62692-41-5

Usage

Uses

Used in Organic Synthesis:
((E)-4-BROMO-BUT-3-ENYL)-BENZENE is used as a synthetic intermediate for the creation of more complex organic molecules. Its unique structure allows it to be a versatile component in the synthesis of a wide range of compounds.
Used in Pharmaceutical Industry:
In the pharmaceutical sector, ((E)-4-BROMO-BUT-3-ENYL)-BENZENE is utilized as a key component in the development of new drugs. Its structural features make it a promising candidate for the design and synthesis of pharmaceutical agents with potential therapeutic applications.
Used in Agrochemical Industry:
((E)-4-BROMO-BUT-3-ENYL)-BENZENE also finds application in the agrochemical industry, where it is employed in the development of crop protection products. Its chemical properties contribute to the creation of effective agents for safeguarding crops against various threats.
Overall, ((E)-4-BROMO-BUT-3-ENYL)-BENZENE is a significant chemical intermediate with broad applications across different industries, particularly in the development of pharmaceuticals and agrochemicals, due to its potential to form complex and useful molecular structures.

InChI:InChI=1/C10H11Br/c11-9-5-4-8-10-6-2-1-3-7-10/h1-3,5-7,9H,4,8H2/b9-5+

Upstream product

• 119405-97-9 4-phenyl-1,1-dibromo-1-butene 
• 65674-14-8 1,2-dibromo-4-phenylbutane 
• 104-53-0 3-phenyl-propionaldehyde 
• 184370-64-7 (4-bromobut-3-yn-1-yl)benzene 
• 75-25-2 Bromoform 
• 16520-62-0 4-Phenyl-1-butyne 
• 55282-95-6 ethyl (2E)-5-phenylpent-2-enoate 
• 24271-22-5 5-phenyl-2(E)-pentenoic acid 
• 138034-97-6 2,3-dibromo-5-phenylpentanoic acid 
• 39598-55-5 (bromomethylene)triphenylphosphorane 
• 1034-49-7 (bromomethyl)triphenyl phosphonium bromide 
• 880634-13-9 5-[(bromomethyl)sulfonyl]-1-phenyl-1H-tetrazole 

Downstream Products

• 62692-41-5 (E)-(4-bromobut-3-en-1-yl) benzene 
• 1021541-67-2 diethyl 2-((E)-1-(trimethylsilyl)-5-phenylpent-1-en-3-yl)malonate 
• 768-56-9 4-Phenylbut-1-ene 
• 184370-59-0 (E)-1-iodo-4-phenyl-1-butene 
• 830345-63-6 (Z)-(5,5-dimethylhex-3-en-1-yl)benzene 

Relevant academic research and scientific papers

Nickel-Catalyzed, Regio- and Enantioselective Benzylic Alkenylation of Olefins with Alkenyl Bromide

A NiH-catalyzed migratory hydroalkenylation reaction of olefins with alkenyl bromides has been developed, affording benzylic alkenylation products with high yields and excellent chemoselectivity. The mild conditions of the reaction preclude olefinic products from undergoing further isomerization or subsequent alkenylation. Catalytic enantioselective hydroalkenylation of styrenes was achieved by using a chiral bisoxazoline ligand.

Zirconium-Catalyzed Synthesis of Alkenylaminoboranes: From a Reliable Preparation of Alkenylboronates to a Direct Stereodivergent Access to Alkenyl Bromides

A simple procedure has been optimized for the preparation of alkenylaminoborane from alkynes using diisopropylaminoborane and HZrCp2Cl. Coupled with a magnesium-catalyzed dehydrogenation, it allowed for the use of air- and moisture-stable diisopropylamine. This synthesis has been extended to a one-pot sequence leading directly to bromoalkenes with controlled stereochemistry. As such, it provides an easy, scalable, cheap process to access alkenylboronates and both (E)- and (Z)-bromoalkenes from commercially available alkynes.

Remote Nucleophilic Allylation by Allylrhodium Chain Walking

Metal migration through a carbon chain is a versatile method for achieving remote functionalization. However, almost all known examples involve the overall net migration of alkylmetal species. Here, we report that allylrhodium species obtained from hydrorhodation of 1,3-dienes undergo chain walking toward esters, amides, or (hetero)arenes over distances of up to eight methylene units. The final, more highly conjugated allylrhodium species undergo nucleophilic allylation with aldehydes and with an imine to give Z-homoallylic alcohols and amines, respectively.

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.

Stereodivergent Olefination of Enantioenriched Boronic Esters

A stereodivergent coupling reaction between vinyl halides and boronic esters is described. This coupling process proceeds without a transition-metal catalyst, instead proceeding by electrophilic selenation or iodination of a vinyl boronate complex followed by stereospecific syn or anti elimination. Chiral, nonracemic boronic esters could be coupled with complete enantiospecificity. The process enables the highly stereoselective synthesis of either the E or Z alkene from a single isomer of a vinyl coupling partner.

Stereoselective Synthesis of Vinyl Iodides through Copper(I)-Catalyzed Finkelstein-Type Halide-Exchange Reaction

An efficient method for the stereoselective synthesis of vinyl iodides is described. The reactions of vinyl bromides with potassium iodide proceed smoothly in the presence of a copper catalyst under mild reaction conditions to produce the corresponding vinyl iodides stereospecifically and in satisfactory to excellent yields.

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.

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.

A new entry of highly nucleophilic CHBr3-TiCl4-Mg system for the stereoselective synthesis of 1-alkenyl bromides

This TiCl4-Mg promoted coupling of CHBr3 with various aldehydes and ketones, especially in sterically hindered or enolizable ketones, provides a simple, practical, and stereoselective carbonyl-bromomethylenation leading primarily to (E)-vinyl bromides.

TBAF-promoted elimination of vicinal dibromides having an adjacent O-functional group: Syntheses of 2-bromoalk-1-enes and alkynes

Syntheses of 2-bromoalk-1-enes and alkynes were achieved in good yields by dehydrobromination of vicinal dibromides with tetrabutylammonium fluoride. Neighboring O-functional-group participation is important in determining elimination reactivity. Georg Thieme Verlag Stuttgart New York.