50870-61-6

Usage

Uses

Used in Pharmaceutical and Agrochemical Industries:
2-Bromocyclohex-2-en-1-one is utilized as a key intermediate in the synthesis of pharmaceuticals and agrochemicals for its ability to facilitate the creation of complex organic molecules that are otherwise challenging to produce. Its reactivity and structural properties make it a valuable component in the development of new drugs and agricultural products.
Used in Fragrance and Flavor Industries:
In the fragrance and flavor industry, 2-Bromocyclohex-2-en-1-one is employed as a building block for creating unique and complex scents and tastes. Its chemical structure allows for the development of novel compounds that can enhance or alter the sensory profiles of consumer products.
Used in Specialty Chemicals Production:
2-Bromocyclohex-2-en-1-one is also used in the production of specialty chemicals, where its unique properties can be leveraged to create high-value compounds for specific applications in various industries, such as coatings, adhesives, and materials science.
Safety and Handling:
It is crucial to handle 2-Bromocyclohex-2-en-1-one with care due to its classification as a possible human carcinogen and its potential to cause skin and eye irritation. Additionally, it is reactive with strong oxidizing agents, which necessitates proper safety measures to prevent hazardous reactions. Exposure should be limited, and appropriate personal protective equipment should be worn during its use.

InChI:InChI=1/C6H7BrO/c7-5-3-1-2-4-6(5)8/h3H,1-2,4H2

Upstream product

• 6705-49-3 7-oxabicyclo[4.1.0]heptan-2-one 
• 57204-95-2 2-(phenylselanyl)cyclohex-2-en-1-one 
• 168985-70-4 2,3-dibromocyclohexanone 
• 104994-78-7 2-<(dimethylthiocarbamoyl)oxy>-2-cyclohexen-1-one 
• 930-68-7 cyclohexenone 
• 109380-07-6 2-bromocyclohex-2-en-1-ol 
• 115534-65-1 trans-3-chloro-2-phenylselenenylcyclohexanone 
• 3242-56-6 2-diazocyclohexanone 
• 10316-66-2 2-hydroxy-2-cyclohexen-1-one 
• 83769-13-5 ((1S,2S)-2-Bromo-3-oxo-cyclohexyl)-dimethyl-sulfonium; bromide 

Downstream Products

• 72162-99-3 2-(trimethylsilyl)cyclohex-2-enone 
• 56974-20-0 2-bromocyclohex-1-enyl acetate 
• 83633-78-7 2-bromo-3-methylcyclohex-1-enyl acetate 
• 219780-64-0 2-bromo-6-triethylsiloxy-2-cyclohexenone 
• 156496-84-3 3-(2,6-Dichlorophenyl)-5,6-dihydro-1,2-benzisoxazol-7(4H)-one 
• 396718-70-0 2-Bromo-1-((Z)-2-ethoxy-vinyl)-cyclohex-2-enol 
• 423764-28-7 Propionic acid 2-bromo-1-((E)-propenyl)-cyclohex-2-enyl ester 
• 423764-49-2 Butyric acid 2-bromo-1-((E)-propenyl)-cyclohex-2-enyl ester 
• 176042-31-2 2′-nitro-4,5-dihydro-[1,1′-biphenyl]-2(3H)-one 
• 61426-49-1 (S)-2-bromo-cyclohex-2-en-1-ol 
• 864672-46-8 isobutyric acid 2-bromo-1-isopropenyl-cyclohex-2-enyl ester 

Relevant academic research and scientific papers

Overcoming equilibrium issues with carbonyl reductase enzymes

We report herein the screening, optimisation and scale up to 100 g of a bioreduction process that employs an in situ product removal (ISPR) technique to overcome the inherent equilibrium problem associated with the coupled-substrate approach to biocatalyt

Diels-Alder routes to angularly halogenated cis-fused bicyclic ketones: Readily accessible cyclynone intermediates

We have developed an efficient Lewis acid-catalyzed Diels-Alder route to a series of cis-fused bicyclic ketones bearing quaternary halogenation at the angular position. We have also developed a Diels-Alder-based one-flask method for the regioselective pre

New 3-vinylation products of indole and investigation of its Diels-Alder reactivity: synthesis of unusual Morita-Baylis-Hillman-type products

3-Vinylindoles as precursors of carbazole and bis-indole derivatives were synthesized. Then, to form new carbazoles, Diels-Alder reactivity of these vinylindoles was studied with various dienophiles. During the cycloaddition reaction, unusual Morita-Baylis-Hillman-type products were observed. The structure and the formation mechanism of the products is discussed.

