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<span>Production</span> </div> </a> <button aria-controls="toc-Production-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Production subsection</span> </button> <ul id="toc-Production-sublist" class="vector-toc-list"> <li id="toc-Synthesis_of_furans" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Synthesis_of_furans"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.1</span> <span>Synthesis of furans</span> </div> </a> <ul id="toc-Synthesis_of_furans-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Structure_and_bonding" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Structure_and_bonding"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Structure and bonding</span> </div> </a> <ul id="toc-Structure_and_bonding-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Reactivity" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Reactivity"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Reactivity</span> </div> </a> <ul id="toc-Reactivity-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Safety" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Safety"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Safety</span> </div> </a> <ul id="toc-Safety-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-See_also" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#See_also"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>See also</span> </div> </a> <ul id="toc-See_also-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-External_links" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#External_links"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</span> <span>External links</span> </div> </a> <ul id="toc-External_links-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav aria-label="Contents" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" > <input type="checkbox" id="vector-page-titlebar-toc-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-titlebar-toc" class="vector-dropdown-checkbox " aria-label="Toggle the table of contents" > <label id="vector-page-titlebar-toc-label" for="vector-page-titlebar-toc-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" ><span class="vector-icon mw-ui-icon-listBullet mw-ui-icon-wikimedia-listBullet"></span> <span class="vector-dropdown-label-text">Toggle the table of contents</span> </label> <div class="vector-dropdown-content"> <div id="vector-page-titlebar-toc-unpinned-container" class="vector-unpinned-container"> </div> </div> </div> </nav> <h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Furan</span></h1> <div id="p-lang-btn" class="vector-dropdown mw-portlet mw-portlet-lang" > <input type="checkbox" id="p-lang-btn-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-p-lang-btn" class="vector-dropdown-checkbox mw-interlanguage-selector" aria-label="Go to an article in another language. Available in 48 languages" > <label id="p-lang-btn-label" for="p-lang-btn-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--action-progressive mw-portlet-lang-heading-48" aria-hidden="true" ><span class="vector-icon mw-ui-icon-language-progressive mw-ui-icon-wikimedia-language-progressive"></span> <span class="vector-dropdown-label-text">48 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-af mw-list-item"><a href="https://af.wikipedia.org/wiki/Furaan" title="Furaan – Afrikaans" lang="af" hreflang="af" data-title="Furaan" data-language-autonym="Afrikaans" data-language-local-name="Afrikaans" class="interlanguage-link-target"><span>Afrikaans</span></a></li><li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D9%81%D9%88%D8%B1%D8%A7%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="فوران (مركب كيميائي) – Arabic" lang="ar" hreflang="ar" data-title="فوران (مركب كيميائي)" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-az mw-list-item"><a href="https://az.wikipedia.org/wiki/Furan" title="Furan – Azerbaijani" lang="az" hreflang="az" data-title="Furan" data-language-autonym="Azərbaycanca" data-language-local-name="Azerbaijani" class="interlanguage-link-target"><span>Azərbaycanca</span></a></li><li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%D9%81%D9%88%D8%B1%D8%A7%D9%86" title="فوران – South Azerbaijani" lang="azb" hreflang="azb" data-title="فوران" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-be mw-list-item"><a href="https://be.wikipedia.org/wiki/%D0%A4%D1%83%D1%80%D0%B0%D0%BD" title="Фуран – Belarusian" lang="be" hreflang="be" data-title="Фуран" data-language-autonym="Беларуская" data-language-local-name="Belarusian" class="interlanguage-link-target"><span>Беларуская</span></a></li><li class="interlanguage-link interwiki-bg mw-list-item"><a href="https://bg.wikipedia.org/wiki/%D0%A4%D1%83%D1%80%D0%B0%D0%BD" title="Фуран – Bulgarian" lang="bg" hreflang="bg" data-title="Фуран" data-language-autonym="Български" data-language-local-name="Bulgarian" class="interlanguage-link-target"><span>Български</span></a></li><li class="interlanguage-link interwiki-bs mw-list-item"><a href="https://bs.wikipedia.org/wiki/Furan" title="Furan – Bosnian" lang="bs" hreflang="bs" data-title="Furan" data-language-autonym="Bosanski" data-language-local-name="Bosnian" class="interlanguage-link-target"><span>Bosanski</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Furan" title="Furan – Catalan" lang="ca" hreflang="ca" data-title="Furan" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target"><span>Català</span></a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Furan" title="Furan – Czech" lang="cs" hreflang="cs" data-title="Furan" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Furan" title="Furan – German" lang="de" hreflang="de" data-title="Furan" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-et mw-list-item"><a href="https://et.wikipedia.org/wiki/Furaan" title="Furaan – Estonian" lang="et" hreflang="et" data-title="Furaan" data-language-autonym="Eesti" data-language-local-name="Estonian" class="interlanguage-link-target"><span>Eesti</span></a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/%CE%A6%CE%BF%CF%85%CF%81%CE%AC%CE%BD%CE%B9%CE%BF" title="Φουράνιο – Greek" lang="el" hreflang="el" data-title="Φουράνιο" data-language-autonym="Ελληνικά" data-language-local-name="Greek" class="interlanguage-link-target"><span>Ελληνικά</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Furano" title="Furano – Spanish" lang="es" hreflang="es" data-title="Furano" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-eo mw-list-item"><a href="https://eo.wikipedia.org/wiki/Furano" title="Furano – Esperanto" lang="eo" hreflang="eo" data-title="Furano" data-language-autonym="Esperanto" data-language-local-name="Esperanto" class="interlanguage-link-target"><span>Esperanto</span></a></li><li class="interlanguage-link interwiki-eu mw-list-item"><a href="https://eu.wikipedia.org/wiki/Furano" title="Furano – Basque" lang="eu" hreflang="eu" data-title="Furano" data-language-autonym="Euskara" data-language-local-name="Basque" class="interlanguage-link-target"><span>Euskara</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D9%81%D9%88%D8%B1%D8%A7%D9%86" title="فوران – Persian" lang="fa" hreflang="fa" data-title="فوران" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Furane" title="Furane – French" lang="fr" hreflang="fr" data-title="Furane" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-ga mw-list-item"><a href="https://ga.wikipedia.org/wiki/F%C3%BAr%C3%A1n" title="Fúrán – Irish" lang="ga" hreflang="ga" data-title="Fúrán" data-language-autonym="Gaeilge" data-language-local-name="Irish" class="interlanguage-link-target"><span>Gaeilge</span></a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/Furano" title="Furano – Galician" lang="gl" hreflang="gl" data-title="Furano" data-language-autonym="Galego" data-language-local-name="Galician" class="interlanguage-link-target"><span>Galego</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%ED%93%A8%EB%9E%80" title="퓨란 – Korean" lang="ko" hreflang="ko" data-title="퓨란" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-hy mw-list-item"><a href="https://hy.wikipedia.org/wiki/%D5%96%D5%B8%D6%82%D6%80%D5%A1%D5%B6" title="Ֆուրան – Armenian" lang="hy" hreflang="hy" data-title="Ֆուրան" data-language-autonym="Հայերեն" data-language-local-name="Armenian" class="interlanguage-link-target"><span>Հայերեն</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Furan" title="Furan – Indonesian" lang="id" hreflang="id" data-title="Furan" data-language-autonym="Bahasa Indonesia" data-language-local-name="Indonesian" class="interlanguage-link-target"><span>Bahasa Indonesia</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Furano" title="Furano – Italian" lang="it" hreflang="it" data-title="Furano" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-ka mw-list-item"><a href="https://ka.wikipedia.org/wiki/%E1%83%A4%E1%83%A3%E1%83%A0%E1%83%90%E1%83%9C%E1%83%98" title="ფურანი – Georgian" lang="ka" hreflang="ka" data-title="ფურანი" data-language-autonym="ქართული" data-language-local-name="Georgian" class="interlanguage-link-target"><span>ქართული</span></a></li><li class="interlanguage-link interwiki-ky mw-list-item"><a href="https://ky.wikipedia.org/wiki/%D0%A4%D1%83%D1%80%D0%B0%D0%BD" title="Фуран – Kyrgyz" lang="ky" hreflang="ky" data-title="Фуран" data-language-autonym="Кыргызча" data-language-local-name="Kyrgyz" class="interlanguage-link-target"><span>Кыргызча</span></a></li><li class="interlanguage-link interwiki-lv mw-list-item"><a href="https://lv.wikipedia.org/wiki/Fur%C4%81ns" title="Furāns – Latvian" lang="lv" hreflang="lv" data-title="Furāns" data-language-autonym="Latviešu" data-language-local-name="Latvian" class="interlanguage-link-target"><span>Latviešu</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Fur%C3%A1n" title="Furán – Hungarian" lang="hu" hreflang="hu" data-title="Furán" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-mk mw-list-item"><a href="https://mk.wikipedia.org/wiki/%D0%A4%D1%83%D1%80%D0%B0%D0%BD" title="Фуран – Macedonian" lang="mk" hreflang="mk" data-title="Фуран" data-language-autonym="Македонски" data-language-local-name="Macedonian" class="interlanguage-link-target"><span>Македонски</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Furaan" title="Furaan – Dutch" lang="nl" hreflang="nl" data-title="Furaan" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%83%95%E3%83%A9%E3%83%B3_(%E5%8C%96%E5%AD%A6)" title="フラン (化学) – Japanese" lang="ja" hreflang="ja" data-title="フラン (化学)" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-no mw-list-item"><a href="https://no.wikipedia.org/wiki/Furan" title="Furan – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Furan" data-language-autonym="Norsk bokmål" data-language-local-name="Norwegian Bokmål" class="interlanguage-link-target"><span>Norsk bokmål</span></a></li><li class="interlanguage-link interwiki-uz mw-list-item"><a href="https://uz.wikipedia.org/wiki/Furan" title="Furan – Uzbek" lang="uz" hreflang="uz" data-title="Furan" data-language-autonym="Oʻzbekcha / ўзбекча" data-language-local-name="Uzbek" class="interlanguage-link-target"><span>Oʻzbekcha / ўзбекча</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Furan" title="Furan – Polish" lang="pl" hreflang="pl" data-title="Furan" data-language-autonym="Polski" data-language-local-name="Polish" class="interlanguage-link-target"><span>Polski</span></a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/Furano_(qu%C3%ADmica)" title="Furano (química) – Portuguese" lang="pt" hreflang="pt" data-title="Furano (química)" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target"><span>Português</span></a></li><li class="interlanguage-link interwiki-ro mw-list-item"><a href="https://ro.wikipedia.org/wiki/Furan" title="Furan – Romanian" lang="ro" hreflang="ro" data-title="Furan" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%A4%D1%83%D1%80%D0%B0%D0%BD" title="Фуран – Russian" lang="ru" hreflang="ru" data-title="Фуран" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sk mw-list-item"><a href="https://sk.wikipedia.org/wiki/Fur%C3%A1n" title="Furán – Slovak" lang="sk" hreflang="sk" data-title="Furán" data-language-autonym="Slovenčina" data-language-local-name="Slovak" class="interlanguage-link-target"><span>Slovenčina</span></a></li><li class="interlanguage-link interwiki-sl mw-list-item"><a href="https://sl.wikipedia.org/wiki/Furan" title="Furan – Slovenian" lang="sl" hreflang="sl" data-title="Furan" data-language-autonym="Slovenščina" data-language-local-name="Slovenian" class="interlanguage-link-target"><span>Slovenščina</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Furan" title="Furan – Serbian" lang="sr" hreflang="sr" data-title="Furan" data-language-autonym="Српски / srpski" data-language-local-name="Serbian" class="interlanguage-link-target"><span>Српски / srpski</span></a></li><li class="interlanguage-link interwiki-sh mw-list-item"><a href="https://sh.wikipedia.org/wiki/Furan" title="Furan – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Furan" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Furaani" title="Furaani – Finnish" lang="fi" hreflang="fi" data-title="Furaani" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-sv mw-list-item"><a href="https://sv.wikipedia.org/wiki/Furan" title="Furan – Swedish" lang="sv" hreflang="sv" data-title="Furan" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-ta mw-list-item"><a href="https://ta.wikipedia.org/wiki/%E0%AE%AA%E0%AE%BF%E0%AE%AF%E0%AF%82%E0%AE%B0%E0%AE%BE%E0%AE%A9%E0%AF%8D" title="பியூரான் – Tamil" lang="ta" hreflang="ta" data-title="பியூரான்" data-language-autonym="தமிழ்" data-language-local-name="Tamil" class="interlanguage-link-target"><span>தமிழ்</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Furan" title="Furan – Turkish" lang="tr" hreflang="tr" data-title="Furan" data-language-autonym="Türkçe" data-language-local-name="Turkish" class="interlanguage-link-target"><span>Türkçe</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%A4%D1%83%D1%80%D0%B0%D0%BD" title="Фуран – Ukrainian" lang="uk" hreflang="uk" data-title="Фуран" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-vi mw-list-item"><a href="https://vi.wikipedia.org/wiki/Furan" title="Furan – Vietnamese" lang="vi" hreflang="vi" data-title="Furan" data-language-autonym="Tiếng Việt" data-language-local-name="Vietnamese" class="interlanguage-link-target"><span>Tiếng Việt</span></a></li><li class="interlanguage-link interwiki-wuu mw-list-item"><a href="https://wuu.wikipedia.org/wiki/%E5%91%8B%E5%96%83" title="呋喃 – Wu" lang="wuu" hreflang="wuu" data-title="呋喃" data-language-autonym="吴语" data-language-local-name="Wu" class="interlanguage-link-target"><span>吴语</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E5%91%8B%E5%96%83" title="呋喃 – Chinese" lang="zh" hreflang="zh" data-title="呋喃" data-language-autonym="中文" data-language-local-name="Chinese" class="interlanguage-link-target"><span>中文</span></a></li> </ul> <div class="after-portlet after-portlet-lang"><span class="wb-langlinks-edit wb-langlinks-link"><a href="https://www.wikidata.org/wiki/Special:EntityPage/Q243992#sitelinks-wikipedia" title="Edit interlanguage links" class="wbc-editpage">Edit links</a></span></div> </div> </div> </div> </header> <div class="vector-page-toolbar"> <div class="vector-page-toolbar-container"> <div id="left-navigation"> <nav aria-label="Namespaces"> <div id="p-associated-pages" class="vector-menu vector-menu-tabs mw-portlet mw-portlet-associated-pages" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="ca-nstab-main" 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class="vector-body" aria-labelledby="firstHeading" data-mw-ve-target-container> <div class="vector-body-before-content"> <div class="mw-indicators"> </div> <div id="siteSub" class="noprint">From Wikipedia, the free encyclopedia</div> </div> <div id="contentSub"><div id="mw-content-subtitle"></div></div> <div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Heterocyclic organic compound,</div> <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 industrial chemical compound. For other uses, see <a href="/wiki/Furan_(disambiguation)" class="mw-disambig" title="Furan (disambiguation)">Furan (disambiguation)</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> <table class="infobox ib-chembox"> <caption>Furan </caption> <tbody><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:Furan-2D-full.svg" class="mw-file-description" title="Full structural formula of furan"><img alt="Full structural formula of furan" src="//upload.wikimedia.org/wikipedia/commons/thumb/2/2b/Furan-2D-full.svg/110px-Furan-2D-full.svg.png" decoding="async" width="110" height="83" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/2b/Furan-2D-full.svg/165px-Furan-2D-full.