91911-21-6

Basic information

• Product Name: Cyclohexanone, 2-[(2-bromophenyl)methyl]-
• CAS NO: 91911-21-6
• Molecular Formula: C13H15BrO
• Molecular Weight: 267.166
• Mol File: 91911-21-6.mol
• Article Data: 10

Chemical Properties

• CAS DataBase Reference: Cyclohexanone, 2-[(2-bromophenyl)methyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclohexanone, 2-[(2-bromophenyl)methyl]-(91911-21-6)
• EPA Substance Registry System: Cyclohexanone, 2-[(2-bromophenyl)methyl]-(91911-21-6)

Safety Data

• Hazardous Substances Data: 91911-21-6(Hazardous Substances Data)

Upstream product

• 108-94-1 cyclohexanone 
• 3433-80-5 1-Bromo-2-bromomethyl-benzene 
• 39209-07-9 2-methylcyclohexanone O-methyl oxime 
• 10468-40-3 cyclohexanone N-cyclohexylimine 
• 1125-99-1 1-(1-Cyclohexen-1-yl)pyrrolidine 

Downstream Products

• 1258947-21-5 C₁₆H₂₃BrOSi 
• 17057-95-3 1,2,3,4-tetrahydro-9H-fluorene 
• 141536-35-8 1-methylene-2-(phenylmethyl)cyclohexane 
• 138616-59-8 2-(o-Bromobenzyl)-1-methylenecyclohexane 
• 13694-36-5 2-benzyl-2-cyclohexenone 
• 323199-52-6 2-(2-bromophenylmethyl)-1-ethylidenecyclohexane 
• 323199-49-1 2-(2-bromophenylmethyl)-1-(chloromethylene)cyclohexane 
• 244279-13-8 2-(2-bromophenylmethyl)-1-(phenylthiomethylene)cyclohexane 
• 323199-43-5 2-(2-bromophenylmethyl)-1-(ethoxycarbonylmethylene)cyclohexane 
• 323199-47-9 2-(2-bromophenylmethyl)-1-(methoxymethylene)cyclohexane 
• 323199-45-7 2-(2-bromophenylmethyl)-1-(cyanomethylene)cyclohexane 

Relevant articles and documents

β-Arylation of oxime ethers using diaryliodonium salts through activation of inert C(sp 3)-H bonds using a palladium catalyst

An efficient method of selective β-arylation of oxime ethers was realized by using a palladium catalyst with diaryliodonium salts as the key arylation reagents. The reaction proceeded smoothly through the activation of inert C(sp3)-H bonds to give corresponding ketones and aldehydes. This convenient procedure can be successfully applied to construct new C(sp3)-C(sp2) bonds on a number of complex molecules derived from natural products and thus serves as a practical synthetic tool for direct late-stage C(sp3)-H functionalization.

Palladium-catalyzed intramolecular α-arylation of aliphatic ketone, formyl, and nitro groups

Intramolecular arylation of properly designed substrates bearing a ketone, formyl, or nitro terminating group was achieved by use of a PdCl 2(Ph3P)2-Cs2CO3 reaction system to form a variety of carbocyclic compounds. Arylation in ketone compounds afforded benzene-annulated bridged or spirocycloalkanone derivatives, depending on the structure of the cyclization precursors. Arylation in formyl compounds occurred at the α-position (α-arylation) or at the carbonyl carbon (carbonyl-arylation) depending on the structure of the cyclization precursors and on the reaction solvent. An α-arylated secondary nitro group was partially transformed to ketone in the manner of the Nef reaction, whereas a tertiary nitro group was partially eliminated to afford a styrene-type olefin. Graphical Abstract

Cyclization of aryllithiums tethered to methylenecycloalkanes: Stereoselective synthesis of 4α-substituted cis-hexahydrofluorenes

The cyclization of an aryllithium tethered to a methylenecycloalkane, generated from 2-(o-bromobenzyl)-1-methylenecycloalkanes 1, 2, and 3 by low-temperature lithium-bromine exchange, has been found to be a kinetically slow but thermodynamically favorable process that proceeds at a convenient rate in an exclusively 5-exo fashion when solutions of the aryllithium in n-heptane-di-n-butyl ether (9:1 v/v) are warmed to 45 °C. The cyclization affords stereoisomerically pure cisfused products (7 and 8) when the methylenecycloalkane is five- or six-membered but it is less stereoselective when the methylenecycloalkane is seven-membered. The ring-closure of the aryllithium derived from 2-(o-bromobenzyl)-1-methylenecyclohexane (2) provides an experimentally convenient route to stereoisomerically pure 4a-substituted cis-hexahydrofluorenes in 60-90% isolated yield.