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type="hidden" name="title" value="Special:Search"/> <input class="search skin-minerva-search-trigger" id="searchInput" type="search" name="search" placeholder="Search Wikipedia" aria-label="Search Wikipedia" autocapitalize="sentences" title="Search Wikipedia [f]" accesskey="f"> </div> <button id="searchIcon" class="cdx-button cdx-button--size-large cdx-button--icon-only cdx-button--weight-quiet skin-minerva-search-trigger"> Search </button> </form> <nav class="minerva-user-navigation" aria-label="User navigation"> </nav> </div> </header> <main id="content" class="mw-body"> <div class="banner-container"> <div id="siteNotice"></div> </div> <div class="pre-content heading-holder"> <div class="page-heading"> <h1 id="firstHeading" class="firstHeading mw-first-heading">Benzene</h1> <div class="tagline"></div> </div> <ul id="p-associated-pages" class="minerva__tab-container"> <li class="minerva__tab selected"> <a class="minerva__tab-text" href="/wiki/Benzene" rel="" 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Watch </a> </li> <li id="page-actions-edit" class="page-actions-menu__list-item"> <a role="button" id="ca-edit" href="/w/index.php?title=Benzene&action=edit" data-event-name="menu.edit" data-mw="interface" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet edit-page menu__item--page-actions-edit"> Edit </a> </li> </ul> </nav>  <div id="mw-content-subtitle"></div> </div> <div id="bodyContent" class="content"> <div id="mw-content-text" class="mw-body-content"><script>function mfTempOpenSection(id){var block=document.getElementById("mf-section-"+id);block.className+=" open-block";block.previousSibling.className+=" open-block";}</script><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><section class="mf-section-0" id="mf-section-0"> <style data-mw-deduplicate="TemplateStyles:r1236090951">.mw-parser-output .hatnote{font-style:italic}.mw-parser-output div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">This article is about the chemical compound. For other uses, see <a href="/wiki/Benzene_(disambiguation)" class="mw-disambig" title="Benzene (disambiguation)">Benzene (disambiguation)</a>.</div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Not to be confused with <a href="/wiki/Petroleum_benzine" title="Petroleum benzine">Petroleum benzine</a>.</div> <style data-mw-deduplicate="TemplateStyles:r1084375498">.mw-parser-output .ib-chembox{border-collapse:collapse;text-align:left}.mw-parser-output .ib-chembox td,.mw-parser-output .ib-chembox th{border:1px solid #a2a9b1;width:40%}.mw-parser-output .ib-chembox td+td{width:60%}</style> Benzene is an <a href="/wiki/Organic_compound" title="Organic compound">organic</a> <a href="/wiki/Chemical_compound" title="Chemical compound">chemical compound</a> with the <a href="/wiki/Chemical_formula#Molecular_formula" title="Chemical formula">molecular formula</a> C6H6. The benzene <a href="/wiki/Molecule" title="Molecule">molecule</a> is composed of six <a href="/wiki/Carbon" title="Carbon">carbon</a> atoms joined in a planar hexagonal <a href="/wiki/Ring_(chemistry)" title="Ring (chemistry)">ring</a> with one <a href="/wiki/Hydrogen" title="Hydrogen">hydrogen</a> atom attached to each. Because it contains only <a href="/wiki/Carbon" title="Carbon">carbon</a> and hydrogen atoms, benzene is classed as a <a href="/wiki/Hydrocarbon" title="Hydrocarbon">hydrocarbon</a>. <table class="infobox ib-chembox"> <caption>Benzene </caption> <tbody><tr> <td colspan="2" style="text-align:center; padding:2px;"><a href="/wiki/File:Benzene-3D-vdW.png" class="mw-file-description" title="Benzene molecule"><img alt="Benzene molecule" src="//upload.wikimedia.org/wikipedia/commons/thumb/9/97/Benzene-3D-vdW.png/150px-Benzene-3D-vdW.png" decoding="async" width="150" height="134" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/97/Benzene-3D-vdW.png/225px-Benzene-3D-vdW.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/97/Benzene-3D-vdW.png/300px-Benzene-3D-vdW.png 2x" data-file-width="1100" data-file-height="981"></a> <div style="text-align:center;">Space-filling model</div> </td></tr> <tr> <td colspan="2" class="borderless" style="text-align:center"> <table border="0" style="width:100%;display:inline-table;"> <tbody><tr> <td style="border-right:1px solid #aaa; width:50%;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Benzene_geometrie_(2).svg" class="mw-file-description" title="Skeletal formula detail of benzene."><img alt="Skeletal formula detail of benzene." src="//upload.wikimedia.org/wikipedia/commons/thumb/6/64/Benzene_geometrie_%282%29.svg/130px-Benzene_geometrie_%282%29.svg.png" decoding="async" width="130" height="152" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/64/Benzene_geometrie_%282%29.svg/195px-Benzene_geometrie_%282%29.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/64/Benzene_geometrie_%282%29.svg/260px-Benzene_geometrie_%282%29.svg.png 2x" data-file-width="96" data-file-height="112"></a><figcaption>Skeletal formula detail of benzene.</figcaption></figure><div style="text-align:center">Geometry</div> </td> <td style="width:50%;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Benzene-aromatic-3D-balls.png" class="mw-file-description" title="Benzene ball-and-stick model"><img alt="Benzene ball-and-stick model" src="//upload.wikimedia.org/wikipedia/commons/thumb/5/5a/Benzene-aromatic-3D-balls.png/125px-Benzene-aromatic-3D-balls.png" decoding="async" width="125" height="138" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/5a/Benzene-aromatic-3D-balls.png/188px-Benzene-aromatic-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/5a/Benzene-aromatic-3D-balls.png/250px-Benzene-aromatic-3D-balls.png 2x" data-file-width="995" data-file-height="1100"></a><figcaption>Benzene ball-and-stick model</figcaption></figure><div style="text-align:center">Ball and stick model</div> </td></tr></tbody></table> </td></tr> <tr> <td colspan="2" style="text-align:center; padding:2px;"><a href="/wiki/File:Benzene_sample.jpg" class="mw-file-description" title="Sample of benzene"><img alt="Sample of benzene" src="//upload.wikimedia.org/wikipedia/commons/thumb/3/3a/Benzene_sample.jpg/200px-Benzene_sample.jpg" decoding="async" width="200" height="220" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/3a/Benzene_sample.jpg/300px-Benzene_sample.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/3a/Benzene_sample.jpg/400px-Benzene_sample.jpg 2x" data-file-width="1369" data-file-height="1505"></a> <div style="text-align:center;">Benzene at room temperature</div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Names </th></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Preferred_IUPAC_name" title="Preferred IUPAC name">Preferred IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0; max-width:22em;">Benzene<a href="#cite_note-iupac2013-1">[1]</a></div></div> </td></tr> <tr> <td colspan="2" style="text-align:left;">Other names <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;">Benzol (historic/German) Cyclohexa-1,3,5-triene; 1,3,5-Cyclohexatriene (theoretical resonance isomers) [6]Annulene (not recommended<a href="#cite_note-iupac2013-1">[1]</a>) Phene (historic)</div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Identifiers </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></div> </td> <td><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=71-43-2">71-43-2</a> <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600">Y</li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=c1ccccc1">Interactive image</a></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChEBI" title="ChEBI">ChEBI</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=16716">CHEBI:16716</a> <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600">Y</li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChEMBL" title="ChEMBL">ChEMBL</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembldb/index.php/compound/inspect/ChEMBL277500">ChEMBL277500</a> <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600">Y</li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChemSpider" title="ChemSpider">ChemSpider</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.236.html">236</a> <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600">Y</li></ul></div> </td></tr> <tr> <td><a href="/wiki/ECHA_InfoCard" class="mw-redirect" title="ECHA InfoCard">ECHA InfoCard</a> </td> <td><a rel="nofollow" class="external text" href="https://echa.europa.eu/substance-information/-/substanceinfo/100.000.685">100.000.685</a> <a href="https://www.wikidata.org/wiki/Q2270#P2566" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20"></a> </td></tr> <tr> <td><a href="/wiki/European_Community_number" title="European Community number">EC Number</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li>200-753-7</li></ul></div> </td></tr> <tr> <td><a href="/wiki/KEGG" title="KEGG">KEGG</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://www.kegg.jp/entry/C01407">C01407</a> <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600">Y</li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/PubChem" title="PubChem">PubChem</a> <abbr title="Compound ID">CID</abbr></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/241">241</a></li></ul></div> </td></tr> <tr> <td><a href="/wiki/RTECS" class="mw-redirect" title="RTECS">RTECS number</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li>CY1400000</li></ul></div> </td></tr> <tr> <td><a href="/wiki/Unique_Ingredient_Identifier" title="Unique Ingredient Identifier">UNII</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/J64922108F">J64922108F</a> <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600">Y</li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CompTox_Chemicals_Dashboard" title="CompTox Chemicals Dashboard">CompTox Dashboard</a> (<abbr title="U.S. Environmental Protection Agency">EPA</abbr>)</div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://comptox.epa.gov/dashboard/chemical/details/DTXSID3039242">DTXSID3039242</a> <a href="https://www.wikidata.org/wiki/Q2270#P3117" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20"></a></li></ul></div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal; background:transparent;"><div><a href="/wiki/International_Chemical_Identifier" title="International Chemical Identifier">InChI</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1S/C6H6/c1-2-4-6-5-3-1/h1-6H <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600">Y</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: UHOVQNZJYSORNB-UHFFFAOYSA-N <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600">Y</div></div></li></ul> </div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal; background:transparent;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.6em; word-wrap:break-word; text-indent:-1.5em; text-align:left; font-size:97%; line-height:120%;">c1ccccc1</div></li></ul> </div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Properties </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Chemical_formula" title="Chemical formula">Chemical formula</a></div> </td> <td>C6H6 </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td>78.114 g·mol−1 </td></tr> <tr> <td>Appearance </td> <td>Colorless liquid </td></tr> <tr> <td><a href="/wiki/Odor" title="Odor">Odor</a> </td> <td>sweet aromatic </td></tr> <tr> <td><a href="/wiki/Density" title="Density">Density</a> </td> <td>0.8765(20) g/cm3<a href="#cite_note-handbook13-2">[2]</a> </td></tr> <tr> <td><a href="/wiki/Melting_point" title="Melting point">Melting point</a> </td> <td>5.53 °C (41.95 °F; 278.68 K) </td></tr> <tr> <td><a href="/wiki/Boiling_point" title="Boiling point">Boiling point</a> </td> <td>80.1 °C (176.2 °F; 353.2 K) </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Aqueous_solution" title="Aqueous solution">Solubility in water</a></div> </td> <td>1.53 g/L (0 °C) 1.81 g/L (9 °C) 1.79 g/L (15 °C)<a href="#cite_note-3">[3]</a><a href="#cite_note-4">[4]</a><a href="#cite_note-5">[5]</a> 1.84 g/L (30 °C) 2.26 g/L (61 °C) 3.94 g/L (100 °C) 21.7 g/kg (200 °C, 6.5 MPa) 17.8 g/kg (200 °C, 40 MPa)<a href="#cite_note-chemister-6">[6]</a> </td></tr> <tr> <td><a href="/wiki/Solubility" title="Solubility">Solubility</a> </td> <td>Soluble in <a href="/wiki/Alcohol_(chemistry)" title="Alcohol (chemistry)">alcohol</a>, <a href="/wiki/Chloroform" title="Chloroform">CHCl3</a>, <a href="/wiki/Carbon_tetrachloride" title="Carbon tetrachloride">CCl4</a>, <a href="/wiki/Diethyl_ether" title="Diethyl ether">diethyl ether</a>, <a href="/wiki/Acetone" title="Acetone">acetone</a>, <a href="/wiki/Acetic_acid" title="Acetic acid">acetic acid</a><a href="#cite_note-chemister-6">[6]</a> </td></tr> <tr> <td><a href="/wiki/Solubility" title="Solubility">Solubility</a> in <a href="/wiki/Ethanediol" class="mw-redirect" title="Ethanediol">ethanediol</a> </td> <td>5.83 g/100 g (20 °C) 6.61 g/100 g (40 °C) 7.61 g/100 g (60 °C)<a href="#cite_note-chemister-6">[6]</a> </td></tr> <tr> <td><a href="/wiki/Solubility" title="Solubility">Solubility</a> in <a href="/wiki/Ethanol" title="Ethanol">ethanol</a> </td> <td>20 °C, solution in ethanol: 1.2 mL/L (20% v/v)<a href="#cite_note-sioc-7">[7]</a> </td></tr> <tr> <td><a href="/wiki/Solubility" title="Solubility">Solubility</a> in <a href="/wiki/Acetone" title="Acetone">acetone</a> </td> <td>20 °C, solution in acetone: 7.69 mL/L (38.46% v/v) 49.4 mL/L (62.5% v/v)<a href="#cite_note-sioc-7">[7]</a> </td></tr> <tr> <td><a href="/wiki/Solubility" title="Solubility">Solubility</a> in <a href="/wiki/Diethylene_glycol" title="Diethylene glycol">diethylene glycol</a> </td> <td>52 g/100 g (20 °C)<a href="#cite_note-chemister-6">[6]</a> </td></tr> <tr> <td><a href="/wiki/Partition_coefficient" title="Partition coefficient">log P</a> </td> <td>2.13 </td></tr> <tr> <td><a href="/wiki/Vapor_pressure" title="Vapor pressure">Vapor pressure</a> </td> <td>12.7 kPa (25 °C) 24.4 kPa (40 °C) 181 kPa (100 °C)<a href="#cite_note-nist-8">[8]</a> </td></tr> <tr> <td><a href="/wiki/Conjugate_acid" class="mw-redirect" title="Conjugate acid">Conjugate acid</a> </td> <td><a href="/wiki/Benzenium" class="mw-redirect" title="Benzenium">Benzenium</a><a href="#cite_note-9">[9]</a> </td></tr> <tr> <td><a href="/wiki/Conjugate_base" class="mw-redirect" title="Conjugate base">Conjugate base</a> </td> <td><a href="/w/index.php?title=Arenide_ion&action=edit&redlink=1" class="new" title="Arenide ion (page does not exist)">Benzenide</a><a href="#cite_note-10">[10]</a> </td></tr> <tr> <td><a href="/wiki/Ultraviolet%E2%80%93visible_spectroscopy" title="Ultraviolet–visible spectroscopy">UV-vis</a> (λmax) </td> <td>255 nm </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Magnetic_susceptibility" title="Magnetic susceptibility">Magnetic susceptibility</a> (χ)</div> </td> <td>−54.8·10−6 cm3/mol </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Refractive_index" title="Refractive index">Refractive index</a> (nD)</div> </td> <td>1.5011 (20 °C) 1.4948 (30 °C)<a href="#cite_note-chemister-6">[6]</a> </td></tr> <tr> <td><a href="/wiki/Viscosity" title="Viscosity">Viscosity</a> </td> <td>0.7528 <a href="/wiki/Poise_(unit)" title="Poise (unit)">cP</a> (10 °C) 0.6076 cP (25 °C) 0.4965 cP (40 °C) 0.3075 cP (80 °C) </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Structure </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Molecular_geometry" title="Molecular geometry">Molecular shape</a></div> </td> <td><a href="/wiki/Trigonal_planar_molecular_geometry" title="Trigonal planar molecular geometry">Trigonal planar</a> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Dipole#Molecular_dipoles" title="Dipole">Dipole moment</a></div> </td> <td>0 <a href="/wiki/Debye" title="Debye">D</a> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Thermochemistry </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Heat_capacity" title="Heat capacity">Heat capacity</a> (C)</div> </td> <td>134.8 J/mol·K </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Standard_molar_entropy" title="Standard molar entropy">Std molar entropy</a> (S⦵298)</div> </td> <td>173.26 J/mol·K<a href="#cite_note-nist-8">[8]</a> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Standard_enthalpy_change_of_formation" class="mw-redirect" title="Standard enthalpy change of formation">Std enthalpy of formation</a> (ΔfH⦵298)</div> </td> <td>48.7 kJ/mol </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Standard_enthalpy_change_of_combustion" class="mw-redirect" title="Standard enthalpy change of combustion">Std enthalpy of combustion</a> (ΔcH⦵298)</div> </td> <td>-3267.6 kJ/mol<a href="#cite_note-nist-8">[8]</a> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Hazards </th></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;"><a href="/wiki/Occupational_safety_and_health" title="Occupational safety and health">Occupational safety and health</a> (OHS/OSH): </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Main hazards</div> </td> <td>potential occupational carcinogen, flammable </td></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;"><a href="/wiki/Globally_Harmonized_System_of_Classification_and_Labelling_of_Chemicals" title="Globally Harmonized System of Classification and Labelling of Chemicals">GHS labelling</a>: </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/GHS_hazard_pictograms" title="GHS hazard pictograms">Pictograms</a></div> </td> <td><a href="/wiki/File:GHS-pictogram-flamme.svg" class="mw-file-description" title="GHS02: Flammable"><img alt="GHS02: Flammable" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6d/GHS-pictogram-flamme.svg/50px-GHS-pictogram-flamme.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6d/GHS-pictogram-flamme.svg/75px-GHS-pictogram-flamme.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6d/GHS-pictogram-flamme.svg/100px-GHS-pictogram-flamme.svg.png 2x" data-file-width="512" data-file-height="512"></a><a href="/wiki/File:GHS-pictogram-skull.svg" class="mw-file-description" title="GHS06: Toxic"><img alt="GHS06: Toxic" src="//upload.wikimedia.org/wikipedia/commons/thumb/5/58/GHS-pictogram-skull.svg/50px-GHS-pictogram-skull.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/58/GHS-pictogram-skull.svg/75px-GHS-pictogram-skull.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/58/GHS-pictogram-skull.svg/100px-GHS-pictogram-skull.svg.png 2x" data-file-width="724" data-file-height="724"></a><a href="/wiki/File:GHS-pictogram-exclam.svg" class="mw-file-description" title="GHS07: Exclamation mark"><img alt="GHS07: Exclamation mark" src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c3/GHS-pictogram-exclam.svg/50px-GHS-pictogram-exclam.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c3/GHS-pictogram-exclam.svg/75px-GHS-pictogram-exclam.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c3/GHS-pictogram-exclam.svg/100px-GHS-pictogram-exclam.svg.png 2x" data-file-width="512" data-file-height="512"></a><a href="/wiki/File:GHS-pictogram-silhouette.svg" class="mw-file-description" title="GHS08: Health hazard"><img alt="GHS08: Health hazard" src="//upload.wikimedia.org/wikipedia/commons/thumb/2/21/GHS-pictogram-silhouette.svg/50px-GHS-pictogram-silhouette.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/21/GHS-pictogram-silhouette.svg/75px-GHS-pictogram-silhouette.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/21/GHS-pictogram-silhouette.svg/100px-GHS-pictogram-silhouette.svg.png 2x" data-file-width="724" data-file-height="724"></a><a href="/wiki/File:GHS-pictogram-pollu.svg" class="mw-file-description" title="GHS09: Environmental hazard"><img alt="GHS09: Environmental hazard" src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b9/GHS-pictogram-pollu.svg/50px-GHS-pictogram-pollu.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b9/GHS-pictogram-pollu.svg/75px-GHS-pictogram-pollu.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b9/GHS-pictogram-pollu.svg/100px-GHS-pictogram-pollu.svg.png 2x" data-file-width="724" data-file-height="724"></a><a href="#cite_note-sigma-11">[11]</a> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Globally_Harmonized_System_of_Classification_and_Labelling_of_Chemicals#Signal_word" title="Globally Harmonized System of Classification and Labelling of Chemicals">Signal word</a></div> </td> <td>Danger </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/GHS_hazard_statements" title="GHS hazard statements">Hazard statements</a></div> </td> <td><abbr class="abbr" title="H225: Highly flammable liquid and vapour">H225</abbr>, <abbr class="abbr" title="H302: Harmful if swallowed">H302</abbr>, <abbr class="abbr" title="H304: May be fatal if swallowed and enters airways">H304</abbr>, <abbr class="abbr" title="H305: May be harmful if swallowed and enters airways">H305</abbr>, <abbr class="abbr" title="H315: Causes skin irritation">H315</abbr>, <abbr class="abbr" title="H319: Causes serious eye irritation">H319</abbr>, <abbr class="abbr" title="H340: May cause genetic defects">H340</abbr>, <abbr class="abbr" title="H350: May cause cancer">H350</abbr>, <abbr class="abbr" title="H372: Causes damage to organs through prolonged or repeated exposure">H372</abbr>, <abbr class="abbr" title="H410: Very toxic to aquatic life with long lasting effects">H410</abbr><a href="#cite_note-sigma-11">[11]</a> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/GHS_precautionary_statements" title="GHS precautionary statements">Precautionary statements</a></div> </td> <td><abbr class="abbr" title="P201: Obtain special instructions before use.">P201</abbr>, <abbr class="abbr" title="P210: Keep away from heat, hot surfaces, sparks, open flames and other ignition sources. No smoking.">P210</abbr>, <abbr class="abbr" title="P301+P310: IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.">P301+P310</abbr>, <abbr class="abbr" title="P305+P351+P338: IF IN EYES: Rinse continuously with water for several minutes. Remove contact lenses if present and easy to do. Continue rinsing.">P305+P351+P338</abbr>, <abbr class="abbr" title="P308+P313: IF exposed or concerned: Get medical advice/attention.">P308+P313</abbr>, <abbr class="abbr" title="P331: Do NOT induce vomiting.">P331</abbr><a href="#cite_note-sigma-11">[11]</a> </td></tr> <tr> <td><a href="/wiki/NFPA_704" title="NFPA 704">NFPA 704</a> (fire diamond) </td> <td><style data-mw-deduplicate="TemplateStyles:r1170367383">.mw-parser-output .nfpa-704-diamond-ref{float:right;padding:1px;text-align:right}.mw-parser-output .nfpa-704-diamond-container{width:82px;font-family:sans-serif;margin:0 auto}.mw-parser-output .nfpa-704-diamond-container-ref{float:left;margin-left:1em}.mw-parser-output .nfpa-704-diamond-images{float:left;font-size:20px;text-align:center;position:relative;height:80px;width:80px;padding:1px}.mw-parser-output .nfpa-704-diamond-map{position:absolute;height:80px;width:80px}.mw-parser-output .nfpa-704-diamond .noresize{margin:0 auto}.mw-parser-output .nfpa-704-diamond-code{line-height:1em;text-align:center;position:absolute}.mw-parser-output .nfpa-704-diamond-code>a{color:black}.mw-parser-output .nfpa-704-diamond-blue{width:13px;top:31px;left:15px}.mw-parser-output .nfpa-704-diamond-red{width:12px;top:12px;left:35px}.mw-parser-output .nfpa-704-diamond-yellow{width:13px;top:31px;left:54px}.mw-parser-output .nfpa-704-diamond-white-image{position:relative;top:51px;left:0}.mw-parser-output .nfpa-704-diamond-white-text{vertical-align:middle;text-align:center;line-height:80%;position:absolute;top:52px}.mw-parser-output .nfpa-704-diamond-white-text a>span{position:absolute;color:black}.mw-parser-output .nfpa-704-diamond-white-wors{font-size:15px;width:23px;left:29px}.mw-parser-output .nfpa-704-diamond-white-wox{font-size:15px;font-stretch:condensed;width:21px;line-height:80%;top:-4px;left:29px}.mw-parser-output .nfpa-704-diamond-white-abcp{font-size:13.5px;font-stretch:condensed;width:28px;left:26px}.mw-parser-output .nfpa-704-diamond-white-ac{font-size:10px;width:30px;left:25px}.mw-parser-output .nfpa-704-diamond-white-strike{text-decoration:line-through}</style><div class="nfpa-704-diamond notheme"><div class="nfpa-704-diamond-container"><div class="nfpa-704-diamond-images nounderlines"> <div class="nfpa-704-diamond-map"><figure class="noresize" typeof="mw:File"><img alt="NFPA 704 four-colored diamond" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/80px-NFPA_704.svg.png" decoding="async" width="80" height="80" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/120px-NFPA_704.