Benzo ( c ) phenanthrene
| Structural formula | ||||||||||||||||
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![Structural formula of benzo [c] phenanthrene](https://de.wikipedia.org/wiki/Datei:Benzo(c)phenanthrene.png)
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| General | ||||||||||||||||
| Surname | Benzo [ c ] phenanthrene | |||||||||||||||
| Molecular formula | C 18 H 12 | |||||||||||||||
| Brief description |
colorless solid |
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| properties | ||||||||||||||||
| Molar mass | 228.29 g mol −1 | |||||||||||||||
| Physical state |
firmly |
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| Melting point |
68 ° C |
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| solubility |
soluble in benzene, chloroform and ethanol |
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| As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . | ||||||||||||||||
Benzo [ c ] phenanthrene is a chemical compound from the group of polycyclic aromatic hydrocarbons and consists of four fused (connected) benzene rings.
Occurrence
Benzo [ c ] phenanthrene occurs naturally in coal tar and cigarette smoke .
Extraction and presentation
Benzo [ c ] phenanthrene can be obtained from an alkylation of the potassium salt of 1,3-cyclohexanedione with 2-iodoethylnaphthalene , subsequent acid-catalyzed cyclization with lithium aluminum hydride and dehydrogenation. Other modes of presentation such as the Diels-Alder reaction of 2-vinylnaphthalene with 1,4-benzoquinone and subsequent reduction with lithium aluminum hydride are also known. The compound is also formed during the pyrolysis of indene .
properties
Benzo [ c ] phenanthrene is a colorless solid that is soluble in benzene , chloroform and ethanol . It has an orthorhombic crystal structure with the space group P 2 1 2 1 2 1 (space group no. 19) . It is weakly carcinogenic.
Individual evidence
- ↑ a b c d e Ronald G. Harvey: Polycyclic Aromatic Hydrocarbons Chemistry and Carcinogenicity . CUP Archive, 1991, ISBN 978-0-521-36458-4 , pp. 386 ( limited preview in Google Book Search).
- ↑ a b c d data sheet Benzo (c) phenanthrene, BCR at Sigma-Aldrich , accessed on October 17, 2015 ( PDF ).
- ^ Serban C. Moldoveanu: Pyrolysis of Organic Molecules Applications to Health and Environmental Issues . Elsevier, 2009, ISBN 978-0-08-093215-6 , pp. 697 ( limited preview in Google Book search).
- ↑ FL Hirshfeld, Selina Sandler, GMJ Schmidt: 398. The structure of overcrowded aromatic compounds. Part VI. The crystal structure of benzo [c] phenanthrene and of 1,12-dimethylbenzo [c] phenanthrene. In: Journal of the Chemical Society (Resumed). 1963, p. 2108, doi : 10.1039 / JR9630002108 .
- ↑ M. Baum, S. Amin, FP Guengerich, SS Hecht, W. Köhl, G. Eisenbrand: Metabolic activation of benzo [c] phenanthrene by cytochrome P450 enzymes in human liver and lung. In: Chem. Res. Toxicol .. 14, 2001, pp. 686-693, PMID 11409939 .