View source for Anthracene

{{chembox
| Watchedfields = changed
| verifiedrevid = 464364595
| Name = Anthracene
| ImageFile_Ref = {{chemboximage|correct|??}}
| ImageFile = Anthracene-numbering.svg
| ImageClass = skin-invert
| ImageName = Skeletal formula and numbering system of anthracene
| ImageFile1 = Anthracene molecule ball.png
| ImageAlt1 = Ball-and-stick model of the anthracene molecule
| ImageFile2 = Anthracene.jpg
| ImageName2 = Anthracene
| IUPACName = Anthracene <!-- Nomenclature of Organic Chemistry – IUPAC Recommendations and Preferred Names 2013 (Blue Book) -->
|Section1={{Chembox Identifiers
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = EH46A1TLD7
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 35298
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB07372
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 8111
| PubChem = 8418
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C14315
| InChI = 1/C14H10/c1-2-6-12-10-14-8-4-3-7-13(14)9-11(12)5-1/h1-10H
| InChIKey = MWPLVEDNUUSJAV-UHFFFAOYAK
| SMILES = c1ccc2cc3ccccc3cc2c1
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 333179
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C14H10/c1-2-6-12-10-14-8-4-3-7-13(14)9-11(12)5-1/h1-10H
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = MWPLVEDNUUSJAV-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 120-12-7
| RTECS = CA9350000
| EINECS = 217-004-5
| Beilstein = 1905429
| Gmelin = 67837
  }}
|Section2={{Chembox Properties
| C=14 | H=10
| Appearance = Colorless
| Odor = Weak aromatic
| Density = 1.28 g/cm<sup>3</sup> (25 °C)<ref name=crc1 /><br /> 0.969 g/cm<sup>3</sup> (220 °C)
| MeltingPtC = 216
| MeltingPt_notes = at 760&nbsp;mmHg
| BoilingPtC = 341.3
| BoilingPt_notes = at 760&nbsp;mmHg
| MeltingPt_ref =<ref name=crc1>Haynes, p. 3.28</ref>
| BoilingPt_ref =<ref name=crc1/>
| Solubility = 0.022 mg/L (0 °C)<br /> 0.044 mg/L (25 °C)<br /> 0.29 mg/L (50 °C)<br /> 0.00045% w/w (100&nbsp;°C, 3.9&nbsp;MPa)<ref>Haynes, p. 5.157</ref>
| SolubleOther = Soluble in [[ethanol|alcohol]], [[diethyl ether|(C<sub>2</sub>H<sub>5</sub>)<sub>2</sub>O]], [[acetone]], [[benzene|C<sub>6</sub>H<sub>6</sub>]], [[chloroform|CHCl<sub>3</sub>]],<ref name=crc1 /> [[carbon disulfide|CS<sub>2</sub>]]<ref name=sioc />
| Solubility1 = 0.76 g/kg (16 °C)<br /> 19 g/kg (19.5 °C)<br /> 3.28 g/kg (25 °C)<ref name=sioc>{{cite book|last1 = Seidell|first1 = Atherton|last2 = Linke|first2 = William F.|year = 1919|title = Solubilities of Inorganic and Organic Compounds|url = https://archive.org/details/solubilitiesino01seidgoog|publisher = D. Van Nostrand Company|place = New York|edition = 2nd|pages = [https://archive.org/details/solubilitiesino01seidgoog/page/n111 81]}}</ref>
| Solvent1 = ethanol
| Solubility2 = 18 g/kg (19.5 °C)<ref name=sioc />
| Solvent2 = methanol
| Solubility3 = 3.7 g/kg<ref name=sioc />