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/160px-NFPA_704.svg.png 2x" data-file-width="512" data-file-height="512" usemap="#ImageMap_9a02d12247c3a88a"><map name="ImageMap_9a02d12247c3a88a"><area href="/wiki/NFPA_704#Blue" shape="poly" coords="23,23,47,47,23,70,0,47" alt="Health 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroform" title="Health 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroform"><area href="/wiki/NFPA_704#Red" shape="poly" coords="47,0,70,23,47,47,23,23" alt="Flammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasoline" title="Flammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasoline"><area href="/wiki/NFPA_704#Yellow" shape="poly" coords="70,23,94,47,70,70,47,47" alt="Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen" title="Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen"><area href="/wiki/NFPA_704#White" shape="poly" coords="47,47,70,70,47,94,23,70" alt="Special hazards (white): no code" title="Special hazards (white): no code"></map><figcaption></figcaption></figure></div><div class="nfpa-704-diamond-code nfpa-704-diamond-blue"> <a href="/wiki/NFPA_704#Blue" title="NFPA 704">2</a></div><div class="nfpa-704-diamond-code nfpa-704-diamond-red"> <a href="/wiki/NFPA_704#Red" title="NFPA 704"><span title="Flammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasoline" class="notheme mw-no-invert">3</a></div><div class="nfpa-704-diamond-code nfpa-704-diamond-yellow"> <a href="/wiki/NFPA_704#Yellow" title="NFPA 704">0</a></div></div></div></div> </td></tr> <tr> <td><a href="/wiki/Flash_point" title="Flash point">Flash point</a> </td> <td>−11.63 °C (11.07 °F; 261.52 K) </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Autoignition_temperature" title="Autoignition temperature">Autoignition temperature</a></div> </td> <td>497.78 °C (928.00 °F; 770.93 K) </td></tr> <tr> <td><a href="/wiki/Explosive_limit" class="mw-redirect" title="Explosive limit">Explosive limits</a> </td> <td>1.2–7.8% </td></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;">Lethal dose or concentration (LD, LC): </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">LD50 (<a href="/wiki/Lethal_dose#LD50" title="Lethal dose">median dose</a>)</div> </td> <td>930 mg/kg (rat, oral)<a href="#cite_note-13">[13]</a> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">LCLo (<a href="/wiki/Lethal_dose#LCLo" title="Lethal dose">lowest published</a>)</div> </td> <td>44,000 ppm (rabbit, 30 min) 44,923 ppm (dog) 52,308 ppm (cat) 20,000 ppm (human, 5 min)<a href="#cite_note-14">[14]</a> </td></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;"><a href="/wiki/National_Institute_for_Occupational_Safety_and_Health" title="National Institute for Occupational Safety and Health">NIOSH</a> (US health exposure limits): </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Permissible_exposure_limit" title="Permissible exposure limit">PEL</a> (Permissible)</div> </td> <td>TWA 1 ppm, ST 5 ppm<a href="#cite_note-PGCH-12">[12]</a> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Recommended_exposure_limit" title="Recommended exposure limit">REL</a> (Recommended)</div> </td> <td>Ca TWA 0.1 ppm ST 1 ppm<a href="#cite_note-PGCH-12">[12]</a> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/IDLH" class="mw-redirect" title="IDLH">IDLH</a> (Immediate danger)</div> </td> <td>500 ppm<a href="#cite_note-PGCH-12">[12]</a> </td></tr> <tr> <td><a href="/wiki/Safety_data_sheet" title="Safety data sheet">Safety data sheet</a> (SDS) </td> <td><a rel="nofollow" class="external text" href="http://www.hmdb.ca/system/metabolites/msds/000/001/365/original/HMDB01505.pdf?1358893540">HMDB</a> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Related compounds </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Related compounds</div> </td> <td><a href="/wiki/Toluene" title="Toluene">Toluene</a> <a href="/wiki/Borazine" title="Borazine">Borazine</a> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Supplementary data page </th></tr> <tr> <td colspan="2" style="text-align:center"><a href="/wiki/Benzene_(data_page)" title="Benzene (data page)">Benzene (data page)</a> </td></tr> <tr> <td colspan="2" style="text-align:left; background:#f8eaba; border:1px solid #a2a9b1;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Except where otherwise noted, data are given for materials in their <a href="/wiki/Standard_state" title="Standard state">standard state</a> (at 25 °C [77 °F], 100 kPa).</div> <div style="margin-top: 0.3em;"><div style="text-align:center;"><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/12px-Yes_check.svg.png" decoding="async" width="12" height="12" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/18px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/24px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600">Y <a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=464365865&page2=Benzene">verify</a> (<a href="/wiki/Wikipedia:WikiProject_Chemicals/Chembox_validation" title="Wikipedia:WikiProject Chemicals/Chembox validation">what is</a> <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600">Y<img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600">N ?) </div></div> <div style="margin-top: 0.3em; text-align: center;"><a href="/wiki/Wikipedia:Chemical_infobox#References" title="Wikipedia:Chemical infobox">Infobox references</a></div> </td></tr> </tbody></table> Benzene is a natural constituent of <a href="/wiki/Petroleum" title="Petroleum">petroleum</a> and is one of the elementary <a href="/wiki/Petrochemical" title="Petrochemical">petrochemicals</a>. Due to the cyclic continuous <a href="/wiki/Pi_bond" title="Pi bond">pi bonds</a> between the carbon atoms, benzene is classed as an <a href="/wiki/Aromatic_hydrocarbon" class="mw-redirect" title="Aromatic hydrocarbon">aromatic hydrocarbon</a>. Benzene is a colorless and highly <a href="/wiki/Combustibility_and_flammability" title="Combustibility and flammability">flammable</a> liquid with a sweet smell, and is partially responsible for the aroma of <a href="/wiki/Gasoline" title="Gasoline">gasoline</a>. It is used primarily as a <a href="/wiki/Precursor_(chemistry)" title="Precursor (chemistry)">precursor</a> to the manufacture of chemicals with more complex structures, such as <a href="/wiki/Ethylbenzene" title="Ethylbenzene">ethylbenzene</a> and <a href="/wiki/Cumene" title="Cumene">cumene</a>, of which billions of kilograms are produced annually. Although benzene is a major <a href="/wiki/Chemical_industry" title="Chemical industry">industrial chemical</a>, it finds limited use in consumer items because of its toxicity. Benzene is a <a href="/wiki/Volatile_organic_compound" title="Volatile organic compound">volatile organic compound</a>.<a href="#cite_note-15">[15]</a> Benzene is classified as a <a href="/wiki/Carcinogen" title="Carcinogen">carcinogen</a>. Its particular effects on <a href="/wiki/Human_health" class="mw-redirect" title="Human health">human health</a>, such as the long-term results of accidental exposure, have been reported on by news organizations such as <a href="/wiki/The_New_York_Times" title="The New York Times">The New York Times</a>. For instance, a 2022 article stated that benzene contamination in the <a href="/wiki/Boston_metropolitan_area" class="mw-redirect" title="Boston metropolitan area">Boston metropolitan area</a> caused hazardous conditions in multiple places, with the publication noting that the compound may eventually cause <a href="/wiki/Leukemia" title="Leukemia">leukemia</a> in some individuals.<a href="#cite_note-16">[16]</a> <div id="toc" class="toc" role="navigation" aria-labelledby="mw-toc-heading"><input type="checkbox" role="button" id="toctogglecheckbox" class="toctogglecheckbox" style="display:none"><div class="toctitle" lang="en" dir="ltr"><h2 id="mw-toc-heading">Contents</h2><label class="toctogglelabel" for="toctogglecheckbox"></label></div> <ul> <li class="toclevel-1 tocsection-1"><a href="#History">1 History</a> <ul> <li class="toclevel-2 tocsection-2"><a href="#Discovery">1.1 Discovery</a></li> <li class="toclevel-2 tocsection-3"><a href="#Ring_formula">1.2 Ring formula</a></li> <li class="toclevel-2 tocsection-4"><a href="#Nomenclature">1.3 Nomenclature</a></li> <li class="toclevel-2 tocsection-5"><a href="#Early_applications">1.4 Early applications</a></li> <li class="toclevel-2 tocsection-6"><a href="#Occurrence">1.5 Occurrence</a></li> </ul> </li> <li class="toclevel-1 tocsection-7"><a href="#Structure">2 Structure</a></li> <li class="toclevel-1 tocsection-8"><a href="#Benzene_derivatives">3 Benzene derivatives</a></li> <li class="toclevel-1 tocsection-9"><a href="#Production">4 Production</a> <ul> <li class="toclevel-2 tocsection-10"><a href="#Catalytic_reforming">4.1 Catalytic reforming</a></li> <li class="toclevel-2 tocsection-11"><a href="#Toluene_hydrodealkylation">4.2 Toluene hydrodealkylation</a></li> <li class="toclevel-2 tocsection-12"><a href="#Toluene_disproportionation">4.3 Toluene disproportionation</a></li> <li class="toclevel-2 tocsection-13"><a href="#Steam_cracking">4.4 Steam cracking</a></li> <li class="toclevel-2 tocsection-14"><a href="#Other_methods">4.5 Other methods</a></li> </ul> </li> <li class="toclevel-1 tocsection-15"><a href="#Uses">5 Uses</a> <ul> <li class="toclevel-2 tocsection-16"><a href="#Component_of_gasoline">5.1 Component of gasoline</a></li> </ul> </li> <li class="toclevel-1 tocsection-17"><a href="#Reactions">6 Reactions</a> <ul> <li class="toclevel-2 tocsection-18"><a href="#Sulfonation,_chlorination,_nitration">6.1 Sulfonation, chlorination, nitration</a></li> <li class="toclevel-2 tocsection-19"><a href="#Hydrogenation">6.2 Hydrogenation</a></li> <li class="toclevel-2 tocsection-20"><a href="#Metal_complexes">6.3 Metal complexes</a></li> </ul> </li> <li class="toclevel-1 tocsection-21"><a href="#Health_effects">7 Health effects</a></li> <li class="toclevel-1 tocsection-22"><a href="#Exposure_to_benzene">8 Exposure to benzene</a> <ul> <li class="toclevel-2 tocsection-23"><a href="#Benzene_exposure_limits">8.1 Benzene exposure limits</a></li> <li class="toclevel-2 tocsection-24"><a href="#Toxicology">8.2 Toxicology</a> <ul> <li class="toclevel-3 tocsection-25"><a href="#Biomarkers_of_exposure">8.2.1 Biomarkers of exposure</a></li> <li class="toclevel-3 tocsection-26"><a href="#Biotransformations">8.2.2 Biotransformations</a></li> <li class="toclevel-3 tocsection-27"><a href="#Molecular_toxicology">8.2.3 Molecular toxicology</a></li> <li class="toclevel-3 tocsection-28"><a href="#Biological_oxidation_and_carcinogenic_activity">8.2.4 Biological oxidation and carcinogenic activity</a></li> </ul> </li> <li class="toclevel-2 tocsection-29"><a href="#Routes_of_exposure">8.3 Routes of exposure</a> <ul> <li class="toclevel-3 tocsection-30"><a href="#Inhalation">8.3.1 Inhalation</a></li> <li class="toclevel-3 tocsection-31"><a href="#Exposure_from_soft_drinks">8.3.2 Exposure from soft drinks</a></li> <li class="toclevel-3 tocsection-32"><a href="#Contamination_of_water_supply">8.3.3 Contamination of water supply</a></li> <li class="toclevel-3 tocsection-33"><a href="#Genocide">8.3.4 Genocide</a></li> </ul> </li> </ul> </li> <li class="toclevel-1 tocsection-34"><a href="#See_also">9 See also</a></li> <li class="toclevel-1 tocsection-35"><a href="#Explanatory_notes">10 Explanatory notes</a></li> <li class="toclevel-1 tocsection-36"><a href="#References">11 References</a></li> <li class="toclevel-1 tocsection-37"><a href="#External_links">12 External links</a></li> </ul> </div> </section><div class="mw-heading mw-heading2 section-heading" onclick="mfTempOpenSection(1)"><h2 id="History">History</h2> <a role="button" href="/w/index.php?title=Benzene&action=edit&section=1" title="Edit section: History" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> edit </a> </div><section class="mf-section-1 collapsible-block" id="mf-section-1"> <div class="mw-heading mw-heading3"><h3 id="Discovery">Discovery</h3> <a role="button" href="/w/index.php?title=Benzene&action=edit&section=2" title="Edit section: Discovery" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> edit </a> </div> The word "benzene" derives from "gum benzoin" (<a href="/wiki/Benzoin_(resin)" title="Benzoin (resin)">benzoin resin</a>), an aromatic resin known since ancient times in Southeast Asia, and later to European pharmacists and perfumers in the 16th century via trade routes.<a href="#cite_note-17">[17]</a> An <a href="/wiki/Acid" title="Acid">acidic</a> material was derived from benzoin by <a href="/wiki/Sublimation_(phase_transition)" title="Sublimation (phase transition)">sublimation</a>, and named "flowers of benzoin", or benzoic acid. The hydrocarbon derived from benzoic acid thus acquired the name benzin, benzol, or benzene.<a href="#cite_note-rocke-18">[18]</a> <a href="/wiki/Michael_Faraday" title="Michael Faraday">Michael Faraday</a> first isolated and identified benzene in 1825 from the oily residue derived from the production of illuminating gas, giving it the name bicarburet of hydrogen.<a href="#cite_note-19">[19]</a><a href="#cite_note-20">[20]</a> In 1833, <a href="/wiki/Eilhard_Mitscherlich" title="Eilhard Mitscherlich">Eilhard Mitscherlich</a> produced it by <a href="/wiki/Distillation" title="Distillation">distilling</a> <a href="/wiki/Benzoic_acid" title="Benzoic acid">benzoic acid</a> (from <a href="/wiki/Benzoin_(resin)" title="Benzoin (resin)">gum benzoin</a>) and <a href="/wiki/Calcium_oxide" title="Calcium oxide">lime</a>. He gave the compound the name benzin.<a href="#cite_note-21">[21]</a> In 1836, the French chemist <a href="/wiki/Auguste_Laurent" title="Auguste Laurent">Auguste Laurent</a> named the substance "phène";<a href="#cite_note-22">[22]</a> this word has become the root of the English word "<a href="/wiki/Phenol" title="Phenol">phenol</a>", which is <a href="/wiki/Hydroxylation" title="Hydroxylation">hydroxylated</a> benzene, and "<a href="/wiki/Phenyl_group" title="Phenyl group">phenyl</a>", the radical formed by abstraction of a hydrogen atom from benzene. In 1845, <a href="/wiki/Charles_Blachford_Mansfield" title="Charles Blachford Mansfield">Charles Blachford Mansfield</a>, working under <a href="/wiki/August_Wilhelm_von_Hofmann" title="August Wilhelm von Hofmann">August Wilhelm von Hofmann</a>, isolated benzene from <a href="/wiki/Coal_tar" title="Coal tar">coal tar</a>.<a href="#cite_note-23">[23]</a> Four years later, Mansfield began the first industrial-scale production of benzene, based on the coal-tar method.<a href="#cite_note-24">[24]</a><a href="#cite_note-25">[25]</a> Gradually, the sense developed among chemists that a number of substances were chemically related to benzene, comprising a diverse chemical family. In 1855, Hofmann was the first to apply the word "<a href="/wiki/Aromaticity" title="Aromaticity">aromatic</a>" to designate this family relationship, after a characteristic property of many of its members.<a href="#cite_note-26">[26]</a> In 1997, benzene was <a href="/wiki/List_of_interstellar_and_circumstellar_molecules" title="List of interstellar and circumstellar molecules">detected in deep space</a>.<a href="#cite_note-Cernicharo_546-27">[27]</a> <div class="mw-heading mw-heading3"><h3 id="Ring_formula">Ring formula</h3> <a role="button" href="/w/index.php?title=Benzene&action=edit&section=3" title="Edit section: Ring formula" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> edit </a> </div> <table class="wikitable" style="text-align:center; font-size:90%; margin-left:20px;" width="50%"> <tbody><tr> <th colspan="6">Historic proposals of benzene structures </th></tr> <tr style="background-color:white"> <td><a href="/wiki/File:Historic_Benzene_Formula_Claus_1867_(original)2.png" class="mw-file-description"><noscript><img src="//upload.wikimedia.org/wikipedia/commons/thumb/1/1b/Historic_Benzene_Formula_Claus_1867_%28original%292.png/120px-Historic_Benzene_Formula_Claus_1867_%28original%292.png" decoding="async" width="120" height="132" class="mw-file-element" data-file-width="334" data-file-height="367"></noscript><span class="lazy-image-placeholder" style="width: 120px;height: 132px;" data-src="//upload.wikimedia.org/wikipedia/commons/thumb/1/1b/Historic_Benzene_Formula_Claus_1867_%28original%292.png/120px-Historic_Benzene_Formula_Claus_1867_%28original%292.png" data-width="120" data-height="132" data-srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/1b/Historic_Benzene_Formula_Claus_1867_%28original%292.png/180px-Historic_Benzene_Formula_Claus_1867_%28original%292.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/1b/Historic_Benzene_Formula_Claus_1867_%28original%292.png/240px-Historic_Benzene_Formula_Claus_1867_%28original%292.png 2x" data-class="mw-file-element"> </a> </td> <td><a href="/wiki/File:Historic_Benzene_Formula_Dewar_1869_(original_Dewar_benzene).png" class="mw-file-description"><noscript><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/9b/Historic_Benzene_Formula_Dewar_1869_%28original_Dewar_benzene%29.png/91px-Historic_Benzene_Formula_Dewar_1869_%28original_Dewar_benzene%29.png" decoding="async" width="91" height="120" class="mw-file-element" data-file-width="348" data-file-height="459"></noscript><span class="lazy-image-placeholder" style="width: 91px;height: 120px;" data-src="//upload.wikimedia.org/wikipedia/commons/thumb/9/9b/Historic_Benzene_Formula_Dewar_1869_%28original_Dewar_benzene%29.png/91px-Historic_Benzene_Formula_Dewar_1869_%28original_Dewar_benzene%29.png" data-width="91" data-height="120" data-srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/9b/Historic_Benzene_Formula_Dewar_1869_%28original_Dewar_benzene%29.png/137px-Historic_Benzene_Formula_Dewar_1869_%28original_Dewar_benzene%29.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/9b/Historic_Benzene_Formula_Dewar_1869_%28original_Dewar_benzene%29.png/182px-Historic_Benzene_Formula_Dewar_1869_%28original_Dewar_benzene%29.png 2x" data-class="mw-file-element"> </a> </td> <td><a href="/wiki/File:Historic_Benzene_Formula_Ladenburg_1869_(original).png" class="mw-file-description"><noscript><img src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a4/Historic_Benzene_Formula_Ladenburg_1869_%28original%29.png/80px-Historic_Benzene_Formula_Ladenburg_1869_%28original%29.png" decoding="async" width="80" height="100" class="mw-file-element" data-file-width="233" data-file-height="290"></noscript><span class="lazy-image-placeholder" style="width: 80px;height: 100px;" data-src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a4/Historic_Benzene_Formula_Ladenburg_1869_%28original%29.png/80px-Historic_Benzene_Formula_Ladenburg_1869_%28original%29.png" data-width="80" data-height="100" data-srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a4/Historic_Benzene_Formula_Ladenburg_1869_%28original%29.png/120px-Historic_Benzene_Formula_Ladenburg_1869_%28original%29.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a4/Historic_Benzene_Formula_Ladenburg_1869_%28original%29.png/160px-Historic_Benzene_Formula_Ladenburg_1869_%28original%29.png 2x" data-class="mw-file-element"> </a> </td></tr> <tr align="center" style="vertical-align:top"> <td>By <a href="/wiki/Adolf_Karl_Ludwig_Claus" title="Adolf Karl Ludwig Claus">Adolf Karl Ludwig Claus</a> (1867)<a href="#cite_note-28">[28]</a> </td> <td>By <a href="/wiki/James_Dewar" title="James Dewar">James Dewar</a> (1869)<a href="#cite_note-29">[29]</a> </td> <td>By <a href="/wiki/Albert_Ladenburg" title="Albert Ladenburg">Albert Ladenburg</a> (1869)<a href="#cite_note-30">[30]</a> </td></tr> <tr> <td colspan="3" style="background:#FFFFFF"><a href="/wiki/File:Historic_Benzene_Formulae_Kekul%C3%A9_(original).png" class="mw-file-description"><noscript><img src="//upload.wikimedia.org/wikipedia/commons/thumb/f/f8/Historic_Benzene_Formulae_Kekul%C3%A9_%28original%29.png/300px-Historic_Benzene_Formulae_Kekul%C3%A9_%28original%29.png" decoding="async" width="300" height="104" class="mw-file-element" data-file-width="1081" data-file-height="375"></noscript><span class="lazy-image-placeholder" style="width: 300px;height: 104px;" data-src="//upload.wikimedia.org/wikipedia/commons/thumb/f/f8/Historic_Benzene_Formulae_Kekul%C3%A9_%28original%29.png/300px-Historic_Benzene_Formulae_Kekul%C3%A9_%28original%29.png" data-width="300" data-height="104" data-srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/f8/Historic_Benzene_Formulae_Kekul%C3%A9_%28original%29.png/450px-Historic_Benzene_Formulae_Kekul%C3%A9_%28original%29.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/f8/Historic_Benzene_Formulae_Kekul%C3%A9_%28original%29.png/600px-Historic_Benzene_Formulae_Kekul%C3%A9_%28original%29.png 2x" data-class="mw-file-element"> </a> </td></tr> <tr align="center" style="vertical-align:top"> <td colspan="3">By <a href="/wiki/August_Kekul%C3%A9" title="August Kekulé">August Kekulé</a> (1865/1872)<a href="#cite_note-Kekul%C3%A91865-31">[31]</a><a href="#cite_note-32">[32]</a> </td></tr> <tr style="background-color:white"> <td><a href="/wiki/File:Historic_Benzene_Formulae_Armstrong_(original).png" class="mw-file-description"><noscript><img src="//upload.wikimedia.org/wikipedia/commons/thumb/1/1b/Historic_Benzene_Formulae_Armstrong_%28original%29.png/130px-Historic_Benzene_Formulae_Armstrong_%28original%29.png" decoding="async" width="130" height="117" class="mw-file-element" data-file-width="504" data-file-height="453"></noscript><span class="lazy-image-placeholder" style="width: 130px;height: 117px;" data-src="//upload.wikimedia.org/wikipedia/commons/thumb/1/1b/Historic_Benzene_Formulae_Armstrong_%28original%29.png/130px-Historic_Benzene_Formulae_Armstrong_%28original%29.png" data-width="130" data-height="117" data-srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/1b/Historic_Benzene_Formulae_Armstrong_%28original%29.png/195px-Historic_Benzene_Formulae_Armstrong_%28original%29.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/1b/Historic_Benzene_Formulae_Armstrong_%28original%29.png/260px-Historic_Benzene_Formulae_Armstrong_%28original%29.png 2x" data-class="mw-file-element"> </a> </td> <td><a href="/wiki/File:Historic_Benzene_Formula_Baeyer_1888_(original).png" class="mw-file-description"><noscript><img src="//upload.wikimedia.org/wikipedia/commons/thumb/2/21/Historic_Benzene_Formula_Baeyer_1888_%28original%29.png/150px-Historic_Benzene_Formula_Baeyer_1888_%28original%29.png" decoding="async" width="150" height="129" class="mw-file-element" data-file-width="444" data-file-height="381"></noscript><span class="lazy-image-placeholder" style="width: 150px;height: 129px;" data-src="//upload.wikimedia.org/wikipedia/commons/thumb/2/21/Historic_Benzene_Formula_Baeyer_1888_%28original%29.png/150px-Historic_Benzene_Formula_Baeyer_1888_%28original%29.png" data-width="150" data-height="129" data-srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/21/Historic_Benzene_Formula_Baeyer_1888_%28original%29.png/225px-Historic_Benzene_Formula_Baeyer_1888_%28original%29.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/21/Historic_Benzene_Formula_Baeyer_1888_%28original%29.png/300px-Historic_Benzene_Formula_Baeyer_1888_%28original%29.png 2x" data-class="mw-file-element"> </a> </td> <td><a href="/wiki/File:Historic_Benzene_Formula_Thiele_1899_(original).png" class="mw-file-description"><noscript><img src="//upload.wikimedia.org/wikipedia/commons/thumb/5/55/Historic_Benzene_Formula_Thiele_1899_%28original%29.png/90px-Historic_Benzene_Formula_Thiele_1899_%28original%29.png" decoding="async" width="90" height="158" class="mw-file-element" data-file-width="201" data-file-height="352"></noscript><span class="lazy-image-placeholder" style="width: 90px;height: 158px;" data-src="//upload.wikimedia.org/wikipedia/commons/thumb/5/55/Historic_Benzene_Formula_Thiele_1899_%28original%29.png/90px-Historic_Benzene_Formula_Thiele_1899_%28original%29.png" data-width="90" data-height="158" data-srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/55/Historic_Benzene_Formula_Thiele_1899_%28original%29.png/135px-Historic_Benzene_Formula_Thiele_1899_%28original%29.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/55/Historic_Benzene_Formula_Thiele_1899_%28original%29.png/180px-Historic_Benzene_Formula_Thiele_1899_%28original%29.png 2x" data-class="mw-file-element"> </a> </td></tr> <tr align="center" style="vertical-align:top"> <td>By <a href="/wiki/Henry_Edward_Armstrong" title="Henry Edward Armstrong">Henry Edward Armstrong</a> (1887)<a href="#cite_note-33">[33]</a><a href="#cite_note-34">[34]</a> </td> <td>By <a href="/wiki/Adolf_von_Baeyer" title="Adolf von Baeyer">Adolf von Baeyer</a> (1888)<a href="#cite_note-35">[35]</a> </td> <td>By <a href="/wiki/Johannes_Thiele_(chemist)" title="Johannes Thiele (chemist)">Friedrich Karl Johannes Thiele</a> (1899)<a href="#cite_note-36">[36]</a> </td></tr></tbody></table> The <a href="/wiki/Empirical_formula" title="Empirical formula">empirical formula</a> for benzene was long known, but its highly <a href="/wiki/Saturated_and_unsaturated_compounds" title="Saturated and unsaturated compounds">polyunsaturated</a> structure, with just one <a href="/wiki/Hydrogen" title="Hydrogen">hydrogen</a> atom for each <a href="/wiki/Carbon" title="Carbon">carbon</a> atom, was challenging to determine. <a href="/wiki/Archibald_Scott_Couper" title="Archibald Scott Couper">Archibald Scott Couper</a> in 1858 and <a href="/wiki/Johann_Josef_Loschmidt" title="Johann Josef Loschmidt">Johann Josef Loschmidt</a> in 1861<a href="#cite_note-37">[37]</a> suggested possible structures that contained multiple double bonds or multiple rings, but in these years very little was known about aromatic chemistry, and so chemists were unable to adduce appropriate evidence to favor any particular formula. But many chemists had begun to work on aromatic substances, especially in Germany, and relevant data was coming fast. In 1865, the German chemist <a href="/wiki/Friedrich_August_Kekul%C3%A9" class="mw-redirect" title="Friedrich August Kekulé">Friedrich August Kekulé</a> published a paper in French (for he was then teaching in Francophone Belgium) suggesting that the structure contained a ring of six carbon atoms with alternating single and double bonds. The next year he published a much longer paper in German on the same subject.