115665-71-9

Basic information

• Product Name: (E)-1-(2-Bromovinyl)-3-chlorobenzene
• Synonyms: (E)-β-bromo-3-chlorostyrene;(E)-1-(2-bromovinyl)-3-chlorobenzene;(E)-1-chloro-3-(2-bromovinyl)benzene;1-((E)-2-Bromo-vinyl)-3-chloro-benzene
• CAS NO: 115665-71-9
• Molecular Formula: C₈H₆BrCl
• Molecular Weight: 217.493
• Mol File: 115665-71-9.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 265.3 °C at 760 mmHg
• Flash Point: 126.6 °C
• Density: 1.564 g/cm³
• CAS DataBase Reference: (E)-1-(2-Bromovinyl)-3-chlorobenzene(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-1-(2-Bromovinyl)-3-chlorobenzene(115665-71-9)
• EPA Substance Registry System: (E)-1-(2-Bromovinyl)-3-chlorobenzene(115665-71-9)

Safety Data

• Hazardous Substances Data: 115665-71-9(Hazardous Substances Data)

Usage

Description

(E)-1-(2-Bromovinyl)-3-chlorobenzene, with the molecular formula C8H6BrCl, is a chemical compound featuring a benzene ring with a chloro group and a bromovinyl group attached to it. This colorless to pale yellow liquid exhibits a slightly sweet and floral odor and is known for its use in organic synthesis and pharmaceutical applications.

Uses

Used in Organic Synthesis:
(E)-1-(2-Bromovinyl)-3-chlorobenzene is used as a starting material for the production of various functionalized benzene derivatives. Its unique structure allows for further chemical reactions to create a range of compounds with different properties and applications.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (E)-1-(2-Bromovinyl)-3-chlorobenzene serves as an intermediate in the synthesis of biologically active compounds. Its role in creating these compounds is crucial for developing new drugs and therapies.
Safety Precautions:
Due to its incompatibility with strong oxidizing agents, it is essential to handle (E)-1-(2-Bromovinyl)-3-chlorobenzene with care and follow proper safety precautions when working with it. This ensures the safety of those involved in its production, use, and handling.

Upstream product

• 1866-38-2 m-Chlorocinnamic acid 
• 587-04-2 m-Chlorobenzaldehyde 
• 2039-85-2 3-Chlorostyrene 
• 1866-38-2 3-chlorocinnamic acid 
• 117538-45-1 2-bromo-1-(3-chlorophenyl)ethanol 

Downstream Products

• 1381775-28-5 (E)-3-chloro-β-iodostyrene 

Relevant articles and documents

A Simplified Protocol for the Stereospecific Nickel-Catalyzed C-S Vinylation Using NiX 2 Salts and Alkyl Phosphites

A Ni-catalyzed C-S cross-coupling using only NiI 2 (0.5-2.5 molpercent) and P(O i Pr) 3 (2.0-10.0 molpercent) is reported. Using an air-stable Ni(II) precatalyst, and a cheap and commercially available ligand, a scalable and robust method was developed to cross-couple various thiophenols and styryl bromides, including some sterically encumbered thiols, an α-bromocinnamaldehyde as well as a thiolation-cyclization.

Facile Synthesis of β-Bromostyrenes by Direct Bromination of Styrenes with N -Bromosuccinimide and Sodium Persulfate

A new, direct, efficient, and transition-metal-free method is reported for the synthesis of β-bromostyrenes from styrenes by using N -bromosuccinimide as the brominating reagent and sodium persulfate (Na 2S 2O 8) as the oxidant. This convenient and concise reaction is practical, operationally simple, and can be adapted for large-scale syntheses.

TsNBr2 promoted decarboxylative bromination of α,β-unsaturated carboxylic acids

A rapid process for decarboxylative bromination of α,β-unsaturated carboxylic acids have been developed using N,N-dibromo-p-toluenesulfonamide (TsNBr2). Treatment of cinnamic acids with TsNBr2 in presence of potassium carbonate in acetonitrile produces corresponding β-bromostyrenes at room temperature. Exclusive formation of (E)-β-bromostyrenes was observed in a stereoselective manner within a very short period of time (5–15 min). This method was further extended for obtaining 1-bromoalkynes from corresponding propiolic acids. Instantaneous formation of bromoalkynes was observed when the reaction was carried out in presence of DBU as a base in acetonitrile at room temperature. A wide variety of cinnamic acids and propiolic acids could be converted to corresponding β-bromostyrenes and 1-bromoalkynes respectively under mild reaction condition with high to excellent yield.