1597602-60-2

Basic information

• Product Name: 2-methoxy-3,8-dinitro-5-(hex-1’-yl)-6-phenylphenanthridinium chloride
• Synonyms: 2-methoxy-3,8-dinitro-5-(hex-1’-yl)-6-phenylphenanthridinium chloride
• CAS NO: 1597602-60-2
• Molecular Weight: 495.963
• Mol File: 1597602-60-2.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 2-methoxy-3,8-dinitro-5-(hex-1’-yl)-6-phenylphenanthridinium chloride(CAS DataBase Reference)
• NIST Chemistry Reference: 2-methoxy-3,8-dinitro-5-(hex-1’-yl)-6-phenylphenanthridinium chloride(1597602-60-2)
• EPA Substance Registry System: 2-methoxy-3,8-dinitro-5-(hex-1’-yl)-6-phenylphenanthridinium chloride(1597602-60-2)

Safety Data

• Hazardous Substances Data: 1597602-60-2(Hazardous Substances Data)

Upstream product

• 1597602-39-5 C₂₆H₂₆FN₃O₅ 
• 406482-19-7 2-fluoro-5-methoxyphenylboronic acid 
• 403615-35-0 1-(2-iodo-5-nitro-phenyl)-1-phenyl-methanone 
• 1597602-20-4 2-(2-fluoro-4-nitro-5-methoxyphenyl)-5-nitrobenzophenone 
• 1597602-17-9 2-(2-fluoro-5-methoxyphenyl)-5-nitrobenzophenone 

Relevant articles and documents

Expanding the palette of phenanthridinium cations

5,6-Disubstituted phenanthridinium cations have a range of redox, fluorescence and biological properties. Some properties rely on phenanthridiniums intercalating into DNA, but the use of these cations as exomarkers for the reactive oxygen species (ROS), superoxide, and as inhibitors of acetylcholine esterase (AChE) do not require intercalation. A versatile modular synthesis of 5,6-disubstituted phenanthridiniums that introduces diversity by Suzuki-Miyaura coupling, imine formation and microwave-assisted cyclisation is presented. Computational modelling at the density functional theory (DFT) level reveals that the novel displacement of the aryl halide by an acyclic N-alkylimine proceeds by an SNAr mechanism rather than electrocyclisation. It is found that the displacement of halide is concerted and there is no stable Meisenheimer intermediate, provided the calculations consistently use a polarisable solvent model and a diffuse basis set.