| Solvent3 = hexane
| Solubility4 = 9.2 g/kg (16.5 °C)<br /> 129.4 g/kg (100 °C)<ref name=sioc />
| Solvent4 = toluene
| Solubility5 = 7.32 g/kg<ref name=sioc />
| Solvent5 = carbon tetrachloride
| VaporPressure = 0.01 kPa (125.9 °C)<br /> 0.1 kPa (151.5 °C)<ref>Haynes, p. 6.116</ref><br /> 13.4 kPa (250 °C)<ref name=nist />
| HenryConstant = 0.0396 L·atm/mol<ref>Haynes, p. 5.157</ref>
| LogP = 4.56
| ThermalConductivity = 0.1416 W/(m·K) (240 °C)<br /> 0.1334 W/(m·K) (270 °C)<br /> 0.1259 W/(m·K) (300 °C)<ref name=wileyfr>{{cite web|url = http://www.infotherm.com/static/molpages/02/32/mol23245.html|title = Properties of Anthracene|website = www.infotherm.com|publisher = Wiley Information Services GmbH|access-date = 2014-06-22|archive-url = https://web.archive.org/web/20141101132638/http://www.infotherm.com/static/molpages/02/32/mol23245.html|archive-date = 2014-11-01}}</ref>
| Viscosity = 0.602 cP (240 °C)<br /> 0.498 cP (270 °C)<br /> 0.429 cP (300 °C)<ref name=wileyfr />
| LambdaMax = 345.6 nm, 363.2 nm<ref name=nist />
| MagSus = −129.8{{e|−6}} cm<sup>3</sup>/mol<ref>Haynes, p. 3.579</ref>
  }}
|Section3={{Chembox Structure
| CrystalStruct = [[monoclinic crystal system|Monoclinic]] (290 K)<ref name=sccs>{{cite book|url = https://books.google.com/books?id=hYRCAAAAQBAJ&pg=PA289|title = Structure and Chemistry of Crystalline Solids|last1 = Douglas|first1 = Bodie E.|last2 = Ho|first2 = Shih-Ming|publisher = Springer Science+Business Media, Inc.|year = 2007|isbn = 978-0-387-26147-8|place = New York|page = 289}}</ref>
| SpaceGroup = P2<sub>1</sub>/b<ref name=sccs />
| PointGroup = D{{sup sub|5|2h}}<ref name=sccs />
| LattConst_a = 8.562&nbsp;Å
| LattConst_b = 6.038&nbsp;Å
| LattConst_c = 11.184&nbsp;Å<ref name=sccs />
| LattConst_alpha = 
| LattConst_beta = 124.7
| LattConst_gamma = 
  }}
|Section4={{Chembox Thermochemistry
| Thermochemistry_ref =<ref>Haynes, p. 5.41</ref>
| HeatCapacity = 210.5 J/(mol·K)
| Entropy = 207.5 J/(mol·K)
| DeltaHf = 129.2 kJ/mol
| DeltaHc = 7061 kJ/mol<ref name=nist>{{nist|name=Anthracene|id=C120127|access-date=2014-06-22|mask=FFFF|units=SI}}</ref>
  }}
|Section7={{Chembox Hazards
| GHSPictograms = {{GHS07}}{{GHS09}}<ref name="sigma">{{Sigma-Aldrich|id=141062|name=Anthracene|access-date=2014-06-22}}</ref>
| GHSSignalWord = Warning
| HPhrases = {{H-phrases|302|305|315|319|335|410}}<ref name="sigma" />
| PPhrases = {{P-phrases|261|273|305+351+338|501}}<ref name="sigma" />
| FlashPtC = 121
| FlashPt_ref = <ref name="sigma" />
| AutoignitionPtC = 540
| AutoignitionPt_ref = <ref name="sigma" />
| NFPA-H = 1
| NFPA-F = 1
| NFPA-R = 0
| NFPA_ref =<ref name="fca">{{cite web|url = https://www.fishersci.ca/viewmsds.do?catNo=AC104860050|title = MSDS of Anthracene|website = www.fishersci.ca|access-date = 2014-06-22|publisher = Fisher Scientific}}</ref>
| LD50 = 100-149 mg/kg (rats, oral)
  }}
}}

