Benzo(c)phenanthrene

Benzo[c]phenanthrene

Names
IUPAC name benzo[c]phenanthrene
Other names 3,4-Benzphenanthrene, [4]Helicene
Identifiers
CAS Number	195-19-7
3D model (Jmol)	Interactive image
ChEBI	CHEBI:82292
ChemSpider	8782
ECHA InfoCard	100.005.362
KEGG	C19197
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/h1-12H Key: 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/h1-12H Key: TUAHORSUHVUKBD-UHFFFAOYAU
SMILES c3cc2ccc1ccccc1c2c4ccccc34
Properties
Chemical formula	C18H12
Molar mass	228.2879
Density	1.19 g/cm^3
Boiling point	436.7 °C (818.1 °F; 709.8 K) @760mmHg
Hazards
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 [77 °F], 100 kPa).
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Infobox references

Benzo[c]phenanthrene 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^[1][2] consisting of the fusion of four fused benzene rings. The compound is of mainly theoretical interest but it is environmentally occurring^[3] and weakly carcinogenic.^[4]

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 benzo[c]phenanthrene and of 1,12-dimethylbenzo[c]phenanthrene". Journal of the Chemical Society (Resumed) (0). doi:10.1039/jr9630002108. ISSN 0368-1769.
2. M. Levy , Melvin S. Newman , M. Szwarc "Methyl Affinities of Non-planar Aromatic Hydrocarbons" J. Am. Chem. Soc., 1955, 77 (16), pp 4225–4225 {{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.
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 benzo[c]phenanthrene and benzo[g]chrysene". Cancer Research. 58 (23): 5340–5343. ISSN 0008-5472. PMID 9850062.