Phenanthridine

Phenanthridine
IUPAC name

phenanthridine
Identifiers
CAS number 229-87-8 Y
PubChem 9189
Jmol-3D images Image 1
Properties
Molecular formula C13H9N
Molar mass 179.217 g/mol
Melting point

107.4°C
Boiling point

348.9°C
Solubility in water slightly soluble[1]
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Phenanthridine is a nitrogen heterocyclic compound that is the basis of DNA-binding fluorescent dyes through intercalation. Examples of such dyes are ethidium bromide and propidium iodide. Acridine is an isomer of phenanthridine.

Phenanthridine was discovered by Amé Pictet and H. J. Ankersmit in 1891 by pyrolysis of the condensation product of benzaldehyde and aniline [2]. In the Pictet-Hubert reaction (1899) the compound is formed in a reaction of the 2-aminobiphenyl - formaldehyde adduct (an N-acyl-o-xenylamine) with zinc chloride at elevated temperatures [3]. The reaction conditions were improved by Morgan and Walls in 1931, replacing the metal by phosphorus oxychloride and using nitrobenzene as a reaction solvent [4]. For this reason the reaction is also called the Morgan-Walls reaction [5].

The reaction is similar to the Bischler–Napieralski reaction and the Pictet–Spengler reaction.

References

  1. ^ Lide, David R. (1998), Handbook of Chemistry and Physics (87 ed.), Boca Raton, FL: CRC Press, pp. 3–460, ISBN 0-8493-0594-2 
  2. ^ Mittheilung Ueber das Phenanthridin Amé Pictet, H. J. Ankersmit Chemisches Laboratorium der Universität Genf Justus Liebigs Annalen der Chemie Volume 266 Issue 1-2, Pages 138 - 153 doi:10.1002/jlac.18912660107
  3. ^ Mittheilungen Ueber eine neue Synthese der Phenanthridinbasen Amé Pictet, A. Hubert Berichte der deutschen chemischen Gesellschaft Volume 29 Issue 2, Pages 1182 - 1189 1896 doi:10.1002/cber.18960290206
  4. ^ CCCXXXV.—Researches in the phenanthridine series. Part I. A new synthesis of phenanthridine homologues and derivatives Gilbert T. Morgan, Leslie Percy Walls, J. Chem. Soc., 1931, 2447-2456 doi:10.1039/JR9310002447
  5. ^ Name reactions in heterocyclic chemistry, Jie Jack Li