:Benzo(c)phenanthrene

{{short description|Organic molecule (C18H12) made of four fused benzene rings}}

{{DISPLAYTITLE:Benzo(c)phenanthrene}}

{{correct title|reason=bracket|edit=substitution|Benzo[c]phenanthrene}}

{{Chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 437570118

| Name = {{nowrap|Benzo[c]phenanthrene}}

| ImageFileL1 = Benzo(c)phenanthrene.png

| ImageFileR1 = Benzo(c)phenanthrene-3D-balls.png

| ImageFile2 = Benzo(c)phenanthrene-3D-spacefill.png

| PIN = Benzo[c]phenanthrene

| OtherNames = 3,4-Benzophenanthrene; Benzo[e]phenanthrene; Tetrahelicene

|Section1={{Chembox Identifiers

| InChIKey = TUAHORSUHVUKBD-UHFFFAOYAU

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = TUAHORSUHVUKBD-UHFFFAOYSA-N

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo = 195-19-7

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 8782

| 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

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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

| SMILES = c3cc2ccc1ccccc1c2c4ccccc34

| MeSHName =

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = C19197

| ChEBI_Ref = {{ebicite|changed|EBI}}

| ChEBI = 82292

| PubChem = 9136

| EC_number = 205-896-9

| UNII = H22XVR3V8A

}}

|Section2={{Chembox Properties

| C=18|H=12

| MolarMass =

| Appearance = white solid

| Density = 1.19 g/cm³

| MeltingPtC = 68

| BoilingPtC = 436.7

| BoilingPt_notes = @760mmHg

}}

|Section3={{Chembox Hazards

| FlashPtC = 209.1

| GHSPictograms = {{GHS07}}{{GHS08}}

| GHSSignalWord = Warning

| HPhrases = {{H-phrases|302|312|315|319|332|335|341|351}}

| PPhrases = {{P-phrases|201|202|261|264|270|271|280|281|301+312|302+352|304+312|304+340|305+351+338|308+313|312|321|322|330|332+313|337+313|362|363|403+233|405|501}}

}}

}}

Benzo[c]phenanthrene is a polycyclic aromatic hydrocarbon with the chemical formula {{chem2|C18H12}}. It is a white solid that is soluble in nonpolar organic solvents. It is a nonplanar molecule{{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 benzo[c]phenanthrene and of 1,12-dimethylbenzo[c]phenanthrene|journal=Journal of the Chemical Society (Resumed)|language=en|pages=2108|doi=10.1039/jr9630002108|issn=0368-1769}}{{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}} consisting of the fusion of four fused benzene rings. The compound is of mainly theoretical interest but it is environmentally occurring{{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}} and weakly carcinogenic.{{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 benzo[c]phenanthrene and benzo[g]chrysene|journal=Cancer Research|volume=58|issue=23|pages=5340–5343|issn=0008-5472|pmid=9850062}}