<a href="#cite_note-Kekul%C3%A91865-31">[31]</a><a href="#cite_note-38">[38]</a> Kekulé used evidence that had accumulated in the intervening years—namely, that there always appeared to be only one <a href="/wiki/Isomer" title="Isomer">isomer</a> of any <a href="/wiki/Derivative_(chemistry)" title="Derivative (chemistry)">monoderivative</a> of benzene, and that there always appeared to be exactly three isomers of every disubstituted derivative—now understood to correspond to the ortho, meta, and para patterns of <a href="/wiki/Arene_substitution_pattern" title="Arene substitution pattern">arene substitution</a>—to argue in support of his proposed structure.<a href="#cite_note-39">[39]</a> Kekulé's symmetrical ring could explain these curious facts, as well as benzene's 1:1 carbon-hydrogen ratio. <ul class="gallery mw-gallery-packed"> <li class="gallerybox" style="width: 348px"> <div class="thumb" style="width: 346px;"><a href="/wiki/File:Historic_Benzene_Formulae_Kekul%C3%A9_(original).png" class="mw-file-description" title="Kekulé's 1872 modification of his 1865 theory, illustrating rapid alternation of double bonds[note 1]"><noscript><img alt="Kekulé's 1872 modification of his 1865 theory, illustrating rapid alternation of double bonds[note 1]" src="//upload.wikimedia.org/wikipedia/commons/thumb/f/f8/Historic_Benzene_Formulae_Kekul%C3%A9_%28original%29.png/519px-Historic_Benzene_Formulae_Kekul%C3%A9_%28original%29.png" decoding="async" width="346" height="120" class="mw-file-element" data-file-width="1081" data-file-height="375"></noscript><span class="lazy-image-placeholder" style="width: 346px;height: 120px;" data-src="//upload.wikimedia.org/wikipedia/commons/thumb/f/f8/Historic_Benzene_Formulae_Kekul%C3%A9_%28original%29.png/519px-Historic_Benzene_Formulae_Kekul%C3%A9_%28original%29.png" data-alt="Kekulé's 1872 modification of his 1865 theory, illustrating rapid alternation of double bonds[note 1]" data-width="346" data-height="120" data-srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/f8/Historic_Benzene_Formulae_Kekul%C3%A9_%28original%29.png/779px-Historic_Benzene_Formulae_Kekul%C3%A9_%28original%29.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/f8/Historic_Benzene_Formulae_Kekul%C3%A9_%28original%29.png/1038px-Historic_Benzene_Formulae_Kekul%C3%A9_%28original%29.png 2x" data-class="mw-file-element"> </a></div> <div class="gallerytext">Kekulé's 1872 modification of his 1865 theory, illustrating rapid alternation of double bonds<a href="#cite_note-40">[note 1]</a></div> </li> </ul> The new understanding of benzene, and hence of all aromatic compounds, proved to be so important for both pure and applied chemistry that in 1890 the <a href="/wiki/German_Chemical_Society" title="German Chemical Society">German Chemical Society</a> organized an elaborate appreciation in Kekulé's honor, celebrating the twenty-fifth anniversary of his first benzene paper. Here Kekulé spoke of the creation of the theory. He said that he had discovered the ring shape of the benzene molecule after having a reverie or day-dream of a snake biting its own tail (a symbol in ancient cultures known as the <a href="/wiki/Ouroboros" title="Ouroboros">ouroboros</a>).<a href="#cite_note-41">[40]</a> This vision, he said, came to him after years of studying the nature of carbon-carbon bonds. This was seven years after he had solved the problem of how carbon atoms could bond to up to four other atoms at the same time. Curiously, a similar, humorous depiction of benzene had appeared in 1886 in a pamphlet entitled Berichte der Durstigen Chemischen Gesellschaft (Journal of the Thirsty Chemical Society), a parody of the Berichte der Deutschen Chemischen Gesellschaft, only the parody had monkeys seizing each other in a circle, rather than snakes as in Kekulé's anecdote.<a href="#cite_note-42">[41]</a> Some historians have suggested that the parody was a lampoon of the snake anecdote, possibly already well known through oral transmission even if it had not yet appeared in print.<a href="#cite_note-rocke-18">[18]</a> Kekulé's 1890 speech<a href="#cite_note-43">[42]</a> in which this anecdote appeared has been translated into English.<a href="#cite_note-44">[43]</a> If the anecdote is the memory of a real event, circumstances mentioned in the story suggest that it must have happened early in 1862.<a href="#cite_note-45">[44]</a> In 1929, the cyclic nature of benzene was finally confirmed by the <a href="/wiki/Crystallography" title="Crystallography">crystallographer</a> <a href="/wiki/Kathleen_Lonsdale" title="Kathleen Lonsdale">Kathleen Lonsdale</a> using <a href="/wiki/X-ray_diffraction" title="X-ray diffraction">X-ray diffraction</a> methods.<a href="#cite_note-46">[45]</a><a href="#cite_note-47">[46]</a> Using large crystals of <a href="/wiki/Hexamethylbenzene" title="Hexamethylbenzene">hexamethylbenzene</a>, a benzene derivative with the same core of six carbon atoms, Lonsdale obtained diffraction patterns. Through calculating more than thirty parameters, Lonsdale demonstrated that the benzene ring could not be anything but a flat hexagon, and provided accurate distances for all carbon-carbon bonds in the molecule.<a href="#cite_note-48">[47]</a> <div class="mw-heading mw-heading3"><h3 id="Nomenclature">Nomenclature</h3> <a role="button" href="/w/index.php?title=Benzene&action=edit&section=4" title="Edit section: Nomenclature" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> edit </a> </div> The German chemist <a href="/wiki/Wilhelm_K%C3%B6rner" title="Wilhelm Körner">Wilhelm Körner</a> suggested the prefixes ortho-, meta-, para- to distinguish di-substituted benzene derivatives in 1867; however, he did not use the prefixes to distinguish the relative positions of the substituents on a benzene ring.<a href="#cite_note-49">[48]</a><a href="#cite_note-50">[49]</a> It was the German chemist <a href="/wiki/Carl_Gr%C3%A4be" class="mw-redirect" title="Carl Gräbe">Carl Gräbe</a> who, in 1869, first used the prefixes ortho-, meta-, para- to denote specific relative locations of the substituents on a di-substituted aromatic ring (viz, naphthalene).<a href="#cite_note-51">[50]</a> In 1870, the German chemist <a href="/wiki/Viktor_Meyer" title="Viktor Meyer">Viktor Meyer</a> first applied Gräbe's nomenclature to benzene.<a href="#cite_note-52">[51]</a> <div class="mw-heading mw-heading3"><h3 id="Early_applications">Early applications</h3> <a role="button" href="/w/index.php?title=Benzene&action=edit&section=5" title="Edit section: Early applications" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> edit </a> </div> In 1903, <a href="/wiki/Ludwig_Roselius" title="Ludwig Roselius">Ludwig Roselius</a> popularized the use of benzene to <a href="/wiki/Decaffeination" title="Decaffeination">decaffeinate</a> <a href="/wiki/Coffee" title="Coffee">coffee</a>. This discovery led to the production of <a href="/wiki/Sanka" title="Sanka">Sanka</a>. This process was later discontinued. Benzene was historically used as a significant component in many consumer products such as <a href="/wiki/Penetrating_oil" title="Penetrating oil">liquid wrench</a>, several <a href="/wiki/Paint_stripper" title="Paint stripper">paint strippers</a>, <a href="/wiki/Rubber_cement" title="Rubber cement">rubber cements</a>, spot removers, and other products. Manufacture of some of these benzene-containing formulations ceased in about 1950, although Liquid Wrench continued to contain significant amounts of benzene until the late 1970s.<a href="#cite_note-53">[52]</a> <div class="mw-heading mw-heading3"><h3 id="Occurrence">Occurrence</h3> <a role="button" href="/w/index.php?title=Benzene&action=edit&section=6" title="Edit section: Occurrence" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> edit </a> </div> Trace amounts of benzene are found in petroleum and coal. It is a byproduct of the incomplete combustion of many materials. For commercial use, until <a href="/wiki/World_War_II" title="World War II">World War II</a>, much of benzene was obtained as a by-product of <a href="/wiki/Coke_(fuel)" title="Coke (fuel)">coke</a> production (or "coke-oven light oil") for the <a href="/wiki/Steel" title="Steel">steel</a> industry. However, in the 1950s, increased demand for benzene, especially from the growing <a href="/wiki/Polymer" title="Polymer">polymers</a> industry, necessitated the production of benzene from petroleum. Today, most benzene comes from the <a href="/wiki/Petrochemical_industry" title="Petrochemical industry">petrochemical industry</a>, with only a small fraction being produced from coal.<a href="#cite_note-Ullmann-54">[53]</a> Benzene has been detected on <a href="/wiki/Mars" title="Mars">Mars</a>.<a href="#cite_note-NYT-20180607-55">[54]</a><a href="#cite_note-SCI-20180608a-56">[55]</a><a href="#cite_note-SCI-20180608c-57">[56]</a> </section><div class="mw-heading mw-heading2 section-heading" onclick="mfTempOpenSection(2)"><h2 id="Structure">Structure</h2> <a role="button" href="/w/index.php?title=Benzene&action=edit&section=7" title="Edit section: Structure" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> edit </a> </div><section class="mf-section-2 collapsible-block" id="mf-section-2"> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Aromaticity" title="Aromaticity">Aromaticity</a></div> <figure typeof="mw:File/Thumb"><a href="/wiki/File:Benzene_Representations.svg" class="mw-file-description"><noscript><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/9a/Benzene_Representations.svg/400px-Benzene_Representations.svg.png" decoding="async" width="400" height="225" class="mw-file-element" data-file-width="1600" data-file-height="900"></noscript><span class="lazy-image-placeholder" style="width: 400px;height: 225px;" data-src="//upload.wikimedia.org/wikipedia/commons/thumb/9/9a/Benzene_Representations.svg/400px-Benzene_Representations.svg.png" data-width="400" data-height="225" data-srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/9a/Benzene_Representations.svg/600px-Benzene_Representations.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/9a/Benzene_Representations.svg/800px-Benzene_Representations.svg.png 2x" data-class="mw-file-element"> </a><figcaption>The various representations of benzene.</figcaption></figure> <a href="/wiki/X-ray_diffraction" title="X-ray diffraction">X-ray diffraction</a> shows that all six carbon-carbon bonds in benzene are of the same length, at 140 <a href="/wiki/Picometre" title="Picometre">picometres</a> (pm).<a href="#cite_note-58">[57]</a> The C–C <a href="/wiki/Bond_length" title="Bond length">bond lengths</a> are greater than a double bond (135 pm) but shorter than a single bond (147 pm). This intermediate distance is caused by electron <a href="/wiki/Delocalized_electron" title="Delocalized electron">delocalization</a>: the electrons for C=C bonding are distributed equally between each of the six carbon atoms. Benzene has 6 hydrogen atoms, fewer than the corresponding parent <a href="/wiki/Alkane" title="Alkane">alkane</a>, <a href="/wiki/Hexane" title="Hexane">hexane</a>, which has 14. Benzene and <a href="/wiki/Cyclohexane" title="Cyclohexane">cyclohexane</a> have a similar structure, only the ring of delocalized electrons and the loss of one hydrogen per carbon distinguishes it from cyclohexane. The molecule is planar.<a href="#cite_note-59">[58]</a> The molecular orbital description involves the formation of three delocalized <a href="/wiki/Pi_bond" title="Pi bond">π orbitals</a> spanning all six carbon atoms, while the valence bond description involves a superposition of <a href="/wiki/Resonance_(chemistry)" title="Resonance (chemistry)">resonance structures</a>.<a href="#cite_note-60">[59]</a><a href="#cite_note-61">[60]</a><a href="#cite_note-62">[61]</a><a href="#cite_note-63">[62]</a> It is likely that this stability contributes to the peculiar molecular and chemical properties known as <a href="/wiki/Aromaticity" title="Aromaticity">aromaticity</a>. To reflect the delocalized nature of the bonding, benzene is often depicted with a circle inside a hexagonal arrangement of carbon atoms. Derivatives of benzene occur sufficiently often as a component of organic molecules, so much so that the <a href="/wiki/Unicode" title="Unicode">Unicode</a> Consortium has allocated a symbol in the <a href="/wiki/Miscellaneous_Technical_(Unicode)" class="mw-redirect" title="Miscellaneous Technical (Unicode)">Miscellaneous Technical</a> block with the code U+232C (⌬) to represent it with three double bonds,<a href="#cite_note-64">[63]</a> and U+23E3 (⏣) for a delocalized version.<a href="#cite_note-65">[64]</a> </section><div class="mw-heading mw-heading2 section-heading" onclick="mfTempOpenSection(3)"><h2 id="Benzene_derivatives">Benzene derivatives</h2> <a role="button" href="/w/index.php?title=Benzene&action=edit&section=8" title="Edit section: Benzene derivatives" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> edit </a> </div><section class="mf-section-3 collapsible-block" id="mf-section-3"> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main articles: <a href="/wiki/Aromatic_hydrocarbons" class="mw-redirect" title="Aromatic hydrocarbons">Aromatic hydrocarbons</a> and <a href="/wiki/Alkylbenzenes" class="mw-redirect" title="Alkylbenzenes">Alkylbenzenes</a></div> Many important chemical compounds are derived from benzene by replacing one or more of its hydrogen atoms with another <a href="/wiki/Functional_group" title="Functional group">functional group</a>. Examples of simple benzene derivatives are <a href="/wiki/Phenol" title="Phenol">phenol</a>, <a href="/wiki/Toluene" title="Toluene">toluene</a>, and <a href="/wiki/Aniline" title="Aniline">aniline</a>, abbreviated PhOH, PhMe, and PhNH2, respectively. Linking benzene rings gives <a href="/wiki/Biphenyl" title="Biphenyl">biphenyl</a>, C6H5–C6H5. Further loss of hydrogen gives "fused" aromatic hydrocarbons, such as <a href="/wiki/Naphthalene" title="Naphthalene">naphthalene</a>, <a href="/wiki/Anthracene" title="Anthracene">anthracene</a>, <a href="/wiki/Phenanthrene" title="Phenanthrene">phenanthrene</a>, and <a href="/wiki/Pyrene" title="Pyrene">pyrene</a>. The limit of the fusion process is the hydrogen-free allotrope of carbon, <a href="/wiki/Graphite" title="Graphite">graphite</a>. In <a href="/wiki/Heterocyclic_chemistry" class="mw-redirect" title="Heterocyclic chemistry">heterocycles</a>, carbon atoms in the benzene ring are replaced with other elements. The most important variations contain <a href="/wiki/Nitrogen" title="Nitrogen">nitrogen</a>. Replacing one CH with N gives the compound <a href="/wiki/Pyridine" title="Pyridine">pyridine</a>, C5H5N. Although benzene and pyridine are structurally related, benzene cannot be converted into pyridine. Replacement of a second CH bond with N gives, depending on the location of the second N, <a href="/wiki/Pyridazine" title="Pyridazine">pyridazine</a>, <a href="/wiki/Pyrimidine" title="Pyrimidine">pyrimidine</a>, or <a href="/wiki/Pyrazine" title="Pyrazine">pyrazine</a>.<a href="#cite_note-66">[65]</a> </section><div class="mw-heading mw-heading2 section-heading" onclick="mfTempOpenSection(4)"><h2 id="Production">Production</h2> <a role="button" href="/w/index.php?title=Benzene&action=edit&section=9" title="Edit section: Production" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> edit </a> </div><section class="mf-section-4 collapsible-block" id="mf-section-4"> Four chemical processes contribute to industrial benzene production: <a href="/wiki/Catalytic_reforming" title="Catalytic reforming">catalytic reforming</a>, <a href="/wiki/Toluene" title="Toluene">toluene</a> hydrodealkylation, toluene disproportionation, and <a href="/wiki/Steam_cracking" title="Steam cracking">steam cracking</a> etc. According to the <a href="/wiki/ATSDR" class="mw-redirect" title="ATSDR">ATSDR</a> Toxicological Profile for benzene, between 1978 and 1981, catalytic reformates accounted for approximately 44–50% of the total U.S. benzene production.<a href="#cite_note-Ullmann-54">[53]</a> <div class="mw-heading mw-heading3"><h3 id="Catalytic_reforming">Catalytic reforming</h3> <a role="button" href="/w/index.php?title=Benzene&action=edit&section=10" title="Edit section: Catalytic reforming" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> edit </a> </div> In catalytic reforming, a mixture of <a href="/wiki/Hydrocarbon" title="Hydrocarbon">hydrocarbons</a> with boiling points between 60 and 200 °C is blended with <a href="/wiki/Hydrogen" title="Hydrogen">hydrogen</a> gas and then exposed to a <a href="/wiki/Bifunctional" class="mw-redirect" title="Bifunctional">bifunctional</a> <a href="/wiki/Platinum(II)_chloride" title="Platinum(II) chloride">platinum chloride</a> or <a href="/wiki/Rhenium" title="Rhenium">rhenium</a> chloride <a href="/wiki/Catalyst" class="mw-redirect" title="Catalyst">catalyst</a> at 500–525 °C and pressures ranging from 8–50 atm. Under these conditions, <a href="/wiki/Aliphatic" class="mw-redirect" title="Aliphatic">aliphatic</a> hydrocarbons form rings and lose hydrogen to become aromatic hydrocarbons. The aromatic products of the reaction are then separated from the reaction mixture (or reformate) by <a href="/wiki/Liquid-liquid_extraction" class="mw-redirect" title="Liquid-liquid extraction">extraction</a> with any one of a number of <a href="/wiki/Solvent" title="Solvent">solvents</a>, including <a href="/wiki/Diethylene_glycol" title="Diethylene glycol">diethylene glycol</a> or <a href="/wiki/Sulfolane" title="Sulfolane">sulfolane</a>, and benzene is then separated from the other aromatics by distillation. The extraction step of aromatics from the reformate is designed to produce aromatics with lowest non-aromatic components. Recovery of the aromatics, commonly referred to as <a href="/wiki/BTX_(chemistry)" title="BTX (chemistry)">BTX</a> (benzene, toluene and xylene isomers), involves such extraction and distillation steps. In similar fashion to this catalytic reforming, <a href="/wiki/UOP_LLC" class="mw-redirect" title="UOP LLC">UOP</a> and <a href="/wiki/BP" title="BP">BP</a> commercialized a method from LPG (mainly propane and butane) to aromatics. <div class="mw-heading mw-heading3"><h3 id="Toluene_hydrodealkylation">Toluene hydrodealkylation</h3> <a role="button" href="/w/index.php?title=Benzene&action=edit&section=11" title="Edit section: Toluene hydrodealkylation" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> edit </a> </div> Toluene <a href="/wiki/Hydrodealkylation" title="Hydrodealkylation">hydrodealkylation</a> converts <a href="/wiki/Toluene" title="Toluene">toluene</a> to benzene. In this hydrogen-intensive process, toluene is mixed with hydrogen, then passed over a <a href="/wiki/Chromium" title="Chromium">chromium</a>, <a href="/wiki/Molybdenum" title="Molybdenum">molybdenum</a>, or <a href="/wiki/Platinum" title="Platinum">platinum</a> <a href="/wiki/Oxide" title="Oxide">oxide</a> catalyst at 500–650 °C and 20–60 atm pressure. Sometimes, higher temperatures are used instead of a catalyst (at the similar reaction condition). Under these conditions, toluene undergoes dealkylation to benzene and <a href="/wiki/Methane" title="Methane">methane</a>: <dl><dd><math xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle {\ce {C6H5CH3 + H2 -> C6H6 + CH4}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <msubsup> <mtext>C</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>6</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <msubsup> <mtext>H</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>5</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>3</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <mo>+</mo> <msubsup> <mtext>H</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <mo stretchy="false">⟶</mo> <msubsup> <mtext>C</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>6</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <msubsup> <mtext>H</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>6</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <mo>+</mo> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>4</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\ce {C6H5CH3 + H2 -> C6H6 + CH4}}}</annotation> </semantics> </math><noscript><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/eda6fc15cac8ac7985a6c7e927f598540d5b501e" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -1.005ex; width:33.584ex; height:2.843ex;" alt="{\displaystyle {\ce {C6H5CH3 + H2 -> C6H6 + CH4}}}"></noscript><span class="lazy-image-placeholder" style="width: 33.584ex;height: 2.843ex;vertical-align: -1.005ex;" data-src="https://wikimedia.org/api/rest_v1/media/math/render/svg/eda6fc15cac8ac7985a6c7e927f598540d5b501e" data-alt="{\displaystyle {\ce {C6H5CH3 + H2 -> C6H6 + CH4}}}" data-class="mwe-math-fallback-image-inline mw-invert skin-invert"> </dd></dl> This irreversible reaction is accompanied by an equilibrium side reaction that produces <a href="/wiki/Biphenyl" title="Biphenyl">biphenyl</a> (aka diphenyl) at higher temperature: <dl><dd>2 C 6H 6 ⇌ H 2 + C 6H 5–C 6H 5</dd></dl> If the raw material stream contains much non-aromatic components (paraffins or naphthenes), those are likely decomposed to lower hydrocarbons such as methane, which increases the consumption of hydrogen. A typical reaction yield exceeds 95%. Sometimes, <a href="/wiki/Xylene" title="Xylene">xylenes</a> and heavier aromatics are used in place of toluene, with similar efficiency. This is often called "on-purpose" methodology to produce benzene, compared to conventional BTX (benzene-toluene-xylene) extraction processes. <div class="mw-heading mw-heading3"><h3 id="Toluene_disproportionation">Toluene disproportionation</h3> <a role="button" href="/w/index.php?title=Benzene&action=edit&section=12" title="Edit section: Toluene disproportionation" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> edit </a> </div> Toluene <a href="/wiki/Disproportionation" title="Disproportionation">disproportionation</a> (TDP) is the conversion of toluene to benzene and <a href="/wiki/Xylene" title="Xylene">xylene</a>.<a href="#cite_note-67">[66]</a> Given that demand for para-xylene (<a href="/wiki/P-Xylene" title="P-Xylene">p-xylene</a>) substantially exceeds demand for other xylene isomers, a refinement of the TDP process called Selective TDP (STDP) may be used. In this process, the xylene stream exiting the TDP unit is approximately 90% p-xylene. In some systems, even the benzene-to-xylenes ratio is modified to favor xylenes. <div class="mw-heading mw-heading3"><h3 id="Steam_cracking">Steam cracking</h3> <a role="button" href="/w/index.php?title=Benzene&action=edit&section=13" title="Edit section: Steam cracking" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> edit </a> </div> <a href="/wiki/Steam_cracking" title="Steam cracking">Steam cracking</a> is the process for producing <a href="/wiki/Ethylene" title="Ethylene">ethylene</a> and other <a href="/wiki/Alkene" title="Alkene">alkenes</a> from <a href="/wiki/Aliphatic_compound" title="Aliphatic compound">aliphatic hydrocarbons</a>. Depending on the feedstock used to produce the olefins, steam cracking can produce a benzene-rich liquid by-product called <a href="/wiki/Pyrolysis_gasoline" title="Pyrolysis gasoline">pyrolysis gasoline</a>. Pyrolysis gasoline can be blended with other hydrocarbons as a gasoline additive, or routed through an extraction process to recover <a href="/wiki/BTX_(chemistry)" title="BTX (chemistry)">BTX</a> aromatics (benzene, toluene and xylenes). <div class="mw-heading mw-heading3"><h3 id="Other_methods">Other methods</h3> <a role="button" href="/w/index.php?title=Benzene&action=edit&section=14" title="Edit section: Other methods" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> edit </a> </div> Although of no commercial significance, many other routes to benzene exist. <a href="/wiki/Phenol" title="Phenol">Phenol</a> and <a href="/wiki/Halobenzene" title="Halobenzene">halobenzenes</a> can be reduced with metals. <a href="/wiki/Benzoic_acid" title="Benzoic acid">Benzoic acid</a> and its salts undergo <a href="/wiki/Decarboxylation" title="Decarboxylation">decarboxylation</a> to benzene. The reaction of the <a href="/wiki/Diazonium_compound" title="Diazonium compound">diazonium compound</a> derived from <a href="/wiki/Aniline" title="Aniline">aniline</a> with <a href="/wiki/Hypophosphorus_acid" class="mw-redirect" title="Hypophosphorus acid">hypophosphorus acid</a> gives benzene. <a href="/wiki/Alkyne_trimerisation" title="Alkyne trimerisation">Alkyne trimerisation</a> of <a href="/wiki/Acetylene" title="Acetylene">acetylene</a> gives benzene. Complete <a href="/wiki/Decarboxylation" title="Decarboxylation">decarboxylation</a> of <a href="/wiki/Mellitic_acid" title="Mellitic acid">mellitic acid</a> gives benzene. </section><div class="mw-heading mw-heading2 section-heading" onclick="mfTempOpenSection(5)"><h2 id="Uses">Uses</h2> <a role="button" href="/w/index.php?title=Benzene&action=edit&section=15" title="Edit section: Uses" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> edit </a> </div><section class="mf-section-5 collapsible-block" id="mf-section-5"> Benzene is used mainly as an intermediate to make other chemicals, above all <a href="/wiki/Ethylbenzene" title="Ethylbenzene">ethylbenzene</a> (and other <a href="/wiki/Alkylbenzenes" class="mw-redirect" title="Alkylbenzenes">alkylbenzenes</a>), <a href="/wiki/Cumene" title="Cumene">cumene</a>, <a href="/wiki/Cyclohexane" title="Cyclohexane">cyclohexane</a>, and <a href="/wiki/Nitrobenzene" title="Nitrobenzene">nitrobenzene</a>. In 1988 it was reported that two-thirds of all chemicals on the <a href="/wiki/American_Chemical_Society" title="American Chemical Society">American Chemical Society</a>'s lists contained at least one benzene ring.