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href="#Synthesis"> <div class="vector-toc-text"> 3 Synthesis </div> </a> <button aria-controls="toc-Synthesis-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> Toggle Synthesis subsection </button> <ul id="toc-Synthesis-sublist" class="vector-toc-list"> <li id="toc-Early_methods" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Early_methods"> <div class="vector-toc-text"> 3.1 Early methods </div> </a> <ul id="toc-Early_methods-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Via_alkali_cyclopentadienide" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Via_alkali_cyclopentadienide"> <div class="vector-toc-text"> 3.2 Via alkali cyclopentadienide </div> </a> <ul id="toc-Via_alkali_cyclopentadienide-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Properties" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Properties"> <div class="vector-toc-text"> 4 Properties </div> </a> <ul id="toc-Properties-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Reactions" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Reactions"> <div class="vector-toc-text"> 5 Reactions </div> </a> <button aria-controls="toc-Reactions-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> Toggle Reactions subsection </button> <ul id="toc-Reactions-sublist" class="vector-toc-list"> <li id="toc-With_electrophiles" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#With_electrophiles"> <div class="vector-toc-text"> 5.1 With electrophiles </div> </a> <ul id="toc-With_electrophiles-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Lithiation" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Lithiation"> <div class="vector-toc-text"> 5.2 Lithiation </div> </a> <ul id="toc-Lithiation-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Redox_chemistry" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Redox_chemistry"> <div class="vector-toc-text"> 5.3 Redox chemistry </div> </a> <ul id="toc-Redox_chemistry-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Stereochemistry_of_substituted_ferrocenes" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Stereochemistry_of_substituted_ferrocenes"> <div class="vector-toc-text"> 6 Stereochemistry of substituted ferrocenes </div> </a> <ul id="toc-Stereochemistry_of_substituted_ferrocenes-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Applications_of_ferrocene_and_its_derivatives" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Applications_of_ferrocene_and_its_derivatives"> <div class="vector-toc-text"> 7 Applications of ferrocene and its derivatives </div> </a> <button aria-controls="toc-Applications_of_ferrocene_and_its_derivatives-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> Toggle Applications of ferrocene and its derivatives subsection </button> <ul id="toc-Applications_of_ferrocene_and_its_derivatives-sublist" class="vector-toc-list"> <li id="toc-Ligand_scaffolds" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Ligand_scaffolds"> <div class="vector-toc-text"> 7.1 Ligand scaffolds </div> </a> <ul id="toc-Ligand_scaffolds-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Fuel_additives" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Fuel_additives"> <div class="vector-toc-text"> 7.2 Fuel additives </div> </a> <ul id="toc-Fuel_additives-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Pharmaceuticals" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Pharmaceuticals"> <div class="vector-toc-text"> 7.3 Pharmaceuticals </div> </a> <ul id="toc-Pharmaceuticals-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Solid_rocket_propellant" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Solid_rocket_propellant"> <div class="vector-toc-text"> 7.4 Solid rocket propellant </div> </a> <ul id="toc-Solid_rocket_propellant-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Derivatives_and_variations" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Derivatives_and_variations"> <div class="vector-toc-text"> 8 Derivatives and variations </div> </a> <button aria-controls="toc-Derivatives_and_variations-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> Toggle Derivatives and variations subsection </button> <ul id="toc-Derivatives_and_variations-sublist" class="vector-toc-list"> <li id="toc-Materials_chemistry" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Materials_chemistry"> <div class="vector-toc-text"> 8.1 Materials chemistry </div> </a> <ul id="toc-Materials_chemistry-sublist" class="vector-toc-list"> </ul> </li> </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"> 9 See also </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"> 10 References </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"> 11 External links </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 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Available in 31 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-31" aria-hidden="true" > 31 languages </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/Ferroseen" title="Ferroseen – Afrikaans" lang="af" hreflang="af" data-title="Ferroseen" data-language-autonym="Afrikaans" data-language-local-name="Afrikaans" class="interlanguage-link-target">Afrikaans</a></li><li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D9%81%D8%B1%D9%88%D8%B3%D9%8A%D9%86" title="فروسين – Arabic" lang="ar" hreflang="ar" data-title="فروسين" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target">العربية</a></li><li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%D9%81%D8%B1%D9%88%D8%B3%D9%86" title="فروسن – South Azerbaijani" lang="azb" hreflang="azb" data-title="فروسن" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target">تۆرکجه</a></li><li class="interlanguage-link interwiki-bn mw-list-item"><a href="https://bn.wikipedia.org/wiki/%E0%A6%AB%E0%A7%87%E0%A6%B0%E0%A7%8B%E0%A6%B8%E0%A6%BF%E0%A6%A8" title="ফেরোসিন – Bangla" lang="bn" hreflang="bn" data-title="ফেরোসিন" data-language-autonym="বাংলা" data-language-local-name="Bangla" class="interlanguage-link-target">বাংলা</a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Ferroc%C3%A8" title="Ferrocè – Catalan" lang="ca" hreflang="ca" data-title="Ferrocè" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target">Català</a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Ferrocen" title="Ferrocen – Czech" lang="cs" hreflang="cs" data-title="Ferrocen" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target">Čeština</a></li><li class="interlanguage-link interwiki-de badge-Q17437798 badge-goodarticle mw-list-item" title="good article badge"><a href="https://de.wikipedia.org/wiki/Ferrocen" title="Ferrocen – German" lang="de" hreflang="de" data-title="Ferrocen" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target">Deutsch</a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Ferroceno" title="Ferroceno – Spanish" lang="es" hreflang="es" data-title="Ferroceno" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target">Español</a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D9%81%D8%B1%D9%88%D8%B3%D9%86" title="فروسن – Persian" lang="fa" hreflang="fa" data-title="فروسن" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target">فارسی</a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Ferroc%C3%A8ne" title="Ferrocène – French" lang="fr" hreflang="fr" data-title="Ferrocène" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target">Français</a></li><li class="interlanguage-link interwiki-ga mw-list-item"><a href="https://ga.wikipedia.org/wiki/Fear%C3%B3ic%C3%A9in" title="Fearóicéin – Irish" lang="ga" hreflang="ga" data-title="Fearóicéin" data-language-autonym="Gaeilge" data-language-local-name="Irish" class="interlanguage-link-target">Gaeilge</a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%ED%8E%98%EB%A1%9C%EC%84%BC" title="페로센 – Korean" lang="ko" hreflang="ko" data-title="페로센" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target">한국어</a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Ferosena" title="Ferosena – Indonesian" lang="id" hreflang="id" data-title="Ferosena" data-language-autonym="Bahasa Indonesia" data-language-local-name="Indonesian" class="interlanguage-link-target">Bahasa Indonesia</a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Ferrocene" title="Ferrocene – Italian" lang="it" hreflang="it" data-title="Ferrocene" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target">Italiano</a></li><li class="interlanguage-link interwiki-ky mw-list-item"><a href="https://ky.wikipedia.org/wiki/%D0%A4%D0%B5%D1%80%D1%80%D0%BE%D1%86%D0%B5%D0%BD" title="Ферроцен – Kyrgyz" lang="ky" hreflang="ky" data-title="Ферроцен" data-language-autonym="Кыргызча" data-language-local-name="Kyrgyz" class="interlanguage-link-target">Кыргызча</a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Ferroc%C3%A9n" title="Ferrocén – Hungarian" lang="hu" hreflang="hu" data-title="Ferrocén" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target">Magyar</a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Ferroceen" title="Ferroceen – Dutch" lang="nl" hreflang="nl" data-title="Ferroceen" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target">Nederlands</a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%83%95%E3%82%A7%E3%83%AD%E3%82%BB%E3%83%B3" title="フェロセン – Japanese" lang="ja" hreflang="ja" data-title="フェロセン" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target">日本語</a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Ferrocen" title="Ferrocen – Polish" lang="pl" hreflang="pl" data-title="Ferrocen" data-language-autonym="Polski" data-language-local-name="Polish" class="interlanguage-link-target">Polski</a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/Ferroceno" title="Ferroceno – Portuguese" lang="pt" hreflang="pt" data-title="Ferroceno" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target">Português</a></li><li class="interlanguage-link interwiki-ro mw-list-item"><a href="https://ro.wikipedia.org/wiki/Ferocen" title="Ferocen – Romanian" lang="ro" hreflang="ro" data-title="Ferocen" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target">Română</a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%A4%D0%B5%D1%80%D1%80%D0%BE%D1%86%D0%B5%D0%BD" title="Ферроцен – Russian" lang="ru" hreflang="ru" data-title="Ферроцен" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target">Русский</a></li><li class="interlanguage-link interwiki-sl mw-list-item"><a