10412-66-5

Basic information

• Product Name: 1,2-trans-bromocyclohexylphthalimide
• CAS NO: 10412-66-5
• Molecular Weight: 308.175
• Mol File: 10412-66-5.mol

Chemical Properties

• CAS DataBase Reference: 1,2-trans-bromocyclohexylphthalimide(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-trans-bromocyclohexylphthalimide(10412-66-5)
• EPA Substance Registry System: 1,2-trans-bromocyclohexylphthalimide(10412-66-5)

Safety Data

• Hazardous Substances Data: 10412-66-5(Hazardous Substances Data)

Upstream product

• 2439-85-2 N-bromophthalimide 
• 110-83-8 cyclohexene 
• 2133-65-5 N-cyclohexylphthalimide 
• 85-44-9 phthalic anhydride 
• 108-91-8 cyclohexylamine 

Relevant articles and documents

Catalytic intermolecular haloamidation of simple alkenes with N-halophthalimide as both nitrogen and halogen source

A simple, efficient, and highly atom economic haloamidation of simple alkenes has been developed, using AgBF4 or InBr3/AgBF 4 (1:3) as catalyst and N-halophthalimide as both nitrogen and halogen source. A broad range of olefins can be applied to afford vicinal haloamines in good yields and with high regioselectivity and diastereoselectivity.

Site-selective aliphatic C-H bromination using N -bromoamides and visible light

Transformations that selectively functionalize aliphatic C-H bonds hold significant promise to streamline complex molecule synthesis. Despite the potential for site-selective C-H functionalization, few intermolecular processes of preparative value exist. Herein, we report an approach to unactivated, aliphatic C-H bromination using readily available N-bromoamide reagents and visible light. These halogenations proceed in useful chemical yields, with substrate as the limiting reagent. The site selectivities of these radical-mediated C-H functionalizations are comparable (or superior) to the most selective intermolecular C-H functionalizations known. With the broad utility of alkyl bromides as synthetic intermediates, this convenient approach will find general use in chemical synthesis.

Stereoselectivity of Radical Additions of N-Haloimides to Cyclic Alkenes

The addition of N-haloimides (1-5) to alkenes 9 via imidyl radicals 6-8 introduces a halogen atom and an imidyl moiety to vicinal C-atoms of a carbon chain. With cyclic alkenes, the trans/cis-stereoselectivity depends on the nature of the imidyl unit, on the halogen atom, and on the alkene and varied between 58 : 42 and >95 : 5. Temperature dependend studies showed higher trans/cis-selectivities at elevated temperatures, which may be caused by different conformations of the adduct radicals 10-12, each of them exhibiting a different stereoselectivity.