'''Anthracene''' is a solid [[polycyclic aromatic hydrocarbon]] (PAH) of formula C<sub>14</sub>H<sub>10</sub>, consisting of three fused [[benzene]] rings. It is a component of [[coal tar]]. Anthracene is used in the [[Economic production|production]] of the red [[dye]] [[alizarin]] and other dyes, as a [[scintillator]] to detect high energy particles, as production of pharmaceutical drugs. Anthracene is colorless but exhibits a blue (400–500&nbsp;nm peak) [[fluorescence]] under [[ultraviolet]] radiation.<ref>{{cite web|last=Lindsey |first=Jonathan |display-authors=etal |title=Anthracene |url=http://omlc.ogi.edu/spectra/PhotochemCAD/html/022.html |work=PhotochemCAD |access-date=20 February 2014}}</ref>

== History and etymology ==
Crude anthracene (with a melting point of only 180°) was discovered in 1832 by [[Jean-Baptiste Dumas]] and [[Auguste Laurent]]<ref name=":0">{{Cite journal |last=Wisniak |first=Jaime |date=2009 |title=Auguste Laurent: Radical and radicals |journal=Educación química |language=en |volume=20 |issue=2 |pages=166–175 |doi=10.1016/S0187-893X(18)30023-5 |issn=0187-893X|doi-access=free }}</ref> who crystalized it from a fraction of coal tar later known as "anthracene oil". Since their (inaccurate) measurements showed the proportions of carbon and hydrogen of it to be the same as in [[naphthalene]], Laurent called it ''paranaphtaline'' in his 1835 publication of the discovery,<ref>{{Cite wikisource|title=fr:Comptes rendus de l'Académie des sciences/Tome 1, 1835/7 décembre}}</ref> which is translated to English as '''paranaphthalene'''.<ref name=":0" /> Two years later, however, he decided to rename the compound to its modern name derived from {{Langx|grc|ἄνθραξ|lit=coal|translit=anthrax}} because after discovering other polyaromatic hydrocarbons he decided it was only one of isomers of naphthalene.<ref>{{Cite book |url=https://books.google.com/books?id=wZg5AAAAcAAJ&pg=PA149 |title=Annales de chimie et de physique |date=1837 |language=fr}}</ref> This notion was disproved in 1850s and 1860s.<ref>{{Cite web |title=À propos de l'anthracène et de l'alizarine - p3 - N°467 - L'Actualité Chimique, le journal de la SCF |url=https://new.societechimiquedefrance.fr/numero/a-propos-de-lanthracene-et-de-lalizarine-p3-n467 |access-date=2024-11-11 |website=Société Chimique de France (SCF) |language=fr-FR}}</ref><ref>{{Cite journal |last1=Jackson |first1=C. Loring |last2=White |first2=J. Fleming |date=1880 |title=Researches on the Substituted Benzyl Compounds. Ninth Paper. The Synthesis of Anthracene and Phenanthrene from Orthobrombenzylbromide |url=https://www.jstor.org/stable/25138602 |journal=Proceedings of the American Academy of Arts and Sciences |volume=16 |pages=63–77 |doi=10.2307/25138602 |jstor=25138602 |issn=0199-9818|url-access=subscription }}</ref>

==Occurrence and production==
Anthracene, as many other [[polycyclic aromatic hydrocarbons]], is generated during combustion processes. Most human exposure is through [[tobacco smoke]] or ingestion of [[charring|charred]] food.

The mineral form of anthracene is called freitalite and is related to a coal deposit.<ref>Freitalite, Mindat, https://www.mindat.org/min-54360.html</ref> Coal tar, which contains around 1.5% anthracene, remains a major industrial source of this material.  Common impurities are [[phenanthrene]] and [[carbazole]]. 

A classic laboratory method for the preparation of anthracene is by cyclodehydration of o-methyl- or o-methylene-substituted diarylketones in the so-called [[Elbs reaction]], for example from ''o''-tolyl phenyl ketone.<ref>{{Cite web |title=Anthracene |url=https://www.acs.org/content/acs/en/molecule-of-the-week/archive/a/anthracene.html |access-date=2022-09-14 |website=American Chemical Society |language=en}}</ref>

==Reactions==
===Reduction===
Reduction of anthracene with alkali metals yields the deeply colored radical anion salts M<sup>+</sup>[anthracene]<sup>−</sup> (M = Li, Na, K).   Reduction with sodium in ethanol gives 9,10-[[dihydroanthracene]], preserving the aromaticity of the two flanking rings.<ref>{{OrgSynth|first = K. C.|last = Bass|title = 9,10-Dihydroanthracene|year = 1962|volume = 42|page = 48|doi = 10.15227/orgsyn.042.0048}}</ref>

===Cycloadditions===
In any solvent except water,<ref>{{Kirk-Othmer|title=Liquid salts for reactions|first1=Keith E.|last1=Johnson|first2=Richard M.|last2=Pagni|doi=10.1002/0471238961.liqupagn.a01|p=28}}</ref> anthracene [[photochemistry|photodimerize]]s by the action of [[ultraviolet|UV]] light:
:[[Image:Anthracene Photodimerisation.svg|class=skin-invert-image|360px|Anthracene dimer]]

The [[Dimer (chemistry)|dimer]], called dianthracene (or sometimes paranthracene), is connected by a pair of new carbon-carbon bonds, the result of the [4+4] [[cycloaddition]]. It reverts to anthracene thermally or with [[ultraviolet|UV]] irradiation below {{val|300|u=nm}}. Substituted anthracene derivatives behave similarly. The reaction is affected by the presence of [[oxygen]].<ref>{{cite book|author=Rickborn, Bruce |chapter=The Retro–Diels–Alder Reaction Part I. C-C Dienophiles |title=Organic Reactions|pages=1–393|doi=10.1002/0471264180.or052.01|year=1998|isbn=978-0-471-26418-7}}</ref><ref>{{cite journal |author=Bouas-Laurent, Henri |author2=Desvergne, Jean-Pierre |author3=Castellan, Alain |author4=Lapouyade, Rene |title=Photodimerization of anthracenes in fluid solution: Structural aspects|journal=Chemical Society Reviews|volume=29|pages=43–55|doi=10.1039/a801821i|year=2000}}</ref>