Highly enantioselective and regioselective carbonyl reduction of cyclic α,β-unsaturated ketones using TarB-N02 and sodium borohydride

Asymmetric 1,2-reduction of α,β-unsaturated ketones using TarB-NO2 and NaBH4 Is reported. Simple cycloalkenones give products In low enantiomeric excess. However, cycloalkenones with a-substituents, such as halides, alkyl, and aryl, have been enantioselectively reduced with this system to yield chiral allylic alcohols In enantiomeric excess up to 99%. The starting materials for TarB-N02 are inexpensive, and the boronlc acid can be easily recovered In high yield by a simple acid extraction.

The palladium-catalyzed aerobic kinetic resolution of secondary alcohols: Reaction development, scope, and applications

The first palladium-catalyzed enantioselective oxidation of secondary alcohols has been developed, utilizing the readily available diamine (-)-sparteine as a chiral ligand and molecular oxygen as the stoichiometric oxidant. Mechanistic insights regarding the role of the base and hydrogen-bond donors have resulted in several improvements to the original system. Namely, addition of cesium carbonate and tert-butyl alcohol greatly enhances reaction rates, promoting rapid resolutions. The use of chloroform as solvent allows the use of ambient air as the terminal oxidant at 23°C, resulting in enhanced catalyst selectivity. These improved reaction conditions have permitted the successful kinetic resolution of benzylic, allylic, and cyclopropyl secondary alcohols to high enantiomeric excess with good-toexcellent selectivity factors. This catalyst system has also been applied to the desymmetrization of meso-diols, providing high yields of enantioenriched hydroxyketones.

A convenient halogenation of α,β-unsaturated carbonyl compounds with OXONE and hydrohalic acid (HBr,HCl)

Mixtures of OXONE and hydrobromic acid or hydrochloric acid afford solutions of bromine or chlorine, respectively, α-Bromo- or α-chloro-α,β-unsaturated carbonyl compounds were prepared by addition of hydrobromic acid or hydrochloric acid to the mixture of

Electrochemical and yeast-catalysed ring-opening of isoxazoles in the synthesis of analogues of the herbicide Grasp

Isoxazoles substituted with an electron-withdrawing group at the 4-position undergo electrochemical and yeast-catalysed N-O bond cleavage. The electrolysis is much more efficient and, with acyl- and alkoxycarbonyl-substituted isoxazoles, it affords the enolised dicarbonylimine functionality characteristic of the herbicide Grasp. Regioisomeric 4- and 5-substituted isoxazoles are accessible through nitrile oxide cycloaddition chemistry, using halogen as a steric auxiliary to control the regiochemistry of reaction. Crystal data for compounds 11 and 19b are presented.

Trifluoromethanesulfonic anhydride-promoted α-bromination of ketones with Grignard reagent or magnesium bromide

The direct α-bromination of various ketones using trifluoromethanesulfonic anhydride and Grignard reagent or magnesium bromide in ether gave the corresponding α-bromo ketones in moderate to good yields under mild reaction conditions.

A radical based addition-elimination route for the preparation of indoles

Indoles, including tricyclic derivatives, are produced by cyclisations of aryl radicals onto vinyl halides followed by elimination of halide radical and tautomerism of the resulting product; the aryl radicals are produced using "clean methodology" either by reaction of iodide ions with arenediazonium salts or by reaction of phosphorus-centred radicals with aryl iodides. The Royal Society of Chemistry 2000.

A mild preparation of α-halo-α,β-enones from cyclic enones

A simple one pot procedure flor the selective transformation of cyclic enones into α-halo-α,β-enones is reported using dimethyldioxirane and metal halides/Amberlyst 15. The method appears particularly appealing for the preparation of labelled molecules for use with the CMIA technique.