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/2b/Furan-2D-full.svg/220px-Furan-2D-full.svg.png 2x" data-file-width="300" data-file-height="225" /></a><figcaption>Full structural formula of furan</figcaption></figure> </td> <td style="width:50%;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Furan-2D-numbered.svg" class="mw-file-description" title="Skeletal formula showing numbering convention"><img alt="Skeletal formula showing numbering convention" src="//upload.wikimedia.org/wikipedia/commons/thumb/0/0a/Furan-2D-numbered.svg/110px-Furan-2D-numbered.svg.png" decoding="async" width="110" height="110" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/0a/Furan-2D-numbered.svg/165px-Furan-2D-numbered.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/0a/Furan-2D-numbered.svg/220px-Furan-2D-numbered.svg.png 2x" data-file-width="300" data-file-height="300" /></a><figcaption>Skeletal formula showing numbering convention</figcaption></figure> </td></tr></tbody></table> </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:Furan-CRC-MW-3D-balls-A.png" class="mw-file-description" title="Ball-and-stick model"><img alt="Ball-and-stick model" src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c9/Furan-CRC-MW-3D-balls-A.png/110px-Furan-CRC-MW-3D-balls-A.png" decoding="async" width="110" height="91" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c9/Furan-CRC-MW-3D-balls-A.png/165px-Furan-CRC-MW-3D-balls-A.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c9/Furan-CRC-MW-3D-balls-A.png/220px-Furan-CRC-MW-3D-balls-A.png 2x" data-file-width="1100" data-file-height="908" /></a><figcaption>Ball-and-stick model</figcaption></figure> </td> <td style="width:50%;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Furan-CRC-MW-3D-vdW.png" class="mw-file-description" title="Space-filling model"><img alt="Space-filling model" src="//upload.wikimedia.org/wikipedia/commons/thumb/5/54/Furan-CRC-MW-3D-vdW.png/110px-Furan-CRC-MW-3D-vdW.png" decoding="async" width="110" height="98" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/54/Furan-CRC-MW-3D-vdW.png/165px-Furan-CRC-MW-3D-vdW.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/54/Furan-CRC-MW-3D-vdW.png/220px-Furan-CRC-MW-3D-vdW.png 2x" data-file-width="1100" data-file-height="983" /></a><figcaption>Space-filling model</figcaption></figure> </td></tr></tbody></table> </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;">Furan<sup id="cite_ref-iupac2013_1-0" class="reference"><a href="#cite_note-iupac2013-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup></div></div> </td></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Chemical_nomenclature#Systematic_name" title="Chemical nomenclature">Systematic 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;">1,4-Epoxybuta-1,3-diene<br />1-Oxacyclopenta-2,4-diene</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;">Oxole<br />Oxa[5]annulene<br />1,4-Epoxy-1,3-butadiene<br />5-Oxacyclopenta-1,3-diene<br />5-Oxacyclo-1,3-pentadiene<br />Furfuran<br />Divinylene oxide</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><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=110-00-9">110-00-9</a></span><sup> <span typeof="mw:File"><span><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" /></span></span><span style="display:none">Y</span></sup></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><span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=c1ccoc1">Interactive image</a></span></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Beilstein_database" title="Beilstein database">Beilstein Reference</a></div> </td> <td>103221 </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><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=35559">CHEBI:35559</a></span><sup> <span typeof="mw:File"><span><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" /></span></span><span style="display:none">Y</span></sup></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><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembl/explore/compound/ChEMBL278980">ChEMBL278980</a></span><sup> <span typeof="mw:File"><span><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" /></span></span><span style="display:none">Y</span></sup></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><span title="www.chemspider.com"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.7738.html">7738</a></span><sup> <span typeof="mw:File"><span><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" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ECHA_InfoCard" class="mw-redirect" title="ECHA InfoCard"><span title="echa.europa.eu">ECHA InfoCard</span></a> </td> <td><a rel="nofollow" class="external text" href="https://echa.europa.eu/substance-information/-/substanceinfo/100.003.390">100.003.390</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q243992#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></span> </td></tr> <tr> <td><a href="/wiki/European_Community_number" title="European Community number"><span title="European Community number (chemical identifier)">EC Number</span></a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li>203-727-3</li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Gmelin_database" title="Gmelin database">Gmelin Reference</a></div> </td> <td>25716 </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><span title="www.kegg.jp"><a rel="nofollow" class="external text" href="https://www.kegg.jp/entry/C14275">C14275</a></span><sup> <span typeof="mw:File"><span><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" /></span></span><span style="display:none">Y</span></sup></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><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/8029">8029</a></span></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>LT8524000</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><span title="precision.fda.gov"><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/UC0XV6A8N9">UC0XV6A8N9</a></span><sup> <span typeof="mw:File"><span><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" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/UN_number" title="UN number">UN number</a> </td> <td>2389 </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> <span style="font-weight:normal">(<abbr title="U.S. Environmental Protection Agency">EPA</abbr>)</span></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="comptox.epa.gov"><a rel="nofollow" class="external text" href="https://comptox.epa.gov/dashboard/chemical/details/DTXSID6020646">DTXSID6020646</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q243992#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></span></span></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/C4H4O/c1-2-4-5-3-1/h1-4H<sup> <span typeof="mw:File"><span><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" /></span></span><span style="display:none">Y</span></sup></div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: YLQBMQCUIZJEEH-UHFFFAOYSA-N<sup> <span typeof="mw:File"><span><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" /></span></span><span style="display:none">Y</span></sup></div></div></li><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=1/C4H4O/c1-2-4-5-3-1/h1-4H</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: YLQBMQCUIZJEEH-UHFFFAOYAC</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%;">c1ccoc1</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><span title="Carbon">C</span><sub>4</sub><span title="Hydrogen">H</span><sub>4</sub><span title="Oxygen">O</span> </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td><span class="nowrap"><span data-sort-value="7001680750000000000♠"></span>68.075</span> g·mol<sup>−1</sup>   </td></tr> <tr> <td>Appearance </td> <td>Colorless, volatile liquid </td></tr> <tr> <td><a href="/wiki/Density" title="Density">Density</a> </td> <td>0.936 g/mL </td></tr> <tr> <td><a href="/wiki/Melting_point" title="Melting point">Melting point</a> </td> <td>−85.6 °C (−122.1 °F; 187.6 K) </td></tr> <tr> <td><a href="/wiki/Boiling_point" title="Boiling point">Boiling point</a> </td> <td>31.3 °C (88.3 °F; 304.4 