Anthracene also reacts with dienophile [[singlet oxygen]] in a [4+2]-cycloaddition ([[Diels–Alder reaction]]):
:[[Image:Anthracene singlet oxygen Diels-Alder reaction.svg|class=skin-invert-image|360px|none|Diels alder reaction of anthracene with singlet oxygen]]

===With electrophiles===
Chemical [[oxidation]] occurs readily, giving [[anthraquinone]], C<sub>14</sub>H<sub>8</sub>O<sub>2</sub> (below), for example using [[hydrogen peroxide]] and [[vanadyl acetylacetonate]].<ref>{{cite journal|doi=10.1021/ed100843a|title=Coordination Complexes as Catalysts: The Oxidation of Anthracene by Hydrogen Peroxide in the Presence of VO(acac)2|journal=Journal of Chemical Education|volume=88|issue=8|pages=1155–1157|year=2011|last1=Charleton|first1=Kimberly D. M.|last2=Prokopchuk|first2=Ernest M.|bibcode=2011JChEd..88.1155C}}</ref>
:[[Image:Anthraquinone acsv.svg|class=skin-invert-image|120px|none|Anthraquione]]

Electrophilic substitution of anthracene occurs at the 9 position.  For example, formylation affords [[9-Anthracenecarboxaldehyde|9-anthracenecarboxaldehyde]].  Substitution at other positions is effected indirectly, for example starting with anthroquinone.<ref>{{cite journal|doi=10.1016/j.tet.2017.08.038|title=Synthesis of asymmetrically disubstituted anthracenes|journal=Tetrahedron|volume=73|issue=40|pages=5892–5899|year=2017|last1=Škalamera|first1=Đani|last2=Veljković|first2=Jelena|last3=Ptiček|first3=Lucija|last4=Sambol|first4=Matija|last5=Mlinarić-Majerski|first5=Kata|last6=Basarić|first6=Nikola}}</ref>  Bromination of anthracene gives 9,10-dibromoanthracene.<ref>{{cite journal |doi=10.15227/orgsyn.003.0041|first1=I. M.|last1=Heilbron|first2=J. S.|last2=Heaton|title=9,10-Dibromoanthracene|journal=Organic Syntheses|year=1923|volume=3|page=41}}</ref>

==Uses==
Anthracene proper has application as an [[organic semiconductor]] and [[chemical feedstock]] for various preservatives and dyes.  

===Electronics===
[[File:Fluorescence of Anthracene under UV light.jpg|thumb|left|Fluorescence of anthracene under UV light]]
Anthracene is a wide band-gap [[organic semiconductor]], with an [[emission spectrum]] peaking between [[dark violet|400&nbsp;nm and 440&nbsp;nm]].  Organic [[field-effect transistor]]s have been constructed from it.  In [[particle physics]], it is used as a [[scintillator]] to detect high-energy [[photon]]s, [[electron]]s, or [[alpha particle]]s.<ref>{{Cite web |title=Anthracene |url=https://www.acs.org/molecule-of-the-week/archive/a/anthracene.html |access-date=2025-01-18 |website=American Chemical Society |language=en}}</ref>  Plastics, such as [[polyvinyltoluene]], can be doped with anthracene to produce an approximately water-equivalent scintillator in [[radiation therapy]] [[dosimetry]].  

Anthracene is commonly used as a UV tracer in conformal coatings applied to printed wiring boards.  The anthracene tracer allows the conformal coating to be inspected under UV light.<ref>Zeitler, Alex (2012-06-27) [https://www.smta.org/chapters/files/UpperMidwest_BTW_Conformal_Coating_June_27th_2012.pdf Conformal Coating 101: General Overview, Process Development, and Control Methods]. BTW, Inc.</ref>

It is also used in [[wood]] [[preservative]]s, [[insecticide]]s, and coating [[commodity|materials]].{{Citation needed|date=September 2010}}

