Chrysene

{{short description|Chemical compound}}

{{chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 455522715

| Reference = Merck Index, 11th Edition, 2259.

| ImageFile = Chryzen.svg

| ImageName = Skeletal structure

| ImageFile1 = Chrysene molecule ball.png

| ImageAlt1 = Ball-and-stick model of the chrysene molecule

| PIN = Chrysene{{cite book |author=International Union of Pure and Applied Chemistry |date=2014 |title=Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 |publisher=The Royal Society of Chemistry |pages=206 |doi=10.1039/9781849733069 |isbn=978-0-85404-182-4}}

| OtherNames = 1,2-Benzophenanthrene; 1,2-Benzphenanthrene; Benzo[a]phenanthrene; NSC 6175; [4]Phenacene

|Section1={{Chembox Identifiers

| Abbreviations =

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

| ChemSpiderID = 8817

| InChIKey = WDECIBYCCFPHNR-UHFFFAOYAK

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 85685

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

| StdInChI = 1S/C18H12/c1-3-7-15-13(5-1)9-11-18-16-8-4-2-6-14(16)10-12-17(15)18/h1-12H

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

| StdInChIKey = WDECIBYCCFPHNR-UHFFFAOYSA-N

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

| CASNo = 218-01-9

| EINECS = 205-923-4

| PubChem = 9171

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 084HCM49PT

| SMILES = c1ccc2c(c1)ccc3c2ccc4c3cccc4

| InChI = 1/C18H12/c1-3-7-15-13(5-1)9-11-18-16-8-4-2-6-14(16)10-12-17(15)18/h1-12H

| RTECS = GC0700000

| MeSHName =

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI = 51687

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

| KEGG = C14222

| Beilstein = 1909297

| Gmelin = 262600

}}

|Section2={{Chembox Properties

| C=18 | H=12

| Appearance = white solid

| Density = 1.274 g/cm³

| MeltingPtC = 254

| MeltingPt_notes =

| BoilingPtC = 448

| BoilingPt_notes =

| Solubility = Insoluble

| SolubleOther = 1 g/1300 mLMerck Index, 14th edition

| Solvent = ethanol

| pKa =

| pKb =

| MagSus = −166.67·10⁻⁶ cm³/mol}}

|Section7={{Chembox Hazards

| MainHazards =

| NFPA-H =

| NFPA-F =

| NFPA-R =

| NFPA-S =

| FlashPt =

| AutoignitionPt =

| ExploLimits =

| PEL = }}

|Section8={{Chembox Related

| OtherAnions =

| OtherCations =

| OtherFunction =

Pyrene, Tetracene, Triphenylene

| OtherFunction_label = PAHs

| OtherCompounds =

}}

}}

Chrysene is a polycyclic aromatic hydrocarbon (PAH) with the molecular formula {{chem|C|18|H|12}}{{cite EB1911|wstitle=Chrysene|volume=6|page=319}} that consists of four fused benzene rings. It is a natural constituent of coal tar, from which it was first isolated and characterized. It is also found in creosote at levels of 0.5–6 mg/kg.Anja Sörensen and Bodo Wichert "Asphalt and Bitumen" in Ullmann's Encyclopedia of Industrial Chemistry Wiley-VCH, Weinheim, 2009. {{doi|10.1002/14356007.a03_169.pub2}}http://www.qrpoil.com/site/?bitumen {{Webarchive|url=https://web.archive.org/web/20160304042118/http://www.qrpoil.com/site/?bitumen |date=2016-03-04 }}

The name "chrysene" originates from Greek Χρύσoς (chrysos), meaning "gold", and is due to the golden-yellow color of the crystals of the hydrocarbon, thought to be the proper color of the compound at the time of its isolation and characterization. However, high purity chrysene is colorless, the yellow hue being due to the traces of its yellow-orange isomer tetracene, which cannot be separated easily.