6607-46-1

Usage

Uses

Used in Organic Synthesis:
((E)-1,2-DIBROMO-VINYL)-BENZENE is used as a key intermediate in organic synthesis for the production of various organic compounds. Its unique structure allows for versatile chemical reactions, making it a valuable component in the synthesis of a wide range of products.
Used in Pharmaceutical Production:
In the pharmaceutical industry, ((E)-1,2-DIBROMO-VINYL)-BENZENE is used as an intermediate in the synthesis of various drugs. Its reactivity and structural properties enable the development of new pharmaceutical agents with potential therapeutic applications.
Used in Agrochemical Production:
((E)-1,2-DIBROMO-VINYL)-BENZENE is also utilized in the agrochemical sector as an intermediate for the synthesis of pesticides and other agricultural chemicals. Its role in the production of these compounds contributes to the development of effective solutions for crop protection and management.
Used in Polymer Production:
In the polymer industry, ((E)-1,2-DIBROMO-VINYL)-BENZENE serves as a building block for the creation of various polymers and industrial materials. Its incorporation into these materials can enhance their properties, such as strength, durability, and resistance to environmental factors.
Used in Other Industrial Applications:
Beyond the aforementioned industries, ((E)-1,2-DIBROMO-VINYL)-BENZENE finds use in other areas, including the production of dyes, fragrances, and other specialty chemicals. Its versatility and reactivity make it a valuable component in a diverse range of industrial applications.

InChI:InChI=1/C8H6Br2/c9-6-8(10)7-4-2-1-3-5-7/h1-6H/b8-6+

Upstream product

• 7020-20-4 α,β-bibromo-chalcone 
• 861362-81-4 2,3,3-tribromo-3-phenyl-propionic acid 
• 121-69-7 N,N-dimethyl-aniline 
• 71-43-2 benzene 
• 861346-09-0 2,2,3-tribromo-3-phenyl-propionic acid 
• 7166-19-0 (2-bromo-2-nitroethenyl)benzene 
• 536-74-3 phenylacetylene 
• 79-15-2 N-bromoacetamide 
• 67-68-5 dimethyl sulfoxide 
• 3712-44-5 2,2,2-tribromo-1,3,2-benzodioxaphosphole 
• 67-66-3 chloroform 
• 7726-95-6 bromine 
• 7789-69-7 phosphorus pentabromide 
• 70-11-1 α-bromoacetophenone 

Downstream Products

• 536-74-3 phenylacetylene 
• 3489-31-4 4-phenyl-1,3-dithiolane-2-thione 
• 1707-03-5 diphenyl-phosphinic acid 
• 795-47-1 (E)-diphenyl(styryl)phosphine oxide 
• 1885-38-7 cinnamic nitrile 
• 24840-05-9 (Z)-cinnamonitrile 
• 1823-91-2 1-phenylethyl cyanide 
• 100-42-5 styrene 
• 65-85-0 benzoic acid 
• 103-82-2 phenylacetic acid 
• 1483-82-5 phenylethynyl chloride 
• 1522-13-0 1,1,3-triphenylprop-2-yn-1-ol 
• 932-88-7 1-iodo-2-phenylethyne 
• 17655-74-2 β-ethoxystyrene 

Relevant academic research and scientific papers

TEMPO-Regulated Regio- and Stereoselective Cross-Dihalogenation with Dual Electrophilic X+ Reagents

A TEMPO catalyzed cross-dihalogenation reaction was established via redox-regulation of the otherwise complex system of dual electrophilic X+ reagents. Formally, the ICl, BrCl, I2 and Br2 were generated in-situ, which enabled high regio- or stereoselective access to a myriad of iodochlorination, bromochlorination and homo-dihalogenation products with a wide spectrum of functionalities. With its mild conditions and operational simplicity, this method could enable wide applications in organic synthesis, which was exemplified by divergent synthesis of two pharmaceuticals. Detailed mechanistic investigations via radical clock reaction, pinacol ring expansion and Hammett experiments were conducted, which confirmed the intermediacy of halonium ion. In addition, a dynamic catalytic model based on the versatile catalytic role of TEMPO was proposed to explain the selective outcomes.

Green bromination method

The invention discloses a green bromination method, and belongs to the field of green organic chemistry. Under the conditions of room temperature, opening and neutrality, reaction raw materials are aromatic hydrocarbon, olefin, alkyne, tryptamine, tryptophane and derivatives thereof with different functional groups, a bromine source is MBrx (M is Fe , Fe , Ce and the like, and x is 2-3), and the unique oxidant is H2O2. Brominated alkanes, alkenes, aromatic hydrocarbons, pyrrolo-indolines and furo-indolines and derivatives thereof can be produced. The bromination reaction is carried out by using easily available and cheap reagents (such as FeBr2, CeB3 and H2O2) in the market and the solvent, and the method has the characteristics of mild reaction conditions, wide substrate application range, simple steps, easiness in operation and no need of separation, is a green, environment-friendly and safe bromination reaction method, and has a good application prospect.

