactive. Previous studies have shown that catechins form dimers on oxidation, and there seem to be distinct regioselective effects. However, the dimerization mechanism and regioselectivity are not well understood. Therefore, we investigated the oxidation of four pyrogallol-type model compounds of epigallocatechin (EGC) having various substituents with 1 equiv of copper chloride and 30% dioxane in water. Compounds having 2C-2C or 2C-4C bonds in the B-ring were obtained in different product ratios. Comparison of the oxidation rates of each compound revealed that the model compounds having an oxygen atom corresponding to the 1-position of the C-ring of EGC underwent slow oxidation. In addition, using density functional theory calculations, we found that the highest occupied molecular orbital energies of these compounds were higher than those of the others. Further, the 2C-2C-bonded oxidation product having an A-ring and an oxygen atom at the C-ring 1-position was confirmed to have the highest thermodynamic stability. From these results, it is suggested that the regioselective condensation reaction of the catechin B-ring is related to interactions between the A-rings, as indicated by earlier studies, and the presence of oxygen at the 1-position of the C-ring in EGC.

2-arylvinyl-cyclic amine derivative, preparation method and applications thereof

The invention belongs to the technical field of medicines, and discloses a 2-arylvinyl-cyclic amine derivative, a preparation method and applications thereof. The biological activity test results showthat the 2-arylvinyl-cyclic amine derivative has selective M1 receptor antagonism activity. The compounds can be used as a pharmaceutically active ingredient in treatment of diseases mediated by a M1receptor. According to the method, the 2-arylvinyl-cyclic amine derivative can be obtained by reacting -diarylalkylene bromide and cyclic tertiary amine, and the simple and efficient method for synthesizing the 2-aryl vinyl-cyclic amine derivative is provided.

Iron-Catalyzed Reductive Vinylation of Tertiary Alkyl Oxalates with Activated Vinyl Halides

We present herein a rare and efficient method for the creation of vinylated all carbon quaternary centers via Fe-catalyzed cross-electrophile coupling of vinyl halides with tertiary alkyl methyl oxalates. The reaction displays excellent functional group tolerance and broad substrate scope, which allows cascade radical cyclization and vinylation to afford complex bicyclic and spiral structural motifs. The reaction proceeds via tertiary alkyl radicals, and the putative vinyl-Br/Fe complexation appears to be crucial for activating the alkene and enabling a possibly concerted radical addition/C-Fe forming process.