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Benzo(c)phenanthrene

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Organic molecule (C18H12) made of four fused benzene rings The correct title of this article is Benzophenanthrene. The substitution of any brackets is due to technical restrictions.
Benzophenanthrene
Names
Preferred IUPAC name Benzophenanthrene
Other names 3,4-Benzophenanthrene; Benzophenanthrene; Tetrahelicene
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.005.362 Edit this at Wikidata
EC Number
  • 205-896-9
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C18H12/c1-3-7-16-13(5-1)9-11-15-12-10-14-6-2-4-8-17(14)18(15)16/h1-12HKey: TUAHORSUHVUKBD-UHFFFAOYSA-N
  • InChI=1/C18H12/c1-3-7-16-13(5-1)9-11-15-12-10-14-6-2-4-8-17(14)18(15)16/h1-12HKey: TUAHORSUHVUKBD-UHFFFAOYAU
SMILES
  • c3cc2ccc1ccccc1c2c4ccccc34
Properties
Chemical formula C18H12
Molar mass 228.294 g·mol
Appearance white solid
Density 1.19 g/cm
Melting point 68 °C (154 °F; 341 K)
Boiling point 436.7 °C (818.1 °F; 709.8 K) @760mmHg
Hazards
GHS labelling:
Pictograms GHS07: Exclamation markGHS08: Health hazard
Signal word Warning
Hazard statements H302, H312, H315, H319, H332, H335, H341, H351
Precautionary statements P201, P202, P261, P264, P270, P271, P280, P281, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P308+P313, P312, P321, P322, P330, P332+P313, P337+P313, P362, P363, P403+P233, P405, P501
Flash point 209.1 °C (408.4 °F; 482.2 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Benzophenanthrene is a polycyclic aromatic hydrocarbon with the chemical formula C18H12. It is a white solid that is soluble in nonpolar organic solvents. It is a nonplanar molecule consisting of the fusion of four fused benzene rings. The compound is of mainly theoretical interest but it is environmentally occurring and weakly carcinogenic.

References

  1. Hirshfeld, F. L.; Sandler, Selina; Schmidt, G. M. J. (1963-01-01). "398. The structure of overcrowded aromatic compounds. Part VI. The crystal structure of benzophenanthrene and of 1,12-dimethylbenzophenanthrene". Journal of the Chemical Society (Resumed): 2108. doi:10.1039/jr9630002108. ISSN 0368-1769.
  2. Levy, M.; Newman, Melvin S.; Szwarc, M. (1955). "Methyl Affinities of Non-planar Aromatic Hydrocarbons". J. Am. Chem. Soc. 77 (16): 4225. doi:10.1021/ja01621a015.
  3. Tolosa, Imma; de Mora, Stephen; Sheikholeslami, Mohammad Reza; Villeneuve, Jean-Pierre; Bartocci, Jean; Cattini, Chantal (2004-01-01). "Aliphatic and aromatic hydrocarbons in coastal caspian Sea sediments". Marine Pollution Bulletin. 48 (1–2): 44–60. doi:10.1016/S0025-326X(03)00255-8. PMID 14725875.
  4. Hu, X.; Xia, H.; Srivastava, S. K.; Pal, A.; Awasthi, Y. C.; Zimniak, P.; Singh, S. V. (1998-12-01). "Catalytic efficiencies of allelic variants of human glutathione S-transferase P1-1 toward carcinogenic anti-diol epoxides of benzophenanthrene and benzochrysene". Cancer Research. 58 (23): 5340–5343. ISSN 0008-5472. PMID 9850062.
Polycyclic aromatic hydrocarbons
2 rings
3 rings
4 rings
5 rings
6 rings
7+ rings
General classes


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