67478-59-5

Usage

Uses

Used in Chemical Synthesis:
[(E)-2-bromoethenyl]cyclohexane is used as a synthetic intermediate for the production of various organic compounds. Its bromine atom allows it to participate in substitution and elimination reactions, making it a versatile building block in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used as a Solvent:
In some applications, [(E)-2-bromoethenyl]cyclohexane can be used as a solvent due to its liquid state and ability to dissolve certain substances. It may be employed in specific chemical reactions or processes where a solvent with its particular properties is required.
Used in Industrial Processes:
[(E)-2-bromoethenyl]cyclohexane may also be utilized in various industrial processes, where its unique chemical structure and reactivity can be advantageous. These processes could include the production of polymers, coatings, or other materials that require the specific properties of [(E)-2-bromoethenyl]cyclohexane.

Upstream product

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

Downstream Products

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

Relevant academic research and scientific papers

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.

Synthesis of α,ω-Bis-Enones by the Double Addition of Alkenyl Grignard Reagents to Diacid Weinreb Amides

An efficient double addition of substituted alkenylmagnesium bromides to bis-Weinreb amides has been developed, giving α,ω-bis-enones that are building blocks for certain drugs and polymers. Furthermore, reliable protocols for the preparation of the requi

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.

A Convenient Stereoselective Reduction of Gem-Dibromides with a Combination of Dimethyl Phosphite and Potassium Carbonate

An efficient and highly stereoselective reduction of a gem-dibromocyclopropane to the corresponding monobromocyclopropane under mild reaction conditions was developed using a combination of dimethyl phosphite and potassium carbonate. This reaction provided a simple and practical way for the synthesis of the valuable monobromocyclopropanes and β-monobromoalkenes.

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.

Nickel(II)-magnesium-catalyzed cross-coupling of 1,1-dibromo-1-alkenes with diphenylphosphine oxide: One-pot synthesis of (E)-1-alkenylphosphine oxides or bisphosphine oxides

A novel nickel(II)-magnesium-mediated cross-coupling of diphenylphosphine oxide with a variety of 1,1-dibromo-1-alkenes has been developed, which provides a powerful and general methodology for the stereoselective synthesis of various (E)-1-alkenylphosphine oxides or bisphosphine oxides, with operational simplicity of the procedure, good to high yields and broad substrate applicability. Mechanistic studies reveal that the reaction might involve a Hirao reduction, cross-coupling and Michael addition. Copyright

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.

Ruthenium-catalyzed transformation of aryl and alkenyl triflates to halides

Aryl triflates were transformed to aryl bromides/iodides simply by treating them with LiBr/NaI and [Cp*Ru(MeCN)3]OTf. The ruthenium complex also catalyzed the transformation of alkenyl sulfonates and phosphates to alkenyl halides under mild conditions. Aryl and alkenyl triflates undergo oxidative addition to a ruthenium(II) complex to form η'1- arylruthenium and 1-ruthenacyclopropene intermediates, respectively, which are transformed to the corresponding halides.

A novel method for bromodecarboxylation of α,β-unsaturated carboxylic acids using catalytic sodium nitrite

A first novel synthetic utility of catalytic sodium nitrite in combination with aqueous HBr, for bromo decarboxylation of α,β-unsaturated carboxylic acid is described. α,β-Unsaturated carboxylic acid compounds successfully converted into corresponding bromo compounds. The advantages of this protocol are shorter reaction time and moderate to good yields.

Transfer of alk-1-enyl group from boron to tin: A highly stereoselective synthesis of (E)-alk-1-enyltributylstannanes

Treatment of (E)-alk-1-enyldicyclohexylboranes with tributyltin methoxide in the presence of galvinoxyl (1 mol%) at room temperature results in transfer of the alk-1-enyl group from boron to tin to give (E)-alk-1- enyltributylstannanes in a highly stereoselective fashion. Subsequent halodestannylation of (E)-alk-1-enyltributylstannanes is allowed to proceed in a one-pot manner to produce the corresponding (E)-1-iodoalk-1-enes and (E)-1-bromoalk-1-enes in good to high yields, respectively. Georg Thieme Verlag Stuttgart.