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
• Article Data: 35

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

• 75-25-2 Bromoform 
• 1122-91-4 4-bromo-benzaldehyde 
• 136350-66-8 1-bromo-4-(2,2-dibromovinyl)benzene 
• 117465-34-6 2-bromo-1-(4-bromophenyl)ethanol 
• 766-96-1 4-bromo-1-ethynylbenzene 
• 2039-82-9 1-bromo-4-ethenyl-benzene 
• 1242770-51-9 (E)-1-(4’,4’,5’,5’-tetramethyl)-1’,3’,2’-dioxaboronalyl-2-(4’’-bromophenyl)ethene 
• 1200-07-3 3-(4-bromophenyl)acrylic acid 
• 778641-02-4 1-bromo-4-(2-bromovinyl)benzene 
• 112595-55-8 (2RS,3SR)-2,3-dibromo-3-(4-bromophenyl)propanoic acid 
• 1200-07-3 trans-4-bromocinnamic acid 
• 57477-93-7 hydrazone of p-bromobenzaldehyde 
• 112595-55-8 2,3-Dibromo-3-(4-bromophenyl)propionic acid 
• 94397-78-1 (E)-trimethyl<2-(4-bromophenyl)ethenyl>silane 

Downstream Products

• 766-96-1 4-bromo-1-ethynylbenzene 
• 56361-12-7 (E)-4-bromostyryl phenyl sulfone 
• 1201221-02-4 (E)-1-(4-bromophenyl)-4-phenyl-but-1-en-3-yne 
• 1201221-05-7 C₁₇H₁₃Br 
• 1243726-59-1 (S,E)-(+)-tert-butyl 2-cinnamyl-4,4-dimethylpyrrolidine-1-carboxylate 
• 1243726-49-9 (R,Z)-(+)-tert-butyl 2-(3-phenylallyl)pyrrolidine-1-carboxylate 
• 1310582-72-9 (E)-5-chloro-6-(4-(3-(p-tolyl)prop-1-en-1-yl)benzyl)benzo[d][1,3]dioxole 
• 1191300-38-5 (E)-1-bromo-4-(3-(p-tolyl)prop-1-en-1-yl)benzene 
• 1393689-83-2 (E)-4-bromo-N-(4-bromostyryl)benzamide 
• 13041-70-8 (E)-4-bromostilbene 
• 21175-18-8 (E)-4-phenylstilbene 
• 1567951-98-7 C₁₇H₁₂BrNO₂ 
• 27549-93-5 (E)-3-(4-bromophenyl)acrylonitrile 
• 58177-59-6 (2Z)-3-(4-bromophenyl)prop-2-enenitrile 

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.

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.