K) </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>-43.09·10<sup>−6</sup> cm<sup>3</sup>/mol </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/Globally_Harmonized_System_of_Classification_and_Labelling_of_Chemicals" title="Globally Harmonized System of Classification and Labelling of Chemicals"><b>GHS</b> 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><span typeof="mw:File"><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></span><span typeof="mw:File"><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></span><span typeof="mw:File"><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></span> </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><b>Danger</b> </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="H224: Extremely flammable liquid and vapour">H224</abbr>, <abbr class="abbr" title="H302: Harmful if swallowed">H302</abbr>, <abbr class="abbr" title="H315: Causes skin irritation">H315</abbr>, <abbr class="abbr" title="H332: Harmful if inhaled">H332</abbr>, <abbr class="abbr" title="H341: Suspected of causing genetic defects">H341</abbr>, <abbr class="abbr" title="H350: May cause cancer">H350</abbr>, <abbr class="abbr" title="H373: May cause damage to organs through prolonged or repeated exposure">H373</abbr>, <abbr class="abbr" title="H412: Harmful to aquatic life with long lasting effects">H412</abbr> </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="P202: Do not handle until all safety precautions have been read and understood.">P202</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="P233: Keep container tightly closed.">P233</abbr>, <abbr class="abbr" title="P240: Ground and bond container and receiving equipment.">P240</abbr>, <abbr class="abbr" title="P241: Use explosion-proof electrical/ventilating/light/.../equipment.">P241</abbr>, <abbr class="abbr" title="P242: Use only non-sparking tools.">P242</abbr>, <abbr class="abbr" title="P243: Take precautionary measures to prevent static discharges.">P243</abbr>, <abbr class="abbr" title="P260: Do not breathe dust/fume/gas/mist/vapours/spray.">P260</abbr>, <abbr class="abbr" title="P261: Avoid breathing dust/fume/gas/mist/vapours/spray.">P261</abbr>, <abbr class="abbr" title="P264: Wash ... thoroughly after handling.">P264</abbr>, <abbr class="abbr" title="P270: Do not eat, drink or smoke when using this product.">P270</abbr>, <abbr class="abbr" title="P271: Use only outdoors or in a well-ventilated area.">P271</abbr>, <abbr class="abbr" title="P273: Avoid release to the environment.">P273</abbr>, <abbr class="abbr" title="P280: Wear protective gloves/protective clothing/eye protection/face protection.">P280</abbr>, <abbr class="abbr" title="P281: Use personal protective equipment as required.">P281</abbr>, <abbr class="abbr" title="P301+P312: IF SWALLOWED: Call a POISON CENTER or doctor/physician if you feel unwell.">P301+P312</abbr>, <abbr class="abbr" title="P302+P352: IF ON SKIN: Wash with soap and water.">P302+P352</abbr>, <abbr class="abbr" title="P303+P361+P353: IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water [or shower].">P303+P361+P353</abbr>, <abbr class="abbr" title="P304+P312: IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.">P304+P312</abbr>, <abbr class="abbr" title="P304+P340: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing.">P304+P340</abbr>, <abbr class="abbr" title="P308+P313: IF exposed or concerned: Get medical advice/attention.">P308+P313</abbr>, <abbr class="abbr" title="P312: Call a POISON CENTER or doctor/physician if you feel unwell.">P312</abbr>, <abbr class="abbr" title="P314: Get Medical advice/attention if you feel unwell.">P314</abbr>, <abbr class="abbr" title="P321: Specific treatment (see ... on this label).">P321</abbr>, <abbr class="abbr" title="P330: Rinse mouth.">P330</abbr>, <abbr class="abbr" title="P332+P313: If skin irritation occurs: Get medical advice/attention.">P332+P313</abbr>, <abbr class="abbr" title="P362: Take off contaminated clothing.">P362</abbr>, <abbr class="abbr" title="P370+P378: In case of fire: Use ... to extinguish.">P370+P378</abbr>, <abbr class="abbr" title="P403+P235: Store in a well ventilated place. Keep cool.">P403+P235</abbr>, <abbr class="abbr" title="P405: Store locked up.">P405</abbr>, <abbr class="abbr" title="P501: Dispose of contents/container to ...">P501</abbr> </td></tr> <tr> <td><a href="/wiki/NFPA_704" title="NFPA 704"><b>NFPA 704</b></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"><span><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_a9232b9eb3d1a5a0" /></span><map name="ImageMap_a9232b9eb3d1a5a0"><area href="/wiki/NFPA_704#Blue" shape="poly" coords="23,23,47,47,23,70,0,47" alt="Health 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gas" title="Health 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gas" /><area href="/wiki/NFPA_704#Red" shape="poly" coords="47,0,70,23,47,47,23,23" alt="Flammability 4: Will rapidly or completely vaporize at normal atmospheric pressure and temperature, or is readily dispersed in air and will burn readily. Flash point below 23 °C (73 °F). E.g. propane" title="Flammability 4: Will rapidly or completely vaporize at normal atmospheric pressure and temperature, or is readily dispersed in air and will burn readily. Flash point below 23 °C (73 °F). E.g. propane" /><area href="/wiki/NFPA_704#Yellow" shape="poly" coords="70,23,94,47,70,70,47,47" alt="Instability 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calcium" title="Instability 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calcium" /><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"><span title="Health 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gas" class="notheme mw-no-invert">3</span></a></div><div class="nfpa-704-diamond-code nfpa-704-diamond-red"> <a href="/wiki/NFPA_704#Red" title="NFPA 704"><span title="Flammability 4: Will rapidly or completely vaporize at normal atmospheric pressure and temperature, or is readily dispersed in air and will burn readily. Flash point below 23 °C (73 °F). E.g. propane" class="notheme mw-no-invert">4</span></a></div><div class="nfpa-704-diamond-code nfpa-704-diamond-yellow"> <a href="/wiki/NFPA_704#Yellow" title="NFPA 704"><span title="Instability 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calcium" class="notheme mw-no-invert">1</span></a></div></div></div></div> </td></tr> <tr> <td><a href="/wiki/Flash_point" title="Flash point">Flash point</a> </td> <td>−36 °C (−33 °F; 237 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<br />temperature</a></div> </td> <td>390 °C (734 °F; 663 K) </td></tr> <tr> <td><a href="/wiki/Explosive_limit" class="mw-redirect" title="Explosive limit">Explosive limits</a> </td> <td>Lower: 2.3%<br />Upper: 14.3% at 20 °C </td></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;"><b>Lethal dose</b> or concentration (LD, LC): </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">LD<sub>50</sub> (<a href="/wiki/Lethal_dose#LD50" title="Lethal dose">median dose</a>)</div> </td> <td>> 2 g/kg (rat) </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="https://web.archive.org/web/20171124235603/http://www.pennakem.com/msds/110-00-9_Furan_PAK_msds.pdf">Pennakem</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 <a href="/wiki/Heterocycle" class="mw-redirect" title="Heterocycle">heterocycles</a></div> </td> <td><a href="/wiki/Pyrrole" title="Pyrrole">Pyrrole</a><br /><a href="/wiki/Thiophene" title="Thiophene">Thiophene</a> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Related compounds</div> </td> <td><a href="/wiki/Tetrahydrofuran" title="Tetrahydrofuran">Tetrahydrofuran</a> (THF)<br /><a href="/wiki/2,5-Dimethylfuran" title="2,5-Dimethylfuran">2,5-Dimethylfuran</a><br /><a href="/wiki/Benzofuran" title="Benzofuran">Benzofuran</a><br /><a href="/wiki/Dibenzofuran" title="Dibenzofuran">Dibenzofuran</a> </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_symmetry" title="Molecular symmetry">Point group</a></div> </td> <td>C<sub>2v</sub> </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;"><span typeof="mw:File"><span><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" /></span></span><span style="display:none">Y</span> <span class="reflink plainlinks nourlexpansion"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=477167468&page2=Furan">verify</a></span> (<a