<a href="#cite_note-nyt-68">[67]</a> More than half of the entire benzene production is processed into ethylbenzene, a precursor to <a href="/wiki/Styrene" title="Styrene">styrene</a>, which is used to make polymers and plastics like <a href="/wiki/Polystyrene" title="Polystyrene">polystyrene</a>. Some 20% of the benzene production is used to manufacture cumene, which is needed to produce <a href="/wiki/Phenol" title="Phenol">phenol</a> and acetone for resins and adhesives. <a href="/wiki/Cyclohexane" title="Cyclohexane">Cyclohexane</a> consumes around 10% of the world's benzene production; it is primarily used in the manufacture of nylon fibers, which are processed into textiles and engineering plastics. Smaller amounts of benzene are used to make some types of <a href="/wiki/Rubber" class="mw-redirect" title="Rubber">rubbers</a>, <a href="/wiki/Lubricant" title="Lubricant">lubricants</a>, <a href="/wiki/Dye" title="Dye">dyes</a>, <a href="/wiki/Detergent" title="Detergent">detergents</a>, <a href="/wiki/Drug" title="Drug">drugs</a>, <a href="/wiki/Explosive" title="Explosive">explosives</a>, and <a href="/wiki/Pesticide" title="Pesticide">pesticides</a>. In 2013, the biggest consumer country of benzene was China, followed by the USA. Benzene production is currently expanding in the Middle East and in Africa, whereas production capacities in Western Europe and North America are stagnating.<a href="#cite_note-Ceresana-69">[68]</a> <a href="/wiki/Toluene" title="Toluene">Toluene</a> is now often used as a substitute for benzene, for instance as a fuel additive. The solvent-properties of the two are similar, but toluene is less toxic and has a wider liquid range. Toluene is also processed into benzene.<a href="#cite_note-CeresanaB-70">[69]</a> <figure class="mw-halign-center noresize" typeof="mw:File/Thumb"><noscript><img src="//upload.wikimedia.org/wikipedia/commons/thumb/5/54/Benzene_uses.png/600px-Benzene_uses.png" decoding="async" width="600" height="374" class="mw-file-element" data-file-width="2788" data-file-height="1737" usemap="#ImageMap_ef38bf12dc61fe65" resource="/wiki/File:Benzene_uses.png"></noscript><span class="lazy-image-placeholder" style="width: 600px;height: 374px;" data-src="//upload.wikimedia.org/wikipedia/commons/thumb/5/54/Benzene_uses.png/600px-Benzene_uses.png" data-width="600" data-height="374" data-srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/54/Benzene_uses.png/900px-Benzene_uses.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/54/Benzene_uses.png/1200px-Benzene_uses.png 2x" data-class="mw-file-element" data-usemap="#ImageMap_ef38bf12dc61fe65"> <map name="ImageMap_ef38bf12dc61fe65"><area href="#Uses" shape="rect" coords="8,142,94,174" alt="Benzene" title="Benzene"><area href="/wiki/Ethylbenzene" shape="rect" coords="143,13,229,45" alt="Ethylbenzene" title="Ethylbenzene"><area href="/wiki/Cumene" shape="rect" coords="143,92,229,125" alt="Cumene" title="Cumene"><area href="/wiki/Cyclohexane" shape="rect" coords="143,171,229,203" alt="Cyclohexane" title="Cyclohexane"><area href="/wiki/Aniline" shape="rect" coords="143,250,229,283" alt="Aniline" title="Aniline"><area href="/wiki/Chlorobenzene" shape="rect" coords="143,330,229,363" alt="Chlorobenzene" title="Chlorobenzene"><area href="/wiki/Acetone" shape="rect" coords="262,74,347,107" alt="Acetone" title="Acetone"><area href="/wiki/Phenol" shape="rect" coords="262,137,347,169" alt="Phenol" title="Phenol"><area href="/wiki/Styrene" shape="rect" coords="380,12,466,45" alt="Styrene" title="Styrene"><area href="/wiki/Bisphenol_A" shape="rect" coords="380,93,466,126" alt="Bisphenol A" title="Bisphenol A"><area href="/wiki/Adipic_acid" shape="rect" coords="380,233,466,265" alt="Adipic acid" title="Adipic acid"><area href="/wiki/Caprolactam" shape="rect" coords="380,287,466,319" alt="Caprolactam" title="Caprolactam"><area href="/wiki/Polystyrene" shape="rect" coords="498,12,584,45" alt="Polystyrene" title="Polystyrene"><area href="/wiki/Polycarbonate" shape="rect" coords="498,68,584,99" alt="Polycarbonate" title="Polycarbonate"><area href="/wiki/Epoxy_resin" shape="rect" coords="498,123,584,154" alt="Epoxy resin" title="Epoxy resin"><area href="/wiki/Phenolic_resin" shape="rect" coords="498,177,584,210" alt="Phenolic resin" title="Phenolic resin"><area href="/wiki/Nylon_6-6" shape="rect" coords="498,233,584,265" alt="Nylon 6-6" title="Nylon 6-6"><area href="/wiki/Nylon_6" shape="rect" coords="498,287,584,320" alt="Nylon 6" title="Nylon 6"></map><figcaption>Major commodity chemicals and polymers derived from benzene. Clicking on the image loads the appropriate article</figcaption></figure> <div class="mw-heading mw-heading3"><h3 id="Component_of_gasoline">Component of gasoline</h3> <a role="button" href="/w/index.php?title=Benzene&action=edit&section=16" title="Edit section: Component of gasoline" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> edit </a> </div> As a <a href="/wiki/Gasoline" title="Gasoline">gasoline</a> (petrol) additive, benzene increases the <a href="/wiki/Octane_rating" title="Octane rating">octane rating</a> and reduces <a href="/wiki/Engine_knocking" title="Engine knocking">knocking</a>. As a consequence, gasoline often contained several percent benzene before the 1950s, when <a href="/wiki/Tetraethyl_lead" class="mw-redirect" title="Tetraethyl lead">tetraethyl lead</a> replaced it as the most widely used antiknock additive. With the global phaseout of leaded gasoline, benzene has made a comeback as a gasoline additive in some nations. In the <a href="/wiki/United_States" title="United States">United States</a>, concern over its negative health effects and the possibility of benzene entering the <a href="/wiki/Groundwater" title="Groundwater">groundwater</a> has led to stringent regulation of gasoline's benzene content, with limits typically around 1%.<a href="#cite_note-71">[70]</a> European petrol specifications now contain the same 1% limit on benzene content. The <a href="/wiki/United_States_Environmental_Protection_Agency" title="United States Environmental Protection Agency">United States Environmental Protection Agency</a> introduced new regulations in 2011 that lowered the benzene content in gasoline to 0.62%.<a href="#cite_note-72">[71]</a> In some European languages, the word for petroleum or gasoline is an exact cognate of "benzene". For instance in <a href="/wiki/Catalan_language" title="Catalan language">Catalan</a> the word 'benzina' can be used for gasoline, though now it is relatively rare. </section><div class="mw-heading mw-heading2 section-heading" onclick="mfTempOpenSection(6)"><h2 id="Reactions">Reactions</h2> <a role="button" href="/w/index.php?title=Benzene&action=edit&section=17" title="Edit section: Reactions" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> edit </a> </div><section class="mf-section-6 collapsible-block" id="mf-section-6"> The most common reactions of benzene involve substitution of a proton by other groups.<a href="#cite_note-StranksEtAl1970-73">[72]</a> <a href="/wiki/Electrophilic_aromatic_substitution" title="Electrophilic aromatic substitution">Electrophilic aromatic substitution</a> is a general method of derivatizing benzene. Benzene is sufficiently <a href="/wiki/Nucleophile" title="Nucleophile">nucleophilic</a> that it undergoes substitution by <a href="/wiki/Acylium" class="mw-redirect" title="Acylium">acylium</a> ions and alkyl <a href="/wiki/Carbocation" title="Carbocation">carbocations</a> to give substituted derivatives. <dl><dd><figure class="mw-halign-center" typeof="mw:File/Thumb"><a href="/wiki/File:OChem-Mech-ElectrophilicAromaticSubstitution-General.png" class="mw-file-description"><noscript><img src="//upload.wikimedia.org/wikipedia/commons/thumb/5/57/OChem-Mech-ElectrophilicAromaticSubstitution-General.png/450px-OChem-Mech-ElectrophilicAromaticSubstitution-General.png" decoding="async" width="450" height="75" class="mw-file-element" data-file-width="712" data-file-height="118"></noscript><span class="lazy-image-placeholder" style="width: 450px;height: 75px;" data-src="//upload.wikimedia.org/wikipedia/commons/thumb/5/57/OChem-Mech-ElectrophilicAromaticSubstitution-General.png/450px-OChem-Mech-ElectrophilicAromaticSubstitution-General.png" data-width="450" data-height="75" data-srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/57/OChem-Mech-ElectrophilicAromaticSubstitution-General.png/675px-OChem-Mech-ElectrophilicAromaticSubstitution-General.png 1.5x, //upload.wikimedia.org/wikipedia/commons/5/57/OChem-Mech-ElectrophilicAromaticSubstitution-General.png 2x" data-class="mw-file-element"> </a><figcaption>Electrophilic aromatic substitution of benzene</figcaption></figure></dd></dl> The most widely practiced example of this reaction is the <a href="/wiki/Ethylation" class="mw-redirect" title="Ethylation">ethylation</a> of benzene. <dl><dd><dl><dd><a href="/wiki/File:EtC6H5route.png" class="mw-file-description"><noscript><img src="//upload.wikimedia.org/wikipedia/commons/thumb/4/47/EtC6H5route.png/320px-EtC6H5route.png" decoding="async" width="320" height="65" class="mw-file-element" data-file-width="1453" data-file-height="297"></noscript><span class="lazy-image-placeholder" style="width: 320px;height: 65px;" data-src="//upload.wikimedia.org/wikipedia/commons/thumb/4/47/EtC6H5route.png/320px-EtC6H5route.png" data-width="320" data-height="65" data-srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/47/EtC6H5route.png/480px-EtC6H5route.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/47/EtC6H5route.png/640px-EtC6H5route.png 2x" data-class="mw-file-element"> </a></dd></dl></dd></dl> Approximately 24,700,000 tons were produced in 1999.<a href="#cite_note-74">[73]</a> Highly instructive but of far less industrial significance is the <a href="/wiki/Friedel-Crafts_alkylation" class="mw-redirect" title="Friedel-Crafts alkylation">Friedel-Crafts alkylation</a> of benzene (and many other aromatic rings) using an <a href="/wiki/Alkyl_halide" class="mw-redirect" title="Alkyl halide">alkyl halide</a> in the presence of a strong Lewis acid catalyst. Similarly, the <a href="/wiki/Friedel-Crafts_acylation" class="mw-redirect" title="Friedel-Crafts acylation">Friedel-Crafts acylation</a> is a related example of <a href="/wiki/Electrophilic_aromatic_substitution" title="Electrophilic aromatic substitution">electrophilic aromatic substitution</a>. The reaction involves the <a href="/wiki/Acylation" title="Acylation">acylation</a> of benzene (or many other aromatic rings) with an <a href="/wiki/Acyl_chloride" title="Acyl chloride">acyl chloride</a> using a strong <a href="/wiki/Lewis_acid" class="mw-redirect" title="Lewis acid">Lewis acid</a> <a href="/wiki/Catalyst" class="mw-redirect" title="Catalyst">catalyst</a> such as <a href="/wiki/Aluminium_chloride" title="Aluminium chloride">aluminium chloride</a> or <a href="/wiki/Iron(III)_chloride" title="Iron(III) chloride">Iron(III) chloride</a>. <figure class="mw-halign-center" typeof="mw:File/Thumb"><a href="/wiki/File:Benzen_acylowany.svg" class="mw-file-description"><noscript><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/8b/Benzen_acylowany.svg/300px-Benzen_acylowany.svg.png" decoding="async" width="300" height="77" class="mw-file-element" data-file-width="3371" data-file-height="869"></noscript><span class="lazy-image-placeholder" style="width: 300px;height: 77px;" data-src="//upload.wikimedia.org/wikipedia/commons/thumb/8/8b/Benzen_acylowany.svg/300px-Benzen_acylowany.svg.png" data-width="300" data-height="77" data-srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/8b/Benzen_acylowany.svg/450px-Benzen_acylowany.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/8b/Benzen_acylowany.svg/600px-Benzen_acylowany.svg.png 2x" data-class="mw-file-element"> </a><figcaption>Friedel-Crafts acylation of benzene by acetyl chloride</figcaption></figure> <div class="mw-heading mw-heading3"><h3 id="Sulfonation,_chlorination,_nitration">Sulfonation, chlorination, nitration</h3> <a role="button" href="/w/index.php?title=Benzene&action=edit&section=18" title="Edit section: Sulfonation, chlorination, nitration" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> edit </a> </div> Using electrophilic aromatic substitution, many functional groups are introduced onto the benzene framework. <a href="/wiki/Aromatic_sulfonation" title="Aromatic sulfonation">Sulfonation</a> of benzene involves the use of <a href="/wiki/Oleum" title="Oleum">oleum</a>, a mixture of sulfuric acid with <a href="/wiki/Sulfur_trioxide" title="Sulfur trioxide">sulfur trioxide</a>. Sulfonated benzene derivatives are useful <a href="/wiki/Detergent" title="Detergent">detergents</a>. In <a href="/wiki/Nitration" title="Nitration">nitration</a>, benzene reacts with nitronium ions (NO2+), which is a strong electrophile produced by combining sulfuric and nitric acids. <a href="/wiki/Nitrobenzene" title="Nitrobenzene">Nitrobenzene</a> is the precursor to <a href="/wiki/Aniline" title="Aniline">aniline</a>. Chlorination is achieved with chlorine to give <a href="/wiki/Chlorobenzene" title="Chlorobenzene">chlorobenzene</a> in the presence of a Lewis acid catalyst such as aluminium tri-chloride. <div class="mw-heading mw-heading3"><h3 id="Hydrogenation">Hydrogenation</h3> <a role="button" href="/w/index.php?title=Benzene&action=edit&section=19" title="Edit section: Hydrogenation" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> edit </a> </div> Via <a href="/wiki/Hydrogenation" title="Hydrogenation">hydrogenation</a>, benzene and its derivatives convert to <a href="/wiki/Cyclohexane" title="Cyclohexane">cyclohexane</a> and derivatives. This reaction is achieved by the use of high pressures of <a href="/wiki/Hydrogen" title="Hydrogen">hydrogen</a> in the presence of <a href="/wiki/Heterogeneous_catalyst" class="mw-redirect" title="Heterogeneous catalyst">heterogeneous catalysts</a>, such as finely divided <a href="/wiki/Nickel" title="Nickel">nickel</a>. Whereas alkenes can be hydrogenated near room temperatures, benzene and related compounds are more reluctant substrates, requiring temperatures >100 °C. This reaction is practiced on a large scale industrially. In the absence of the catalyst, benzene is impervious to hydrogen. Hydrogenation cannot be stopped to give cyclohexene or cyclohexadienes as these are superior substrates. <a href="/wiki/Birch_reduction" title="Birch reduction">Birch reduction</a>, a non catalytic process, however selectively hydrogenates benzene to the diene. <div class="mw-heading mw-heading3"><h3 id="Metal_complexes">Metal complexes</h3> <a role="button" href="/w/index.php?title=Benzene&action=edit&section=20" title="Edit section: Metal complexes" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> edit </a> </div> Benzene is an excellent <a href="/wiki/Ligand" title="Ligand">ligand</a> in the <a href="/wiki/Complex_(chemistry)" class="mw-redirect" title="Complex (chemistry)">organometallic</a> chemistry of low-valent metals. Important examples include the sandwich and half-sandwich complexes, respectively, <a href="/wiki/Bis(benzene)chromium" title="Bis(benzene)chromium">Cr(C6H6)2</a> and <a href="/wiki/(Benzene)ruthenium_dichloride_dimer" title="(Benzene)ruthenium dichloride dimer">[RuCl2(C6H6)]2</a>. </section><div class="mw-heading mw-heading2 section-heading" onclick="mfTempOpenSection(7)"><h2 id="Health_effects">Health effects</h2> <a role="button" href="/w/index.php?title=Benzene&action=edit&section=21" title="Edit section: Health effects" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> edit </a> </div><section class="mf-section-7 collapsible-block" id="mf-section-7"> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Benzol.JPG" class="mw-file-description"><noscript><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/8f/Benzol.JPG/220px-Benzol.JPG" decoding="async" width="220" height="308" class="mw-file-element" data-file-width="414" data-file-height="580"></noscript><span class="lazy-image-placeholder" style="width: 220px;height: 308px;" data-src="//upload.wikimedia.org/wikipedia/commons/thumb/8/8f/Benzol.JPG/220px-Benzol.JPG" data-width="220" data-height="308" data-srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/8f/Benzol.JPG/330px-Benzol.JPG 1.5x, //upload.wikimedia.org/wikipedia/commons/8/8f/Benzol.JPG 2x" data-class="mw-file-element"> </a><figcaption>A bottle of benzene. The warnings show benzene is a toxic and flammable liquid.</figcaption></figure> Benzene is classified as a <a href="/wiki/Carcinogen" title="Carcinogen">carcinogen</a>, which increases the risk of <a href="/wiki/Cancer" title="Cancer">cancer</a> and other illnesses, and is also a notorious cause of <a href="/wiki/Bone_marrow_failure" title="Bone marrow failure">bone marrow failure</a>. Substantial quantities of epidemiologic, clinical, and laboratory data link benzene to aplastic anemia, acute <a href="/wiki/Leukemia" title="Leukemia">leukemia</a>, bone marrow abnormalities and cardiovascular disease.<a href="#cite_note-75">[74]</a><a href="#cite_note-76">[75]</a><a href="#cite_note-Bard_2014_Jun_16;9(6)-77">[76]</a> The specific hematologic malignancies that benzene is associated with include: acute myeloid leukemia (AML), aplastic anemia, myelodysplastic syndrome (MDS), acute lymphoblastic leukemia (ALL), and chronic myeloid leukemia (CML).<a href="#cite_note-Smith_2010_133%E2%80%9348-78">[77]</a> Carcinogenic activity of benzene was discovered by Swedish pharmacologist <a href="/w/index.php?title=Carl_Gustaf_Santesson_(farmakolog)&action=edit&redlink=1" class="new" title="Carl Gustaf Santesson (farmakolog) (page does not exist)">C. G. Santesson</a> [<a href="https://se.wikipedia.org/wiki/Carl_Gustaf_Santesson" class="extiw" title="se:Carl Gustaf Santesson">se</a>] in 1897 on female workers of a tire-making factory.<a href="#cite_note-79">[78]</a><a href="#cite_note-80">[79]</a> The <a href="/wiki/American_Petroleum_Institute" title="American Petroleum Institute">American Petroleum Institute</a> (API) stated in 1948 that "it is generally considered that the only absolutely safe concentration for benzene is zero".<a href="#cite_note-81">[80]</a> There is no safe exposure level; even tiny amounts can cause harm.<a href="#cite_note-82">[81]</a> The <a href="/wiki/US_Department_of_Health_and_Human_Services" class="mw-redirect" title="US Department of Health and Human Services">US Department of Health and Human Services</a> (DHHS) classifies benzene as a human carcinogen. Long-term exposure to excessive levels of benzene in the air causes leukemia, a potentially fatal cancer of the blood-forming organs. In particular, <a href="/wiki/Acute_myeloid_leukemia" title="Acute myeloid leukemia">acute myeloid leukemia</a> or <a href="/wiki/Acute_nonlymphocytic_leukemia" class="mw-redirect" title="Acute nonlymphocytic leukemia">acute nonlymphocytic leukemia</a> (AML & ANLL) is caused by benzene.<a href="#cite_note-83">[82]</a> IARC rated benzene as "known to be carcinogenic to humans" (<a href="/wiki/IARC_group_1_Carcinogens" title="IARC group 1 Carcinogens">Group 1</a>). As benzene is ubiquitous in gasoline and hydrocarbon fuels that are in use everywhere, human exposure to benzene is a global health problem. Benzene targets the liver, kidney, lung, heart and brain and can cause <a href="/wiki/DNA" title="DNA">DNA</a> strand breaks and <a href="/wiki/Chromosomal" class="mw-redirect" title="Chromosomal">chromosomal</a> damage, hence is <a href="/wiki/Teratology#Teratogenesis" title="Teratology">teratogenic</a> and <a href="/wiki/Mutagen" title="Mutagen">mutagenic</a>. Benzene causes cancer in animals including humans. Benzene has been shown to cause cancer in both sexes of multiple species of laboratory animals exposed via various routes.<a href="#cite_note-84">[83]</a><a href="#cite_note-85">[84]</a> </section><div class="mw-heading mw-heading2 section-heading" onclick="mfTempOpenSection(8)"><h2 id="Exposure_to_benzene">Exposure to benzene</h2> <a role="button" href="/w/index.php?title=Benzene&action=edit&section=22" title="Edit section: Exposure to benzene" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> edit </a> </div><section class="mf-section-8 collapsible-block" id="mf-section-8"> According to the <a href="/wiki/Agency_for_Toxic_Substances_and_Disease_Registry" title="Agency for Toxic Substances and Disease Registry">Agency for Toxic Substances and Disease Registry</a> (ATSDR) (2007), benzene is both a synthetically made and naturally occurring chemical from processes that include: volcanic eruptions, wild fires, synthesis of chemicals such as <a href="/wiki/Phenol" title="Phenol">phenol</a>, production of <a href="/wiki/Synthetic_fiber" title="Synthetic fiber">synthetic fibers</a>, and fabrication of <a href="/wiki/Rubber" class="mw-redirect" title="Rubber">rubbers</a>, <a href="/wiki/Lubricant" title="Lubricant">lubricants</a>, <a href="/wiki/Pesticide" title="Pesticide">pesticides</a>, medications, and <a href="/wiki/Dye" title="Dye">dyes</a>. The major sources of benzene exposure are <a href="/wiki/Tobacco" title="Tobacco">tobacco</a> smoke, automobile service stations, exhaust from motor vehicles, and industrial emissions; however, ingestion and dermal absorption of benzene can also occur through contact with contaminated water. Benzene is hepatically metabolized and excreted in the <a href="/wiki/Urine" title="Urine">urine</a>. Measurement of air and water levels of benzene is accomplished through collection via <a href="/wiki/Activated_charcoal" class="mw-redirect" title="Activated charcoal">activated charcoal</a> tubes, which are then analyzed with a <a href="/wiki/Gas_chromatograph" class="mw-redirect" title="Gas chromatograph">gas chromatograph</a>. The measurement of benzene in humans can be accomplished via <a href="/wiki/Urine_test" title="Urine test">urine</a>, <a href="/wiki/Blood_test" title="Blood test">blood</a>, and <a href="/wiki/Breath_test" title="Breath test">breath tests</a>; however, all of these have their limitations because benzene is rapidly metabolized in the human body.<a href="#cite_note-86">[85]</a> Exposure to benzene may lead progressively to aplastic <a href="/wiki/Anemia" title="Anemia">anemia</a>, <a href="/wiki/Leukaemia" class="mw-redirect" title="Leukaemia">leukaemia</a>, and <a href="/wiki/Multiple_myeloma" title="Multiple myeloma">multiple myeloma</a>.<a href="#cite_note-87">[86]</a> <a href="/wiki/Occupational_Safety_and_Health_Administration" title="Occupational Safety and Health Administration">OSHA</a> regulates levels of benzene in the workplace.<a href="#cite_note-88">[87]</a> The maximum allowable amount of benzene in workroom air during an 8-hour workday, 40-hour workweek is 1 ppm. As benzene can cause <a href="/wiki/Cancer" title="Cancer">cancer</a>, <a href="/wiki/National_Institute_for_Occupational_Safety_and_Health" title="National Institute for Occupational Safety and Health">NIOSH</a> recommends that all workers wear special <a href="/wiki/Self-contained_breathing_apparatus" title="Self-contained breathing apparatus">breathing equipment</a> when they are likely to be exposed to benzene at levels exceeding the recommended (8-hour) exposure limit of 0.1 ppm.<a href="#cite_note-89">[88]</a> <div class="mw-heading mw-heading3"><h3 id="Benzene_exposure_limits">Benzene exposure limits</h3> <a role="button" href="/w/index.php?title=Benzene&action=edit&section=23" title="Edit section: Benzene exposure limits" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> edit </a> </div> The <a href="/wiki/United_States_Environmental_Protection_Agency" title="United States Environmental Protection Agency">United States Environmental Protection Agency</a> has set a <a href="/wiki/Maximum_contaminant_level" title="Maximum contaminant level">maximum contaminant level</a> for benzene in <a href="/wiki/Drinking_water" title="Drinking water">drinking water</a> at 0.005 mg/L (5 ppb), as promulgated via the U.S. National Primary Drinking Water Regulations.<a href="#cite_note-90">[89]</a> This regulation is based on preventing benzene <a href="/wiki/Leukemogenesis" class="mw-redirect" title="Leukemogenesis">leukemogenesis</a>. The maximum contaminant level goal (<a href="/w/index.php?title=MCLG&action=edit&redlink=1" class="new" title="MCLG (page does not exist)">MCLG</a>), a nonenforceable health goal that would allow an adequate margin of safety for the prevention of adverse effects, is zero benzene concentration in drinking water. The EPA requires that spills or accidental releases into the environment of 10 pounds (4.5 kg) or more of benzene be reported. The U.S. <a href="/wiki/Occupational_Safety_and_Health_Administration" title="Occupational Safety and Health Administration">Occupational Safety and Health Administration</a> (OSHA) has set a permissible exposure limit of 1 part of benzene per million parts of air (1 ppm) in the workplace during an 8-hour workday, 40-hour workweek. The short term exposure limit for airborne benzene is 5 ppm for 15 minutes.