22460-52-2

Basic information

• Product Name: 4-BroMocyclohexanone
• Synonyms: 4-BroMocyclohexanone
• CAS NO: 22460-52-2
• Molecular Formula: C₆H₉BrO
• Molecular Weight: 177.03906
• Mol File: 22460-52-2.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 95-100℃ (5 Torr)
• Appearance: /
• Density: 1.509±0.06 g/cm3(Predicted)
• CAS DataBase Reference: 4-BroMocyclohexanone(CAS DataBase Reference)
• NIST Chemistry Reference: 4-BroMocyclohexanone(22460-52-2)
• EPA Substance Registry System: 4-BroMocyclohexanone(22460-52-2)

Safety Data

• Hazardous Substances Data: 22460-52-2(Hazardous Substances Data)

Usage

Uses

4-Bromocyclohexanone is an organic building block, used as a reactant in the preparation of alkylbenzenes via nickel-catalyzed cross-coupling with arylfluorosilanes.

Upstream product

• 279-49-2 7-oxabicyclo(2.2.1)heptane 
• 23511-04-8 4-oxocyclohexyl 4-methylbenzenesulfonate 
• 13482-22-9 4-hydroxycyclohexanone 
• 556-48-9 1,4-Cyclohexanediol 
• 89599-47-3 4-bromocyclohexanol 

Downstream Products

• 5309-16-0 4-(4-methoxyphenyl)cyclohexanone 
• 58753-02-9 4-benzoylcyclohexanone 
• 4894-75-1 1-phenyl-4-cyclohexanone 
• 61203-82-5 4-butylcyclohexanone 
• 110174-56-6 4-bromo-1-phenyl-1-cyclohexene 
• 40503-88-6 4-(2-methylphenyl)cyclohexan-1-one 
• 110174-57-7 4-bromo-1-phenyl-1-cyclohexanol 

Relevant articles and documents

Ni-Catalyzed Formal Cross-Electrophile Coupling of Alcohols with Aryl Halides

Direct coupling of unactivated alcohols remains a challenge in current synthetic chemistry. We herein demonstrate a strategy building upon in situ halogenation/reductive coupling of alcohols with aryl halides to forge Csp2-Csp3 bonds. The combination of 2-chloro-3-ethylbenzo[d]oxazol-3-ium salt (CEBO) and TBAB as the mild bromination reagents enables rapid transformation of a wide range of alcohols to their bromide counterparts within one to 5 min in CH3CN and DMF, which is compatible with the Ni-catalyzed cross-electrophile coupling conditions in the presence of a chemical reductant. The present method is suitable for arylation of a myriad of structurally complex alcohols with no need for prepreparation of alkyl halides. More importantly, the mild and kinetically rapid bromination process has shown good selectivity in the bromination/arylation of symmetric diols and less sterically hindered hydroxyl groups in polyols, thus offering promise for selective functionalization of diols and polyols without laborious protecting/deprotecting operations. The practicality of this work is also evident in the arylation of a number of carbohydrates, drug compounds, and naturally occurring alcohols.

Fluorescence Quenching and Photoreactions of 2,3-Diazabicyclooct-2-enes. A Case of Charge Transfer and Hydrogen Atom Transfer

A variety of organic compounds have been found to quench the long-lived fluorescence of 2,3-diazabicyclooct-2-ene (DBO), but photochemical reactions take place only with good hydrogen atom donors and tetrahalomethanes.A hydrogen isotope effect on kq of 1.7-3.0 was observed with 1,3- and 1,4-cyclohexadiene.While both quenchers photoreduced DBO, the 1,3-isomer also dimerized to a mixture characteristic of triplet diene.The results are rationalized in terms of the usual encounter complex and ion pair except that the former can undergo hydrogen transfer or react with 1,3-cyclohexadiene.A second case of photochemically induced electron transfer fragmentation was found in the reaction of 1-phenyl-DBO with bromotrichloromethane.