href="https://sl.wikipedia.org/wiki/Ferocen" title="Ferocen – Slovenian" lang="sl" hreflang="sl" data-title="Ferocen" data-language-autonym="Slovenščina" data-language-local-name="Slovenian" class="interlanguage-link-target">Slovenščina</a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Ferocen" title="Ferocen – Serbian" lang="sr" hreflang="sr" data-title="Ferocen" data-language-autonym="Српски / srpski" data-language-local-name="Serbian" class="interlanguage-link-target">Српски / srpski</a></li><li class="interlanguage-link interwiki-sh mw-list-item"><a href="https://sh.wikipedia.org/wiki/Ferocen" title="Ferocen – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Ferocen" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target">Srpskohrvatski / српскохрватски</a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Ferroseeni" title="Ferroseeni – Finnish" lang="fi" hreflang="fi" data-title="Ferroseeni" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target">Suomi</a></li><li class="interlanguage-link interwiki-sv mw-list-item"><a href="https://sv.wikipedia.org/wiki/Ferrocen" title="Ferrocen – Swedish" lang="sv" hreflang="sv" data-title="Ferrocen" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target">Svenska</a></li><li class="interlanguage-link interwiki-th mw-list-item"><a href="https://th.wikipedia.org/wiki/%E0%B9%80%E0%B8%9F%E0%B8%AD%E0%B8%A3%E0%B9%8C%E0%B9%82%E0%B8%A3%E0%B8%8B%E0%B8%B5%E0%B8%99" title="เฟอร์โรซีน – Thai" lang="th" hreflang="th" data-title="เฟอร์โรซีน" data-language-autonym="ไทย" data-language-local-name="Thai" class="interlanguage-link-target">ไทย</a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Ferrosen" title="Ferrosen – Turkish" lang="tr" hreflang="tr" data-title="Ferrosen" data-language-autonym="Türkçe" data-language-local-name="Turkish" class="interlanguage-link-target">Türkçe</a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%A4%D0%B5%D1%80%D0%BE%D1%86%D0%B5%D0%BD" title="Фероцен – Ukrainian" lang="uk" hreflang="uk" data-title="Фероцен" data-language-autonym="Українська" 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dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Organometallic compound: Fe(II) sandwiched between two cyclopentadienyl rings</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>Ferrocene </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:Ferrocene.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e9/Ferrocene.svg/110px-Ferrocene.svg.png" decoding="async" width="110" height="186" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e9/Ferrocene.svg/165px-Ferrocene.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e9/Ferrocene.svg/220px-Ferrocene.svg.png 2x" data-file-width="103" data-file-height="174" /></a><figcaption></figcaption></figure> </td> <td style="width:50%;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Ferrocene-from-xtal-3D-balls.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/7a/Ferrocene-from-xtal-3D-balls.png/110px-Ferrocene-from-xtal-3D-balls.png" decoding="async" width="110" height="121" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/7a/Ferrocene-from-xtal-3D-balls.png/165px-Ferrocene-from-xtal-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/7a/Ferrocene-from-xtal-3D-balls.png/220px-Ferrocene-from-xtal-3D-balls.png 2x" data-file-width="1002" data-file-height="1100" /></a><figcaption></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:Ferrocene_3d_model_2.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/4/42/Ferrocene_3d_model_2.png/110px-Ferrocene_3d_model_2.png" decoding="async" width="110" height="98" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/42/Ferrocene_3d_model_2.png/165px-Ferrocene_3d_model_2.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/42/Ferrocene_3d_model_2.png/220px-Ferrocene_3d_model_2.png 2x" data-file-width="1088" data-file-height="968" /></a><figcaption></figcaption></figure> </td> <td style="width:50%;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Photo_of_Ferrocene_(powdered).JPG" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c9/Photo_of_Ferrocene_%28powdered%29.JPG/110px-Photo_of_Ferrocene_%28powdered%29.JPG" decoding="async" width="110" height="70" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c9/Photo_of_Ferrocene_%28powdered%29.JPG/165px-Photo_of_Ferrocene_%28powdered%29.JPG 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c9/Photo_of_Ferrocene_%28powdered%29.JPG/220px-Photo_of_Ferrocene_%28powdered%29.JPG 2x" data-file-width="906" data-file-height="573" /></a><figcaption></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;">Ferrocene<a href="#cite_note-1">[1]</a></div></div> </td></tr> <tr> <td colspan="2" style="text-align:left;">Other names <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;"><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>Dicyclopentadienyl