78463-06-6

Usage

Physical state

Colorless liquid

Usage

Organic synthesis and chemical reactions

Cyclohexene ring

A six-membered carbon ring with one double bond

Bromoethenyl group

A vinyl group (C=C) with a bromine atom attached

Bond configuration

(E)-2-bromoethenyl, indicating the position of the bromine atom and the configuration of the double bond

Applications

Intermediate in the production of organic compounds and polymers
Manufacturing of pharmaceuticals and agrochemicals
Key ingredient in the production of specialty chemicals
Reagent in organic chemistry research

Upstream product

• 62072-23-5 ((E)-2-Cyclohex-1-enyl-vinyl)-dicyclohexyl-borane 
• 931-49-7 1-ethenylcyclohexene 
• 75-25-2 Bromoform 
• 1192-88-7 1-cyclohexene-1-carboxaldehyde 

Downstream Products

• 78463-02-2 (E)-diisopropyl 2-(1-cyclohexenyl)vinylphosphonate 
• 78463-01-1 (E)-diethyl cyclohex-2-enylidenemethylphosphonate 

Relevant academic research and scientific papers

Palladium-catalyzed amination of 1-bromo- and 1-chloro-1,3-butadienes: A general method for the synthesis of 1-amino-1,3-butadienes

1-Amino-1,3-butadienes, interesting substrates for [4+2] cycloadditions, are prepared by Pd-catalyzed cross-coupling of secondary amines with readily available 1-halodienes. The optimized catalytic system employs Pd 2(dba)3 as metal

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.

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.

Transfer of alk-1-enyl group from boron to aluminium: A novel way to prepare (E)-alk-1-enyldiisobutylalanes

Treatment of (E)-alk-1-enyldicyclohexylboranes 1 with diisobutylaluminium hydride (DIBAL-H) in the presence of hex-1-ene at room temperature results in transfer of the alk-1-enyl group from boron to aluminium to give (E)-alk-1-enyldiisobutylalanes 2 with retention of configuration at the double bond.