===Derivatives===
[[File:Antracene diradical AFM2.png|thumb|left|False-color [[atomic force microscopy|AFM]] image of anthracene diradical, where hydrogen atoms are removed at carbons 9 and 10]]
A variety of anthracene derivatives find specialized uses.  Industrially, anthracene is converted mainly to [[anthraquinone]], a precursor to dyes.<ref name=Ullmann>Collin, Gerd; Höke, Hartmut and Talbiersky, Jörg (2006) "Anthracene" in ''Ullmann's Encyclopedia of Industrial Chemistry'', Wiley-VCH, Weinheim.  {{doi|10.1002/14356007.a02_343.pub2}}</ref>  Derivatives having a [[Hydroxide|hydroxyl group]] are 1-hydroxyanthracene and 2-hydroxyanthracene, homologous to [[phenol]] and [[naphthol (disambiguation)|naphthol]]s, and hydroxyanthracene (also called anthrol, and anthracenol)<ref>[http://webbook.nist.gov/cgi/cbook.cgi?Name=1-hydroxyanthracene&Units=SI 1-Hydroxyanthracene]. NIST datapage</ref><ref>[http://webbook.nist.gov/cgi/cbook.cgi?Name=2-hydroxyanthracene&Units=SI 2-Hydroxyanthracene]. NIST datapage</ref> are [[pharmacology|pharmacologically]] active.  <!--They are contained in [[aloe]] for example (to be specific, in the aloe latex - the references cited for this are inaccurate as they describe the aloe latex, which is typically not a part of the plant used in commerce or is removed during processing [IASC, 2009].<ref>[http://www.tga.gov.au/docs/html/tganews/news23/chem.htm TGA News]</ref>-->
Anthracene may also be found with multiple hydroxyl groups, as in [[9,10-dihydroxyanthracene]].

Some anthracene derivatives are used as pharmaceutical drugs, including [[bisantrene]], [[trazitiline]], and [[benzoctamine]].


==Toxicology==
Many investigations indicate that anthracene is noncarcinogenic: "consistently negative findings in numerous in vitro and in vivo genotoxicity tests". Early experiments suggested otherwise because crude samples were contaminated with other polycyclic aromatic hydrocarbons.  Furthermore, it is readily biodegraded in soil.  It is especially susceptible to degradation in the presence of light.<ref name=Ullmann/>  The [[International Agency for Research on Cancer]] (IARC) classifies anthracene as [[IARC group 2B]], possibly carcinogenic to humans.<ref>{{Cite web |title=IARC Monographs evaluate the carcinogenicity of anthracene, 2-bromopropane, butyl methacrylate, and dimethyl hydrogen phosphite |url=https://www.iarc.who.int/faq/iarc-monographs-evaluate-the-carcinogenicity-of-anthracene-2-bromopropane-butyl-methacrylate-and-dimethyl-hydrogen-phosphite/#:~:text=Anthracene%20was%20classified%20as%20possibly,for%20cancer%20in%20experimental%20animals. |access-date=2025-01-17 |website=www.iarc.who.int |language=en-US}}</ref>

==See also==
* [[9,10-Dithioanthracene]], derivative with two thiol groups added to the central ring
* [[Phenanthrene]]
* [[Acridine]]
* [[Phenazine]]
* [[Tetracene]]

==References==
{{reflist}}

==Cited sources==
*{{cite book | editor= Haynes, William M. | year = 2011 | title = [[CRC Handbook of Chemistry and Physics]] | edition = 92nd | publisher = [[CRC Press]] | isbn = 978-1-4398-5511-9}}

==External links==
{{Commons category|Anthracenes}}
{{AmCyc Poster}}
* {{ICSC|0825|08}}
* [https://web.archive.org/web/20091114145131/http://monographs.iarc.fr/ENG/Monographs/vol32/volume32.pdf IARC – Monograph 32]
* [https://web.archive.org/web/20060518002254/http://www.npi.gov.au/database/substance-info/profiles/74.html National Pollutant Inventory – Polycyclic Aromatic Hydrocarbon Fact Sheet]
* [https://web.archive.org/web/20110122105255/http://echa.europa.eu/home_en.asp European Chemicals Agency – ECHA]
* {{Cite EB1911|wstitle=Anthracene |short=x}}

{{Hydrocarbons}}
{{Tricyclics}}
{{PAHs}}
{{Molecules detected in outer space}}

{{Authority control}}

[[Category:Organic semiconductors]]
[[Category:Phosphors and scintillators]]
[[Category:IARC Group 2B carcinogens]]
[[Category:Anthracenes| ]]
[[Category:Ionising radiation detectors]]
[[Category:Acenes]]
[[Category:PBT substances]]
[[Category:Polycyclic aromatic hydrocarbons]]