iron</li><li>Bis(η5-cyclopentadienyl)iron</li><li>Iron(II) cyclopentadienide</li></ul></div></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><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=102-54-5">102-54-5</a> <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" />Y</li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChEBI" title="ChEBI">ChEBI</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=30672">CHEBI:30672</a> <img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" />N</li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChemSpider" title="ChemSpider">ChemSpider</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.7329.html">7329</a> <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" />Y</li></ul></div> </td></tr> <tr> <td><a href="/wiki/ECHA_InfoCard" class="mw-redirect" title="ECHA InfoCard">ECHA InfoCard</a> </td> <td><a rel="nofollow" class="external text" href="https://echa.europa.eu/substance-information/-/substanceinfo/100.002.764">100.002.764</a> <a href="https://www.wikidata.org/wiki/Q211972#P2566" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/PubChem" title="PubChem">PubChem</a> <abbr title="Compound ID">CID</abbr></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/11985121">11985121</a></li></ul></div> </td></tr> <tr> <td><a href="/wiki/Unique_Ingredient_Identifier" title="Unique Ingredient Identifier">UNII</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/U96PKG90JQ">U96PKG90JQ</a> <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" />Y</li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CompTox_Chemicals_Dashboard" title="CompTox Chemicals Dashboard">CompTox Dashboard</a> (<abbr title="U.S. Environmental Protection Agency">EPA</abbr>)</div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://comptox.epa.gov/dashboard/chemical/details/DTXSID9025326">DTXSID9025326</a> <a href="https://www.wikidata.org/wiki/Q211972#P3117" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></li></ul></div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal; background:transparent;"><div><a href="/wiki/International_Chemical_Identifier" title="International Chemical Identifier">InChI</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1S/2C5H5.Fe/c2*1-2-4-5-3-1;/h2*1-5H;/q2*-1;+2 <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" />Y</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: KTWOOEGAPBSYNW-UHFFFAOYSA-N <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" />Y</div></div></li><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=1/2C5H5.Fe/c2*1-2-4-5-3-1;/h2*1-5H;/q2*-1;+2</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: KTWOOEGAPBSYNW-UHFFFAOYAZ</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%;">[CH-]1C=CC=C1.[CH-]1C=CC=C1.[Fe+2]</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>C10H10Fe </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td>186.04 g/mol </td></tr> <tr> <td>Appearance </td> <td>light orange powder </td></tr> <tr> <td><a href="/wiki/Odor" title="Odor">Odor</a> </td> <td><a href="/wiki/Camphor" title="Camphor">camphor</a>-like </td></tr> <tr> <td><a href="/wiki/Density" title="Density">Density</a> </td> <td>1.107 g/cm3 (0 °C) 1.490 g/cm3 (20 °C)<a href="#cite_note-2">[2]</a> </td></tr> <tr> <td><a href="/wiki/Melting_point" title="Melting point">Melting point</a> </td> <td>172.5 °C (342.5 °F; 445.6 K)<a href="#cite_note-4">[4]</a> </td></tr> <tr> <td><a href="/wiki/Boiling_point" title="Boiling point">Boiling point</a> </td> <td>249 °C (480 °F; 522 K) </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Aqueous_solution" title="Aqueous solution">Solubility in water</a></div> </td> <td>Insoluble in water, soluble in most organic solvents </td></tr> <tr> <td><a href="/wiki/Partition_coefficient" title="Partition coefficient">log P</a> </td> <td>2.04050<a href="#cite_note-chemsrc-3">[3]</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>D5h (eclipsed) D5d (staggered) </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Molecular_geometry" title="Molecular geometry">Molecular shape</a></div> </td> <td>Sandwich structure with iron centre </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Hazards </th></tr> <tr> <td><a href="/wiki/NFPA_704" title="NFPA 704">NFPA 704</a> (fire diamond) </td> <td><style data-mw-deduplicate="TemplateStyles:r1170367383">.mw-parser-output .nfpa-704-diamond-ref{float:right;padding:1px;text-align:right}.mw-parser-output .nfpa-704-diamond-container{width:82px;font-family:sans-serif;margin:0 auto}.mw-parser-output .nfpa-704-diamond-container-ref{float:left;margin-left:1em}.mw-parser-output .nfpa-704-diamond-images{float:left;font-size:20px;text-align:center;position:relative;height:80px;width:80px;padding:1px}.mw-parser-output .nfpa-704-diamond-map{position:absolute;height:80px;width:80px}.mw-parser-output .nfpa-704-diamond .noresize{margin:0 auto}.mw-parser-output .nfpa-704-diamond-code{line-height:1em;text-align:center;position:absolute}.mw-parser-output .nfpa-704-diamond-code>a{color:black}.mw-parser-output .nfpa-704-diamond-blue{width:13px;top:31px;left:15px}.mw-parser-output .nfpa-704-diamond-red{width:12px;top:12px;left:35px}.mw-parser-output .nfpa-704-diamond-yellow{width:13px;top:31px;left:54px}.mw-parser-output .nfpa-704-diamond-white-image{position:relative;top:51px;left:0}.mw-parser-output .nfpa-704-diamond-white-text{vertical-align:middle;text-align:center;line-height:80%;position:absolute;top:52px}.mw-parser-output .nfpa-704-diamond-white-text a>span{position:absolute;color:black}.mw-parser-output .nfpa-704-diamond-white-wors{font-size:15px;width:23px;left:29px}.mw-parser-output .nfpa-704-diamond-white-wox{font-size:15px;font-stretch:condensed;width:21px;line-height:80%;top:-4px;left:29px}.mw-parser-output .nfpa-704-diamond-white-abcp{font-size:13.5px;font-stretch:condensed;width:28px;left:26px}.mw-parser-output .nfpa-704-diamond-white-ac{font-size:10px;width:30px;left:25px}.mw-parser-output .nfpa-704-diamond-white-strike{text-decoration:line-through}</style><div class="nfpa-704-diamond notheme"><div class="nfpa-74-diamond-refs"><a href="#cite_note-6">[6]</a></div><div class="nfpa-704-diamond-container nfpa-704-diamond-container-ref"><div class="nfpa-704-diamond-images nounderlines"> <div class="nfpa-704-diamond-map"><figure class="noresize" typeof="mw:File"><img alt="NFPA 704 four-colored diamond" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/80px-NFPA_704.svg.png" decoding="async" width="80" height="80" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/120px-NFPA_704.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/160px-NFPA_704.svg.png 2x" data-file-width="512" data-file-height="512" usemap="#ImageMap_953a9591cdee1806" /><map name="ImageMap_953a9591cdee1806"><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 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuel" title="Flammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuel" /><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">3</a></div><div class="nfpa-704-diamond-code nfpa-704-diamond-red"> <a href="/wiki/NFPA_704#Red" title="NFPA 704"><span title="Flammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuel" class="notheme mw-no-invert">2</a></div><div class="nfpa-704-diamond-code nfpa-704-diamond-yellow"> <a href="/wiki/NFPA_704#Yellow" title="NFPA 704">1</a></div></div></div></div> </td></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;"><a href="/wiki/National_Institute_for_Occupational_Safety_and_Health" title="National Institute for Occupational Safety and Health">NIOSH</a> (US health exposure limits): </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Permissible_exposure_limit" title="Permissible exposure limit">PEL</a> (Permissible)</div> </td> <td>TWA 15 mg/m3 (total) TWA 5 mg/m3 (resp)<a href="#cite_note-PGCH-5">[5]</a> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Recommended_exposure_limit" title="Recommended exposure limit">REL</a> (Recommended)</div> </td> <td>TWA 10 mg/m3 (total) TWA 5 mg/m3 (resp)<a href="#cite_note-PGCH-5">[5]</a> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/IDLH" class="mw-redirect" title="IDLH">IDLH</a> (Immediate danger)</div> </td> <td>N.D.<a href="#cite_note-PGCH-5">[5]</a> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Related compounds </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Related compounds</div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a href="/wiki/Metallocene" title="Metallocene">Metallocene</a></li><li><a href="/wiki/F-block_metallocene" title="F-block metallocene">f-block metallocene</a></li><li><a href="/wiki/Actinocene" title="Actinocene">Actinocene</a></li><li><a href="/wiki/Actinocene#Characterised_actinocenes" title="Actinocene">Thorocene</a></li><li><a href="/wiki/Actinocene#Characterised_actinocenes" title="Actinocene">Protactinocene</a></li><li><a href="/wiki/Uranocene" title="Uranocene">Uranocene</a></li><li><a href="/wiki/Neptunocene" title="Neptunocene">Neptunocene</a></li><li><a href="/wiki/Plutonocene" title="Plutonocene">Plutonocene</a></li><li><a href="/wiki/Zirconocene" title="Zirconocene">Zirconocene</a></li><li><a href="/wiki/Vanadocene" title="Vanadocene">Vanadocene</a></li><li><a href="/wiki/Chromocene" title="Chromocene">Chromocene</a></li><li><a href="/wiki/Bis(benzene)chromium" title="Bis(benzene)chromium">Bis(benzene)chromium</a></li><li><a href="/wiki/Manganocene" title="Manganocene">Manganocene</a></li><li><a href="/wiki/Nickelocene" title="Nickelocene">Nickelocene</a></li><li><a href="/wiki/Cobaltocene" title="Cobaltocene">Cobaltocene</a></li><li><a href="/wiki/Ruthenocene" title="Ruthenocene">Ruthenocene</a></li><li><a href="/wiki/Rhodocene" title="Rhodocene">Rhodocene</a></li><li><a href="/wiki/Osmocene" title="Osmocene">Osmocene</a></li><li><a href="/wiki/Hassium#Experimental_chemistry" title="Hassium">Hassocene</a></li><li><a href="/wiki/Stannocene" title="Stannocene">Stannocene</a></li><li><a href="/wiki/Plumbocene" title="Plumbocene">Plumbocene</a></li></ul></div> </td></tr> <tr> <td colspan="2" style="text-align:left; background:#f8eaba; border:1px solid #a2a9b1;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Except where otherwise noted, data are given for materials in their <a href="/wiki/Standard_state" title="Standard state">standard state</a> (at 25 °C [77 °F], 100 kPa).