Phenanthridine was first discovered by Ame Pictet and H. J. Ankersmit in 1891 by pyrolysis of the condensed product of benzaldehyde and aniline. Earlier, phenanathridine and related compounds were prepared using mainly Pictect-Hurbert and modified Morgan-Walls type of condensation reactions.
Phenanthridine is an isomeric compound of acridine. It is a nitrogen heterocycle that is the basis of DNA-binding fluorescent dyes through intercalation. Ethidium bromide and propidium iodide are the examples of such intercalating dyes. It is used as a dye in biological and chemical sensors. It is also used in the study of ecotoxicity and rotational spectroscopic investigations and radio astronomical searches.
Palladium catalyzed synthesis of phenanthridine has been accomplished by Pritchard and coworkers from imidoyl selenides. This was the first report of palladium insertion into the C-Se bond. The palladium insertion into the imidoyl selenides 3.20 followed by intramolecular cyclization and subsequent aromatization via the elimination of HSePh lead to the formation of substituted phenanthridines 3.21.
Pd-catalysed synthesis of phenanathridine
ChEBI: Phenanthridine is an azaarene that is the 9-aza derivative of phenanthrene. The parent of the class of phenanthridines. It is a mancude organic heterotricyclic parent, a polycyclic heteroarene, a member of phenanthridines and an azaarene.
Phenanthridine appears as crystalline needles. Mutagenic.
Sparingly soluble in water.
PHENANTHRIDINE neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen may be generated in combination with strong reducing agents, such as hydrides.
Flash point data are not available for PHENANTHRIDINE, but is probably combustible.
Mutation data reported. When heated to decomposition it emits toxic vapors of NOx.
