Phenanthridine

Chemical properties

white to beige powder

History

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.

The Uses of Phenanthridine

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.

Definition

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.

Preparation

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

Synthesis Reference(s)

Journal of the American Chemical Society, 74, p. 6295, 1952 DOI: 10.1021/ja01144a521
Journal of Heterocyclic Chemistry, 26, p. 865, 1989 DOI: 10.1002/jhet.5570260366
Tetrahedron Letters, 29, p. 5463, 1988 DOI: 10.1016/S0040-4039(00)80787-X

General Description

Phenanthridine appears as crystalline needles. Mutagenic.

Air & Water Reactions

Sparingly soluble in water.

Reactivity Profile

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.

Fire Hazard

Flash point data are not available for PHENANTHRIDINE, but is probably combustible.

Safety Profile

Mutation data reported. When heated to decomposition it emits toxic vapors of NOx.