</div> <div style="margin-top: 0.3em;"><div style="text-align:center;"><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/12px-X_mark.svg.png" decoding="async" width="12" height="14" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/18px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/24px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" />N <a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=457631192&page2=Ferrocene">verify</a> (<a href="/wiki/Wikipedia:WikiProject_Chemicals/Chembox_validation" title="Wikipedia:WikiProject Chemicals/Chembox validation">what is</a> <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" />Y<img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" />N ?) </div></div> <div style="margin-top: 0.3em; text-align: center;"><a href="/wiki/Wikipedia:Chemical_infobox#References" title="Wikipedia:Chemical infobox">Infobox references</a></div> </td></tr> </tbody></table><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Chemical compound</div> Ferrocene is an <a href="/wiki/Organometallic_chemistry" title="Organometallic chemistry">organometallic compound</a> with the formula <style data-mw-deduplicate="TemplateStyles:r1123817410">.mw-parser-output .template-chem2-su{display:inline-block;font-size:80%;line-height:1;vertical-align:-0.35em}.mw-parser-output .template-chem2-su>span{display:block;text-align:left}.mw-parser-output sub.template-chem2-sub{font-size:80%;vertical-align:-0.35em}.mw-parser-output sup.template-chem2-sup{font-size:80%;vertical-align:0.65em}</style>Fe(C5H5)2. The molecule is a <a href="/wiki/Cyclopentadienyl_complex" title="Cyclopentadienyl complex">complex</a> consisting of two <a href="/wiki/Cyclopentadienyl_anion" title="Cyclopentadienyl anion">cyclopentadienyl</a> rings sandwiching a central <a href="/wiki/Iron" title="Iron">iron</a> atom. It is an orange solid with a camphor-like odor that <a href="/wiki/Sublimation_(phase_transition)" title="Sublimation (phase transition)">sublimes</a> above room temperature, and is soluble in most organic solvents. It is remarkable for its stability: it is unaffected by air, water, strong bases, and can be heated to 400 °C without decomposition. In oxidizing conditions it can reversibly react with strong acids to form the ferrocenium <a href="/wiki/Cation" class="mw-redirect" title="Cation">cation</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410">Fe(C5H5)+2.<a href="#cite_note-werner2012-7">[7]</a> Ferrocene and the ferrocenium cation are sometimes abbreviated as Fc and <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410">Fc+ respectively. The first reported synthesis of ferrocene was in 1951. Its unusual stability puzzled chemists, and required the development of new theory to explain its formation and bonding. The discovery of ferrocene and its many <a href="/wiki/Structural_analog" title="Structural analog">analogues</a>, known as <a href="/wiki/Metallocene" title="Metallocene">metallocenes</a>, sparked excitement and led to a rapid growth in the discipline of <a href="/wiki/Organometallic_chemistry" title="Organometallic chemistry">organometallic chemistry</a>. <a href="/wiki/Geoffrey_Wilkinson" title="Geoffrey Wilkinson">Geoffrey Wilkinson</a> and <a href="/wiki/Ernst_Otto_Fischer" title="Ernst Otto Fischer">Ernst Otto Fischer</a>, both of whom worked on elucidating the structure of ferrocene, later shared the 1973 <a href="/wiki/Nobel_Prize_in_Chemistry" title="Nobel Prize in Chemistry">Nobel Prize in Chemistry</a> for their work on organometallic sandwich compounds. Ferrocene itself has no large-scale applications, but has found more niche uses in catalysis, as a fuel additive, and as a tool in undergraduate education. <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="History">History</h2>[<a href="/w/index.php?title=Ferrocene&action=edit&section=1" title="Edit section: History">edit</a>]</div> <div class="mw-heading mw-heading3"><h3 id="Discovery">Discovery</h3>[<a href="/w/index.php?title=Ferrocene&action=edit&section=2" title="Edit section: Discovery">edit</a>]</div> Ferrocene was <a href="/wiki/Role_of_chance_in_scientific_discoveries" title="Role of chance in scientific discoveries">discovered by accident</a> twice. The first known synthesis may have been made in the late 1940s by unknown researchers at <a href="/wiki/Union_Carbide" title="Union Carbide">Union Carbide</a>, who tried to pass hot cyclopentadiene vapor through an iron pipe. The vapor reacted with the pipe wall, creating a "yellow sludge" that clogged the pipe. Years later, a sample of the sludge that had been saved was obtained and analyzed by Eugene O. Brimm, shortly after reading Kealy and Pauson's article, and was found to consist of ferrocene.<a href="#cite_note-werner2012-7">[7]</a><a href="#cite_note-Pauson2001-8">[8]</a> The second time was around 1950, when Samuel A. Miller, John A. Tebboth, and John F. Tremaine, researchers at <a href="/wiki/BOC_(company)" title="BOC (company)">British Oxygen</a>, were attempting to synthesize amines from hydrocarbons and <a href="/wiki/Nitrogen" title="Nitrogen">nitrogen</a> in a modification of the <a href="/wiki/Haber_process" title="Haber process">Haber process</a>. When they tried to react cyclopentadiene with nitrogen at 300 °C, at atmospheric pressure, they were disappointed to see the hydrocarbon react with some source of iron, yielding ferrocene. While they too observed its remarkable stability, they put the observation aside and did not publish it until after Pauson reported his findings.