<a href="#cite_note-OSHASampling2015-91">[90]</a> These legal limits were based on studies demonstrating compelling evidence of health risk to workers exposed to benzene. The risk from exposure to 1 ppm for a working lifetime has been estimated as 5 excess leukemia deaths per 1,000 employees exposed. (This estimate assumes no threshold for benzene's carcinogenic effects.) OSHA has also established an action level of 0.5 ppm to encourage even lower exposures in the workplace.<a href="#cite_note-92">[91]</a> The U.S. <a href="/wiki/National_Institute_for_Occupational_Safety_and_Health" title="National Institute for Occupational Safety and Health">National Institute for Occupational Safety and Health</a> (NIOSH) revised the <a href="/wiki/Immediately_Dangerous_to_Life_and_Health" class="mw-redirect" title="Immediately Dangerous to Life and Health">Immediately Dangerous to Life and Health</a> (IDLH) concentration for benzene to 500 ppm. The current NIOSH definition for an IDLH condition, as given in the NIOSH Respirator Selection Logic, is one that poses a threat of exposure to airborne contaminants when that exposure is likely to cause death or immediate or delayed permanent adverse health effects or prevent escape from such an environment.<a href="#cite_note-NIOSH2004-93">[92]</a> The purpose of establishing an IDLH value is (1) to ensure that the worker can escape from a given contaminated environment in the event of failure of the respiratory protection equipment and (2) is considered a maximum level above which only a highly reliable <a href="/wiki/Self-contained_breathing_apparatus" title="Self-contained breathing apparatus">breathing apparatus</a> providing maximum worker protection is permitted.<a href="#cite_note-NIOSH2004-93">[92]</a><a href="#cite_note-94">[93]</a> In September 1995, NIOSH issued a new policy for developing <a href="/wiki/Recommended_exposure_limit" title="Recommended exposure limit">recommended exposure limits</a> (RELs) for substances, including carcinogens. As benzene can cause cancer, NIOSH recommends that all workers wear special breathing equipment when they are likely to be exposed to benzene at levels exceeding the REL (10-hour) of 0.1 ppm.<a href="#cite_note-95">[94]</a> The NIOSH short-term exposure limit (STEL – 15 min) is 1 ppm. American Conference of Governmental Industrial Hygienists (ACGIH) adopted Threshold Limit Values (TLVs) for benzene at 0.5 ppm TWA and 2.5 ppm STEL.<a href="#cite_note-OSHASampling2015-91">[90]</a> <div class="mw-heading mw-heading3"><h3 id="Toxicology">Toxicology</h3> <a role="button" href="/w/index.php?title=Benzene&action=edit&section=24" title="Edit section: Toxicology" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> edit </a> </div> <div class="mw-heading mw-heading4"><h4 id="Biomarkers_of_exposure">Biomarkers of exposure</h4> <a role="button" href="/w/index.php?title=Benzene&action=edit&section=25" title="Edit section: Biomarkers of exposure" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> edit </a> </div> Several tests can determine exposure to benzene. Benzene itself can be measured in breath, blood or urine, but such testing is usually limited to the first 24 hours post-exposure due to the relatively rapid removal of the chemical by exhalation or biotransformation. Most people in developed countries have measureable baseline levels of benzene and other aromatic petroleum hydrocarbons in their blood. In the body, benzene is enzymatically converted to a series of oxidation products including <a href="/wiki/Muconic_acid" title="Muconic acid">muconic acid</a>, <a href="/w/index.php?title=Phenylmercapturic_acid&action=edit&redlink=1" class="new" title="Phenylmercapturic acid (page does not exist)">phenylmercapturic acid</a>, <a href="/wiki/Phenol" title="Phenol">phenol</a>, <a href="/wiki/Catechol" title="Catechol">catechol</a>, <a href="/wiki/Hydroquinone" title="Hydroquinone">hydroquinone</a> and <a href="/wiki/Hydroxyquinol" title="Hydroxyquinol">1,2,4-trihydroxybenzene</a>. Most of these metabolites have some value as biomarkers of human exposure, since they accumulate in the urine in proportion to the extent and duration of exposure, and they may still be present for some days after exposure has ceased. The current ACGIH biological exposure limits for occupational exposure are 500 μg/g creatinine for muconic acid and 25 μg/g creatinine for phenylmercapturic acid in an end-of-shift urine specimen.<a href="#cite_note-96">[95]</a><a href="#cite_note-97">[96]</a><a href="#cite_note-98">[97]</a><a href="#cite_note-99">[98]</a> <div class="mw-heading mw-heading4"><h4 id="Biotransformations">Biotransformations</h4> <a role="button" href="/w/index.php?title=Benzene&action=edit&section=26" title="Edit section: Biotransformations" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> edit </a> </div> Even if it is not a common substrate for metabolism, benzene can be oxidized by both <a href="/wiki/Bacteria" title="Bacteria">bacteria</a> and <a href="/wiki/Eukaryote" title="Eukaryote">eukaryotes</a>. In bacteria, <a href="/wiki/Dioxygenase" title="Dioxygenase">dioxygenase</a> enzyme can add an <a href="/wiki/Oxygen" title="Oxygen">oxygen</a> to the ring, and the unstable product is immediately reduced (by <a href="/wiki/NADH" class="mw-redirect" title="NADH">NADH</a>) to a cyclic <a href="/wiki/Diol" title="Diol">diol</a> with two double bonds, breaking the aromaticity. Next, the diol is newly reduced by NADH to <a href="/wiki/Catechol" title="Catechol">catechol</a>. The catechol is then metabolized to <a href="/wiki/Acetyl_CoA" class="mw-redirect" title="Acetyl CoA">acetyl CoA</a> and <a href="/wiki/Succinyl_CoA" class="mw-redirect" title="Succinyl CoA">succinyl CoA</a>, used by organisms mainly in the <a href="/wiki/Citric_acid_cycle" title="Citric acid cycle">citric acid cycle</a> for energy production. The pathway for the metabolism of benzene is complex and begins in the liver. Several enzymes are involved. These include <a href="/wiki/Cytochrome_P450" title="Cytochrome P450">cytochrome P450</a> 2E1 (CYP2E1), quinine oxidoreductase (NQ01 or DT-diaphorase or <a href="/wiki/NAD(P)H_dehydrogenase_(quinone_1)" title="NAD(P)H dehydrogenase (quinone 1)">NAD(P)H dehydrogenase (quinone 1)</a>), GSH, and myeloperoxidase (MPO). CYP2E1 is involved at multiple steps: converting benzene to <a href="/wiki/Oxepin" title="Oxepin">oxepin</a> (benzene oxide), <a href="/wiki/Phenol" title="Phenol">phenol</a> to <a href="/wiki/Hydroquinone" title="Hydroquinone">hydroquinone</a>, and hydroquinone to both benzenetriol and <a href="/wiki/Catechol" title="Catechol">catechol</a>. Hydroquinone, benzenetriol and catechol are converted to polyphenols. In the bone marrow, MPO converts these polyphenols to benzoquinones. These intermediates and metabolites induce genotoxicity by multiple mechanisms including inhibition of <a href="/wiki/Type_II_topoisomerase" title="Type II topoisomerase">topoisomerase II</a> (which maintains chromosome structure), disruption of <a href="/wiki/Microtubules" class="mw-redirect" title="Microtubules">microtubules</a> (which maintains cellular structure and organization), generation of oxygen free radicals (unstable species) that may lead to point mutations, increasing oxidative stress, inducing <a href="/wiki/DNA" title="DNA">DNA</a> strand breaks, and altering DNA <a href="/wiki/Methylation" title="Methylation">methylation</a> (which can affect gene expression). NQ01 and GSH shift metabolism away from toxicity. NQ01 metabolizes <a href="/wiki/Benzoquinone" title="Benzoquinone">benzoquinone</a> toward <a href="/wiki/Polyphenols" class="mw-redirect" title="Polyphenols">polyphenols</a> (counteracting the effect of MPO). GSH is involved with the formation of <a href="/w/index.php?title=Phenylmercapturic_acid&action=edit&redlink=1" class="new" title="Phenylmercapturic acid (page does not exist)">phenylmercapturic acid</a>.<a href="#cite_note-Smith_2010_133%E2%80%9348-78">[77]</a><a href="#cite_note-100">[99]</a> Genetic polymorphisms in these enzymes may induce loss of function or gain of function. For example, mutations in CYP2E1 increase activity and result in increased generation of toxic metabolites. NQ01 mutations result in loss of function and may result in decreased detoxification. Myeloperoxidase mutations result in loss of function and may result in decreased generation of toxic metabolites. GSH mutations or deletions result in loss of function and result in decreased detoxification. These genes may be targets for genetic screening for susceptibility to benzene toxicity.<a href="#cite_note-101">[100]</a> <div class="mw-heading mw-heading4"><h4 id="Molecular_toxicology">Molecular toxicology</h4> <a role="button" href="/w/index.php?title=Benzene&action=edit&section=27" title="Edit section: Molecular toxicology" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> edit </a> </div> The paradigm of toxicological assessment of benzene is shifting towards the domain of molecular toxicology as it allows understanding of fundamental biological mechanisms in a better way. <a href="/wiki/Glutathione" title="Glutathione">Glutathione</a> seems to play an important role by protecting against benzene-induced DNA breaks and it is being identified as a new biomarker for exposure and effect.<a href="#cite_note-r3-102">[101]</a> Benzene causes chromosomal aberrations in the peripheral blood leukocytes and bone marrow explaining the higher incidence of leukemia and multiple myeloma caused by chronic exposure. These aberrations can be monitored using <a href="/wiki/Fluorescent_in_situ_hybridization" class="mw-redirect" title="Fluorescent in situ hybridization">fluorescent in situ hybridization</a> (FISH) with DNA probes to assess the effects of benzene along with the hematological tests as markers of hematotoxicity.<a href="#cite_note-r1-103">[102]</a> Benzene metabolism involves enzymes coded for by polymorphic genes. Studies have shown that genotype at these loci may influence susceptibility to the toxic effects of benzene exposure. Individuals carrying variant of NAD(P)H:quinone oxidoreductase 1 (NQO1), microsomal epoxide hydrolase (EPHX) and deletion of the glutathione S-transferase T1 (GSTT1) showed a greater frequency of DNA single-stranded breaks.<a href="#cite_note-r2-104">[103]</a> <div class="mw-heading mw-heading4"><h4 id="Biological_oxidation_and_carcinogenic_activity">Biological oxidation and carcinogenic activity</h4> <a role="button" href="/w/index.php?title=Benzene&action=edit&section=28" title="Edit section: Biological oxidation and carcinogenic activity" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> edit </a> </div> One way of understanding the carcinogenic effects of benzene is by examining the products of biological oxidation. Pure benzene, for example, oxidizes in the body to produce an epoxide, <a href="/wiki/Benzene_oxide" class="mw-redirect" title="Benzene oxide">benzene oxide</a>, which is not excreted readily and can interact with DNA to produce harmful mutations. <div class="mw-heading mw-heading3"><h3 id="Routes_of_exposure">Routes of exposure</h3> <a role="button" href="/w/index.php?title=Benzene&action=edit&section=29" title="Edit section: Routes of exposure" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> edit </a> </div> <div class="mw-heading mw-heading4"><h4 id="Inhalation">Inhalation</h4> <a role="button" href="/w/index.php?title=Benzene&action=edit&section=30" title="Edit section: Inhalation" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> edit </a> </div> Outdoor air may contain low levels of benzene from automobile service stations, wood smoke, tobacco smoke, the transfer of gasoline, exhaust from motor vehicles, and industrial emissions.<a href="#cite_note-105">[104]</a> About 50% of the entire nationwide (United States) exposure to benzene results from smoking tobacco or from exposure to tobacco smoke.<a href="#cite_note-106">[105]</a> After smoking 32 cigarettes per day, the smoker would take in about 1.8 milligrams (mg) of benzene. This amount is about 10 times the average daily intake of benzene by nonsmokers.<a href="#cite_note-107">[106]</a> Inhaled benzene is primarily expelled unchanged through exhalation. In a human study 16.4 to 41.6% of retained benzene was eliminated through the lungs within five to seven hours after a two- to three-hour exposure to 47 to 110 ppm and only 0.07 to 0.2% of the remaining benzene was excreted unchanged in the urine. After exposure to 63 to 405 mg/m3 of benzene for 1 to 5 hours, 51 to 87% was excreted in the urine as phenol over a period of 23 to 50 hours. In another human study, 30% of absorbed dermally applied benzene, which is primarily metabolized in the liver, was excreted as phenol in the urine.<a href="#cite_note-108">[107]</a> <div class="mw-heading mw-heading4"><h4 id="Exposure_from_soft_drinks">Exposure from soft drinks</h4> <a role="button" href="/w/index.php?title=Benzene&action=edit&section=31" title="Edit section: Exposure from soft drinks" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> edit </a> </div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Benzene_in_soft_drinks" title="Benzene in soft drinks">Benzene in soft drinks</a></div> Under specific conditions and in the presence of other chemicals <a href="/wiki/Benzoic_acid" title="Benzoic acid">benzoic acid</a> (a preservative) and <a href="/wiki/Ascorbic_acid" class="mw-redirect" title="Ascorbic acid">ascorbic acid</a> (Vitamin C) may interact to produce benzene. In March 2006, the official <a href="/wiki/Food_Standards_Agency" title="Food Standards Agency">Food Standards Agency</a> in <a href="/wiki/United_Kingdom" title="United Kingdom">United Kingdom</a> conducted a survey of 150 brands of soft drinks. It found that four contained benzene levels above <a href="/wiki/World_Health_Organization" title="World Health Organization">World Health Organization</a> limits. The affected batches were removed from sale. Similar problems were reported by the FDA in the United States.<a href="#cite_note-109">[108]</a> <div class="mw-heading mw-heading4"><h4 id="Contamination_of_water_supply">Contamination of water supply</h4> <a role="button" href="/w/index.php?title=Benzene&action=edit&section=32" title="Edit section: Contamination of water supply" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> edit </a> </div> In 2005, the water supply to the city of <a href="/wiki/Harbin" title="Harbin">Harbin</a> in China with a population of almost nine million people, was cut off because of a major benzene exposure.<a href="#cite_note-Guardian-25Nov2005-110">[109]</a> Benzene leaked into the <a href="/wiki/Songhua_River" title="Songhua River">Songhua River</a>, which supplies drinking water to the city, after <a href="/wiki/Jilin_chemical_plant_explosions_2005" class="mw-redirect" title="Jilin chemical plant explosions 2005">an explosion at a China National Petroleum Corporation (CNPC) factory</a> in the city of Jilin on 13 November 2005. When plastic water pipes are subject to high heat, the water may be contaminated with benzene.<a href="#cite_note-111">[110]</a> <div class="mw-heading mw-heading4"><h4 id="Genocide">Genocide</h4> <a role="button" href="/w/index.php?title=Benzene&action=edit&section=33" title="Edit section: Genocide" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> edit </a> </div> The <a href="/wiki/Nazi_Germany" title="Nazi Germany">Nazi German</a> government used benzene administered via <a href="/wiki/Injection_(medicine)" title="Injection (medicine)">injection</a> as one of their many methods for <a href="/wiki/Murder" title="Murder">killing</a>.<a href="#cite_note-112">[111]</a><a href="#cite_note-113">[112]</a> </section><div class="mw-heading mw-heading2 section-heading" onclick="mfTempOpenSection(9)"><h2 id="See_also">See also</h2> <a role="button" href="/w/index.php?title=Benzene&action=edit&section=34" title="Edit section: See also" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> edit </a> </div><section class="mf-section-9 collapsible-block" id="mf-section-9"> <style data-mw-deduplicate="TemplateStyles:r1239009302">.mw-parser-output .portalbox{padding:0;margin:0.5em 0;display:table;box-sizing:border-box;max-width:175px;list-style:none}.mw-parser-output .portalborder{border:1px solid var(--border-color-base,#a2a9b1);padding:0.1em;background:var(--background-color-neutral-subtle,#f8f9fa)}.mw-parser-output .portalbox-entry{display:table-row;font-size:85%;line-height:110%;height:1.9em;font-style:italic;font-weight:bold}.mw-parser-output .portalbox-image{display:table-cell;padding:0.2em;vertical-align:middle;text-align:center}.mw-parser-output .portalbox-link{display:table-cell;padding:0.2em 0.2em 0.2em 0.3em;vertical-align:middle}@media(min-width:720px){.mw-parser-output .portalleft{clear:left;float:left;margin:0.5em 1em 0.5em 0}.mw-parser-output .portalright{clear:right;float:right;margin:0.5em 0 0.5em 1em}}</style><ul role="navigation" aria-label="Portals" class="noprint portalbox portalborder portalright"> <li class="portalbox-entry"><a href="/wiki/File:Aegopodium_podagraria1_ies.jpg" class="mw-file-description"><noscript><img alt="icon" src="//upload.wikimedia.org/wikipedia/commons/thumb/b/bf/Aegopodium_podagraria1_ies.jpg/32px-Aegopodium_podagraria1_ies.jpg" decoding="async" width="32" height="28" class="mw-file-element" data-file-width="800" data-file-height="700"></noscript><span class="lazy-image-placeholder" style="width: 32px;height: 28px;" data-src="//upload.wikimedia.org/wikipedia/commons/thumb/b/bf/Aegopodium_podagraria1_ies.jpg/32px-Aegopodium_podagraria1_ies.jpg" data-alt="icon" data-width="32" data-height="28" data-srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/bf/Aegopodium_podagraria1_ies.jpg/48px-Aegopodium_podagraria1_ies.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/bf/Aegopodium_podagraria1_ies.jpg/64px-Aegopodium_podagraria1_ies.jpg 2x" data-class="mw-file-element"> </a><a href="/wiki/Portal:Environment" title="Portal:Environment">Environment portal</a></li><li class="portalbox-entry"><noscript><img alt="icon" src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d6/WHO_Rod.svg/12px-WHO_Rod.svg.png" decoding="async" width="12" height="28" class="mw-file-element" data-file-width="107" data-file-height="250"></noscript><span class="lazy-image-placeholder" style="width: 12px;height: 28px;" data-src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d6/WHO_Rod.svg/12px-WHO_Rod.svg.png" data-alt="icon" data-width="12" data-height="28" data-srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/d6/WHO_Rod.svg/18px-WHO_Rod.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/d6/WHO_Rod.svg/24px-WHO_Rod.svg.png 2x" data-class="mw-file-element"> <a href="/wiki/Portal:Medicine" title="Portal:Medicine">Medicine portal</a></li></ul> <ul><li><a href="/wiki/BTEX" class="mw-redirect" title="BTEX">BTEX</a></li> <li><a href="/wiki/1,2,3-Cyclohexatriene" title="1,2,3-Cyclohexatriene">1,2,3-Cyclohexatriene</a></li> <li><a href="/wiki/Industrial_Union_Department_v._American_Petroleum_Institute" title="Industrial Union Department v. American Petroleum Institute">Industrial Union Department v. American Petroleum Institute</a></li> <li>Six-membered aromatic rings with one carbon replaced by another element: <a href="/wiki/Borabenzene" title="Borabenzene">borabenzene</a>, <a href="/wiki/Silabenzene" title="Silabenzene">silabenzene</a>, <a href="/wiki/Germabenzene" title="Germabenzene">germabenzene</a>, <a href="/wiki/Stannabenzene" title="Stannabenzene">stannabenzene</a>, <a href="/wiki/Pyridine" title="Pyridine">pyridine</a>, <a href="/wiki/Phosphorine" title="Phosphorine">phosphorine</a>, <a href="/wiki/Arsabenzene" title="Arsabenzene">arsabenzene</a>, <a href="/wiki/Bismabenzene" title="Bismabenzene">bismabenzene</a>, <a href="/wiki/Pyrylium_salt" class="mw-redirect" title="Pyrylium salt">pyrylium</a>, <a href="/wiki/Thiopyrylium" title="Thiopyrylium">thiopyrylium</a>, <a href="/wiki/Selenopyrylium" title="Selenopyrylium">selenopyrylium</a>, <a href="/wiki/Telluropyrylium" title="Telluropyrylium">telluropyrylium</a></li></ul> </section><div class="mw-heading mw-heading2 section-heading" onclick="mfTempOpenSection(10)"><h2 id="Explanatory_notes">Explanatory notes</h2> <a role="button" href="/w/index.php?title=Benzene&action=edit&section=35" title="Edit section: Explanatory notes" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> edit </a> </div><section class="mf-section-10 collapsible-block" id="mf-section-10"> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap"><ol class="references"> <li id="cite_note-40"><a href="#cite_ref-40">^</a> Critics pointed out a problem with Kekulé's original (1865) structure for benzene: Whenever benzene underwent substitution at the ortho position, two distinguishable isomers should have resulted, depending on whether a double bond or a single bond existed between the carbon atoms to which the substituents were attached; however, no such isomers were observed. In 1872, Kekulé suggested that benzene had two complementary structures and that these forms rapidly interconverted, so that if there were a double bond between any pair of carbon atoms at one instant, that double bond would become a single bond at the next instant (and vice versa). To provide a mechanism for the conversion process, Kekulé proposed that the valency of an atom is determined by the frequency with which it collided with its neighbors in a molecule. As the carbon atoms in the benzene ring collided with each other, each carbon atom would collide twice with one neighbor during a given interval and then twice with its other neighbor during the next interval. Thus, a double bond would exist with one neighbor during the first interval and with the other neighbor during the next interval. Therefore, between the carbon atoms of benzene there were no fixed (i.e., constant) and distinct single or double bonds; instead, the bonds between the carbon atoms were identical. See <a class="external text" href="https://de.wikipedia.org/w/index.php?title=Datei:Kekule_-_Ueber_einige_Condensationsproducte_des_Aldehyds.pdf&page=10">pages 86–89</a> <a rel="nofollow" class="external text" href="https://web.archive.org/web/20200320235654/https://de.wikipedia.org/w/index.php?title=Datei%3AKekule_-_Ueber_einige_Condensationsproducte_des_Aldehyds.pdf&page=10">Archived</a> 2020-03-20 at the <a href="/wiki/Wayback_Machine" title="Wayback Machine">Wayback Machine</a> of Auguste Kekulé (1872) "Ueber einige Condensationsprodukte des Aldehyds" (On some condensation products of aldehydes), Liebig's Annalen der Chemie und Pharmacie, 162(1): 77–124, 309–320. From p. 89: "Das einfachste Mittel aller Stöße eines Kohlenstoffatoms ergiebt sich aus der Summe der Stöße der beiden ersten Zeiteinheiten, die sich dann periodisch wiederholen. … man sieht daher, daß jedes Kohlenstoffatom mit den beiden anderen, … daß diese Verschiedenheit nur eine scheinbare, aber keine wirkliche ist." (The simplest average of all the collisions of a carbon atom [in benzene] comes from the sum of the collisions during the first two units of time, which then periodically repeat. … thus one sees that each carbon atom collides equally often with the two others against which it bumps, [and] thus stands in exactly the same relation with its two neighbors. The usual structural formula for benzene expresses, of course, only the collisions that occur during one unit of time, thus during one phase, and so one is led to the view [that] doubly substituted derivatives [of benzene] must be different at positions 1,2 and 1,6 [of the benzene ring]. If the idea [that was] just presented—or a similar one—can be regarded as correct, then [it] follows therefrom that this difference [between the bonds at positions 1,2 and 1,6] is only an apparent [one], not a real [one].) </li> </ol></div></div> </section><div class="mw-heading mw-heading2 section-heading" onclick="mfTempOpenSection(11)"><h2 id="References">References</h2> <a role="button" href="/w/index.php?title=Benzene&action=edit&section=36" title="Edit section: References" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> edit </a> </div><section class="mf-section-11 collapsible-block" id="mf-section-11"> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239543626"><div class="reflist"> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-iupac2013-1">^ <a href="#cite_ref-iupac2013_1-0">a</a> <a href="#cite_ref-iupac2013_1-1">b</a> <style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite id="CITEREFFavrePowell2014" class="citation book cs1">Favre, Henri A.; Powell, Warren H. (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The <a href="/wiki/Royal_Society_of_Chemistry" title="Royal Society of Chemistry">Royal Society of Chemistry</a>. pp. 10, 22, 204, 494, 577. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1039%2F9781849733069">10.1039/9781849733069</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-85404-182-4" title="Special:BookSources/978-0-85404-182-4"><bdi>978-0-85404-182-4</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Nomenclature+of+Organic+Chemistry%3A+IUPAC+Recommendations+and+Preferred+Names+2013+%28Blue+Book%29&rft.place=Cambridge&rft.pages=10%2C+22%2C+204%2C+494%2C+577&rft.pub=The+Royal+Society+of+Chemistry&rft.date=2014&rft_id=info%3Adoi%2F10.1039%2F9781849733069&rft.isbn=978-0-85404-182-4&rft.aulast=Favre&rft.aufirst=Henri+A.