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. It is an isomer of acridine.
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| Preferred IUPAC name
Phenanthridine[1] | |
| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
| ECHA InfoCard | 100.005.396 |
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PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |
| C13H9N | |
| Molar mass | 179.217 g/mol |
| Melting point | 107.4 °C (225.3 °F; 380.5 K) |
| Boiling point | 348.9 °C (660.0 °F; 622.0 K) |
| slightly soluble[2] | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Phenanthridine was discovered by Amé Pictet and H. J. Ankersmit in 1891 by pyrolysis of the condensation product of benzaldehyde and aniline.[3] 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.[4]
The reaction conditions for the Pictet–Hubert reaction were improved by Morgan and Walls in 1931, replacing the metal by phosphorus oxychloride and using nitrobenzene as a reaction solvent.[5] For this reason, the reaction is also called the Morgan–Walls reaction.[6]
The reaction is similar to the Bischler–Napieralski reaction and the Pictet–Spengler reaction.
References
edit- ^ International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. p. 212. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4.
- ^ Lide, David R. (1998), Handbook of Chemistry and Physics (87 ed.), Boca Raton, FL: CRC Press, pp. 3–460, ISBN 0-8493-0594-2
- ^ Pictet, Amé; Ankersmit, H. J. (1891). "Ueber das Phenanthridin". Justus Liebigs Annalen der Chemie. 266 (1–2): 138–153. doi:10.1002/jlac.18912660107.
- ^ Pictet, Amé; Hubert, A. (1896). "Ueber eine neue Synthese der Phenanthridinbasen". Berichte der Deutschen Chemischen Gesellschaft. 29 (2): 1182–1189. doi:10.1002/cber.18960290206.
- ^ Morgan, Gilbert T.; Walls, Leslie Percy (1931). "CCCXXXV.—Researches in the phenanthridine series. Part I. A new synthesis of phenanthridine homologues and derivatives". J. Chem. Soc.: 2447–2456. doi:10.1039/JR9310002447.
- ^ Jie Jack Li, ed. (2004). Name Reactions in Heterocyclic Chemistry. Wiley.