<a href="#cite_note-werner2012-7">[7]</a><a href="#cite_note-miller-9">[9]</a><a href="#cite_note-laszloRmon-10">[10]</a> Kealy and Pauson were later provided with a sample by Miller et al., who confirmed that the products were the same compound.<a href="#cite_note-Pauson2001-8">[8]</a> In 1951, <a href="/wiki/Peter_L._Pauson" class="mw-redirect" title="Peter L. Pauson">Peter L. Pauson</a> and <a href="/wiki/Thomas_J._Kealy" title="Thomas J. Kealy">Thomas J. Kealy</a> at <a href="/wiki/Duquesne_University" title="Duquesne University">Duquesne University</a> attempted to prepare <a href="/wiki/Fulvalene" title="Fulvalene">fulvalene</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410">(C5H4)2) by oxidative dimerization of <a href="/wiki/Cyclopentadiene" title="Cyclopentadiene">cyclopentadiene</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410">C5H6). To that end, they reacted the <a href="/wiki/Grignard_reagent" title="Grignard reagent">Grignard</a> compound <a href="/wiki/Cyclopentadienyl_magnesium_bromide" title="Cyclopentadienyl magnesium bromide">cyclopentadienyl magnesium bromide</a> in <a href="/wiki/Diethyl_ether" title="Diethyl ether">diethyl ether</a> with <a href="/wiki/Iron(III)_chloride" title="Iron(III) chloride">ferric chloride</a> as an oxidizer.<a href="#cite_note-werner2012-7">[7]</a> However, instead of the expected fulvalene, they obtained a light orange powder of "remarkable stability", with the formula <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410">C10H10Fe.<a href="#cite_note-Pauson2001-8">[8]</a><a href="#cite_note-pauson-11">[11]</a> <div class="mw-heading mw-heading3"><h3 id="Determining_the_structure">Determining the structure</h3>[<a href="/w/index.php?title=Ferrocene&action=edit&section=3" title="Edit section: Determining the structure">edit</a>]</div> <figure class="mw-default-size mw-halign-left" typeof="mw:File/Thumb"><a href="/wiki/File:Ferrocene_kealy.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/d/da/Ferrocene_kealy.svg/220px-Ferrocene_kealy.svg.png" decoding="async" width="220" height="87" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/da/Ferrocene_kealy.svg/330px-Ferrocene_kealy.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/da/Ferrocene_kealy.svg/440px-Ferrocene_kealy.svg.png 2x" data-file-width="312" data-file-height="124" /></a><figcaption>Pauson and Kealy's original (incorrect) notion of ferrocene's molecular structure.<a href="#cite_note-pauson-11">[11]</a></figcaption></figure> Pauson and Kealy conjectured that the compound had two cyclopentadienyl groups, each with a single covalent bond from the saturated carbon atom to the iron atom.<a href="#cite_note-werner2012-7">[7]</a> However, that structure was inconsistent with then-existing bonding models and did not explain the unexpected stability of the compound, and chemists struggled to find the correct structure.<a href="#cite_note-laszloRmon-10">[10]</a><a href="#cite_note-federman-12">[12]</a> The structure was deduced and reported independently by three groups in 1952.<a href="#cite_note-werner2008-13">[13]</a> <a href="/wiki/Robert_Burns_Woodward" title="Robert Burns Woodward">Robert Burns Woodward</a>, <a href="/wiki/Geoffrey_Wilkinson" title="Geoffrey Wilkinson">Geoffrey Wilkinson</a>, et al. deduced observe that the compound was diamagnetic and nonpolar.<a href="#cite_note-wilk52-14">[14]</a> A few months later they described its reactions as being typical of aromatic compounds such as <a href="/wiki/Benzene" title="Benzene">benzene</a>.<a href="#cite_note-15">[15]</a> The name ferrocene was coined by Mark Whiting, a postdoc with Woodward.<a href="#cite_note-16">[16]</a>. <a href="/wiki/Ernst_Otto_Fischer" title="Ernst Otto Fischer">Ernst Otto Fischer</a> and Wolfgang Pfab also noted ferrocene's diamagneticity and high symmetry. They also synthesize <a href="/wiki/Nickelocene" title="Nickelocene">nickelocene</a> and <a href="/wiki/Cobaltocene" title="Cobaltocene">cobaltocene</a> and confirmed they had the same structure.<a href="#cite_note-fischer-17">[17]</a> Fischer described the structure as Doppelkegelstruktur ("double-cone structure"), although the term "sandwich" came to be preferred by British and American chemists.<a href="#cite_note-okuda-18">[18]</a> Philip Frank Eiland and Raymond Pepinsky confirmed the structure through <a href="/wiki/X-ray_crystallography" title="X-ray crystallography">X-ray crystallography</a> and later by <a href="/wiki/Nuclear_magnetic_resonance" title="Nuclear magnetic resonance">NMR</a> spectroscopy.<a href="#cite_note-laszloRmon-10">[10]</a><a href="#cite_note-eiland52-19">[19]</a><a href="#cite_note-dunitz53-20">[20]</a><a href="#cite_note-dunitz56-21">[21]</a> The "sandwich" structure of ferrocene was shockingly novel and led to intensive theoretical studies. Application of <a href="/wiki/Molecular_orbital_theory" title="Molecular orbital theory">molecular orbital theory</a> with the assumption of a Fe2+ centre between two <a href="/wiki/Cyclopentadienide" class="mw-redirect" title="Cyclopentadienide">cyclopentadienide</a> anions <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410">C5H−5 resulted in the successful <a href="/wiki/Dewar%E2%80%93Chatt%E2%80%93Duncanson_model" title="Dewar–Chatt–Duncanson model">Dewar–Chatt–Duncanson model</a>, allowing correct prediction of the geometry of the molecule as well as explaining its remarkable stability.