href="/wiki/Wikipedia:WikiProject_Chemicals/Chembox_validation" title="Wikipedia:WikiProject Chemicals/Chembox validation">what is</a> <sup><span typeof="mw:File"><span><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" /></span></span><span style="display:none">Y</span><span typeof="mw:File"><span><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" /></span></span><span style="display:none">N</span></sup> ?) </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><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Chemical compound</div> <p><b>Furan</b> is a <a href="/wiki/Heterocyclic_compound" title="Heterocyclic compound">heterocyclic</a> <a href="/wiki/Organic_compound" title="Organic compound">organic compound</a>, consisting of a five-membered <a href="/wiki/Aromatic" class="mw-redirect" title="Aromatic">aromatic</a> <a href="/wiki/Ring_(chemistry)" title="Ring (chemistry)">ring</a> with four <a href="/wiki/Carbon" title="Carbon">carbon</a> <a href="/wiki/Atom" title="Atom">atoms</a> and one <a href="/wiki/Oxygen" title="Oxygen">oxygen</a> atom. Chemical compounds containing such rings are also referred to as furans. </p><p>Furan is a colorless, <a href="/wiki/Flammable" class="mw-redirect" title="Flammable">flammable</a>, highly <a href="/wiki/Volatility_(chemistry)" title="Volatility (chemistry)">volatile</a> liquid with a <a href="/wiki/Boiling_point" title="Boiling point">boiling point</a> close to room temperature. It is soluble in common organic <a href="/wiki/Solvent" title="Solvent">solvents</a>, including <a href="/wiki/Ethanol" title="Ethanol">alcohol</a>, <a href="/wiki/Diethyl_ether" title="Diethyl ether">ether</a>, and <a href="/wiki/Acetone" title="Acetone">acetone</a>, and is slightly soluble in <a href="/wiki/Water" title="Water">water</a>.<sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> Its odor is "strong, ethereal; <a href="/wiki/Chloroform" title="Chloroform">chloroform</a>-like".<sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> It is <a href="/wiki/Toxic" class="mw-redirect" title="Toxic">toxic</a> and may be <a href="/wiki/Carcinogenic" class="mw-redirect" title="Carcinogenic">carcinogenic</a> in humans. Furan is used as a starting point for other <a href="/wiki/Speciality_chemicals" title="Speciality chemicals">speciality chemicals</a>.<sup id="cite_ref-ullmann_4-0" class="reference"><a href="#cite_note-ullmann-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="History">History</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Furan&action=edit&section=1" title="Edit section: History"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The name "furan" comes from the <a href="/wiki/Latin" title="Latin">Latin</a> <i>furfur</i>, which means <a href="/wiki/Bran" title="Bran">bran</a><sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> (<a href="/wiki/Furfural" title="Furfural">furfural</a> is produced from bran). The first furan derivative to be described was <a href="/wiki/2-furoic_acid" class="mw-redirect" title="2-furoic acid">2-furoic acid</a>, by <a href="/wiki/Carl_Wilhelm_Scheele" title="Carl Wilhelm Scheele">Carl Wilhelm Scheele</a> in 1780. Another important derivative, <a href="/wiki/Furfural" title="Furfural">furfural</a>, was reported by <a href="/wiki/Johann_Wolfgang_D%C3%B6bereiner" title="Johann Wolfgang Döbereiner">Johann Wolfgang Döbereiner</a> in 1831 and characterised nine years later by <a href="/wiki/John_Stenhouse" title="John Stenhouse">John Stenhouse</a>. Furan itself was first prepared by <a href="/wiki/Heinrich_Limpricht" title="Heinrich Limpricht">Heinrich Limpricht</a> in 1870, although he called it "tetraphenol" (as if it were a four-carbon analog to <a href="/wiki/Phenol" title="Phenol">phenol</a>, C<sub>6</sub>H<sub>5</sub>OH).<sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Production">Production</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Furan&action=edit&section=2" title="Edit section: Production"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Industrially, furan is manufactured by the <a href="/wiki/Palladium" title="Palladium">palladium</a>-catalyzed decarbonylation of <a href="/wiki/Furfural" title="Furfural">furfural</a>, or by the <a href="/wiki/Copper" title="Copper">copper</a>-catalyzed oxidation of <a href="/wiki/1,3-butadiene" class="mw-redirect" title="1,3-butadiene">1,3-butadiene</a>:<sup id="cite_ref-ullmann_4-1" class="reference"><a href="#cite_note-ullmann-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p> <dl><dd><span typeof="mw:File"><a href="/wiki/File:Manufacture_of_furan.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c6/Manufacture_of_furan.png/450px-Manufacture_of_furan.png" decoding="async" width="450" height="69" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c6/Manufacture_of_furan.png/675px-Manufacture_of_furan.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c6/Manufacture_of_furan.png/900px-Manufacture_of_furan.png 2x" data-file-width="2971" data-file-height="454" /></a></span></dd></dl> <p>In the laboratory, furan can be obtained from <a href="/wiki/Furfural" title="Furfural">furfural</a> by oxidation to 2-furoic acid, followed by <a href="/wiki/Decarboxylation" title="Decarboxylation">decarboxylation</a>.<sup id="cite_ref-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> It can also be prepared directly by <a href="/wiki/Thermal_decomposition" title="Thermal decomposition">thermal decomposition</a> of <a href="/wiki/Pentose" title="Pentose">pentose</a>-containing materials, and <a href="/wiki/Cellulose" title="Cellulose">cellulosic</a> solids, especially <a href="/wiki/Pine" title="Pine">pine</a> wood. </p> <div class="mw-heading mw-heading3"><h3 id="Synthesis_of_furans">Synthesis of furans</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Furan&action=edit&section=3" title="Edit section: Synthesis of furans"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The <a href="/wiki/Feist%E2%80%93Benary_synthesis" title="Feist–Benary synthesis">Feist–Benary synthesis</a> is a classic way to synthesize furans. The reaction involves alkylation of 1,3-<a href="/wiki/Diketone" class="mw-redirect" title="Diketone">diketones</a> with α-bromoketones followed by dehydration of an intermediate hydroxy<a href="/wiki/Dihydrofuran" title="Dihydrofuran">dihydrofuran</a>.<sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> The other traditional route involve the reaction of <a href="/wiki/Ketone" title="Ketone">1,4-diketones</a> with <a href="/wiki/Phosphorus_pentoxide" title="Phosphorus pentoxide">phosphorus pentoxide</a> (P<sub>2</sub>O<sub>5</sub>) in the <a href="/wiki/Paal%E2%80%93Knorr_synthesis" title="Paal–Knorr synthesis">Paal–Knorr synthesis</a>.<sup id="cite_ref-Gil_10-0" class="reference"><a href="#cite_note-Gil-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </p><p>Many routes exist for the synthesis of substituted furans.<sup id="cite_ref-11" class="reference"><a href="#cite_note-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-12" class="reference"><a href="#cite_note-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> </p><p><br /> </p> <ul class="gallery mw-gallery-traditional"> <li class="gallerycaption">Furan in nature and commerce</li> <li class="gallerybox" style="width: 215px"> <div class="thumb" style="width: 210px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Ranitidine_Structural_Formulae.png" class="mw-file-description" title="The drug Zantac, also known as ranitidine."><img alt="The drug Zantac, also known as ranitidine." src="//upload.wikimedia.org/wikipedia/commons/thumb/7/7b/Ranitidine_Structural_Formulae.png/180px-Ranitidine_Structural_Formulae.png" decoding="async" width="180" height="43" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/7b/Ranitidine_Structural_Formulae.png/270px-Ranitidine_Structural_Formulae.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/7b/Ranitidine_Structural_Formulae.png/360px-Ranitidine_Structural_Formulae.png 2x" data-file-width="2164" data-file-height="516" /></a></span></div> <div class="gallerytext">The drug Zantac, also known as <a href="/wiki/Ranitidine" title="Ranitidine">ranitidine</a>.