6607-46-1

Basic information

• Product Name: ((E)-1,2-DIBROMO-VINYL)-BENZENE
• Synonyms: ((E)-1,2-DIBROMO-VINYL)-BENZENE;1,2-Dibromo-1-phenylethene;(E)-1,2-Dibromo-1-phenylethene;(E)-1-Phenyl-1,2-dibromoethene;(E)-α,β-Dibromostyrene
• CAS NO: 6607-46-1
• Molecular Formula: C₈H₆Br₂
• Molecular Weight: 261.94124
• Mol File: 6607-46-1.mol
• Article Data: 44

Chemical Properties

• Boiling Point: 270.8°C at 760 mmHg
• Flash Point: 132.2°C
• Appearance: /
• Density: 1.823g/cm³
• Vapor Pressure: 0.0111mmHg at 25°C
• Refractive Index: 1.637
• CAS DataBase Reference: ((E)-1,2-DIBROMO-VINYL)-BENZENE(CAS DataBase Reference)
• NIST Chemistry Reference: ((E)-1,2-DIBROMO-VINYL)-BENZENE(6607-46-1)
• EPA Substance Registry System: ((E)-1,2-DIBROMO-VINYL)-BENZENE(6607-46-1)

Safety Data

• Hazardous Substances Data: 6607-46-1(Hazardous Substances Data)

Usage

General Description

The chemical (E)-1,2-dibromo-vinyl-benzene is a compound with the molecular formula C8H6Br2. It is also known by its systematic name 1,2-dibromo-2-phenylethene. This chemical is a colorless to yellow liquid at room temperature and is insoluble in water. It is commonly used in organic synthesis and as an intermediate in the production of pharmaceuticals, agrochemicals, and other organic compounds. (E)-1,2-dibromo-vinyl-benzene is also used as a building block in the production of polymers and other industrial materials. However, it should be handled with care as it is toxic and may cause irritation to the skin, eyes, and respiratory system.

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

Upstream product

• 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 
• 3712-44-5 2,2,2-tribromo-1,3,2-benzodioxaphosphole 
• 536-74-3 phenylacetylene 
• 67-66-3 chloroform 
• 7726-95-6 bromine 
• 7789-69-7 phosphorus pentabromide 
• 75-61-6 dibromodifluoromethane 
• 932-87-6 1-Bromo-2-phenylacetylene 
• 70-11-1 α-bromoacetophenone 
• 7020-20-4 α,β-bibromo-chalcone 

Downstream Products

• 3489-31-4 4-phenyl-1,3-dithiolane-2-thione 
• 27786-05-6 (E)-(1,2-dibromovinyl)benzene 
• 38908-96-2 3-Phenyl-1,2-dithiet-Radikalkation 
• 536-74-3 phenylacetylene 
• 98-81-7 1-bromovinylbenzene 
• 101-97-3 Ethyl 2-phenylethanoate 
• 122-78-1 phenylacetaldehyde 
• 120-46-7 1,3-diphenylpropanedione 
• 1375415-68-1 N-propyl-N-(phenylethynyl)-4-methylbenzenesulfonamide 
• 1414850-56-8 4-methyl-N-pentyl-N-(phenylethynyl)benzenesulfonamide 
• 1414850-55-7 4-methyl-N-octyl-N-(phenylethynyl)benzenesulfonamide 
• 1174638-31-3 N-cyclopropyl-4-methyl-N-(phenylethynyl)benzenesulfonamide 
• 1414850-54-6 N-(furan-2-ylmethyl)-4-methyl-N-(phenylethynyl)benzenesulfonamide 
• 1414850-53-5 4-methyl-N-(1-phenylethyl)-N-(phenylethynyl)benzenesulfonamide 

Relevant articles and documents

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.

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.

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.