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Benzo(c)phenanthrene

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The correct title of this article is Benzo[c]phenanthrene. The substitution of any brackets is due to technical restrictions.
Benzo[c]phenanthrene
Names
Preferred IUPAC name
Benzo[c]phenanthrene
Other names
3,4-Benzophenanthrene; Benzo[e]phenanthrene; Tetrahelicene
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.005.362 Edit this at Wikidata
EC Number
  • 205-896-9
KEGG
UNII
  • 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 checkY
    Key: TUAHORSUHVUKBD-UHFFFAOYSA-N checkY
  • 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
  • c3cc2ccc1ccccc1c2c4ccccc34
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 labelling:
GHS07: Exclamation markGHS08: Health hazard
Warning
H302, H312, H315, H319, H332, H335, H341, H351
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 [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

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

[edit]
  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): 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 benzo[c]phenanthrene and benzo[g]chrysene". Cancer Research. 58 (23): 5340–5343. ISSN 0008-5472. PMID 9850062.


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