</div> </li> <li class="gallerybox" style="width: 215px"> <div class="thumb" style="width: 210px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Rosefuran-2D-skeletal.png" class="mw-file-description" title="Rosefuran, an aroma compound found in rose oil.[10]"><img alt="Rosefuran, an aroma compound found in rose oil.[10]" src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b6/Rosefuran-2D-skeletal.png/180px-Rosefuran-2D-skeletal.png" decoding="async" width="180" height="104" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b6/Rosefuran-2D-skeletal.png/270px-Rosefuran-2D-skeletal.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b6/Rosefuran-2D-skeletal.png/360px-Rosefuran-2D-skeletal.png 2x" data-file-width="2000" data-file-height="1157" /></a></span></div> <div class="gallerytext"><a href="/wiki/Rosefuran" title="Rosefuran">Rosefuran</a>, an aroma compound found in rose oil.<sup id="cite_ref-Gil_10-1" class="reference"><a href="#cite_note-Gil-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup></div> </li> <li class="gallerybox" style="width: 215px"> <div class="thumb" style="width: 210px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Furfural.svg" class="mw-file-description" title="Furfural, derived from sugars, is the major source of furans"><img alt="Furfural, derived from sugars, is the major source of furans" src="//upload.wikimedia.org/wikipedia/commons/thumb/1/1d/Furfural.svg/171px-Furfural.svg.png" decoding="async" width="171" height="120" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/1d/Furfural.svg/257px-Furfural.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/1d/Furfural.svg/342px-Furfural.svg.png 2x" data-file-width="141" data-file-height="99" /></a></span></div> <div class="gallerytext"><a href="/wiki/Furfural" title="Furfural">Furfural</a>, derived from sugars, is the major source of furans</div> </li> <li class="gallerybox" style="width: 215px"> <div class="thumb" style="width: 210px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:MethanofuranFeb2011.png" class="mw-file-description" title="methanofuran is a cofactor in methanogenesis."><img alt="methanofuran is a cofactor in methanogenesis." src="//upload.wikimedia.org/wikipedia/commons/thumb/e/ea/MethanofuranFeb2011.png/180px-MethanofuranFeb2011.png" decoding="async" width="180" height="32" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/ea/MethanofuranFeb2011.png/270px-MethanofuranFeb2011.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/ea/MethanofuranFeb2011.png/360px-MethanofuranFeb2011.png 2x" data-file-width="2929" data-file-height="514" /></a></span></div> <div class="gallerytext"><a href="/wiki/Methanofuran" title="Methanofuran">methanofuran</a> is a cofactor in <a href="/wiki/Methanogenesis" title="Methanogenesis">methanogenesis</a>.</div> </li> </ul> <div class="mw-heading mw-heading2"><h2 id="Structure_and_bonding">Structure and bonding</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Furan&action=edit&section=4" title="Edit section: Structure and bonding"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Furan has <a href="/wiki/Aromatic" class="mw-redirect" title="Aromatic">aromatic</a> character because one of the <a href="/wiki/Lone_pair" title="Lone pair">lone pairs</a> of <a href="/wiki/Electron" title="Electron">electrons</a> on the oxygen atom is <a href="/wiki/Delocalized_electron" title="Delocalized electron">delocalized</a> into the ring, creating a 4<i>n</i> + 2 aromatic system (see <a href="/wiki/H%C3%BCckel%27s_rule" title="Hückel's rule">Hückel's rule</a>). The aromaticity is modest relative to that for <a href="/wiki/Benzene" title="Benzene">benzene</a> and related heterocycles <a href="/wiki/Thiophene" title="Thiophene">thiophene</a> and <a href="/wiki/Pyrrole" title="Pyrrole">pyrrole</a>. The <a href="/wiki/Resonance_energy" class="mw-redirect" title="Resonance energy">resonance energies</a> of benzene, <a href="/wiki/Pyrrole" title="Pyrrole">pyrrole</a>, <a href="/wiki/Thiophene" title="Thiophene">thiophene</a>, and furan are, respectively, 152, 88, 121, and 67 kJ/mol (36, 21, 29, and 16 kcal/mol). Thus, these heterocycles, especially furan, are far less aromatic than benzene, as is manifested in the lability of these rings.<sup id="cite_ref-13" class="reference"><a href="#cite_note-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> The molecule is flat but the C=C groups attached to oxygen retain significant <a href="/wiki/Double_bond" title="Double bond">double bond</a> character. The other lone pair of electrons of the oxygen atom extends in the plane of the flat ring system. </p><p>Examination of the resonance contributors shows the increased electron density of the ring, leading to increased rates of electrophilic substitution.<sup id="cite_ref-14" class="reference"><a href="#cite_note-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> </p> <dl><dd><dl><dd><span typeof="mw:File"><a href="/wiki/File:Furan_resonance_with_arrows.svg" class="mw-file-description" title="Resonance contributors of furan"><img alt="Resonance contributors of furan" src="//upload.wikimedia.org/wikipedia/commons/thumb/b/bf/Furan_resonance_with_arrows.svg/600px-Furan_resonance_with_arrows.svg.png" decoding="async" width="600" height="86" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/bf/Furan_resonance_with_arrows.svg/900px-Furan_resonance_with_arrows.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/bf/Furan_resonance_with_arrows.svg/1200px-Furan_resonance_with_arrows.svg.png 2x" data-file-width="1526" data-file-height="219" /></a></span></dd></dl></dd></dl> <div class="mw-heading mw-heading2"><h2 id="Reactivity">Reactivity</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Furan&action=edit&section=5" title="Edit section: Reactivity"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Because of its partial aromatic character, furan's behavior is intermediate between that of an enol ether and an aromatic ring. It is dissimilar vs <a href="/wiki/Diethyl_ether" title="Diethyl ether">ethers</a> such as <a href="/wiki/Tetrahydrofuran" title="Tetrahydrofuran">tetrahydrofuran</a>. </p><p>Like enol ethers, 2,5-disubstituted furans are susceptible to hydrolysis to reversibly give 1,4-diketones. </p><p>Furan serves as a <a href="/wiki/Diene" title="Diene">diene</a> in <a href="/wiki/Diels%E2%80%93Alder_reaction" title="Diels–Alder reaction">Diels–Alder reactions</a> with electron-deficient <a href="/wiki/Dienophile" class="mw-redirect" title="Dienophile">dienophiles</a> such as ethyl (<i>E</i>)-3-nitroacrylate.<sup id="cite_ref-15" class="reference"><a href="#cite_note-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> The reaction product is a mixture of isomers with preference for the <a href="/wiki/Endo_isomer" class="mw-redirect" title="Endo isomer"><i>endo</i> isomer</a>: </p> <dl><dd><dl><dd><span typeof="mw:File"><a href="/wiki/File:Furan_cycloaddition.svg" class="mw-file-description" title="Furan Diels–Alder reaction with ethyl (E)-3-nitroacrylate"><img alt="Furan Diels–Alder reaction with ethyl (E)-3-nitroacrylate" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/68/Furan_cycloaddition.svg/600px-Furan_cycloaddition.svg.png" decoding="async" width="600" height="102" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/68/Furan_cycloaddition.svg/900px-Furan_cycloaddition.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/68/Furan_cycloaddition.svg/1200px-Furan_cycloaddition.svg.png 2x" data-file-width="1800" data-file-height="305" /></a></span></dd></dl></dd></dl> <p>Diels-Alder reaction of furan with arynes provides corresponding derivatives of <a href="/w/index.php?title=Dihydronaphthalene&action=edit&redlink=1" class="new" title="Dihydronaphthalene (page does not exist)">dihydronaphthalenes</a>, which are useful intermediates in synthesis of other <a href="/wiki/Polycyclic_aromatic_hydrocarbon" title="Polycyclic aromatic hydrocarbon">polycyclic aromatic compounds</a>.<sup id="cite_ref-16" class="reference"><a href="#cite_note-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> </p> <dl><dd><dl><dd><span typeof="mw:File"><a href="/wiki/File:Reaction_of_furan_with_benzyne.svg" class="mw-file-description" title="Reaction of furan with a benzyne"><img alt="Reaction of furan with a benzyne" src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e8/Reaction_of_furan_with_benzyne.svg/400px-Reaction_of_furan_with_benzyne.svg.png" decoding="async" width="400" height="70" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e8/Reaction_of_furan_with_benzyne.svg/600px-Reaction_of_furan_with_benzyne.