Phenanthridine

Phenanthridine
Names
	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[1]
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	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 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.[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

Lide, David R. (1998), Handbook of Chemistry and Physics (87 ed.), Boca Raton, FL: CRC Press, pp. 3–460, ISBN 0-8493-0594-2
Mittheilung Ueber das Phenanthridin Amé Pictet, H. J. Ankersmit Chemisches Laboratorium der Universität Genf Justus Liebigs Annalen der Chemie Volume 266 Issue 1–2, pp. 138–153 doi:10.1002/jlac.18912660107
Mittheilungen Ueber eine neue Synthese der Phenanthridinbasen Amé Pictet, A. Hubert Berichte der deutschen chemischen Gesellschaft Volume 29 Issue 2, pp. 1182–1189, 1896 doi:10.1002/cber.18960290206
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
Jie Jack Li (ed.), 2004, Name Reactions in Heterocyclic Chemistry, Wiley.

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