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Your current IP address is 8.222.208.146. </p> <div class="paragraphbreak" style="margin-top:0.5em"></div><div style="font-size: 16px;"> <p>Even while globally blocked, you will <i>usually</i> still be able to edit pages on <a href="https://meta.wikimedia.org/wiki/" class="extiw" title="m:">Meta-Wiki</a>. </p> </div> <div class="paragraphbreak" style="margin-top:0.5em"></div><div style="font-size: 16px;"> <p>If you believe you were blocked by mistake, you can find additional information and instructions in the <a href="https://meta.wikimedia.org/wiki/Special:MyLanguage/Stewards/Wizard" class="extiw" title="m:Special:MyLanguage/Stewards/Wizard">Stewards Block Wizard</a>. </p> </div> <p>Other useful links: <a href="https://meta.wikimedia.org/wiki/Global_blocks" class="extiw" title="m:Global blocks">Global blocks</a> · <a href="/wiki/Help:I_have_been_blocked" title="Help:I have been blocked">Help:I have been blocked</a> </p> </div></li></ul><hr /> <div id="viewsourcetext">You can view and copy the source of this page:</div><textarea readonly="" accesskey="," id="wpTextbox1" cols="80" rows="25" style="" class="mw-editfont-monospace" lang="en" dir="ltr" name="wpTextbox1">{{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  |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 |url=https://www.scielo.org.mx/scielo.php?script=sci_arttext&pid=S0187-893X2009000200010 |archive-url=https://web.archive.org/web/20241111201753/https://www.scielo.org.mx/scielo.php?script=sci_arttext&pid=S0187-893X2009000200010 |url-status=dead |archive-date=November 11, 2024 |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}}</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). Hydrogenation 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&nbsp;E.|last1=Johnson|first2=Richard&nbsp;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 300&nbsp;nm. Substituted anthracene derivatives behave similarly. The reaction is affected by the presence of [[oxygen]].<ref>{{cite book|author=Rickborn, Bruce |chapter=The Retro– <SCP>D</SCP> iels– <SCP>A</SCP> lder Reaction Part <SCP>I</SCP> . <SCP>C</SCP>  <SCP>C</SCP> 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.  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]] 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href="/w/index.php?title=Template:Chembox_DeltaHcombust&action=edit" title="Template:Chembox DeltaHcombust">edit</a>) </li><li><a href="/wiki/Template:Chembox_DeltaHform" title="Template:Chembox DeltaHform">Template:Chembox DeltaHform</a> (<a href="/w/index.php?title=Template:Chembox_DeltaHform&action=edit" title="Template:Chembox DeltaHform">view source</a>) (semi-protected)</li><li><a href="/wiki/Template:Chembox_Density" title="Template:Chembox Density">Template:Chembox Density</a> (<a href="/w/index.php?title=Template:Chembox_Density&action=edit" title="Template:Chembox Density">view source</a>) (template editor protected)</li><li><a href="/wiki/Template:Chembox_DrugBank" title="Template:Chembox DrugBank">Template:Chembox DrugBank</a> (<a href="/w/index.php?title=Template:Chembox_DrugBank&action=edit" title="Template:Chembox DrugBank">view source</a>) (template editor protected)</li><li><a href="/wiki/Template:Chembox_DrugBank/format" title="Template:Chembox DrugBank/format">Template:Chembox DrugBank/format</a> (<a href="/w/index.php?title=Template:Chembox_DrugBank/format&action=edit" title="Template:Chembox DrugBank/format">view source</a>) (template editor protected)</li><li><a