Electrochemical synthesis of α,α-dihaloacetophenones from terminal alkyne derivatives

By virtue of electrochemistry, a series of α,α-dihaloacetophenones were easily obtained with good to excellent yields. This electrochemical procedure was taken in a divided cell with constant current in aqueous media. The reaction can be carried out smoothly at room temperature under metal and oxidant free condition, which provides an eco-friendly synthesis for the α,α-dihaloacetophenone derivatives.

Synthesis method for phenylacetylene dibromo compounds

The invention discloses a synthesis method of phenylacetylene dibromo compounds. The method comprises the following specific steps: phenylacetylene compound shown in the formula (I) in the descriptionas a raw material, zinc-aluminum hydrotalcite ZnAl-BrO3

AuIII-Catalyzed Formation of α-Halomethyl Ketones from Terminal Alkynes

A AuIII-catalyzed synthesis of α-halomethyl ketones from terminal alkynes was developed. This approach features excellent functional group compatibility and good yields for both aromatic and aliphatic terminal alkynes. The resulting α-halomethyl ketones were used to prepare heterocyclic indolizine structures. The plausible mechanism of the one-pot reaction is proposed.

Iron(III) catalyzed halo-functionalization of alkynes

Abstract Aromatic and aliphatic alkynes can be halo-functionalized to α,α-dihalodimethyl ketals catalyzed by FeCl3 in excellent yields. MeOH is used as a nucleophilic solvent and N-halosuccinimide as the halogen source for this efficient transformation. The resulting α,α-dibromodimethyl ketals can be converted to the corresponding α,α-dibromoketones by treatment with 8% FeCl3 in silica gel.

Hexamethonium bis(tribromide) (HMBTB) a recyclable and high bromine containing reagent

A recyclable and high bromine containing di-(tribromide) reagent, hexamethonium bis(tribromide) (HMBTB) has been synthesized and utilized for the bromination of various organic substrates. The spent reagent hexamethonium bromide (HMB) can be effectively recycled by regenerating and reusing it without significant loss of activity. The crystalline and stable bis(tribromide) is an effective storehouse of very high percentage of active bromine requiring just half an equivalent of it for complete bromination. Both the Br3- moieties in HMBTB are nearly linear with Br-Br-Br angle of 179.55°.

Halocarbocyclization versus dihalogenation: Substituent directed iodine(iii) catalyzed halogenations

The nucleophilicity of the substituents in iodobenzene pre-catalysts have a huge impact on product selectivity in iodine(iii) triggered halogenations, steering the reactivity from solely carbocyclizations towards dihalogenations. Utilizing this catalyst-dependent reactivity a diastereo- and chemoselective dihalogenation method was established allowing the conversion of structurally and electronically diverse unsaturated compounds in excellent yields.

Brominations with Pr4NBr9 as a solid reagent with high reactivity and selectivity

Tetrapropylammonium nonabromide (Pr4NBr9) is introduced as a room-temperature solid reagent for rapid bromination reactions of various substrates. The reagent exhibits reactivity similar to that of elemental bromine, but shows higher selectivity and it is easier and safer to store and to handle. Georg Thieme Verlag Stuttgart · New York.

An approach to the selenobromination of aryl(thienyl)alkynes: Access to 3-bromobenzo[b]selenophenes and selenophenothiophenes

A novel approach for the cyclization of arylalkynes with selenium(IV) bromide prepared in situ has been elaborated. The use of an alkene additive as a bromine scavenger provides a convenient synthetic pathway for the synthesis of a wide variety of 3-bromobenzo[b]selenophenes. Reactions can be performed open to air without the use of moisture-sensitive reagents, anhydrous solvents, or an inert atmosphere. Selenobromination of ethynylthiophenes has been applied for the preparation of selenopheno[3,2-b]- and selenopheno[2,3-b]thiophenes. The molecular structures of representative derivatives have been confirmed by X-ray crystallographic analysis. The use of an alkene additive as a bromine scavenger under selenobromination conditions provides a convenient synthetic pathway for the synthesis of a wide variety of 3-bromobenzo[b]selenophenes in moderate to high yields. The reactions are not moisture-sensitive and do not require an inert atmosphere. Selenobromination of ethynylthiophenes enables the preparation of selenopheno[b]thiophenes. Copyright