Chemistry:Benzo(c)phenanthrene

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Short description: Organic molecule (C18H12) made of four fused benzene rings


Benzo[c]phenanthrene
Benzo(c)phenanthrene.png
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Names
Preferred IUPAC name
Benzo[c]phenanthrene
Other names
3,4-Benzophenanthrene; Benzo[e]phenanthrene; Tetrahelicene
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
EC Number
  • 205-896-9
KEGG
UNII
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 GHS07: HarmfulGHS08: Health hazard
GHS Signal word Warning
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

Benzo[c]phenanthrene is a polycyclic aromatic hydrocarbon with the chemical formula C
18
H
12
. 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" (in en). 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.