href="/wiki/Template:Chembox_ECHA" title="Template:Chembox ECHA">Template:Chembox ECHA</a> (<a href="/w/index.php?title=Template:Chembox_ECHA&action=edit" title="Template:Chembox ECHA">view source</a>) (template editor protected)</li><li><a href="/wiki/Template:Chembox_ECNumber" title="Template:Chembox ECNumber">Template:Chembox ECNumber</a> (<a href="/w/index.php?title=Template:Chembox_ECNumber&action=edit" title="Template:Chembox ECNumber">view source</a>) (template editor protected)</li><li><a href="/wiki/Template:Chembox_ECNumber/format" title="Template:Chembox ECNumber/format">Template:Chembox ECNumber/format</a> (<a href="/w/index.php?title=Template:Chembox_ECNumber/format&action=edit" title="Template:Chembox ECNumber/format">view source</a>) (template editor protected)</li><li><a href="/wiki/Template:Chembox_Elements" title="Template:Chembox Elements">Template:Chembox Elements</a> (<a href="/w/index.php?title=Template:Chembox_Elements&action=edit" title="Template:Chembox Elements">view source</a>) (template editor protected)</li><li><a href="/wiki/Template:Chembox_Elements/molecular_formula" title="Template:Chembox Elements/molecular formula">Template:Chembox Elements/molecular formula</a> (<a href="/w/index.php?title=Template:Chembox_Elements/molecular_formula&action=edit" title="Template:Chembox Elements/molecular formula">view source</a>) (template editor protected)</li><li><a href="/wiki/Template:Chembox_Entropy" title="Template:Chembox Entropy">Template:Chembox Entropy</a> (<a href="/w/index.php?title=Template:Chembox_Entropy&action=edit" title="Template:Chembox Entropy">view source</a>) (semi-protected)</li><li><a href="/wiki/Template:Chembox_FlashPt" title="Template:Chembox FlashPt">Template:Chembox FlashPt</a> (<a href="/w/index.php?title=Template:Chembox_FlashPt&action=edit" title="Template:Chembox FlashPt">view source</a>) (semi-protected)</li><li><a href="/wiki/Template:Chembox_Footer" title="Template:Chembox Footer">Template:Chembox Footer</a> (<a href="/w/index.php?title=Template:Chembox_Footer&action=edit" title="Template:Chembox Footer">view source</a>) (template editor protected)</li><li><a href="/wiki/Template:Chembox_Footer/tracking" title="Template:Chembox Footer/tracking">Template:Chembox Footer/tracking</a> (<a href="/w/index.php?title=Template:Chembox_Footer/tracking&action=edit" title="Template:Chembox Footer/tracking">view source</a>) (template editor protected)</li><li><a href="/wiki/Template:Chembox_GHS_(set)" title="Template:Chembox GHS (set)">Template:Chembox GHS (set)</a> (<a href="/w/index.php?title=Template:Chembox_GHS_(set)&action=edit" title="Template:Chembox GHS (set)">view source</a>) (extended confirmed protected)</li><li><a href="/wiki/Template:Chembox_Gmelin" title="Template:Chembox Gmelin">Template:Chembox Gmelin</a> (<a href="/w/index.php?title=Template:Chembox_Gmelin&action=edit" title="Template:Chembox Gmelin">view source</a>) (semi-protected)</li><li><a href="/wiki/Template:Chembox_Hazards" title="Template:Chembox Hazards">Template:Chembox Hazards</a> (<a href="/w/index.php?title=Template:Chembox_Hazards&action=edit" title="Template:Chembox Hazards">view source</a>) (template editor protected)</li><li><a href="/wiki/Template:Chembox_HeatCapacity" title="Template:Chembox HeatCapacity">Template:Chembox HeatCapacity</a> (<a href="/w/index.php?title=Template:Chembox_HeatCapacity&action=edit" title="Template:Chembox HeatCapacity">view source</a>) (semi-protected)</li><li><a href="/wiki/Template:Chembox_HenryConstant" title="Template:Chembox HenryConstant">Template:Chembox HenryConstant</a> (<a