870122-74-0

Basic information

• Product Name: (E)-1-(2-bromovinyl)-4-fluorobenzene
• CAS NO: 870122-74-0
• Molecular Formula: C8H6BrF
• Molecular Weight: 201.038
• Mol File: 870122-74-0.mol

Chemical Properties

• CAS DataBase Reference: (E)-1-(2-bromovinyl)-4-fluorobenzene(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-1-(2-bromovinyl)-4-fluorobenzene(870122-74-0)
• EPA Substance Registry System: (E)-1-(2-bromovinyl)-4-fluorobenzene(870122-74-0)

Safety Data

• Hazardous Substances Data: 870122-74-0(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
(E)-1-(2-bromovinyl)-4-fluorobenzene is used as a building block in organic synthesis for creating a variety of complex organic molecules. Its unique combination of fluorine and bromine atoms allows for specific reactivity patterns that can be exploited in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Chemical Research:
In the field of chemical research, (E)-1-(2-bromovinyl)-4-fluorobenzene serves as a model compound for studying the effects of halogen substitution on aromatic systems. It can be used to investigate reaction mechanisms, understand the influence of electron-withdrawing and electron-donating groups, and explore the impact of steric effects on chemical reactivity.
Used in Pharmaceutical Development:
(E)-1-(2-bromovinyl)-4-fluorobenzene is used as a key intermediate in the development of pharmaceuticals. Its unique structure may offer advantages in the design of new drugs, potentially leading to improved pharmacokinetic properties, such as enhanced solubility, bioavailability, or targeted delivery.
Used in Agrochemicals:
In the agrochemical industry, (E)-1-(2-bromovinyl)-4-fluorobenzene may be utilized as a starting material for the synthesis of novel pesticides or herbicides. Its halogenated nature could provide the necessary properties for these applications, such as increased stability, selectivity, or efficacy against target pests.

Upstream product

• 350-35-6 1-(1,2-dibromoethyl)-4-fluorobenzene 
• 405-99-2 para-fluorostyrene 
• 459-32-5 4-fluorocinnamic acid 
• 459-57-4 4-fluorobenzaldehyde 
• 159957-00-3 1-(2,2-dibromovinyl)-4-fluorobenzene 

Downstream Products

• 766-98-3 1-ethynyl-4-fluorobenzene 
• 1206103-20-9 (1E,3E)-1-(4-fluorophenyl)-4-(4-hydroxy-3-methoxyphenyl)-1,3-butadiene 
• 115665-67-3 (E)-1-fluoro-4-(2-bromovinyl)benzene 
• 27530-50-3 trans-3-(4-fluorophenyl)acrylonitrile 
• 1612145-80-8 C₁₃H₁₃FO 
• 1612145-45-5 (R,E)-6-(4-fluorophenyl)-2-phenylhex-5-en-3-yn-2-ol 
• 1342799-89-6 (E)-1-fluoro-4-(4-phenylbut-1-en-3-yn-1-yl)benzene 
• 1380341-57-0 (E)-ethyl 4-(4-fluorophenyl)-2-methylbut-3-enoate 
• 440-40-4 3-Fluorophenanthrene 

Relevant articles and documents

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.

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.

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.

Ni-catalyzed reductive coupling of α-halocarbonyl derivatives with vinyl bromides

This work describes the vinylation of α-halo carbonyl compounds with vinyl bromides under Ni-catalyzed reductive coupling conditions. While aryl-conjugated vinyl bromides entail pyridine as the sole labile ligand, the alkyl-substituted vinyl bromides require both bipyridine and pyridine as the co-ligands.

Preparation of Vinyl Arenes by Nickel-Catalyzed Reductive Coupling of Aryl Halides with Vinyl Bromides

This work emphasizes the synthesis of substituted vinyl arenes by reductive coupling of aryl halides with vinyl bromides under mild and easy-to-operate nickel-catalyzed reaction conditions. A broad range of aryl halides, including heteroaromatics, and vinyl bromides were employed to yielding products in moderate to excellent yields with high functional-group tolerance. The nickel-catalytic system displays good chemoselectivity between the two C(sp2)-halide coupling partners, thus demonstrating a mechanistic pathway distinct from other stepwise protocols.

Ultrasonically Assisted Decarboxylative Bromination of α,β-Unsaturated Carboxylic Acids under Vilsmeier-Haack Conditions

An efficient method for decarboxylative bromination of cinnamic acids (α,β-unsaturated carboxylic acids or 3-arylpropenoic acids) was achieved under relatively mild conditions using Vilsmeier-Haack reagent and KBr in acetonitrile media. Vilsmeier-Haack reagent is prepared by using 1:1 ratio of oxychloride (SOCl2 or POCl3) and DMF under chilled condition. Ultrasonically assisted reactions underwent smoothly with highly significant rate enhancements and afforded bromostyrenes as products in very good yields even though the reactions were too sluggish.

Palladium(0)-catalyzed cross-coupling of 1,1-diboronates with vinyl bromides and 1,1-dibromoalkenes

Palladium-catalyzed cross-coupling reactions of 1,1-diboronates with vinyl bromides and dibromoalkenes were found to afford 1,4-dienes and allenes, respectively. These reactions utilize the high reactivities of both 1,1-diboronates and allylboron intermediates generated in the initial coupling.

Novel system for decarboxylative bromination of α,β-unsaturated carboxylic acids with diacetoxyiodobenzene

A simple and mild method for the conversion of varieties of α,β-unsaturated carboxylic acids to the corresponding bromoalkenes using diacetoxyiodobenzene (IBD) in combination with tetraethyl-ammonium bromide (TEAB) at room temperature is discussed. Advantages of this system are short reaction time, easy work up and gave good to excellent yields.