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e8/Reaction_of_furan_with_benzyne.svg/800px-Reaction_of_furan_with_benzyne.svg.png 2x" data-file-width="1165" data-file-height="205" /></a></span></dd></dl></dd></dl> <ul><li>It is considerably more reactive than <a href="/wiki/Benzene" title="Benzene">benzene</a> in <a href="/wiki/Electrophilic_substitution" title="Electrophilic substitution">electrophilic substitution</a> reactions, due to the electron-donating effects of the oxygen heteroatom. It reacts with bromine at 0 °C to give 2-bromofuran.</li></ul> <ul><li><a href="/wiki/Hydrogenation" title="Hydrogenation">Hydrogenation</a> of furans sequentially affords <a href="/wiki/Dihydrofuran" title="Dihydrofuran">dihydrofurans</a> and <a href="/wiki/Tetrahydrofuran" title="Tetrahydrofuran">tetrahydrofurans</a>.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (September 2023)">citation needed</span></a></i>]</sup></li> <li>In the <a href="/wiki/Achmatowicz_reaction" title="Achmatowicz reaction">Achmatowicz reaction</a>, furans are converted to <a href="/wiki/Dihydropyran" title="Dihydropyran">dihydropyran</a> compounds.</li> <li><a href="/wiki/Pyrrole" title="Pyrrole">Pyrrole</a> can be prepared industrially by treating furan with <a href="/wiki/Ammonia" title="Ammonia">ammonia</a> in the presence of solid acid <a href="/wiki/Catalyst" class="mw-redirect" title="Catalyst">catalysts</a>, such as <a href="/wiki/Silica" class="mw-redirect" title="Silica">SiO<sub>2</sub></a> and <a href="/wiki/Alumina" class="mw-redirect" title="Alumina">Al<sub>2</sub>O<sub>3</sub></a>.<sup id="cite_ref-Ullmann_17-0" class="reference"><a href="#cite_note-Ullmann-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup></li></ul> <div class="mw-heading mw-heading2"><h2 id="Safety">Safety</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Furan&action=edit&section=6" title="Edit section: Safety"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Furan is found in heat-treated commercial foods and is produced through <a href="/wiki/Thermal_degradation" class="mw-redirect" title="Thermal degradation">thermal degradation</a> of natural food constituents.<sup id="cite_ref-18" class="reference"><a href="#cite_note-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Moro_19-0" class="reference"><a href="#cite_note-Moro-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> It can be found in roasted <a href="/wiki/Coffee" title="Coffee">coffee</a>, instant coffee, and processed <a href="/wiki/Baby_food" title="Baby food">baby foods</a>.<sup id="cite_ref-Moro_19-1" class="reference"><a href="#cite_note-Moro-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-20" class="reference"><a href="#cite_note-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-21" class="reference"><a href="#cite_note-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> Research has indicated that coffee made in <a href="/wiki/Espresso" title="Espresso">espresso</a> <a href="/wiki/Espresso_machine" title="Espresso machine">makers</a> and coffee made from <a href="/wiki/Single-serve_coffee_container" title="Single-serve coffee container">capsules</a> contain more furan than that made in traditional <a href="/wiki/Coffeemaker#Electric_drip_coffeemakers" title="Coffeemaker">drip coffee makers</a>, although the levels are still within safe health limits.<sup id="cite_ref-22" class="reference"><a href="#cite_note-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> </p><p>Exposure to furan at doses about 2,000 times the projected level of human exposure from foods increases the risk of <a href="/wiki/Liver_cancer" title="Liver cancer">hepatocellular tumors</a> in rats and mice and <a href="/wiki/Cholangiocarcinoma" title="Cholangiocarcinoma">bile duct tumors</a> in rats.<sup id="cite_ref-Bakhiya_23-0" class="reference"><a href="#cite_note-Bakhiya-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> Furan is therefore listed as a possible human <a href="/wiki/Carcinogen" title="Carcinogen">carcinogen</a>.<sup id="cite_ref-Bakhiya_23-1" class="reference"><a href="#cite_note-Bakhiya-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Furan&action=edit&section=7" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/BS_4994" title="BS 4994">BS 4994</a> – <a href="/wiki/Furan_resin" title="Furan resin">Furan resin</a> as thermoset FRP for chemical process plant equipments</li> <li><a href="/wiki/Furanocoumarin" title="Furanocoumarin">Furanocoumarin</a></li> <li><a href="/wiki/Furanoflavonoid" title="Furanoflavonoid">Furanoflavonoid</a></li> <li><a href="/wiki/Furanose" title="Furanose">Furanose</a></li> <li><a href="/wiki/Furantetracarboxylic_acid" title="Furantetracarboxylic acid">Furantetracarboxylic acid</a></li> <li><a href="/wiki/Simple_aromatic_ring" title="Simple aromatic ring">Simple aromatic rings</a></li> <li><a href="/wiki/Furan_fatty_acids" title="Furan fatty acids">Furan fatty acids</a></li> <li><a href="/wiki/Tetrahydrofuran" title="Tetrahydrofuran">Tetrahydrofuran</a></li></ul> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Furan&action=edit&section=8" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <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 reflist-columns references-column-width" style="column-width: 30em;"> <ol class="references"> <li id="cite_note-iupac2013-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-iupac2013_1-0">^</a></b></span> <span class="reference-text"><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 class="citation book cs1"><i>Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book)</i>. Cambridge: <a href="/wiki/Royal_Society_of_Chemistry" title="Royal Society of Chemistry">The Royal Society of Chemistry</a>. 2014. p. 392. <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-FP001">10.1039/9781849733069-FP001</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=392&rft.pub=The+Royal+Society+of+Chemistry&rft.date=2014&rft_id=info%3Adoi%2F10.1039%2F9781849733069-FP001&rft.isbn=978-0-85404-182-4&rfr_id=info%3Asid%2Fen.wikipedia.org%3AFuran" class="Z3988"></span></span> </li> <li id="cite_note-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-2">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFJakubkeJeschkeit1994" class="citation book cs1">Jakubke, Hans Dieter; Jeschkeit, Hans (1994). <span class="id-lock-registration" title="Free registration required"><a rel="nofollow" class="external text" href="https://archive.org/details/conciseencyclope00eagl/page/1"><i>Concise Encyclopedia of Chemistry</i></a></span>. 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Chem</i>. <b>77</b> (24): 11119–11131. <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%2Fjo302135q">10.1021/jo302135q</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/23205621">23205621</a>. 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title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Archives+of+Toxicology&rft.atitle=Toxicity+and+carcinogenicity+of+furan+in+human+diet&rft.volume=84&rft.issue=7&rft.pages=563-578&rft.date=2010&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A19389984%23id-name%3DS2CID&rft_id=info%3Apmid%2F20237914&rft_id=info%3Adoi%2F10.1007%2Fs00204-010-0531-y&rft.aulast=Bakhiya&rft.aufirst=N.&rft.au=Appel%2C+K.+E.&rft_id=https%3A%2F%2Fmedia.ellinikahoaxes.gr%2Fuploads%2F2016%2F12%2F10.1007%40s00204-010-0531-y.