href="/w/index.php?title=Template:Chembox_HenryConstant&action=edit" title="Template:Chembox HenryConstant">edit</a>) </li><li><a href="/wiki/Template:Chembox_IUPHAR_ligand" title="Template:Chembox IUPHAR ligand">Template:Chembox IUPHAR ligand</a> (<a href="/w/index.php?title=Template:Chembox_IUPHAR_ligand&action=edit" title="Template:Chembox IUPHAR ligand">view source</a>) (template editor protected)</li><li><a href="/wiki/Template:Chembox_IUPHAR_ligand/format" title="Template:Chembox IUPHAR ligand/format">Template:Chembox IUPHAR ligand/format</a> (<a href="/w/index.php?title=Template:Chembox_IUPHAR_ligand/format&action=edit" title="Template:Chembox IUPHAR ligand/format">view source</a>) (template editor protected)</li><li><a href="/wiki/Template:Chembox_Identifiers" title="Template:Chembox Identifiers">Template:Chembox Identifiers</a> (<a href="/w/index.php?title=Template:Chembox_Identifiers&action=edit" title="Template:Chembox Identifiers">view source</a>) (template editor protected)</li><li><a href="/wiki/Template:Chembox_InChI" title="Template:Chembox InChI">Template:Chembox InChI</a> (<a 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title="Template:Chembox Jmol/format">Template:Chembox Jmol/format</a> (<a href="/w/index.php?title=Template:Chembox_Jmol/format&action=edit" title="Template:Chembox Jmol/format">view source</a>) (template editor protected)</li><li><a href="/wiki/Template:Chembox_KEGG" title="Template:Chembox KEGG">Template:Chembox KEGG</a> (<a href="/w/index.php?title=Template:Chembox_KEGG&action=edit" title="Template:Chembox KEGG">view source</a>) (template editor protected)</li><li><a href="/wiki/Template:Chembox_KEGG/format" title="Template:Chembox KEGG/format">Template:Chembox KEGG/format</a> (<a href="/w/index.php?title=Template:Chembox_KEGG/format&action=edit" title="Template:Chembox KEGG/format">view source</a>) (template editor protected)</li><li><a href="/wiki/Template:Chembox_LambdaMax" title="Template:Chembox LambdaMax">Template:Chembox LambdaMax</a> (<a href="/w/index.php?title=Template:Chembox_LambdaMax&action=edit" title="Template:Chembox LambdaMax">edit</a>) </li><li><a href="/wiki/Template:Chembox_LattConst" title="Template:Chembox LattConst">Template:Chembox LattConst</a> (<a href="/w/index.php?title=Template:Chembox_LattConst&action=edit" title="Template:Chembox LattConst">view source</a>) (semi-protected)</li><li><a href="/wiki/Template:Chembox_Lethal_amounts_(set)" title="Template:Chembox Lethal amounts (set)">Template:Chembox Lethal amounts (set)</a> (<a href="/w/index.php?title=Template:Chembox_Lethal_amounts_(set)&action=edit" title="Template:Chembox Lethal amounts (set)">view source</a>) (semi-protected)</li><li><a href="/wiki/Template:Chembox_LogP" title="Template:Chembox LogP">Template:Chembox LogP</a> (<a href="/w/index.php?title=Template:Chembox_LogP&action=edit" title="Template:Chembox LogP">view source</a>) (semi-protected)</li><li><a href="/wiki/Template:Chembox_MagSus" title="Template:Chembox MagSus">Template:Chembox MagSus</a> (<a href="/w/index.php?title=Template:Chembox_MagSus&action=edit" title="Template:Chembox MagSus">view source</a>) (semi-protected)</li><li><a href="/wiki/Template:Chembox_MeltingPt" title="Template:Chembox MeltingPt">Template:Chembox MeltingPt</a> (<a href="/w/index.php?title=Template:Chembox_MeltingPt&action=edit" title="Template:Chembox MeltingPt">view source</a>) (template editor protected)</li><li><a href="/wiki/Template:Chembox_NFPA" title="Template:Chembox NFPA">Template:Chembox NFPA</a> (<a