&rft.au=Powell%2C+Warren+H.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABenzene" class="Z3988"> </li> <li id="cite_note-handbook13-2"><a href="#cite_ref-handbook13_2-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLide2005" class="citation book cs1">Lide, D. R., ed. (2005). CRC Handbook of Chemistry and Physics (86th ed.). Boca Raton (FL): CRC Press. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/0-8493-0486-5" title="Special:BookSources/0-8493-0486-5"><bdi>0-8493-0486-5</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=CRC+Handbook+of+Chemistry+and+Physics&rft.place=Boca+Raton+%28FL%29&rft.edition=86th&rft.pub=CRC+Press&rft.date=2005&rft.isbn=0-8493-0486-5&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABenzene" class="Z3988"> </li> <li id="cite_note-3"><a href="#cite_ref-3">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFArnoldPlankEricksonPike1958" class="citation journal cs1">Arnold, D.; Plank, C.; Erickson, E.; Pike, F. (1958). 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(1990). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC53221">"Surface tension measurements show that chaotropic salting-in denaturants are not just water-structure breakers"</a>. <a href="/wiki/Proceedings_of_the_National_Academy_of_Sciences_of_the_United_States_of_America" title="Proceedings of the National Academy of Sciences of the United States of America">Proceedings of the National Academy of Sciences of the United States of America</a>. 87 (1): 167–9. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/1990PNAS...87..167B">1990PNAS...87..167B</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1073%2Fpnas.87.1.167">10.1073/pnas.87.1.167</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC53221">53221</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/2153285">2153285</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Proceedings+of+the+National+Academy+of+Sciences+of+the+United+States+of+America&rft.atitle=Surface+tension+measurements+show+that+chaotropic+salting-in+denaturants+are+not+just+water-structure+breakers&rft.volume=87&rft.issue=1&rft.pages=167-9&rft.date=1990&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC53221%23id-name%3DPMC&rft_id=info%3Apmid%2F2153285&rft_id=info%3Adoi%2F10.1073%2Fpnas.87.1.167&rft_id=info%3Abibcode%2F1990PNAS...87..167B&rft.aulast=Breslow&rft.aufirst=R.&rft.au=Guo%2C+T.&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC53221&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABenzene" class="Z3988"> </li> <li id="cite_note-5"><a href="#cite_ref-5">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFCokerLudwig2007" class="citation book cs1">Coker, A. Kayode; Ludwig, Ernest E. (2007). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=N8RcH8juG_YC&pg=PA114">Ludwig's Applied Process Design for Chemical And Petrochemical Plants</a>. Vol. 1. Elsevier. p. 114. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-7506-7766-0" title="Special:BookSources/978-0-7506-7766-0"><bdi>978-0-7506-7766-0</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20160312120850/https://books.google.com/books?id=N8RcH8juG_YC&pg=PA114">Archived</a> from the original on 2016-03-12. Retrieved 2012-05-31.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Ludwig%27s+Applied+Process+Design+for+Chemical+And+Petrochemical+Plants&rft.pages=114&rft.pub=Elsevier&rft.date=2007&rft.isbn=978-0-7506-7766-0&rft.aulast=Coker&rft.aufirst=A.+Kayode&rft.au=Ludwig%2C+Ernest+E.&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DN8RcH8juG_YC%26pg%3DPA114&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABenzene" class="Z3988"> </li> <li id="cite_note-chemister-6">^ <a href="#cite_ref-chemister_6-0">a</a> <a href="#cite_ref-chemister_6-1">b</a> <a href="#cite_ref-chemister_6-2">c</a> <a href="#cite_ref-chemister_6-3">d</a> <a href="#cite_ref-chemister_6-4">e</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="http://chemister.ru/Database/properties-en.php?dbid=1&id=644">"Benzol"</a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20140529232137/http://chemister.ru/Database/properties-en.php?dbid=1&id=644">Archived</a> from the original on 2014-05-29. Retrieved 2014-05-29.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Benzol&rft_id=http%3A%2F%2Fchemister.ru%2FDatabase%2Fproperties-en.php%3Fdbid%3D1%26id%3D644&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABenzene" class="Z3988"> </li> <li id="cite_note-sioc-7">^ <a href="#cite_ref-sioc_7-0">a</a> <a href="#cite_ref-sioc_7-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFAtherton_SeidellWilliam_F._Linke1952" class="citation book cs1">Atherton Seidell; William F. Linke (1952). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=k2e5AAAAIAAJ">Solubilities of Inorganic and Organic Compounds: A Compilation of Solubility Data from the Periodical Literature. Supplement</a>. Van Nostrand. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20200311230632/https://books.google.com/books?id=k2e5AAAAIAAJ">Archived</a> from the original on 2020-03-11. Retrieved 2015-06-27.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Solubilities+of+Inorganic+and+Organic+Compounds%3A+A+Compilation+of+Solubility+Data+from+the+Periodical+Literature.+Supplement&rft.pub=Van+Nostrand&rft.date=1952&rft.au=Atherton+Seidell&rft.au=William+F.+Linke&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3Dk2e5AAAAIAAJ&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABenzene" class="Z3988"> </li> <li id="cite_note-nist-8">^ <a href="#cite_ref-nist_8-0">a</a> <a href="#cite_ref-nist_8-1">b</a> <a href="#cite_ref-nist_8-2">c</a> <a rel="nofollow" class="external text" href="http://webbook.nist.gov/cgi/cbook.cgi?ID=C71432&Mask=FFFF&Units=SI">Benzene</a> in Linstrom, Peter J.; Mallard, William G. (eds.); <a rel="nofollow" class="external text" href="http://webbook.nist.gov">NIST Chemistry WebBook</a>, NIST Standard Reference Database Number 69, National Institute of Standards and Technology, Gaithersburg (MD) (retrieved 2014-05-29) </li> <li id="cite_note-9"><a href="#cite_ref-9">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/12533897">"Benzenium (CID 12533897"</a>. <a href="/wiki/PubChem" title="PubChem">PubChem</a>. February 8, 2007. Retrieved September 18, 2022.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Benzenium+%28CID+12533897&rft.pub=PubChem&rft.date=2007-02-08&rft_id=https%3A%2F%2Fpubchem.ncbi.nlm.nih.gov%2Fcompound%2F12533897&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABenzene" class="Z3988"> </li> <li id="cite_note-10"><a href="#cite_ref-10">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/5150480">"Benzenide (CID 5150480)"</a>. <a href="/wiki/PubChem" title="PubChem">PubChem</a>. June 24, 2005. Retrieved September 18, 2022.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Benzenide+%28CID+5150480%29&rft.pub=PubChem&rft.date=2005-06-24&rft_id=https%3A%2F%2Fpubchem.ncbi.nlm.nih.gov%2Fcompound%2F5150480&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABenzene" class="Z3988"> </li> <li id="cite_note-sigma-11">^ <a href="#cite_ref-sigma_11-0">a</a> <a href="#cite_ref-sigma_11-1">b</a> <a href="#cite_ref-sigma_11-2">c</a> <a href="/wiki/Sigma-Aldrich" title="Sigma-Aldrich">Sigma-Aldrich</a> Co., <a rel="nofollow" class="external text" href="http://www.sigmaaldrich.com/catalog/product/sial/401765">Benzene</a> <a rel="nofollow" class="external text" href="https://web.archive.org/web/20161201060259/http://www.hmdb.ca/system/metabolites/msds/000/001/365/original/HMDB01505.pdf?1358893540">Archived</a> 2016-12-01 at the <a href="/wiki/Wayback_Machine" title="Wayback Machine">Wayback Machine</a>. Retrieved on 2014-05-29. </li> <li id="cite_note-PGCH-12">^ <a href="#cite_ref-PGCH_12-0">a</a> <a href="#cite_ref-PGCH_12-1">b</a> <a href="#cite_ref-PGCH_12-2">c</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFNIOSH_Pocket_Guide_to_Chemical_Hazards" class="citation web cs1">NIOSH Pocket Guide to Chemical Hazards. <a rel="nofollow" class="external text" href="https://www.cdc.gov/niosh/npg/npgd0049.html">"#0049"</a>. <a href="/wiki/National_Institute_for_Occupational_Safety_and_Health" title="National Institute for Occupational Safety and Health">National Institute for Occupational Safety and Health</a> (NIOSH).</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=%230049&rft.pub=National+Institute+for+Occupational+Safety+and+Health+%28NIOSH%29&rft.au=NIOSH+Pocket+Guide+to+Chemical+Hazards&rft_id=https%3A%2F%2Fwww.cdc.gov%2Fniosh%2Fnpg%2Fnpgd0049.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABenzene" class="Z3988"> </li> <li id="cite_note-13"><a href="#cite_ref-13">^</a> <a rel="nofollow" class="external text" href="https://fscimage.fishersci.com/msds/02610.htm">MSDS</a> </li> <li id="cite_note-14"><a href="#cite_ref-14">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://www.cdc.gov/niosh/idlh/71432.html">"Benzene"</a>. Immediately Dangerous to Life or Health Concentrations (IDLH). <a href="/wiki/National_Institute_for_Occupational_Safety_and_Health" title="National Institute for Occupational Safety and Health">National Institute for Occupational Safety and Health</a> (NIOSH).</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Immediately+Dangerous+to+Life+or+Health+Concentrations+%28IDLH%29&rft.atitle=Benzene&rft_id=https%3A%2F%2Fwww.cdc.gov%2Fniosh%2Fidlh%2F71432.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABenzene" class="Z3988"> </li> <li id="cite_note-15"><a href="#cite_ref-15">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://www.cdc.gov/biomonitoring/Benzene_FactSheet.html">"Benzene fact sheet"</a>. CDC. 2 September 2021. Retrieved 16 Aug 2023.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=CDC&rft.atitle=Benzene+fact+sheet&rft.date=2021-09-02&rft_id=https%3A%2F%2Fwww.cdc.gov%2Fbiomonitoring%2FBenzene_FactSheet.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABenzene" class="Z3988"> </li> <li id="cite_note-16"><a href="#cite_ref-16">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFShao2022" class="citation news cs1">Shao, Elena (28 June 2022). <a rel="nofollow" class="external text" href="https://www.nytimes.com/2022/06/28/climate/natural-gas-home-toxic-chemicals.html">"Gas Piped into Homes Contains Benzene and Other Risky Chemicals, Study Finds"</a>. The New York Times.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+New+York+Times&rft.atitle=Gas+Piped+into+Homes+Contains+Benzene+and+Other+Risky+Chemicals%2C+Study+Finds&rft.date=2022-06-28&rft.aulast=Shao&rft.aufirst=Elena&rft_id=https%3A%2F%2Fwww.nytimes.com%2F2022%2F06%2F28%2Fclimate%2Fnatural-gas-home-toxic-chemicals.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABenzene" class="Z3988"> </li> <li id="cite_note-17"><a href="#cite_ref-17">^</a> The word "benzoin" is derived from the Arabic expression "luban jawi", or "<a href="/wiki/Frankincense" title="Frankincense">frankincense</a> of <a href="/wiki/Java" title="Java">Java</a>". <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMorris1984" class="citation book cs1">Morris, Edwin T. (1984). Fragrance: The Story of Perfume from Cleopatra to Chanel. Charles Scribner's Sons. p. 101. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0684181950" title="Special:BookSources/978-0684181950"><bdi>978-0684181950</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Fragrance%3A+The+Story+of+Perfume+from+Cleopatra+to+Chanel&rft.pages=101&rft.pub=Charles+Scribner%27s+Sons&rft.date=1984&rft.isbn=978-0684181950&rft.aulast=Morris&rft.aufirst=Edwin+T.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABenzene" class="Z3988"> </li> <li id="cite_note-rocke-18">^ <a href="#cite_ref-rocke_18-0">a</a> <a href="#cite_ref-rocke_18-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFRocke,_A._J.1985" class="citation journal cs1">Rocke, A. J. (1985). "Hypothesis and Experiment in the Early Development of Kekule's Benzene Theory". <a href="/wiki/Annals_of_Science" title="Annals of Science">Annals of Science</a>. 42 (4): 355–81. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1080%2F00033798500200411">10.1080/00033798500200411</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Annals+of+Science&rft.atitle=Hypothesis+and+Experiment+in+the+Early+Development+of+Kekule%27s+Benzene+Theory&rft.volume=42&rft.issue=4&rft.pages=355-81&rft.date=1985&rft_id=info%3Adoi%2F10.1080%2F00033798500200411&rft.au=Rocke%2C+A.+J.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABenzene" class="Z3988"> </li> <li id="cite_note-19"><a href="#cite_ref-19">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFFaraday,_M.1825" class="citation journal cs1"><a href="/wiki/Michael_Faraday" title="Michael Faraday">Faraday, M.</a> (1825). <a rel="nofollow" class="external text" href="http://gallica.bnf.fr/ark:/12148/bpt6k559209/f473.image">"On new compounds of carbon and hydrogen, and on certain other products obtained during the decomposition of oil by heat"</a>. <a href="/wiki/Philosophical_Transactions_of_the_Royal_Society" title="Philosophical Transactions of the Royal Society">Philosophical Transactions of the Royal Society</a>. 115: 440–466. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1098%2Frstl.1825.0022">10.1098/rstl.1825.0022</a>. <a href="/wiki/JSTOR_(identifier)" class="mw-redirect" title="JSTOR (identifier)">JSTOR</a> <a rel="nofollow" class="external text" href="https://www.jstor.org/stable/107752">107752</a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20201121235017/http://gallica.bnf.fr/ark:/12148/bpt6k559209/f473.image">Archived</a> from the original on 2020-11-21. Retrieved 2012-01-15.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Philosophical+Transactions+of+the+Royal+Society&rft.atitle=On+new+compounds+of+carbon+and+hydrogen%2C+and+on+certain+other+products+obtained+during+the+decomposition+of+oil+by+heat&rft.volume=115&rft.pages=440-466&rft.date=1825&rft_id=info%3Adoi%2F10.1098%2Frstl.1825.0022&rft_id=https%3A%2F%2Fwww.jstor.org%2Fstable%2F107752%23id-name%3DJSTOR&rft.au=Faraday%2C+M.&rft_id=http%3A%2F%2Fgallica.bnf.fr%2Fark%3A%2F12148%2Fbpt6k559209%2Ff473.image&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABenzene" class="Z3988"> On pages 443–450, Faraday discusses "bicarburet of hydrogen" (benzene). On pages 449–450, he shows that benzene's empirical formula is C6H6, although he doesn't realize it because he (like most chemists at that time) used the wrong atomic mass for carbon (6 instead of 12). </li> <li id="cite_note-20"><a href="#cite_ref-20">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFKaiser,_R.1968" class="citation journal cs1">Kaiser, R. (1968). "Bicarburet of Hydrogen. Reappraisal of the Discovery of Benzene in 1825 with the Analytical Methods of 1968". Angewandte Chemie International Edition in English. 7 (5): 345–350. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fanie.196803451">10.1002/anie.196803451</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Angewandte+Chemie+International+Edition+in+English&rft.atitle=Bicarburet+of+Hydrogen.+Reappraisal+of+the+Discovery+of+Benzene+in+1825+with+the+Analytical+Methods+of+1968&rft.volume=7&rft.issue=5&rft.pages=345-350&rft.date=1968&rft_id=info%3Adoi%2F10.1002%2Fanie.196803451&rft.au=Kaiser%2C+R.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABenzene" class="Z3988"> </li> <li id="cite_note-21"><a href="#cite_ref-21">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMitscherlich,_E.1834" class="citation journal cs1">Mitscherlich, E. (1834). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=JEs9AAAAcAAJ&pg=PA39">"Über das Benzol und die Säuren der Oel- und Talgarten"</a> [On benzol and oily and fatty types of acids]. <a href="/wiki/Liebigs_Annalen" title="Liebigs Annalen">Annalen der Pharmacie</a>. 9 (1): 39–48. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fjlac.18340090103">10.1002/jlac.18340090103</a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20151123133406/https://books.google.com/books?id=JEs9AAAAcAAJ&pg=PA39">Archived</a> from the original on 2015-11-23. Retrieved 2015-06-27.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Annalen+der+Pharmacie&rft.atitle=%C3%9Cber+das+Benzol+und+die+S%C3%A4uren+der+Oel-+und+Talgarten&rft.volume=9&rft.issue=1&rft.pages=39-48&rft.date=1834&rft_id=info%3Adoi%2F10.1002%2Fjlac.18340090103&rft.au=Mitscherlich%2C+E.&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DJEs9AAAAcAAJ%26pg%3DPA39&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABenzene" class="Z3988"> In a footnote on page 43, Liebig, the journal's editor, suggested changing Mitscherlich's original name for benzene (namely, "benzin") to "benzol", because the suffix "-in" suggested that it was an alkaloid (e.g., Chinin (quinine)), which benzene isn't, whereas the suffix "-ol" suggested that it was oily, which benzene is. Thus on page 44, Mitscherlich states: "Da diese Flüssigkeit aus der Benzoësäure gewonnen wird, und wahrscheinlich mit den Benzoylverbindungen im Zusammenhang steht, so gibt man ihr am besten den Namen Benzol, da der Name Benzoïn schon für die mit dem Bittermandelöl isomerische Verbindung von Liebig und Wöhler gewählt worden ist." (Since this liquid [benzene] is obtained from benzoic acid and probably is related to benzoyl compounds, the best name for it is "benzol", since the name "benzoïn" has already been chosen, by Liebig and Wöhler, for the compound that's isomeric with the oil of bitter almonds [benzaldehyde].) </li> <li id="cite_note-22"><a href="#cite_ref-22">^</a> Laurent, (1836) "Sur la chlorophénise et les acides chlorophénisique et chlorophénèsique," Annales de Chemie et de Physique, vol. 63, pp. 27–45, see <a rel="nofollow" class="external text" href="https://books.google.com/books?id=Lx0AAAAAMAAJ&pg=PA44">p. 44</a> <a rel="nofollow" class="external text" href="https://web.archive.org/web/20150320073432/http://books.google.com/books?id=Lx0AAAAAMAAJ&pg=PA44">Archived</a> 2015-03-20 at the <a href="/wiki/Wayback_Machine" title="Wayback Machine">Wayback Machine</a>: "Je donne le nom de phène au radical fondamental des acides précédens (φαινω, j'éclaire), puisque la benzine se trouve dans le gaz de l'éclairage." (I give the name of "phène" (φαινω, I illuminate) to the fundamental radical of the preceding acids, because benzene is found in illuminating gas.) </li> <li id="cite_note-23"><a href="#cite_ref-23">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHofmann1845" class="citation journal cs1 cs1-prop-foreign-lang-source">Hofmann, A. W. (1845). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=E-1AAAAAYAAJ&pg=PA200">"Ueber eine sichere Reaction auf Benzol"</a> [On a reliable test for benzene]. Annalen der Chemie und Pharmacie (in German). 55 (2): 200–205, especially 204–205. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fjlac.18450550205">10.1002/jlac.18450550205</a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20151122124839/https://books.google.com/books?id=E-1AAAAAYAAJ&pg=PA200">Archived</a> from the original on 2015-11-22.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Annalen+der+Chemie+und+Pharmacie&rft.atitle=Ueber+eine+sichere+Reaction+auf+Benzol&rft.volume=55&rft.issue=2&rft.pages=200-205%2C+especially+204-205&rft.date=1845&rft_id=info%3Adoi%2F10.1002%2Fjlac.18450550205&rft.aulast=Hofmann&rft.aufirst=A.+W.&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DE-1AAAAAYAAJ%26pg%3DPA200&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABenzene" class="Z3988"> </li> <li id="cite_note-24"><a href="#cite_ref-24">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMansfield_Charles_Blachford1849" class="citation journal cs1">Mansfield Charles Blachford (1849). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=kD4aAQAAMAAJ&pg=PA162">"Untersuchung des Steinkohlentheers"</a>. Annalen der Chemie und Pharmacie. 69 (2): 162–180. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fjlac.18490690203">10.1002/jlac.18490690203</a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20151027022228/https://books.google.com/books?id=kD4aAQAAMAAJ&pg=PA162">Archived</a> from the original on 2015-10-27. Retrieved 2015-06-27.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Annalen+der+Chemie+und+Pharmacie&rft.atitle=Untersuchung+des+Steinkohlentheers&rft.volume=69&rft.issue=2&rft.pages=162-180&rft.date=1849&rft_id=info%3Adoi%2F10.1002%2Fjlac.18490690203&rft.au=Mansfield+Charles+Blachford&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DkD4aAQAAMAAJ%26pg%3DPA162&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABenzene" class="Z3988"> </li> <li id="cite_note-25"><a href="#cite_ref-25">^</a> Charles Mansfield filed for (November 11, 1847) and received (May 1848) a patent (no. 11,960) for the fractional distillation of coal tar. </li> <li id="cite_note-26"><a href="#cite_ref-26">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHoffman,_Augustus_W.1856" class="citation journal cs1">Hoffman, Augustus W. (1856). "On insolinic acid". <a href="/wiki/Proceedings_of_the_Royal_Society" title="Proceedings of the Royal Society">Proceedings of the Royal Society</a>. 8: 1–3. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1098%2Frspl.1856.0002">10.1098/rspl.1856.0002</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:97105342">97105342</a>. <q>The existence and mode of formation of insolinic acid prove that to the series of monobasic aromatic acids, Cn2Hn2-8O4, the lowest known term of which is benzoic acid, … .</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Proceedings+of+the+Royal+Society&rft.atitle=On+insolinic+acid&rft.volume=8&rft.pages=1-3&rft.date=1856&rft_id=info%3Adoi%2F10.1098%2Frspl.1856.0002&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A97105342%23id-name%3DS2CID&rft.au=Hoffman%2C+Augustus+W.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABenzene" class="Z3988"> [Note: The empirical formulas of organic compounds that appear in Hofmann's article (p. 3) are based upon an atomic mass of carbon of 6 (instead of 12) and an atomic mass of oxygen of 8 (instead of 16).] </li> <li id="cite_note-Cernicharo_546-27"><a href="#cite_ref-Cernicharo_546_27-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFCernicharoHerasTielensPardo2001" class="citation cs2">Cernicharo, José; et al. (2001), "Infrared Space Observatory's Discovery of C4H2, C6H2, and Benzene in CRL 618", Astrophysical Journal Letters, 546 (2): L123–L126, <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/2001ApJ...546L.123C">2001ApJ...546L.123C</a>, <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1086%2F318871">10.1086/318871</a></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Astrophysical+Journal+Letters&rft.atitle=Infrared+Space+Observatory%27s+Discovery+of+C%3Csub%3E4%3C%2Fsub%3EH%3Csub%3E2%3C%2Fsub%3E%2C+C%3Csub%3E6%3C%2Fsub%3EH%3Csub%3E2%3C%2Fsub%3E%2C+and+Benzene+in+CRL+618&rft.volume=546&rft.issue=2&rft.pages=L123-L126&rft.date=2001&rft_id=info%3Adoi%2F10.1086%2F318871&rft_id=info%3Abibcode%2F2001ApJ...546L.123C&rft.aulast=Cernicharo&rft.aufirst=Jos%C3%A9&rft.au=Heras%2C+Ana+M.&rft.au=Tielens%2C+A.+G.+G.+M.&rft.au=Pardo%2C+Juan+R.&rft.au=Herpin%2C+Fabrice&rft.au=Gu%C3%A9lin%2C+Michel&rft.au=Waters%2C+L.+B.+F.+M.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABenzene" class="Z3988"> </li> <li id="cite_note-28"><a href="#cite_ref-28">^</a> Claus, Adolph K.L. (1867) "Theoretische Betrachtungen und deren Anwendungen zur Systematik der organischen Chemie" (Theoretical considerations and their applications to the classification scheme of organic chemistry), Berichte über die Verhandlungen der Naturforschenden Gesellschaft zu Freiburg im Breisgau (<a href="/w/index.php?title=Reports_of_the_Proceedings_of_the_Scientific_Society_of_Freiburg&action=edit&redlink=1" class="new" title="Reports of the Proceedings of the Scientific Society of Freiburg (page does not exist)">Reports of the Proceedings of the Scientific Society of Freiburg</a> in Breisgau), 4 : 116–381. In the section Aromatischen Verbindungen (aromatic compounds), pp. 315–347, Claus presents Kekulé's hypothetical structure for benzene (<a rel="nofollow" class="external text" href="http://gdz.sub.uni-goettingen.de/en/dms/loader/img/?PID=PPN623920514_0004%7CLOG_0021&physid=PHYS_0339">p. 317</a>), presents objections to it, presents an alternative geometry (<a rel="nofollow" class="external text" href="http://gdz.sub.uni-goettingen.de/en/dms/loader/img/?PID=PPN623920514_0004%7CLOG_0021&physid=PHYS_0342">p. 320</a>), and concludes that his alternative is correct (<a rel="nofollow" class="external text" href="http://gdz.sub.uni-goettingen.de/en/dms/loader/img/?PID=PPN623920514_0004%7CLOG_0021&physid=PHYS_0348">p. 326</a>). See also figures on <a rel="nofollow" class="external text" href="http://gdz.sub.uni-goettingen.de/en/dms/loader/img/?PID=PPN623920514_0004%7CLOG_0021&physid=PHYS_0376">p. 354</a> or <a rel="nofollow" class="external text" href="http://gdz.sub.uni-goettingen.de/en/dms/loader/img/?PID=PPN623920514_0004%7CLOG_0023&physid=PHYS_0401">p. 379.</a> </li> <li id="cite_note-29"><a href="#cite_ref-29">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFDewar_James1869" class="citation journal cs1">Dewar James (1869). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=PmlUAAAAIAAJ&pg=PA82">"On the oxidation of phenyl alcohol, and a mechanical arrangement adapted to illustrate structure in the non-saturated hydrocarbons"</a>. <a href="/wiki/Proceedings_of_the_Royal_Society_of_Edinburgh" class="mw-redirect" title="Proceedings of the Royal Society of Edinburgh">Proceedings of the Royal Society of Edinburgh</a>. 