Phenanthridine
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| Surname | Phenanthridine | |||||||||||||||
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| Molecular formula | C 13 H 9 N | |||||||||||||||
| Brief description |
light brown crystalline solid |
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| properties | ||||||||||||||||
| Molar mass | 179.22 g mol −1 | |||||||||||||||
| Physical state |
firmly |
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| Melting point |
104-107 ° C |
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| boiling point |
349 ° C at 1025 hPa |
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| solubility |
soluble in methanol |
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| As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . | ||||||||||||||||
Phenanthridine is a chemical compound from the group of nitrogen-containing heterocycles .
Extraction and presentation
Phenanthridine was first synthesized in 1889 by Amé Jules Pictet and H. Jan Ankersmit from benzalaniline by pyrolysis in a glow tube. Its derivatives occur naturally in Amaryllidoideae .
In the Pictet-Hubert reaction (1899), the compound is formed from the reaction of a 2-aminobiphenyl - formaldehyde adduct (an N -acyl- o -xenylamine) with zinc chloride at elevated temperatures. The reaction conditions were used by Morgan and Walls in 1931 by replacing the metal with phosphorus oxychloride and using nitrobenzene as the solvent . For this reason the reaction is also called the Morgan Walls reaction .
The reaction is similar to the Bischler-Napieralski reaction and the Pictet-Spengler reaction . Production starting with phenanthraquinone , N -methylcarbazole , fluorenone oxime or phenanthridones is also possible.
Phenanthridine and its derivatives can be synthesized from halogenated benzylarylamines via arynes as an intermediate.
properties
Phenanthridine is a light brown crystalline solid. Phenanthridine and its derivatives are tertiary bases and form mono-acid salts with acids.
use
Phenanthridine is the basic structure of some alkaloids (e.g. fagaronine , more precisely hydrobenzo [ c ] -phenanthridine), medicinal substances (e.g. isometamidium ) and other chemical compounds (e.g. ethidium bromide ).
See also
- Phenanthrene , the nitrogen-free stem core
- Acridine , the non-angular isomer
Individual evidence
- ↑ a b c d e f Datasheet phenanthridine from Sigma-Aldrich , accessed on January 18, 2011 ( PDF ).
- ↑ Entry on phenanthridine at TCI Europe, accessed on June 27, 2011.
- ↑ Amé Pictet, HJ Ankersmit (Chemical Laboratory of the University of Geneva): Mittheilung Ueber das Phenanthridin ; In: Justus Liebigs Annalen der Chemie , Volume 266, Issue 1-2, pp. 138-153 ( doi : 10.1002 / jlac.18912660107 ).
- ↑ Amé Pictet, A. Hubert: Mittheilungen Ueber a new synthesis of phenanthridine bases ; In: Reports of the German Chemical Society , Volume 29, Issue 2, pp. 1182–1189, 1896 ( doi : 10.1002 / cber.18960290206 ).
- ↑ Gilbert T. Morgan, Leslie Percy Walls: CCCXXXV. — Researches in the phenanthridine series. Part I. A new synthesis of phenanthridine homologues and derivatives ; In: J. Chem. Soc. , 1931 , pp. 2447-2456 ( doi : 10.1039 / JR9310002447 ).
- ^ Jie Jack Li: Name Reactions in Heterocyclic Chemistry. 1st edition. 2005, ISBN 0-471-30215-5 .
- ^ CF Allen, Lindsey Allen, Richard Allen: The Chemistry of Heterocyclic Compounds, Six Membered Heterocyclic Nitrogen ; ISBN 978-0-470-37851-9 .
- ↑ SV Kessar: Some new aspects of benzyne and radical mediated cyclisations. (PDF; 214 kB) In: Journal of Chemical Sciences , 1988, Volume 100, No. 2-3, pp. 217-222, doi : 10.1007 / BF02839449 (currently not available) .
- ↑ Raj K. Bansal; Heterocyclic chemistry; ISBN 81-224-1212-2 .
Web links
- Kerstin Schulte: Synthesis of phenanthridine and benzo [ c ] phenanthridine derivatives and investigations into their biological effects. Dissertation, University of Kaiserslautern 2000.