Benzo(c)phenanthrene: Difference between revisions

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	{{short description\|~~Chemical~~ ~~compound~~}}		{{short description\|Organic molecule (C18H12) made of four fused benzene rings}}
	{{DISPLAYTITLE:Benzo(''c'')phenanthrene}}		{{DISPLAYTITLE:Benzo(''c'')phenanthrene}}
	{{correct title\|reason=bracket\|edit=substitution\|Benzophenanthrene}}		{{correct title\|reason=bracket\|edit=substitution\|Benzophenanthrene}}
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	\| verifiedrevid = 437570118		\| verifiedrevid = 437570118
	\| Name = Benzophenanthrene		\| Name = {{nowrap\|Benzophenanthrene}}
	\| ImageFileL1 = Benzo(c)phenanthrene.png		\| ImageFileL1 = Benzo(c)phenanthrene.png
	\| ImageFileR1 = Benzo(c)phenanthrene-3D-balls.png		\| ImageFileR1 = Benzo(c)phenanthrene-3D-balls.png
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	'''Benzophenanthrene''' is a ] with the ] ~~C<sub>18</sub>H<sub>12</sub>~~. It is a white solid that is soluble in nonpolar organic ~~solvents~~. It is a nonplanar molecule<ref>{{Cite journal\|~~last~~=Hirshfeld\|~~first~~=F. L.\|last2=Sandler\|first2=Selina\|last3=Schmidt\|first3=G. M. J.\|date=1963-01-01\|title=398. The structure of overcrowded aromatic compounds. Part VI. The crystal structure of benzophenanthrene and of 1,12-dimethylbenzophenanthrene\|journal=Journal of the Chemical Society (Resumed)\|language=en\|pages=2108\|doi=10.1039/jr9630002108\|issn=0368-1769}}</ref><ref>{{cite journal \|first1=M. \|last1=Levy \|first2= Melvin S. \|last2= Newman \|first3= M. \|last3= Szwarc \|title= Methyl Affinities of Non-planar Aromatic Hydrocarbons \|journal= J. Am. Chem. Soc. \|year= 1955 \|volume= 77 \|issue= 16 \|pages= ~~4225–4225~~ \|doi= 10.1021/ja01621a015}}</ref> consisting of the fusion of four fused ] rings. The compound is of mainly theoretical interest but it is environmentally occurring<ref>{{Cite journal\|~~last~~=Tolosa\|~~first~~=Imma\|last2=de Mora\|first2=Stephen\|last3=Sheikholeslami\|first3=Mohammad Reza\|last4=Villeneuve\|first4=Jean-Pierre\|last5=Bartocci\|first5=Jean\|last6=Cattini\|first6=Chantal\|date=2004-01-01\|title=Aliphatic and aromatic hydrocarbons in coastal caspian Sea sediments\|journal=Marine Pollution Bulletin\|volume=48\|issue=1–2\|pages=44–60\|doi=10.1016/S0025-326X(03)00255-8\|pmid=14725875}}</ref> and weakly ]ic.<ref>{{Cite journal\|~~last~~=Hu\|~~first~~=X.\|last2=Xia\|first2=H.\|last3=Srivastava\|first3=S. K.\|last4=Pal\|first4=A.\|last5=Awasthi\|first5=Y. C.\|last6=Zimniak\|first6=P.\|last7=Singh\|first7=S. V.\|date=1998-12-01\|title=Catalytic efficiencies of allelic variants of human glutathione S-transferase P1-1 toward carcinogenic anti-diol epoxides of benzophenanthrene and benzochrysene\|journal=Cancer Research\|volume=58\|issue=23\|pages=5340–5343\|issn=0008-5472\|pmid=9850062}}</ref>		'''Benzophenanthrene''' is a ] with the ] {{chem2\|C18H12}}. It is a white solid that is soluble in nonpolar ]s. It is a ]<ref>{{Cite journal\|last1=Hirshfeld\|first1=F. L.\|last2=Sandler\|first2=Selina\|last3=Schmidt\|first3=G. M. J.\|date=1963-01-01\|title=398. The structure of overcrowded aromatic compounds. Part VI. The crystal structure of benzophenanthrene and of 1,12-dimethylbenzophenanthrene\|journal=Journal of the Chemical Society (Resumed)\|language=en\|pages=2108\|doi=10.1039/jr9630002108\|issn=0368-1769}}</ref><ref>{{cite journal \|first1=M. \|last1=Levy \|first2= Melvin S. \|last2= Newman \|first3= M. \|last3= Szwarc \|title= Methyl Affinities of Non-planar Aromatic Hydrocarbons \|journal= J. Am. Chem. Soc. \|year= 1955 \|volume= 77 \|issue= 16 \|pages= 4225 \|doi= 10.1021/ja01621a015}}</ref> consisting of the ] of four fused ] rings. The compound is of mainly theoretical interest but it is environmentally occurring<ref>{{Cite journal\|last1=Tolosa\|first1=Imma\|last2=de Mora\|first2=Stephen\|last3=Sheikholeslami\|first3=Mohammad Reza\|last4=Villeneuve\|first4=Jean-Pierre\|last5=Bartocci\|first5=Jean\|last6=Cattini\|first6=Chantal\|date=2004-01-01\|title=Aliphatic and aromatic hydrocarbons in coastal caspian Sea sediments\|journal=Marine Pollution Bulletin\|volume=48\|issue=1–2\|pages=44–60\|doi=10.1016/S0025-326X(03)00255-8\|pmid=14725875}}</ref> and weakly ]ic.<ref>{{Cite journal\|last1=Hu\|first1=X.\|last2=Xia\|first2=H.\|last3=Srivastava\|first3=S. K.\|last4=Pal\|first4=A.\|last5=Awasthi\|first5=Y. C.\|last6=Zimniak\|first6=P.\|last7=Singh\|first7=S. V.\|date=1998-12-01\|title=Catalytic efficiencies of allelic variants of human glutathione S-transferase P1-1 toward carcinogenic anti-diol epoxides of benzophenanthrene and benzochrysene\|journal=Cancer Research\|volume=58\|issue=23\|pages=5340–5343\|issn=0008-5472\|pmid=9850062}}</ref>

