67478-59-5

Basic information

• Product Name: [(E)-2-bromoethenyl]cyclohexane
• CAS NO: 67478-59-5
• Molecular Formula: C₈H₁₃Br
• Molecular Weight: 189.0928
• Mol File: 67478-59-5.mol
• Article Data: 18

Chemical Properties

• Boiling Point: 199.8°C at 760 mmHg
• Flash Point: 85.6°C
• Density: 1.36g/cm³
• Vapor Pressure: 0.474mmHg at 25°C
• Refractive Index: 1.583
• CAS DataBase Reference: [(E)-2-bromoethenyl]cyclohexane(CAS DataBase Reference)
• NIST Chemistry Reference: [(E)-2-bromoethenyl]cyclohexane(67478-59-5)
• EPA Substance Registry System: [(E)-2-bromoethenyl]cyclohexane(67478-59-5)

Safety Data

• Hazardous Substances Data: 67478-59-5(Hazardous Substances Data)

Usage

General Description

[(E)-2-bromoethenyl]cyclohexane, also known as bromoethenylcyclohexane, is a chemical compound with the formula C8H13Br. It is a colorless to pale yellow liquid that is used in various chemical and industrial processes. [(E)-2-bromoethenyl]cyclohexane is a halogenated hydrocarbon, meaning it contains a bromine atom attached to an ethenyl group, which is in turn attached to a cyclohexane ring. The presence of the bromine atom makes [(E)-2-bromoethenyl]cyclohexane useful in organic synthesis, as it can participate in various substitution and elimination reactions. It can also be used as a solvent in some applications. However, due to its halogen content, it is important to handle this compound with proper safety precautions to prevent exposure and potential hazards.

Upstream product

• 60754-49-6 1,1-dibromo-2-cyclohexylethene 
• 66684-39-7 (bromoethynyl)cyclohexane 
• 1034-49-7 (bromomethyl)triphenyl phosphonium bromide 
• 2043-61-0 cyclohexanecarbaldehyde 
• 4484-35-9 3-cyclohexylacrylic acid 
• 66270-60-8 (cyclohexylethynyl)trimethylsilane 
• 95835-71-5 C₁₄H₂₇BO₂ 
• 57002-01-4 (E)-(2-cyclohexylvinyl)boronic acid 
• 75-25-2 Bromoform 
• 66270-65-3 (E)-1-bromo-1-(trimethylsilyl)-2-cyclohexylethene 
• 66270-75-5 (Z)-1-cyclohexyl-2-(trimethylsilyl)ethene 

Downstream Products

• 1404075-64-4 (E)-1-cyclohexyl-5-phenylpent-1-en-3-ol 

Relevant articles and documents

The hydrodebromination of 1,1-dibromoalkenes via visible light catalysis

Vinyl bromides are versatile synthetic intermediates and widely applied in organic synthesis and pharmaceuticals. Herein, a hydrodebromination reaction of 1,1-dibromoalkenes was established via visible light catalysis. A variety of structurally different vinyl bromides were obtained in moderate to excellent yields.

Ohmic Heating and Ionic Liquids in Combination for the Indium-Promoted Synthesis of 1-Halo Alkenyl Compounds: Applications to Pd-Catalysed Cross-Coupling Reactions

We have explored the combination of ohmic heating (ΩH) with ionic liquids for indium-promoted reactions and report herein the indium-promoted dehalogenation of gem-dibromo alkenes and the indium-mediated reductive elimination of chlorohydrins for the synthesis of 1-halo alkenyl derivatives. Heck, Stille, Suzuki, Kumada and Sonogashira couplings of the resulting 1-halo-1-alkenes with appropriate reagents were carried out to give alkenes, dienes and enynes. We report herein the combination of ohmic heating (ΩH) with ionic liquids for the indium-promoted dehalogenation of gem-dibromo alkenes and the indium-mediated reductive elimination of chlorohydrins. The 1-halo alkenyl derivatives synthesized were then submitted to a series of cross-coupling reactions to give conjugated alkenes, dienes and enynes.

Nickel-catalyzed asymmetric reductive cross-coupling between vinyl and benzyl electrophiles

A Ni-catalyzed asymmetric reductive cross-coupling between vinyl bromides and benzyl chlorides has been developed. This method provides direct access to enantioenriched products bearing aryl-substituted tertiary allylic stereogenic centers from simple, stable starting materials. A broad substrate scope is achieved under mild reaction conditions that preclude the pregeneration of organometallic reagents and the regioselectivity issues commonly associated with asymmetric allylic arylation.