6: 82–86. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1017%2FS0370164600045387">10.1017/S0370164600045387</a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20151124162938/https://books.google.com/books?id=PmlUAAAAIAAJ&pg=PA82">Archived</a> from the original on 2015-11-24. Retrieved 2015-06-27.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Proceedings+of+the+Royal+Society+of+Edinburgh&rft.atitle=On+the+oxidation+of+phenyl+alcohol%2C+and+a+mechanical+arrangement+adapted+to+illustrate+structure+in+the+non-saturated+hydrocarbons&rft.volume=6&rft.pages=82-86&rft.date=1869&rft_id=info%3Adoi%2F10.1017%2FS0370164600045387&rft.au=Dewar+James&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DPmlUAAAAIAAJ%26pg%3DPA82&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABenzene" class="Z3988"> </li> <li id="cite_note-30"><a href="#cite_ref-30">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLadenburg_Albert1869" class="citation journal cs1">Ladenburg Albert (1869). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=Epg8AAAAIAAJ&pg=PA140">"Bemerkungen zur aromatischen Theorie"</a> [Observations on the aromatic theory]. Berichte der Deutschen Chemischen Gesellschaft. 2: 140–142. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fcber.18690020171">10.1002/cber.18690020171</a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20151122175439/https://books.google.com/books?id=Epg8AAAAIAAJ&pg=PA140">Archived</a> from the original on 2015-11-22. Retrieved 2015-06-27.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Berichte+der+Deutschen+Chemischen+Gesellschaft&rft.atitle=Bemerkungen+zur+aromatischen+Theorie&rft.volume=2&rft.pages=140-142&rft.date=1869&rft_id=info%3Adoi%2F10.1002%2Fcber.18690020171&rft.au=Ladenburg+Albert&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DEpg8AAAAIAAJ%26pg%3DPA140&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABenzene" class="Z3988"> </li> <li id="cite_note-Kekulé1865-31">^ <a href="#cite_ref-Kekul%C3%A91865_31-0">a</a> <a href="#cite_ref-Kekul%C3%A91865_31-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFKekulé,_F._A.1865" class="citation journal cs1"><a href="/wiki/Friedrich_August_Kekul%C3%A9_von_Stradonitz" class="mw-redirect" title="Friedrich August Kekulé von Stradonitz">Kekulé, F. A.</a> (1865). <a rel="nofollow" class="external text" href="https://gallica.bnf.fr/ark:/12148/bpt6k281952v/f102">"Sur la constitution des substances aromatiques"</a>. Bulletin de la Société Chimique de Paris. 3: 98–110. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20151114102723/https://books.google.com/books?id=bFsSAAAAYAAJ&pg=PA98">Archived</a> from the original on 2015-11-14. Retrieved 2015-06-27.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Bulletin+de+la+Soci%C3%A9t%C3%A9+Chimique+de+Paris&rft.atitle=Sur+la+constitution+des+substances+aromatiques&rft.volume=3&rft.pages=98-110&rft.date=1865&rft.au=Kekul%C3%A9%2C+F.+A.&rft_id=https%3A%2F%2Fgallica.bnf.fr%2Fark%3A%2F12148%2Fbpt6k281952v%2Ff102&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABenzene" class="Z3988"> On p. 100, Kekulé suggests that the carbon atoms of benzene could form a "chaîne fermée" (closed chain). </li> <li id="cite_note-32"><a href="#cite_ref-32">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFAug._Kekulé1872" class="citation cs2 cs1-prop-foreign-lang-source">Aug. Kekulé (1872), <a class="external text" href="https://upload.wikimedia.org/wikipedia/commons/5/5d/Kekule_-_Ueber_einige_Condensationsproducte_des_Aldehyds.pdf">"Ueber einige Condensationsproducte des Aldehyds"</a> (PDF), <a href="/wiki/Annalen_der_Chemie_und_Pharmacie" class="mw-redirect" title="Annalen der Chemie und Pharmacie">Annalen der Chemie und Pharmacie</a> (in German), vol. 162, no. 1, pp. 77–124, <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fjlac.18721620110">10.1002/jlac.18721620110</a></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Annalen+der+Chemie+und+Pharmacie&rft.atitle=Ueber+einige+Condensationsproducte+des+Aldehyds&rft.volume=162&rft.issue=1&rft.pages=pp.-77-124&rft.date=1872&rft_id=info%3Adoi%2F10.1002%2Fjlac.18721620110&rft.au=Aug.+Kekul%C3%A9&rft_id=https%3A%2F%2Fupload.wikimedia.org%2Fwikipedia%2Fcommons%2F5%2F5d%2FKekule_-_Ueber_einige_Condensationsproducte_des_Aldehyds.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABenzene" class="Z3988"> </li> <li id="cite_note-33"><a href="#cite_ref-33">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFArmstrong_Henry_E1887" class="citation journal cs1">Armstrong Henry E (1887). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=4QbzAAAAMAAJ&pg=PA258">"An explanation of the laws which govern substitution in the case of benzenoid compounds"</a>. Journal of the Chemical Society. 51: 258–268 [264]. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1039%2Fct8875100258">10.1039/ct8875100258</a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20151022073257/https://books.google.com/books?id=4QbzAAAAMAAJ&pg=PA258">Archived</a> from the original on 2015-10-22. Retrieved 2015-06-27.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+the+Chemical+Society&rft.atitle=An+explanation+of+the+laws+which+govern+substitution+in+the+case+of+benzenoid+compounds&rft.volume=51&rft.pages=258-268+264&rft.date=1887&rft_id=info%3Adoi%2F10.1039%2Fct8875100258&rft.au=Armstrong+Henry+E&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D4QbzAAAAMAAJ%26pg%3DPA258&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABenzene" class="Z3988"> </li> <li id="cite_note-34"><a href="#cite_ref-34">^</a> In his 1890 paper, Armstrong represented benzene nuclei within polycyclic benzenoids by placing inside the benzene nuclei a letter "C", an abbreviation of the word "centric". Centric affinities (i.e., bonds) acted within a designated cycle of carbon atoms. From p. 102: " … benzene, according to this view, may be represented by a double ring, in fact." See: <ul><li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation journal cs1">Armstrong, H.E. (1890). <a rel="nofollow" class="external text" href="https://babel.hathitrust.org/cgi/pt?id=pst.000052368141;view=1up;seq=319">"The structure of cycloid hydrocarbons"</a>. <a href="/wiki/Proceedings_of_the_Chemical_Society" title="Proceedings of the Chemical Society">Proceedings of the Chemical Society</a>. 6: 101–105. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20211116024104/https://babel.hathitrust.org/cgi/pt?id=pst.000052368141;view=1up;seq=319">Archived</a> from the original on 2021-11-16. Retrieved 2018-02-17.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Proceedings+of+the+Chemical+Society&rft.atitle=The+structure+of+cycloid+hydrocarbons&rft.volume=6&rft.pages=101-105&rft.date=1890&rft.aulast=Armstrong&rft.aufirst=H.E.&rft_id=https%3A%2F%2Fbabel.hathitrust.org%2Fcgi%2Fpt%3Fid%3Dpst.000052368141%3Bview%3D1up%3Bseq%3D319&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABenzene" class="Z3988"></li></ul> The use of a circle to denote a benzene nucleus first appeared in: <ul><li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation journal cs1">Armit, James Wilson; Robinson, Robert (1925). "Polynuclear heterocyclic aromatic types. Part II. Some anhydronium bases". Journal of the Chemical Society, Transactions. 127: 1604–1618. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1039%2Fct9252701604">10.1039/ct9252701604</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+the+Chemical+Society%2C+Transactions&rft.atitle=Polynuclear+heterocyclic+aromatic+types.+Part+II.+Some+anhydronium+bases&rft.volume=127&rft.pages=1604-1618&rft.date=1925&rft_id=info%3Adoi%2F10.1039%2Fct9252701604&rft.aulast=Armit&rft.aufirst=James+Wilson&rft.au=Robinson%2C+Robert&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABenzene" class="Z3988"></li></ul> A history of the determination of benzene's structure is recounted in: <ul><li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation journal cs1">Balaban, Alexandru T.; Schleyer, Paul v. R.; Rzepa, Henry S. (2005). <a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fcr0300946">"Crocker, Not Armit and Robinson, Begat the Six Aromatic Electrons"</a>. Chemical Reviews. 105 (10): 3436–3447. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fcr0300946">10.1021/cr0300946</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/16218557">16218557</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Chemical+Reviews&rft.atitle=Crocker%2C+Not+Armit+and+Robinson%2C+Begat+the+Six+Aromatic+Electrons&rft.volume=105&rft.issue=10&rft.pages=3436-3447&rft.date=2005&rft_id=info%3Adoi%2F10.1021%2Fcr0300946&rft_id=info%3Apmid%2F16218557&rft.aulast=Balaban&rft.aufirst=Alexandru+T.&rft.au=Schleyer%2C+Paul+v.+R.&rft.au=Rzepa%2C+Henry+S.&rft_id=https%3A%2F%2Fdoi.org%2F10.1021%252Fcr0300946&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABenzene" class="Z3988"></li></ul> </li> <li id="cite_note-35"><a href="#cite_ref-35">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFAdolf_Baeyer1888" class="citation cs2 cs1-prop-foreign-lang-source">Adolf Baeyer (1888), <a rel="nofollow" class="external text" href="https://zenodo.org/record/1851261">"Über die Constitution des Benzols"</a>, <a href="/wiki/Justus_Liebigs_Annalen_der_Chemie" class="mw-redirect" title="Justus Liebigs Annalen der Chemie">Justus Liebigs Annalen der Chemie</a> (in German), vol. 245, no. 1–2, pp. 103–190, <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fjlac.18882450110">10.1002/jlac.18882450110</a></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Justus+Liebigs+Annalen+der+Chemie&rft.atitle=%C3%9Cber+die+Constitution+des+Benzols&rft.volume=245&rft.issue=1%E2%80%932&rft.pages=pp.-103-190&rft.date=1888&rft_id=info%3Adoi%2F10.1002%2Fjlac.18882450110&rft.au=Adolf+Baeyer&rft_id=https%3A%2F%2Fzenodo.org%2Frecord%2F1851261&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABenzene" class="Z3988"> </li> <li id="cite_note-36"><a href="#cite_ref-36">^</a> Thiele, Johannes (1899) "Zur Kenntnis der ungesättigten Verbindungen" (On our knowledge of unsaturated compounds), Justus Liebig’s Annalen der Chemie306: 87–142; see: <a rel="nofollow" class="external text" href="https://books.google.com/books?id=NYw8AAAAIAAJ&pg=RA1-PA125">"VIII. Die aromatischen Verbindungen. Das Benzol." (VIII. The aromatic compounds. Benzene.), pp. 125–129.</a> <a rel="nofollow" class="external text" href="https://web.archive.org/web/20200310154749/https://books.google.com/books?id=NYw8AAAAIAAJ&pg=RA1-PA125">Archived</a> 2020-03-10 at the <a href="/wiki/Wayback_Machine" title="Wayback Machine">Wayback Machine</a> See further: Thiele (1901) <a rel="nofollow" class="external text" href="https://babel.hathitrust.org/cgi/pt?id=hvd.hx3kjj;view=1up;seq=543">"Zur Kenntnis der ungesättigen Verbindungen,"</a> <a rel="nofollow" class="external text" href="https://web.archive.org/web/20211226183108/https://babel.hathitrust.org/cgi/pt?id=hvd.hx3kjj;view=1up;seq=543">Archived</a> 2021-12-26 at the <a href="/wiki/Wayback_Machine" title="Wayback Machine">Wayback Machine</a> Justus Liebig’s Annalen der Chemie, 319: 129–143. </li> <li id="cite_note-37"><a href="#cite_ref-37">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLoschmidt1861" class="citation book cs1 cs1-prop-foreign-lang-source">Loschmidt, J. (1861). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=ksw5AAAAcAAJ&pg=PA30">Chemische Studien</a> (in German). Vienna, Austria-Hungary: Carl Gerold's Sohn. pp. 30, 65. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20160507144736/https://books.google.com/books?id=ksw5AAAAcAAJ&pg=PA30">Archived</a> from the original on 2016-05-07. Retrieved 2015-06-27.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Chemische+Studien&rft.place=Vienna%2C+Austria-Hungary&rft.pages=30%2C+65&rft.pub=Carl+Gerold%27s+Sohn&rft.date=1861&rft.aulast=Loschmidt&rft.aufirst=J.&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3Dksw5AAAAcAAJ%26pg%3DPA30&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABenzene" class="Z3988"> </li> <li id="cite_note-38"><a href="#cite_ref-38">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFKekulé,_F._A.1866" class="citation journal cs1">Kekulé, F. A. (1866). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=pNryAAAAMAAJ&pg=PA129">"Untersuchungen über aromatische Verbindungen (Investigations of aromatic compounds)"</a>. Liebigs Annalen der Chemie und Pharmacie. 137 (2): 129–36. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fjlac.18661370202">10.1002/jlac.18661370202</a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20211226183108/https://books.google.com/books?id=pNryAAAAMAAJ&pg=PA129">Archived</a> from the original on 2021-12-26. Retrieved 2021-12-25.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Liebigs+Annalen+der+Chemie+und+Pharmacie&rft.atitle=Untersuchungen+%C3%BCber+aromatische+Verbindungen+%28Investigations+of+aromatic+compounds%29&rft.volume=137&rft.issue=2&rft.pages=129-36&rft.date=1866&rft_id=info%3Adoi%2F10.1002%2Fjlac.18661370202&rft.au=Kekul%C3%A9%2C+F.+A.&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DpNryAAAAMAAJ%26pg%3DPA129&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABenzene" class="Z3988"> </li> <li id="cite_note-39"><a href="#cite_ref-39">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFRocke2010" class="citation book cs1">Rocke, A. J. (2010). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=U5iHmP_dTLwC&pg=PA186">Image and Reality: Kekule, Kopp, and the Scientific Imagination</a>. University of Chicago Press. pp. 186–227. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0226723358" title="Special:BookSources/978-0226723358"><bdi>978-0226723358</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20200727092623/https://books.google.com/books?id=U5iHmP_dTLwC&pg=PA186">Archived</a> from the original on 2020-07-27. Retrieved 2020-05-15.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Image+and+Reality%3A+Kekule%2C+Kopp%2C+and+the+Scientific+Imagination&rft.pages=186-227&rft.pub=University+of+Chicago+Press&rft.date=2010&rft.isbn=978-0226723358&rft.aulast=Rocke&rft.aufirst=A.+J.&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DU5iHmP_dTLwC%26pg%3DPA186&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABenzene" class="Z3988"> </li> <li id="cite_note-41"><a href="#cite_ref-41">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFRead1995" class="citation book cs1">Read, John (1995). <a rel="nofollow" class="external text" href="https://archive.org/details/fromalchemytoche00read_063">From alchemy to chemistry</a>. New York: Dover Publications. pp. <a rel="nofollow" class="external text" href="https://archive.org/details/fromalchemytoche00read_063/page/n210">179</a>–180. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9780486286907" title="Special:BookSources/9780486286907"><bdi>9780486286907</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=From+alchemy+to+chemistry&rft.place=New+York&rft.pages=179-180&rft.pub=Dover+Publications&rft.date=1995&rft.isbn=9780486286907&rft.aulast=Read&rft.aufirst=John&rft_id=https%3A%2F%2Farchive.org%2Fdetails%2Ffromalchemytoche00read_063&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABenzene" class="Z3988"> </li> <li id="cite_note-42"><a href="#cite_ref-42">^</a> English translation <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFWilcoxGreenbaum1965" class="citation journal cs1">Wilcox, David H.; Greenbaum, Frederick R. (1965). "Kekule's benzene ring theory: A subject for lighthearted banter". Journal of Chemical Education. 42 (5): 266–67. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/1965JChEd..42..266W">1965JChEd..42..266W</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fed042p266">10.1021/ed042p266</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Chemical+Education&rft.atitle=Kekule%27s+benzene+ring+theory%3A+A+subject+for+lighthearted+banter&rft.volume=42&rft.issue=5&rft.pages=266-67&rft.date=1965&rft_id=info%3Adoi%2F10.1021%2Fed042p266&rft_id=info%3Abibcode%2F1965JChEd..42..266W&rft.aulast=Wilcox&rft.aufirst=David+H.&rft.au=Greenbaum%2C+Frederick+R.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABenzene" class="Z3988"> </li> <li id="cite_note-43"><a href="#cite_ref-43">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFKekulé,_F._A.1890" class="citation journal cs1">Kekulé, F. 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data-srcset="//upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/45px-Commons-logo.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/59px-Commons-logo.svg.png 2x" data-class="mw-file-element"> </div> <div class="side-box-text plainlist"><a href="/wiki/Wikimedia_Commons" title="Wikimedia Commons">Wikimedia Commons</a> has media related to: <a href="https://commons.wikimedia.org/wiki/Benzene" class="extiw" title="commons:Benzene">Benzene</a> (<a href="https://commons.wikimedia.org/wiki/Category:Benzene" class="extiw" title="commons:Category:Benzene">category</a>)</div></div> </div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1235681985"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1237033735"><div class="side-box side-box-right plainlinks sistersitebox"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"> <div class="side-box-flex"> <div class="side-box-image"><noscript><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/9/99/Wiktionary-logo-en-v2.svg/40px-Wiktionary-logo-en-v2.svg.png" decoding="async" width="40" height="40" class="mw-file-element" data-file-width="512" data-file-height="512"></noscript><span class="lazy-image-placeholder" style="width: 40px;height: 40px;" data-src="//upload.wikimedia.org/wikipedia/commons/thumb/9/99/Wiktionary-logo-en-v2.svg/40px-Wiktionary-logo-en-v2.svg.png" data-alt="" data-width="40" data-height="40" data-srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/99/Wiktionary-logo-en-v2.svg/60px-Wiktionary-logo-en-v2.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/99/Wiktionary-logo-en-v2.svg/80px-Wiktionary-logo-en-v2.svg.png 2x" data-class="mw-file-element"> </div> <div class="side-box-text plainlist">Look up <a href="https://en.wiktionary.org/wiki/benzene" class="extiw" title="wiktionary:benzene">benzene</a> in Wiktionary, the free dictionary.</div></div> </div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1235681985"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1237033735"><div class="side-box side-box-right plainlinks sistersitebox"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"> <div class="side-box-flex"> <div class="side-box-image"><noscript><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/f/fa/Wikiquote-logo.svg/34px-Wikiquote-logo.svg.png" decoding="async" width="34" height="40" class="mw-file-element" data-file-width="300" data-file-height="355"></noscript><span class="lazy-image-placeholder" style="width: 34px;height: 40px;" data-src="//upload.wikimedia.org/wikipedia/commons/thumb/f/fa/Wikiquote-logo.svg/34px-Wikiquote-logo.svg.png" data-alt="" data-width="34" data-height="40" data-srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/fa/Wikiquote-logo.svg/51px-Wikiquote-logo.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/fa/Wikiquote-logo.svg/68px-Wikiquote-logo.svg.png 2x" data-class="mw-file-element"> </div> <div class="side-box-text plainlist">Wikiquote has quotations related to <a href="https://en.wikiquote.org/wiki/Special:Search/Benzene" class="extiw" title="q:Special:Search/Benzene">Benzene</a>.</div></div> </div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1235681985"><div class="side-box metadata side-box-right"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"> <div class="side-box-flex"> <div class="side-box-image"><noscript><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/3/32/Scholia_logo.svg/40px-Scholia_logo.svg.png" decoding="async" width="40" height="39" class="mw-file-element" data-file-width="107" data-file-height="104"></noscript><span class="lazy-image-placeholder" style="width: 40px;height: 39px;" data-src="//upload.wikimedia.org/wikipedia/commons/thumb/3/32/Scholia_logo.svg/40px-Scholia_logo.svg.png" data-alt="" data-width="40" data-height="39" data-srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/32/Scholia_logo.svg/60px-Scholia_logo.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/32/Scholia_logo.svg/80px-Scholia_logo.svg.png 2x" data-class="mw-file-element"> </div> <div class="side-box-text plainlist"><a href="https://www.wikidata.org/wiki/Wikidata:Scholia" class="extiw" title="d:Wikidata:Scholia">Scholia</a> has a chemical profile for <a href="https://iw.toolforge.org/scholia/chemical/Q2270" class="extiw" title="toolforge:scholia/chemical/Q2270">Benzene</a>.</div></div> </div> <ul><li><a rel="nofollow" class="external text" href="http://www.periodicvideos.com/videos/mv_benzene.htm">Benzene</a> at <a href="/wiki/The_Periodic_Table_of_Videos" class="mw-redirect" title="The Periodic Table of Videos">The Periodic Table of Videos</a> (University of Nottingham)</li> <li><a rel="nofollow" class="external text" href="http://www.inchem.org/documents/icsc/icsc/eics0015.htm">International Chemical Safety Card 0015</a></li> <li><a rel="nofollow" class="external text" href="http://www.epa.gov/iris/subst/0276.htm">USEPA Summary of Benzene Toxicity</a></li> <li><a rel="nofollow" class="external text" href="https://www.cdc.gov/niosh/npg/npgd0049.html">NIOSH Pocket Guide to Chemical Hazards</a></li> <li><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/241">Benzene</a> from <a href="/wiki/PubChem" title="PubChem">PubChem</a></li> <li><a rel="nofollow" class="external text" href="https://web.archive.org/web/20070301122020/http://ntp.niehs.nih.gov/index.cfm?objectid=0707525C-0F07-05BF-A16CAC7B0ECC97B5">Dept. of Health and Human Services: TR-289: Toxicology and Carcinogenesis Studies of Benzene</a></li> <li><a rel="nofollow" class="external text" href="http://www.ch.ic.ac.uk/video/faraday_l.m4v">Video Podcast</a> of Sir John Cadogan giving a lecture on Benzene since Faraday, in 1991</li> <li><a rel="nofollow" class="external text" href="https://web.archive.org/web/20070224171424/http://ntp.niehs.nih.gov/ntp/roc/eleventh/profiles/s019benz.pdf">Substance profile</a></li> <li><a rel="nofollow" class="external text" href="http://toxnet.nlm.nih.gov/cgi-bin/sis/search/a?dbs+hsdb:@term+@DOCNO+35">NLM Hazardous Substances Databank – Benzene</a></li></ul> <div class="navbox-styles"><style data-mw-deduplicate="TemplateStyles:r1129693374">.mw-parser-output .hlist dl,.mw-parser-output .hlist ol,.mw-parser-output .hlist ul{margin:0;padding:0}.mw-parser-output .hlist dd,.mw-parser-output .hlist dt,.mw-parser-output .hlist li{margin:0;display:inline}.mw-parser-output .hlist.inline,.mw-parser-output .hlist.inline dl,.mw-parser-output .hlist.inline ol,.mw-parser-output .hlist.inline ul,.mw-parser-output .hlist dl dl,.mw-parser-output .hlist dl ol,.mw-parser-output .hlist dl ul,.mw-parser-output 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src="https://login.m.wikimedia.org/wiki/Special:CentralAutoLogin/start?type=1x1&mobile=1" alt="" width="1" height="1" style="border: none; position: absolute;"></noscript> <div class="printfooter" data-nosnippet="">Retrieved from "<a dir="ltr" href="https://en.wikipedia.org/w/index.php?title=Benzene&oldid=1258182655">https://en.wikipedia.org/w/index.php?title=Benzene&oldid=1258182655</a>"</div></div> </div> <div class="post-content" id="page-secondary-actions"> </div> </main> <footer class="mw-footer minerva-footer" role="contentinfo"> <a class="last-modified-bar" href="/w/index.php?title=Benzene&action=history"> <div class="post-content last-modified-bar__content"> Last edited on 18 November 2024, at 15:55 </div> </a> <div class="post-content footer-content"> <div id='mw-data-after-content'> <div class="read-more-container"></div> </div> <div id="p-lang"> <h4>Languages</h4> <section> <ul id="p-variants" class="minerva-languages"></ul> <ul class="minerva-languages"><li class="interlanguage-link interwiki-af mw-list-item"><a href="https://af.wikipedia.org/wiki/Benseen" title="Benseen – Afrikaans" lang="af" hreflang="af" data-title="Benseen" data-language-autonym="Afrikaans" data-language-local-name="Afrikaans" class="interlanguage-link-target">Afrikaans</a></li><li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D8%A8%D9%86%D8%B2%D9%8A%D9%86_(%D9%85%D8%B1%D9%83%D8%A8_%D9%83%D9%8A%D9%85%D9%8A%D8%A7%D8%A6%D9%8A)" title="بنزين (مركب كيميائي) – Arabic" lang="ar" hreflang="ar" data-title="بنزين (مركب كيميائي)" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target">العربية</a></li><li class="interlanguage-link interwiki-an mw-list-item"><a href="https://an.wikipedia.org/wiki/Benzeno" title="Benzeno – Aragonese" lang="an" hreflang="an" data-title="Benzeno" data-language-autonym="Aragonés" data-language-local-name="Aragonese" class="interlanguage-link-target">Aragonés</a></li><li class="interlanguage-link interwiki-ast mw-list-item"><a href="https://ast.wikipedia.org/wiki/Bencenu" title="Bencenu – Asturian" lang="ast" hreflang="ast" data-title="Bencenu" data-language-autonym="Asturianu" data-language-local-name="Asturian" class="interlanguage-link-target">Asturianu</a></li><li class="interlanguage-link interwiki-az mw-list-item"><a