	==References==		==References==

Latest revision as of 19:22, 30 January 2024

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

195-19-7

3D model (JSmol)

Interactive image

ChEBI

CHEBI:82292

ChemSpider

8782

ECHA InfoCard

100.005.362

EC Number

205-896-9

KEGG

C19197

PubChem CID

9136

UNII

H22XVR3V8A

CompTox Dashboard (EPA)

DTXSID4075459

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

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

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.
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.
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 benzophenanthrene and benzochrysene". Cancer Research. 58 (23): 5340–5343. ISSN 0008-5472. PMID 9850062.

v t e Polycyclic aromatic hydrocarbons
2 rings	Butalene Azulene Naphthalene
3 rings	Acenaphthene Acenaphthylene Anthracene Fluorene Phenalene Phenanthrene
4 rings	Benzanthracene Benzofluorene Benzofluorene Benzophenanthrene Chrysene Fluoranthene Pyrene Tetracene Triphenylene Tricyclobutabenzene
5 rings	Benzacephenanthrylene Benzopyrene Benzopyrene Benzopyrene 6H-Benzopyrene(Olympicene) Benzofluoranthene Benzofluoranthene Benzofluoranthene Benzofluoranthene trans-Bicalicene Dibenzanthracene Dibenzanthracene Pentacene Pentaphene Perylene Picene Tetraphenylene
6 rings	Anthanthrene Benzoperylene Corannulene Dibenzopyrenes Hexacene Triangulene Zethrene
7+ rings	Coronene Dicoronylene Diindenoperylene Heptacene Hexabenzocoronene (Hexa-cata-) Kekulene Ovalene Rubicene Rubrene Sumanene Superphenalene Trinaphthylene Truxene
General classes	Acene Circulene Cyclacene Helicene Phenacene

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