href="/w/index.php?title=Template:Chembox_NFPA&action=edit" title="Template:Chembox NFPA">view source</a>) (template editor protected)</li><li><a href="/wiki/Template:Chembox_Odour" title="Template:Chembox Odour">Template:Chembox Odour</a> (<a href="/w/index.php?title=Template:Chembox_Odour&action=edit" title="Template:Chembox Odour">view source</a>) (semi-protected)</li><li><a href="/wiki/Template:Chembox_PointGroup" title="Template:Chembox PointGroup">Template:Chembox PointGroup</a> (<a href="/w/index.php?title=Template:Chembox_PointGroup&action=edit" title="Template:Chembox PointGroup">edit</a>) </li><li><a href="/wiki/Template:Chembox_Properties" title="Template:Chembox Properties">Template:Chembox Properties</a> (<a href="/w/index.php?title=Template:Chembox_Properties&action=edit" title="Template:Chembox Properties">view source</a>) (template editor protected)</li><li><a href="/wiki/Template:Chembox_PubChem" title="Template:Chembox PubChem">Template:Chembox PubChem</a> (<a href="/w/index.php?title=Template:Chembox_PubChem&action=edit" title="Template:Chembox PubChem">view source</a>) (template editor protected)</li><li><a href="/wiki/Template:Chembox_PubChem/format" title="Template:Chembox PubChem/format">Template:Chembox PubChem/format</a> (<a href="/w/index.php?title=Template:Chembox_PubChem/format&action=edit" title="Template:Chembox PubChem/format">view source</a>) (template editor protected)</li><li><a href="/wiki/Template:Chembox_RTECS" title="Template:Chembox RTECS">Template:Chembox RTECS</a> (<a 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href="/wiki/Template:Chembox_Solubility" title="Template:Chembox Solubility">Template:Chembox Solubility</a> (<a href="/w/index.php?title=Template:Chembox_Solubility&action=edit" title="Template:Chembox Solubility">view source</a>) (template editor protected)</li><li><a href="/wiki/Template:Chembox_SolubilityInWater" title="Template:Chembox SolubilityInWater">Template:Chembox SolubilityInWater</a> (<a href="/w/index.php?title=Template:Chembox_SolubilityInWater&action=edit" title="Template:Chembox SolubilityInWater">view source</a>) (template editor protected)</li><li><a href="/wiki/Template:Chembox_SpaceGroup" title="Template:Chembox SpaceGroup">Template:Chembox SpaceGroup</a> (<a href="/w/index.php?title=Template:Chembox_SpaceGroup&action=edit" title="Template:Chembox SpaceGroup">view source</a>) (semi-protected)</li><li><a href="/wiki/Template:Chembox_Structure" title="Template:Chembox Structure">Template:Chembox Structure</a> (<a 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source</a>) (template editor protected)</li><li><a href="/wiki/Template:Chembox_image" title="Template:Chembox image">Template:Chembox image</a> (<a href="/w/index.php?title=Template:Chembox_image&action=edit" title="Template:Chembox image">view source</a>) (template editor protected)</li><li><a href="/wiki/Template:Chembox_image_cell" title="Template:Chembox image cell">Template:Chembox image cell</a> (<a href="/w/index.php?title=Template:Chembox_image_cell&action=edit" title="Template:Chembox image cell">view source</a>) (template editor protected)</li><li><a href="/wiki/Template:Chembox_image_sbs" title="Template:Chembox image sbs">Template:Chembox image sbs</a> (<a href="/w/index.php?title=Template:Chembox_image_sbs&action=edit" title="Template:Chembox image sbs">view source</a>) (template editor protected)</li><li><a href="/wiki/Template:Chembox_parametercheck" title="Template:Chembox parametercheck">Template:Chembox parametercheck</a> (<a 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