Phenanthridine

Phenanthridine
Names
	Preferred IUPAC name Phenanthridine
Identifiers
CAS Number	229-87-8 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:36421 ;
ChemSpider	8834 ;
ECHA InfoCard	100.005.396
EC Number	205-934-4;
PubChem CID	9189;
UNII	62QGS7CPS6 ;
CompTox Dashboard (EPA)	DTXSID3074288 ;
	InChI InChI=1S/C13H9N/c1-2-6-11-10(5-1)9-14-13-8-4-3-7-12(11)13/h1-9H Key: RDOWQLZANAYVLL-UHFFFAOYSA-N ; InChI=1/C13H9N/c1-2-6-11-10(5-1)9-14-13-8-4-3-7-12(11)13/h1-9H Key: RDOWQLZANAYVLL-UHFFFAOYAL;
	SMILES C1=CC=C2C(=C1)C=NC3=CC=CC=C23;
Properties
Chemical formula	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)
Solubility in water	slightly soluble
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) 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. It is an isomer of acridine.

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

^ 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.

[1] 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.

[hand-2] Lide, David R. (1998), Handbook of Chemistry and Physics (87 ed.), Boca Raton, FL: CRC Press, pp. 3–460, ISBN 0-8493-0594-2

[3] Pictet, Amé; Ankersmit, H. J. (1891). "Ueber das Phenanthridin". Justus Liebigs Annalen der Chemie. 266 (1–2): 138–153. doi:10.1002/jlac.18912660107.

[4] 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.

[5] 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.

[6] Jie Jack Li, ed. (2004). Name Reactions in Heterocyclic Chemistry. Wiley.

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