Benzo(c)phenanthrene
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]
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Names | |||
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IUPAC name
benzo[c]phenanthrene | |||
Other names
3,4-Benzophenanthrene; Benzo[e]phenanthrene; Tetrahelicene | |||
Identifiers | |||
3D model (JSmol) |
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ChEBI | |||
ChemSpider | |||
ECHA InfoCard | 100.005.362 | ||
EC Number |
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KEGG | |||
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CompTox Dashboard (EPA) |
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Properties | |||
C18H12 | |||
Molar mass | 228.294 g·mol−1 | ||
Appearance | white solid | ||
Density | 1.19 g/cm3 | ||
Melting point | 68 °C (154 °F; 341 K) | ||
Boiling point | 436.7 °C (818.1 °F; 709.8 K) @760mmHg | ||
Hazards | |||
GHS pictograms | ![]() ![]() | ||
GHS Signal word | Warning | ||
GHS hazard statements |
H302, H312, H315, H319, H332, H335, H341, H351 | ||
P201, P202, P261, P264, P270, P271, P280, P281, P301+312, P302+352, P304+312, P304+340, P305+351+338, P308+313, P312, P321, P322, P330, P332+313, P337+313, P362, P363, P403+233, 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 [77 °F], 100 kPa). | |||
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Infobox references | |||
References
- 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): 2108. doi:10.1039/jr9630002108. ISSN 0368-1769.
- Levy, M.; Newman, Melvin S.; Szwarc, M. (1955). "Methyl Affinities of Non-planar Aromatic Hydrocarbons". J. Am. Chem. Soc. 77 (16): 4225–4225. doi:10.1021/ja01621a015.
- 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.
- 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.
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