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3AFuran" class="Z3988"></span></span> </li> </ol></div> <div class="mw-heading mw-heading2"><h2 id="External_links">External links</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Furan&action=edit&section=9" title="Edit section: External links"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style 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.mw-parser-output .navbox{display:none!important}}</style></div><div role="navigation" class="navbox" aria-labelledby="Simple_aromatic_rings" style="padding:3px"><table class="nowraplinks mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><style data-mw-deduplicate="TemplateStyles:r1239400231">.mw-parser-output .navbar{display:inline;font-size:88%;font-weight:normal}.mw-parser-output .navbar-collapse{float:left;text-align:left}.mw-parser-output .navbar-boxtext{word-spacing:0}.mw-parser-output .navbar ul{display:inline-block;white-space:nowrap;line-height:inherit}.mw-parser-output .navbar-brackets::before{margin-right:-0.125em;content:"[ "}.mw-parser-output .navbar-brackets::after{margin-left:-0.125em;content:" ]"}.mw-parser-output .navbar li{word-spacing:-0.125em}.mw-parser-output .navbar a>span,.mw-parser-output .navbar a>abbr{text-decoration:inherit}.mw-parser-output .navbar-mini abbr{font-variant:small-caps;border-bottom:none;text-decoration:none;cursor:inherit}.mw-parser-output .navbar-ct-full{font-size:114%;margin:0 7em}.mw-parser-output .navbar-ct-mini{font-size:114%;margin:0 4em}html.skin-theme-clientpref-night .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}@media(prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}}@media print{.mw-parser-output .navbar{display:none!important}}</style><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Simple_aromatic_rings" title="Template:Simple aromatic rings"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Simple_aromatic_rings" title="Template talk:Simple aromatic rings"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Simple_aromatic_rings" title="Special:EditPage/Template:Simple aromatic rings"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Simple_aromatic_rings" style="font-size:114%;margin:0 4em"><a href="/wiki/Simple_aromatic_ring" title="Simple aromatic ring">Simple aromatic rings</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%">1 ring</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%">Three-membered</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Borirene" class="mw-redirect" title="Borirene">Borirene</a></li> <li><a href="/wiki/Cyclopropenone" title="Cyclopropenone">Cyclopropenone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Five-membered</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a class="mw-selflink selflink">Furan</a></li> <li><a href="/wiki/Pyrrole" title="Pyrrole">Pyrrole</a></li> <li><a href="/wiki/Imidazole" title="Imidazole">Imidazole</a></li> <li><a href="/wiki/Thiophene" title="Thiophene">Thiophene</a></li> <li><a href="/wiki/Phosphole" title="Phosphole">Phosphole</a></li> <li><a href="/wiki/Pyrazole" title="Pyrazole">Pyrazole</a></li> <li><a href="/wiki/Oxazole" title="Oxazole">Oxazole</a></li> <li><a href="/wiki/Isoxazole" title="Isoxazole">Isoxazole</a></li> <li><a href="/wiki/Thiazole" title="Thiazole">Thiazole</a></li> <li><a href="/wiki/Isothiazole" title="Isothiazole">Isothiazole</a></li> <li><a href="/wiki/Triazole" title="Triazole">Triazole</a></li> <li><a href="/wiki/Tetrazole" title="Tetrazole">Tetrazole</a></li> <li><a href="/wiki/Pentazole" title="Pentazole">Pentazole</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Six-membered</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Benzene" title="Benzene">Benzene</a></li> <li><a href="/wiki/Pyridine" title="Pyridine">Pyridine</a></li> <li><a href="/wiki/Pyrazine" title="Pyrazine">Pyrazine</a></li> <li><a href="/wiki/Pyrimidine" title="Pyrimidine">Pyrimidine</a></li> <li><a href="/wiki/Pyridazine" title="Pyridazine">Pyridazine</a></li> <li><a href="/wiki/Triazine" title="Triazine">Triazine</a></li> <li><a href="/wiki/Tetrazine" title="Tetrazine">Tetrazine</a></li> <li><a href="/wiki/Pentazine" title="Pentazine">Pentazine</a></li> <li><a href="/wiki/Hexazine" title="Hexazine">Hexazine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Seven-membered</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Borepin" title="Borepin">Borepin</a></li> <li><a href="/wiki/Tropone" title="Tropone">Tropone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Nine-membered</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Azonine" title="Azonine">Azonine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">18-membered</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cyclooctadecanonaene" title="Cyclooctadecanonaene">Cyclooctadecanonaene</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">2 rings</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%">Five + Five</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Diazapentalene" title="Diazapentalene">Diazapentalene</a></li> <li><a href="/wiki/Thienothiophene" title="Thienothiophene">Thienothiophene</a></li> <li><a href="/wiki/Trithiapentalene" title="Trithiapentalene">Trithiapentalene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Five + Six</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Benzofuran" title="Benzofuran">Benzofuran</a></li> <li><a href="/wiki/Isobenzofuran" title="Isobenzofuran">Isobenzofuran</a></li> <li><a href="/wiki/Indole" title="Indole">Indole</a></li> <li><a href="/wiki/Isoindole" title="Isoindole">Isoindole</a></li> <li><a href="/wiki/Benzothiophene" title="Benzothiophene">Benzothiophene</a></li> <li><a href="/wiki/Benzo(c)thiophene" title="Benzo(c)thiophene">Benzo(c)thiophene</a></li> <li><a href="/wiki/Benzophosphole" title="Benzophosphole">Benzophosphole</a></li> <li><a href="/wiki/Benzimidazole" title="Benzimidazole">Benzimidazole</a></li> <li><a href="/wiki/Purine" title="Purine">Purine</a></li> <li><a href="/wiki/Indazole" title="Indazole">Indazole</a></li> <li><a href="/wiki/Benzoxazole" title="Benzoxazole">Benzoxazole</a></li> <li><a href="/wiki/Benzisoxazole" title="Benzisoxazole">Benzisoxazole</a></li> <li><a href="/wiki/Benzothiazole" title="Benzothiazole">Benzothiazole</a></li> <li><a href="/wiki/5-Aza-7-deazapurine" title="5-Aza-7-deazapurine">5-Aza-7-deazapurine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Six + Six</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Naphthalene" title="Naphthalene">Naphthalene</a></li> <li><a href="/wiki/Quinoline" title="Quinoline">Quinoline</a></li> <li><a href="/wiki/Isoquinoline" title="Isoquinoline">Isoquinoline</a></li> <li><a href="/wiki/Quinoxaline" title="Quinoxaline">Quinoxaline</a></li> <li><a href="/wiki/Quinazoline" title="Quinazoline">Quinazoline</a></li> <li><a href="/wiki/Cinnoline" title="Cinnoline">Cinnoline</a></li> <li><a href="/wiki/Phthalazine" title="Phthalazine">Phthalazine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Five + Seven</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Azulene" title="Azulene">Azulene</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"><style data-mw-deduplicate="TemplateStyles:r1038841319">.mw-parser-output .tooltip-dotted{border-bottom:1px dotted;cursor:help}</style><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1038841319"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1038841319"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1038841319"></div><div role="navigation" class="navbox authority-control" aria-label="Navbox" style="padding:3px"><table class="nowraplinks hlist navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Help:Authority_control" title="Help:Authority control">Authority control databases</a>: National <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q243992#identifiers" 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></span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"><ul><li><span class="uid"><a rel="nofollow" class="external text" href="https://d-nb.info/gnd/4539288-2">Germany</a></span></li><li><span class="uid"><span class="rt-commentedText tooltip tooltip-dotted" title="Furans"><a rel="nofollow" class="external text" href="https://id.loc.gov/authorities/sh85052502">United States</a></span></span></li><li><span class="uid"><span class="rt-commentedText tooltip tooltip-dotted" title="Furane"><a rel="nofollow" class="external text" href="https://catalogue.bnf.fr/ark:/12148/cb13185611x">France</a></span></span></li><li><span class="uid"><span class="rt-commentedText tooltip tooltip-dotted" title="Furane"><a rel="nofollow" class="external text" href="https://data.bnf.fr/ark:/12148/cb13185611x">BnF data</a></span></span></li><li><span class="uid"><a rel="nofollow" class="external text" href="https://id.ndl.go.jp/auth/ndlna/00563686">Japan</a></span></li><li><span class="uid"><span class="rt-commentedText tooltip tooltip-dotted" title="furan"><a rel="nofollow" class="external text" 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