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Chemical compound From Wikipedia, the free encyclopedia
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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ChEBI | |
ChemSpider | |
ECHA InfoCard | 100.005.396 |
EC Number |
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PubChem CID |
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UNII | |
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.
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