href="https://az.wikipedia.org/wiki/Benzol" title="Benzol – Azerbaijani" lang="az" hreflang="az" data-title="Benzol" data-language-autonym="Azərbaycanca" data-language-local-name="Azerbaijani" class="interlanguage-link-target">Azərbaycanca</a></li><li class="interlanguage-link interwiki-bn mw-list-item"><a href="https://bn.wikipedia.org/wiki/%E0%A6%AC%E0%A7%87%E0%A6%A8%E0%A6%9C%E0%A6%BF%E0%A6%A8" title="বেনজিন – Bangla" lang="bn" hreflang="bn" data-title="বেনজিন" data-language-autonym="বাংলা" data-language-local-name="Bangla" class="interlanguage-link-target">বাংলা</a></li><li class="interlanguage-link interwiki-zh-min-nan mw-list-item"><a href="https://zh-min-nan.wikipedia.org/wiki/Benzene" title="Benzene – Minnan" lang="nan" hreflang="nan" data-title="Benzene" data-language-autonym="閩南語 / Bân-lâm-gú" data-language-local-name="Minnan" class="interlanguage-link-target">閩南語 / Bân-lâm-gú</a></li><li class="interlanguage-link interwiki-ba mw-list-item"><a href="https://ba.wikipedia.org/wiki/%D0%91%D0%B5%D0%BD%D0%B7%D0%BE%D0%BB" title="Бензол – Bashkir" lang="ba" hreflang="ba" data-title="Бензол" data-language-autonym="Башҡортса" data-language-local-name="Bashkir" class="interlanguage-link-target">Башҡортса</a></li><li class="interlanguage-link interwiki-be mw-list-item"><a href="https://be.wikipedia.org/wiki/%D0%91%D0%B5%D0%BD%D0%B7%D0%BE%D0%BB" title="Бензол – Belarusian" lang="be" hreflang="be" data-title="Бензол" data-language-autonym="Беларуская" data-language-local-name="Belarusian" class="interlanguage-link-target">Беларуская</a></li><li class="interlanguage-link interwiki-be-x-old mw-list-item"><a href="https://be-tarask.wikipedia.org/wiki/%D0%91%D1%8D%D0%BD%D0%B7%D0%BE%D0%BB" title="Бэнзол – Belarusian (Taraškievica orthography)" lang="be-tarask" hreflang="be-tarask" data-title="Бэнзол" data-language-autonym="Беларуская (тарашкевіца)" data-language-local-name="Belarusian (Taraškievica orthography)" class="interlanguage-link-target">Беларуская (тарашкевіца)</a></li><li class="interlanguage-link interwiki-bcl mw-list-item"><a href="https://bcl.wikipedia.org/wiki/Benzene" title="Benzene – Central Bikol" lang="bcl" hreflang="bcl" data-title="Benzene" data-language-autonym="Bikol Central" data-language-local-name="Central Bikol" class="interlanguage-link-target">Bikol Central</a></li><li class="interlanguage-link interwiki-bg mw-list-item"><a href="https://bg.wikipedia.org/wiki/%D0%91%D0%B5%D0%BD%D0%B7%D0%B5%D0%BD" title="Бензен – Bulgarian" lang="bg" hreflang="bg" data-title="Бензен" data-language-autonym="Български" data-language-local-name="Bulgarian" class="interlanguage-link-target">Български</a></li><li class="interlanguage-link interwiki-bs mw-list-item"><a href="https://bs.wikipedia.org/wiki/Benzen" title="Benzen – Bosnian" lang="bs" hreflang="bs" data-title="Benzen" data-language-autonym="Bosanski" data-language-local-name="Bosnian" class="interlanguage-link-target">Bosanski</a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Benz%C3%A8" title="Benzè – Catalan" lang="ca" hreflang="ca" data-title="Benzè" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target">Català</a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Benzen" title="Benzen – Czech" lang="cs" hreflang="cs" data-title="Benzen" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target">Čeština</a></li><li class="interlanguage-link interwiki-cy mw-list-item"><a href="https://cy.wikipedia.org/wiki/Bensen" title="Bensen – Welsh" lang="cy" hreflang="cy" data-title="Bensen" data-language-autonym="Cymraeg" data-language-local-name="Welsh" class="interlanguage-link-target">Cymraeg</a></li><li class="interlanguage-link interwiki-da mw-list-item"><a href="https://da.wikipedia.org/wiki/Benzen" title="Benzen – Danish" lang="da" hreflang="da" data-title="Benzen" data-language-autonym="Dansk" data-language-local-name="Danish" class="interlanguage-link-target">Dansk</a></li><li class="interlanguage-link interwiki-de badge-Q17437796 badge-featuredarticle mw-list-item" title="featured article badge"><a href="https://de.wikipedia.org/wiki/Benzol" title="Benzol – German" lang="de" hreflang="de" data-title="Benzol" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target">Deutsch</a></li><li class="interlanguage-link interwiki-et mw-list-item"><a href="https://et.wikipedia.org/wiki/Benseen" title="Benseen – Estonian" lang="et" hreflang="et" data-title="Benseen" data-language-autonym="Eesti" data-language-local-name="Estonian" class="interlanguage-link-target">Eesti</a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/%CE%92%CE%B5%CE%BD%CE%B6%CF%8C%CE%BB%CE%B9%CE%BF" title="Βενζόλιο – Greek" lang="el" hreflang="el" data-title="Βενζόλιο" data-language-autonym="Ελληνικά" data-language-local-name="Greek" class="interlanguage-link-target">Ελληνικά</a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Benceno" title="Benceno – Spanish" lang="es" hreflang="es" data-title="Benceno" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target">Español</a></li><li class="interlanguage-link interwiki-eo mw-list-item"><a href="https://eo.wikipedia.org/wiki/Benzeno" title="Benzeno – Esperanto" lang="eo" hreflang="eo" data-title="Benzeno" data-language-autonym="Esperanto" data-language-local-name="Esperanto" class="interlanguage-link-target">Esperanto</a></li><li class="interlanguage-link interwiki-eu mw-list-item"><a href="https://eu.wikipedia.org/wiki/Bentzeno" title="Bentzeno – Basque" lang="eu" hreflang="eu" data-title="Bentzeno" data-language-autonym="Euskara" data-language-local-name="Basque" class="interlanguage-link-target">Euskara</a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%A8%D9%86%D8%B2%D9%86" title="بنزن – Persian" lang="fa" hreflang="fa" data-title="بنزن" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target">فارسی</a></li><li class="interlanguage-link interwiki-fr badge-Q17437796 badge-featuredarticle mw-list-item" title="featured article badge"><a href="https://fr.wikipedia.org/wiki/Benz%C3%A8ne" title="Benzène – French" lang="fr" hreflang="fr" data-title="Benzène" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target">Français</a></li><li class="interlanguage-link interwiki-ga mw-list-item"><a href="https://ga.wikipedia.org/wiki/Beins%C3%A9in" title="Beinséin – Irish" lang="ga" hreflang="ga" data-title="Beinséin" data-language-autonym="Gaeilge" data-language-local-name="Irish" class="interlanguage-link-target">Gaeilge</a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/Benceno" title="Benceno – Galician" lang="gl" hreflang="gl" data-title="Benceno" data-language-autonym="Galego" data-language-local-name="Galician" class="interlanguage-link-target">Galego</a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EB%B2%A4%EC%A0%A0" title="벤젠 – Korean" lang="ko" hreflang="ko" data-title="벤젠" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target">한국어</a></li><li class="interlanguage-link interwiki-ha mw-list-item"><a href="https://ha.wikipedia.org/wiki/Benzene" title="Benzene – Hausa" lang="ha" hreflang="ha" data-title="Benzene" data-language-autonym="Hausa" data-language-local-name="Hausa" class="interlanguage-link-target">Hausa</a></li><li class="interlanguage-link interwiki-hy mw-list-item"><a href="https://hy.wikipedia.org/wiki/%D4%B2%D5%A5%D5%B6%D5%A6%D5%B8%D5%AC" title="Բենզոլ – Armenian" lang="hy" hreflang="hy" data-title="Բենզոլ" data-language-autonym="Հայերեն" data-language-local-name="Armenian" class="interlanguage-link-target">Հայերեն</a></li><li class="interlanguage-link interwiki-hi mw-list-item"><a href="https://hi.wikipedia.org/wiki/%E0%A4%AC%E0%A5%87%E0%A4%82%E0%A4%9C%E0%A5%80%E0%A4%A8" title="बेंजीन – Hindi" lang="hi" hreflang="hi" data-title="बेंजीन" data-language-autonym="हिन्दी" data-language-local-name="Hindi" class="interlanguage-link-target">हिन्दी</a></li><li class="interlanguage-link interwiki-hr mw-list-item"><a href="https://hr.wikipedia.org/wiki/Benzen" title="Benzen – Croatian" lang="hr" hreflang="hr" data-title="Benzen" data-language-autonym="Hrvatski" data-language-local-name="Croatian" class="interlanguage-link-target">Hrvatski</a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Benzena" title="Benzena – Indonesian" lang="id" hreflang="id" data-title="Benzena" data-language-autonym="Bahasa Indonesia" data-language-local-name="Indonesian" class="interlanguage-link-target">Bahasa Indonesia</a></li><li class="interlanguage-link interwiki-is mw-list-item"><a href="https://is.wikipedia.org/wiki/Bensen" title="Bensen – Icelandic" lang="is" hreflang="is" data-title="Bensen" data-language-autonym="Íslenska" data-language-local-name="Icelandic" class="interlanguage-link-target">Íslenska</a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Benzene" title="Benzene – Italian" lang="it" hreflang="it" data-title="Benzene" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target">Italiano</a></li><li class="interlanguage-link interwiki-he mw-list-item"><a href="https://he.wikipedia.org/wiki/%D7%91%D7%A0%D7%96%D7%9F" title="בנזן – Hebrew" lang="he" hreflang="he" data-title="בנזן" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target">עברית</a></li><li class="interlanguage-link interwiki-kn mw-list-item"><a href="https://kn.wikipedia.org/wiki/%E0%B2%AC%E0%B3%86%E0%B2%82%E0%B2%9C%E0%B3%80%E0%B2%BC%E0%B2%A8%E0%B3%8D" title="ಬೆಂಜೀ಼ನ್ – Kannada" lang="kn" hreflang="kn" data-title="ಬೆಂಜೀ಼ನ್" data-language-autonym="ಕನ್ನಡ" data-language-local-name="Kannada" class="interlanguage-link-target">ಕನ್ನಡ</a></li><li class="interlanguage-link interwiki-ka mw-list-item"><a href="https://ka.wikipedia.org/wiki/%E1%83%91%E1%83%94%E1%83%9C%E1%83%96%E1%83%9D%E1%83%9A%E1%83%98" title="ბენზოლი – Georgian" lang="ka" hreflang="ka" data-title="ბენზოლი" data-language-autonym="ქართული" data-language-local-name="Georgian" class="interlanguage-link-target">ქართული</a></li><li class="interlanguage-link interwiki-kk mw-list-item"><a href="https://kk.wikipedia.org/wiki/%D0%91%D0%B5%D0%BD%D0%B7%D0%BE%D0%BB" title="Бензол – Kazakh" lang="kk" hreflang="kk" data-title="Бензол" data-language-autonym="Қазақша" data-language-local-name="Kazakh" class="interlanguage-link-target">Қазақша</a></li><li class="interlanguage-link interwiki-ky mw-list-item"><a href="https://ky.wikipedia.org/wiki/%D0%91%D0%B5%D0%BD%D0%B7%D0%BE%D0%BB" title="Бензол – Kyrgyz" lang="ky" hreflang="ky" data-title="Бензол" data-language-autonym="Кыргызча" data-language-local-name="Kyrgyz" class="interlanguage-link-target">Кыргызча</a></li><li class="interlanguage-link interwiki-la mw-list-item"><a href="https://la.wikipedia.org/wiki/Benzenum" title="Benzenum – Latin" lang="la" hreflang="la" data-title="Benzenum" data-language-autonym="Latina" data-language-local-name="Latin" class="interlanguage-link-target">Latina</a></li><li class="interlanguage-link interwiki-lv mw-list-item"><a href="https://lv.wikipedia.org/wiki/Benzols" title="Benzols – Latvian" lang="lv" hreflang="lv" data-title="Benzols" data-language-autonym="Latviešu" data-language-local-name="Latvian" class="interlanguage-link-target">Latviešu</a></li><li class="interlanguage-link interwiki-lb mw-list-item"><a href="https://lb.wikipedia.org/wiki/Benzol" title="Benzol – Luxembourgish" lang="lb" hreflang="lb" data-title="Benzol" data-language-autonym="Lëtzebuergesch" data-language-local-name="Luxembourgish" class="interlanguage-link-target">Lëtzebuergesch</a></li><li class="interlanguage-link interwiki-lt mw-list-item"><a href="https://lt.wikipedia.org/wiki/Benzenas" title="Benzenas – Lithuanian" lang="lt" hreflang="lt" data-title="Benzenas" data-language-autonym="Lietuvių" data-language-local-name="Lithuanian" class="interlanguage-link-target">Lietuvių</a></li><li class="interlanguage-link interwiki-li mw-list-item"><a href="https://li.wikipedia.org/wiki/Benzeen" title="Benzeen – Limburgish" lang="li" hreflang="li" data-title="Benzeen" data-language-autonym="Limburgs" data-language-local-name="Limburgish" class="interlanguage-link-target">Limburgs</a></li><li class="interlanguage-link interwiki-lmo mw-list-item"><a href="https://lmo.wikipedia.org/wiki/Benzen" title="Benzen – Lombard" lang="lmo" hreflang="lmo" data-title="Benzen" data-language-autonym="Lombard" data-language-local-name="Lombard" class="interlanguage-link-target">Lombard</a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Benzol" title="Benzol – Hungarian" lang="hu" hreflang="hu" data-title="Benzol" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target">Magyar</a></li><li class="interlanguage-link interwiki-mk mw-list-item"><a href="https://mk.wikipedia.org/wiki/%D0%91%D0%B5%D0%BD%D0%B7%D0%B5%D0%BD" title="Бензен – Macedonian" lang="mk" hreflang="mk" data-title="Бензен" data-language-autonym="Македонски" data-language-local-name="Macedonian" class="interlanguage-link-target">Македонски</a></li><li class="interlanguage-link interwiki-ml mw-list-item"><a href="https://ml.wikipedia.org/wiki/%E0%B4%AC%E0%B5%86%E0%B5%BB%E0%B4%B8%E0%B5%80%E0%B5%BB" title="ബെൻസീൻ – Malayalam" lang="ml" hreflang="ml" data-title="ബെൻസീൻ" data-language-autonym="മലയാളം" data-language-local-name="Malayalam" class="interlanguage-link-target">മലയാളം</a></li><li class="interlanguage-link interwiki-ms mw-list-item"><a href="https://ms.wikipedia.org/wiki/Benzena" title="Benzena – Malay" lang="ms" hreflang="ms" data-title="Benzena" data-language-autonym="Bahasa Melayu" data-language-local-name="Malay" class="interlanguage-link-target">Bahasa Melayu</a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Benzeen" title="Benzeen – Dutch" lang="nl" hreflang="nl" data-title="Benzeen" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target">Nederlands</a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%83%99%E3%83%B3%E3%82%BC%E3%83%B3" title="ベンゼン – Japanese" lang="ja" hreflang="ja" data-title="ベンゼン" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target">日本語</a></li><li class="interlanguage-link interwiki-no mw-list-item"><a href="https://no.wikipedia.org/wiki/Benzen" title="Benzen – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Benzen" data-language-autonym="Norsk bokmål" data-language-local-name="Norwegian Bokmål" class="interlanguage-link-target">Norsk bokmål</a></li><li class="interlanguage-link interwiki-nn mw-list-item"><a href="https://nn.wikipedia.org/wiki/Benzen" title="Benzen – Norwegian Nynorsk" lang="nn" hreflang="nn" data-title="Benzen" data-language-autonym="Norsk nynorsk" data-language-local-name="Norwegian Nynorsk" class="interlanguage-link-target">Norsk nynorsk</a></li><li class="interlanguage-link interwiki-oc mw-list-item"><a href="https://oc.wikipedia.org/wiki/Benz%C3%A8n" title="Benzèn – Occitan" lang="oc" hreflang="oc" data-title="Benzèn" data-language-autonym="Occitan" data-language-local-name="Occitan" class="interlanguage-link-target">Occitan</a></li><li class="interlanguage-link interwiki-uz mw-list-item"><a href="https://uz.wikipedia.org/wiki/Benzol" title="Benzol – Uzbek" lang="uz" hreflang="uz" data-title="Benzol" data-language-autonym="Oʻzbekcha / ўзбекча" data-language-local-name="Uzbek" class="interlanguage-link-target">Oʻzbekcha / ўзбекча</a></li><li class="interlanguage-link interwiki-pa mw-list-item"><a href="https://pa.wikipedia.org/wiki/%E0%A8%AC%E0%A9%88%E0%A8%A8%E0%A8%9C%E0%A8%BC%E0%A9%80%E0%A8%A8" title="ਬੈਨਜ਼ੀਨ – Punjabi" lang="pa" hreflang="pa" data-title="ਬੈਨਜ਼ੀਨ" data-language-autonym="ਪੰਜਾਬੀ" data-language-local-name="Punjabi" class="interlanguage-link-target">ਪੰਜਾਬੀ</a></li><li class="interlanguage-link interwiki-pnb mw-list-item"><a href="https://pnb.wikipedia.org/wiki/%D8%A8%DB%8C%D9%86%D8%B2%DB%8C%D9%86" title="بینزین – Western Punjabi" lang="pnb" hreflang="pnb" data-title="بینزین" data-language-autonym="پنجابی" data-language-local-name="Western Punjabi" class="interlanguage-link-target">پنجابی</a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Benzen" title="Benzen – Polish" lang="pl" hreflang="pl" data-title="Benzen" data-language-autonym="Polski" data-language-local-name="Polish" class="interlanguage-link-target">Polski</a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/Benzeno" title="Benzeno – Portuguese" lang="pt" hreflang="pt" data-title="Benzeno" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target">Português</a></li><li class="interlanguage-link interwiki-ro badge-Q17437796 badge-featuredarticle mw-list-item" title="featured article badge"><a href="https://ro.wikipedia.org/wiki/Benzen" title="Benzen – Romanian" lang="ro" hreflang="ro" data-title="Benzen" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target">Română</a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%91%D0%B5%D0%BD%D0%B7%D0%BE%D0%BB" title="Бензол – Russian" lang="ru" hreflang="ru" data-title="Бензол" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target">Русский</a></li><li class="interlanguage-link interwiki-sco mw-list-item"><a href="https://sco.wikipedia.org/wiki/Benzene" title="Benzene – Scots" lang="sco" hreflang="sco" data-title="Benzene" data-language-autonym="Scots" data-language-local-name="Scots" class="interlanguage-link-target">Scots</a></li><li class="interlanguage-link interwiki-sq mw-list-item"><a href="https://sq.wikipedia.org/wiki/Benzeni" title="Benzeni – Albanian" lang="sq" hreflang="sq" data-title="Benzeni" data-language-autonym="Shqip" data-language-local-name="Albanian" class="interlanguage-link-target">Shqip</a></li><li class="interlanguage-link interwiki-si mw-list-item"><a href="https://si.wikipedia.org/wiki/%E0%B6%B6%E0%B7%99%E0%B6%B1%E0%B7%8A%E0%B7%83%E0%B7%93%E0%B6%B1%E0%B7%8A" title="බෙන්සීන් – Sinhala" lang="si" hreflang="si" data-title="බෙන්සීන්" data-language-autonym="සිංහල" data-language-local-name="Sinhala" class="interlanguage-link-target">සිංහල</a></li><li class="interlanguage-link interwiki-simple mw-list-item"><a href="https://simple.wikipedia.org/wiki/Benzene" title="Benzene – Simple English" lang="en-simple" hreflang="en-simple" data-title="Benzene" data-language-autonym="Simple English" data-language-local-name="Simple English" class="interlanguage-link-target">Simple English</a></li><li class="interlanguage-link interwiki-sk mw-list-item"><a href="https://sk.wikipedia.org/wiki/Benz%C3%A9n" title="Benzén – Slovak" lang="sk" hreflang="sk" data-title="Benzén" data-language-autonym="Slovenčina" data-language-local-name="Slovak" class="interlanguage-link-target">Slovenčina</a></li><li class="interlanguage-link interwiki-sl badge-Q17437796 badge-featuredarticle mw-list-item" title="featured article badge"><a href="https://sl.wikipedia.org/wiki/Benzen" title="Benzen – Slovenian" lang="sl" hreflang="sl" data-title="Benzen" data-language-autonym="Slovenščina" data-language-local-name="Slovenian" class="interlanguage-link-target">Slovenščina</a></li><li class="interlanguage-link interwiki-ckb mw-list-item"><a href="https://ckb.wikipedia.org/wiki/%D8%A8%DB%95%D9%86%D8%B2%DB%8C%D9%86_(%D8%A6%DB%95%DA%B5%D9%82%DB%95)" title="بەنزین (ئەڵقە) – Central Kurdish" lang="ckb" hreflang="ckb" data-title="بەنزین (ئەڵقە)" data-language-autonym="کوردی" data-language-local-name="Central Kurdish" class="interlanguage-link-target">کوردی</a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/%D0%91%D0%B5%D0%BD%D0%B7%D0%B5%D0%BD" title="Бензен – Serbian" lang="sr" hreflang="sr" data-title="Бензен" data-language-autonym="Српски / srpski" data-language-local-name="Serbian" class="interlanguage-link-target">Српски / srpski</a></li><li class="interlanguage-link interwiki-sh mw-list-item"><a href="https://sh.wikipedia.org/wiki/Benzen" title="Benzen – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Benzen" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target">Srpskohrvatski / српскохрватски</a></li><li class="interlanguage-link interwiki-su mw-list-item"><a href="https://su.wikipedia.org/wiki/B%C3%A9nz%C3%A9na" title="Bénzéna – Sundanese" lang="su" hreflang="su" data-title="Bénzéna" data-language-autonym="Sunda" data-language-local-name="Sundanese" class="interlanguage-link-target">Sunda</a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Bentseeni" title="Bentseeni – Finnish" lang="fi" hreflang="fi" data-title="Bentseeni" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target">Suomi</a></li><li class="interlanguage-link interwiki-sv mw-list-item"><a href="https://sv.wikipedia.org/wiki/Bensen" title="Bensen – Swedish" lang="sv" hreflang="sv" data-title="Bensen" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target">Svenska</a></li><li class="interlanguage-link interwiki-ta mw-list-item"><a href="https://ta.wikipedia.org/wiki/%E0%AE%AA%E0%AF%86%E0%AE%A9%E0%AF%8D%E0%AE%9A%E0%AF%80%E0%AE%A9%E0%AF%8D" title="பென்சீன் – Tamil" lang="ta" hreflang="ta" data-title="பென்சீன்" data-language-autonym="தமிழ்" data-language-local-name="Tamil" class="interlanguage-link-target">தமிழ்</a></li><li class="interlanguage-link interwiki-tt mw-list-item"><a href="https://tt.wikipedia.org/wiki/Benzol" title="Benzol – Tatar" lang="tt" hreflang="tt" data-title="Benzol" data-language-autonym="Татарча / tatarça" data-language-local-name="Tatar" class="interlanguage-link-target">Татарча / tatarça</a></li><li class="interlanguage-link interwiki-te mw-list-item"><a href="https://te.wikipedia.org/wiki/%E0%B0%AC%E0%B1%86%E0%B0%82%E0%B0%9C%E0%B1%80%E0%B0%A8%E0%B1%8D" title="బెంజీన్ – Telugu" lang="te" hreflang="te" data-title="బెంజీన్" data-language-autonym="తెలుగు" data-language-local-name="Telugu" class="interlanguage-link-target">తెలుగు</a></li><li class="interlanguage-link interwiki-th mw-list-item"><a href="https://th.wikipedia.org/wiki/%E0%B9%80%E0%B8%9A%E0%B8%99%E0%B8%8B%E0%B8%B5%E0%B8%99" title="เบนซีน – Thai" lang="th" hreflang="th" data-title="เบนซีน" data-language-autonym="ไทย" data-language-local-name="Thai" class="interlanguage-link-target">ไทย</a></li><li class="interlanguage-link interwiki-tg mw-list-item"><a href="https://tg.wikipedia.org/wiki/%D0%91%D0%B5%D0%BD%D0%B7%D0%BE%D0%BB" title="Бензол – Tajik" lang="tg" hreflang="tg" data-title="Бензол" data-language-autonym="Тоҷикӣ" data-language-local-name="Tajik" class="interlanguage-link-target">Тоҷикӣ</a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Benzen" title="Benzen – Turkish" lang="tr" hreflang="tr" data-title="Benzen" data-language-autonym="Türkçe" data-language-local-name="Turkish" class="interlanguage-link-target">Türkçe</a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%91%D0%B5%D0%BD%D0%B7%D0%B5%D0%BD" title="Бензен – Ukrainian" lang="uk" hreflang="uk" data-title="Бензен" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target">Українська</a></li><li class="interlanguage-link interwiki-ur mw-list-item"><a href="https://ur.wikipedia.org/wiki/%D8%A8%D9%86%D8%B2%DB%8C%D9%86" title="بنزین – Urdu" lang="ur" hreflang="ur" data-title="بنزین" data-language-autonym="اردو" data-language-local-name="Urdu" class="interlanguage-link-target">اردو</a></li><li class="interlanguage-link interwiki-vi mw-list-item"><a href="https://vi.wikipedia.org/wiki/Benzen" title="Benzen – Vietnamese" lang="vi" hreflang="vi" data-title="Benzen" data-language-autonym="Tiếng Việt" data-language-local-name="Vietnamese" class="interlanguage-link-target">Tiếng Việt</a></li><li class="interlanguage-link interwiki-zh-classical mw-list-item"><a href="https://zh-classical.wikipedia.org/wiki/%E8%8B%AF" title="苯 – Literary Chinese" lang="lzh" hreflang="lzh" data-title="苯" data-language-autonym="文言" data-language-local-name="Literary Chinese" class="interlanguage-link-target">文言</a></li><li class="interlanguage-link interwiki-war mw-list-item"><a href="https://war.wikipedia.org/wiki/Benzeno" title="Benzeno – Waray" lang="war" hreflang="war" data-title="Benzeno" data-language-autonym="Winaray" data-language-local-name="Waray" class="interlanguage-link-target">Winaray</a></li><li class="interlanguage-link interwiki-wuu mw-list-item"><a href="https://wuu.wikipedia.org/wiki/%E8%8B%AF" title="苯 – Wu" lang="wuu" hreflang="wuu" data-title="苯" data-language-autonym="吴语" data-language-local-name="Wu" class="interlanguage-link-target">吴语</a></li><li class="interlanguage-link interwiki-zh-yue mw-list-item"><a href="https://zh-yue.wikipedia.org/wiki/%E8%8B%AF" title="苯 – Cantonese" lang="yue" hreflang="yue" data-title="苯" data-language-autonym="粵語" data-language-local-name="Cantonese" class="interlanguage-link-target">粵語</a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E8%8B%AF" title="苯 – Chinese" lang="zh" hreflang="zh" data-title="苯" data-language-autonym="中文" data-language-local-name="Chinese" class="interlanguage-link-target">中文</a></li></ul> </section> </div> <div class="minerva-footer-logo"><img src="/static/images/mobile/copyright/wikipedia-wordmark-en.svg" alt="Wikipedia" width="120" height="18" style="width: 7.5em; height: 1.125em;"/> </div> <ul id="footer-info" class="footer-info hlist hlist-separated"> <li id="footer-info-lastmod"> This page was last edited on 18 November 2024, at 15:55 (UTC).</li> <li id="footer-info-copyright">Content is available under <a class="external" rel="nofollow" href="https://creativecommons.org/licenses/by-sa/4.0/deed.en">CC BY-SA 4.0</a> unless otherwise noted.</li> </ul> <ul id="footer-places" class="footer-places hlist hlist-separated"> <li id="footer-places-privacy"><a href="https://foundation.wikimedia.org/wiki/Special:MyLanguage/Policy:Privacy_policy">Privacy policy</a></li> <li id="footer-places-about"><a href="/wiki/Wikipedia:About">About Wikipedia</a></li> <li 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