17613-37-5

Basic information

• Product Name: 2-bromophenanthridine
• CAS NO: 17613-37-5
• Molecular Formula: C₁₃H₈BrN
• Molecular Weight: 258.1133
• Mol File: 17613-37-5.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 402.9°C at 760 mmHg
• Flash Point: 197.5°C
• Density: 1.544g/cm³
• Vapor Pressure: 2.46E-06mmHg at 25°C
• Refractive Index: 1.744
• CAS DataBase Reference: 2-bromophenanthridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-bromophenanthridine(17613-37-5)
• EPA Substance Registry System: 2-bromophenanthridine(17613-37-5)

Safety Data

• Hazardous Substances Data: 17613-37-5(Hazardous Substances Data)

Upstream product

• 56-23-5 tetrachloromethane 
• 128-08-5 N-Bromosuccinimide 
• 229-87-8 phenanthridine 
• 105904-31-2 N-(5-bromo-biphenyl-2-yl)-formamide 
• 40138-16-7 2-formylbenzene boronic acid 

Relevant articles and documents

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Domino Suzuki coupling and condensation reaction: An efficient strategy towards synthesis of phenanthridines

A short and convenient hetero-annulation protocol has been developed for the synthesis of substituted phenanthridines via domino Suzuki coupling and condensation between N-(2-iodo-aryl)-formamide derivatives and 2-formylphenylboronic acid in the presence of Pd(OAc)2, Cs2CO3 and PPh3 as catalytic system in dry DMF at 85-90 °C for 6-7 h. The intermediate after Suzuki coupling and deprotection of nitrogen under the same catalytic system, furnishes the corresponding phenanthridines in good yields after immediate condensation and dehydration.

Intramolecular Addition of Aryl Radicals to Carbon-Nitrogen Double Bonds

Cyclisation of radicals 6a,b is highly regioselective towards a 5-exo process; 6-endo ring closure is a minor route and their ratio depends on the substituents.No ring expansion of the five-membered radical intermediates 7a,b was observed.Radicals 27a,b give rise to 5-exo cyclisation regiospecifically.A competitive 1,5-hydrogen shift leading to imidoyl radicals was noticed.An analogous behaviour is also exhibited by vinyl radicals when allowed to add to carbon-nitrogen double bonds.