91720-92-2

Basic information

• Product Name: 2-(4-BroMophenyl)cyclohexanone
• Synonyms: 2-(4-BroMophenyl)cyclohexanone
• CAS NO: 91720-92-2
• Molecular Formula: C₁₂H₁₃BrO
• Molecular Weight: 253.13502
• Product Categories: Miscellaneous Reagents
• Mol File: 91720-92-2.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-(4-BroMophenyl)cyclohexanone(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-BroMophenyl)cyclohexanone(91720-92-2)
• EPA Substance Registry System: 2-(4-BroMophenyl)cyclohexanone(91720-92-2)

Safety Data

• Hazardous Substances Data: 91720-92-2(Hazardous Substances Data)

Usage

Uses

2-(4-Bromophenyl)cyclohexanone is used in the synthesis of arylcyclohexanones.

Upstream product

• 92-66-0 4-bromo-1,1'-biphenyl 
• 822-87-7 2-Chlorocyclohexanone 
• 589-15-1 1-bromomethyl-4-bromobenzene 
• 16885-20-4 4-(1',3'-dithian-2'-yl)but-1-ene 
• 1267522-95-1 C₁₂H₁₅BrO 
• 286-20-4 cyclohexane-1,2-epoxide 
• 22480-64-4 4-bromophenyllithium 
• 5467-74-3 4-Bromophenylboronic acid 
• 586961-56-0 1-(4-bromophenyl)-5-hexen-2-one 

Downstream Products

• 1402080-65-2 (-)-(S)-2-(4-bromophenyl)cyclohexanone 
• 1402080-74-3 (+)-(R)-3-(4-bromophenyl)oxepan-2-one 
• 1402080-84-5 7-(4-bromophenyl)oxepan-2-one 
• 1070898-76-8 di-tert-butyl 1-(1-(4-bromophenyl)-2-oxocyclohexyl)hydrazine-1,2-dicarboxylate 
• 102862-52-2 6-(4-bromophenyl)-6-oxohexanoic acid 

Relevant articles and documents

Selective C-C Bond Cleavage of Cycloalkanones by NaNO2/HCl

A novel selective fragmentation of cycloalkanones by NaNO2/HCl has been established. The C-C bond cleavage reaction proceeds smoothly under mild conditions, selectively affording versatile keto acids or oxime acids. The methodology can streamline the synthesis of valuable chiral molecules and isocoumarins from readily available feedstocks.

Diversity-Oriented Synthesis of Bioactive Azaspirocycles

A collection of novel azaspirocyclic β-arylethylamines was prepared in good yield and excellent diastereoselectivity by an expedient strategy that features condensation of a cyclic ketone with an amino allylsilane and a tandem aza-Sakurai cyclization to generate several different spirocyclic N-heterocycles. Subsequent elaboration of the spirocyclic scaffold was achieved via Pictet-Spengler cyclizations, Suzuki cross-coupling reactions, N-functionalizations, and olefin refunctionalization reactions to create a diverse library of compounds, several of which have nanomolar affinity for the sigma 1 receptor and transmembrane protein 97 (TMEM97).

p-Toluenesulfonic acid catalysed fluorination of α-branched ketones for the construction of fluorinated quaternary carbon centres

A p-toluenesulfonic acid catalyzed fluorination of α-branched ketones for the construction of fluorinated quaternary carbon centers has been developed, featuring a broad substrate scope, environmentally benign reaction conditions, and operational simplicity.

Enantioselective Synthesis of Chiral Oxime Ethers: Desymmetrization and Dynamic Kinetic Resolution of Substituted Cyclohexanones

Axially chiral cyclohexylidene oxime ethers exhibit unique chirality because of the restricted rotation of C=N. The first catalytic enantioselective synthesis of novel axially chiral cyclohexylidene oximes has been developed by catalytic desymmetrization of 4-substituted cyclohexanones with O-arylhydroxylamines and is catalyzed by a chiral BINOL-derived strontium phosphate with excellent yields and good enantioselectivities. In addition, chiral BINOL-derived phosphoric acid catalyzed dynamic kinetic resolution of α-substituted cyclohexanones has been performed and yields versatile intermediates in high yields and enantioselectivities.

Palladium-catalyzed intramolecular hydroalkylation of alkenyl- β-keto esters, α-aryl ketones, and alkyl ketones in the presence of Me 3SiCl or HCI

Reaction of 3-butenyl β-keto esters or 3-butenyl α-aryl ketones with a catalytic amount of [PdCl2(CH3CN)2] (2) and a stoichiometric amount of Me3SiCl or Me3SiCl/ CuCl2 in dioxane at 25-70°C formed 2-substituted cyclohexanones in good yield with high regioselectivity. This protocol tolerated a number of ester and aryl groups and tolerated substitution at the allylic, enolic, and cis and trans terminal olefinic positions. In situ NMR experiments indicated that the chlorosilane was not directly involved in palladium-catalyzed hydroalkylation, but rather served as a source of HCl, which presumably catalyzes enolization of the ketone. Identification of HCl as the active promoter of palladium-catalyzed hydroalkylation led to the development of an effective protocol for the hydroalkylation of alkyl 3-butenyl ketones that employed sub-stoichiometric amounts of 2, HCl, and CuCl2 in a sealed tube at 70°C.

Palladium-catalyzed intramolecular hydroalkylation of unactivated olefins with dialkyl ketones

(Matrix presented) Treatment of 3-butenyl heptyl ketone with substoichiometric amounts of PdCl2(CH3CN)2 (10 mol%), HCl (0.1 equiv), and CuCl2 (0.3 equiv) in dioxane at 70°C for 12 h in a sealed tube formed 2-hexylcyclohexanone in 77% isolated yield. A number of alkyl 3-butenyl ketones underwent hydroalkylation under these conditions to form 2-substituted cyclohexanones in moderate to good yield.