<a href="#cite_note-mingos-22">[22]</a><a href="#cite_note-mehr-23">[23]</a> <div class="mw-heading mw-heading3"><h3 id="Impact">Impact</h3>[<a href="/w/index.php?title=Ferrocene&action=edit&section=4" title="Edit section: Impact">edit</a>]</div> The discovery of ferrocene was considered so significant that Wilkinson and Fischer shared the 1973 <a href="/wiki/Nobel_Prize_in_Chemistry" title="Nobel Prize in Chemistry">Nobel Prize in Chemistry</a> "for their pioneering work, performed independently, on the chemistry of the organometallic, called <a href="/wiki/Sandwich_compound" title="Sandwich compound">sandwich compounds</a>".<a href="#cite_note-24">[24]</a> <div class="mw-heading mw-heading2"><h2 id="Structure_and_bonding">Structure and bonding</h2>[<a href="/w/index.php?title=Ferrocene&action=edit&section=5" title="Edit section: Structure and bonding">edit</a>]</div> <a href="/wiki/M%C3%B6ssbauer_spectroscopy" title="Mössbauer spectroscopy">Mössbauer spectroscopy</a> indicates that the iron center in ferrocene should be assigned the +2 oxidation state. Each cyclopentadienyl (Cp) ring should then be allocated a single negative charge. Thus ferrocene could be described as iron(II) bis(<a href="/wiki/Cyclopentadienide" class="mw-redirect" title="Cyclopentadienide">cyclopentadienide</a>), <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410">Fe2+[C5H−5]2. Each ring has six π-electrons, which makes them <a href="/wiki/Aromaticity" title="Aromaticity">aromatic</a> according to <a href="/wiki/H%C3%BCckel%27s_rule" title="Hückel's rule">Hückel's rule</a>. These π-electrons are then shared with the metal via covalent bonding. Since Fe2+ has six d-electrons, the complex attains an <a href="/wiki/18-electron_rule" title="18-electron rule">18-electron</a> configuration, which accounts for its stability. In modern notation, this sandwich structural model of the ferrocene molecule is denoted as <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410">Fe(η5-C5H5)2, where η denotes <a href="/wiki/Hapticity" title="Hapticity">hapticity</a>, the number of atoms through which each ring binds. The carbon–carbon bond distances around each five-membered ring are all 1.40 Å, and all Fe–C bond distances are 2.04 Å. From room temperature down to 164 K, <a href="/wiki/X-ray_crystallography" title="X-ray crystallography">X-ray crystallography</a> yields the monoclinic space group; the cyclopentadienide rings are a staggered conformation, resulting in a centrosymmetric molecule, with <a href="/wiki/Symmetry_group" title="Symmetry group">symmetry group</a> D5d.<a href="#cite_note-eiland52-19">[19]</a> However, below 110 K, ferrocene crystallizes in an orthorhombic crystal lattice in which the Cp rings are ordered and eclipsed, so that the molecule has symmetry group D5h.<a href="#cite_note-seiler-25">[25]</a> In the gas phase, <a href="/wiki/Electron_diffraction" title="Electron diffraction">electron diffraction</a><a href="#cite_note-haal68-26">[26]</a> and computational studies<a href="#cite_note-coriani-27">[27]</a> show that the Cp rings are eclipsed. While ferrocene has no permanent dipole moment at room temperature, between 172.8 and 163.5 K the molecule exhibits an "incommensurate modulation", breaking the D5 symmetry and acquiring an electric dipole.<a href="#cite_note-28">[28]</a> The Cp rings rotate with a low barrier about the Cp(centroid)–Fe–Cp(centroid) axis, as observed by measurements on substituted derivatives of ferrocene using 1H and 13C <a href="/wiki/Nuclear_magnetic_resonance" title="Nuclear magnetic resonance">nuclear magnetic resonance</a> spectroscopy. For example, methylferrocene (CH3C5H4FeC5H5) exhibits a singlet for the C5H5 ring.<a href="#cite_note-29">[29]</a> In solution, and at room temperature, eclipsed D5h ferrocene was determined to dominate over the staggered D5d conformer, as suggested by both <a href="/wiki/Fourier-transform_infrared_spectroscopy" title="Fourier-transform infrared spectroscopy">Fourier-transform infrared spectroscopy</a> and <a href="/wiki/Density_functional_theory" title="Density functional theory">DFT</a> calculations.<a href="#cite_note-30">[30]</a> <div class="mw-heading mw-heading2"><h2 id="Synthesis">Synthesis</h2>[<a href="/w/index.php?title=Ferrocene&action=edit&section=6" title="Edit section: Synthesis">edit</a>]</div> <div class="mw-heading mw-heading3"><h3 id="Early_methods">Early methods</h3>[<a href="/w/index.php?title=Ferrocene&action=edit&section=7" title="Edit section: Early methods">edit</a>]</div> The first reported syntheses of ferrocene were nearly simultaneous. Pauson and Kealy synthesised ferrocene using iron(III) chloride and cyclopentadienyl magnesium bromide.<a href="#cite_note-pauson-11">[11]</a> A <a href="/wiki/Redox" title="Redox">redox reaction</a> produces iron(II) chloride. The formation of fulvalene, the intended outcome does not occur.<a href="#cite_note-Pauson2001-8">[8]</a> <dl><dd><a href="/wiki/File:Kealy_and_Pauson_synthesis_of_ferrocene_v2.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/2/2b/Kealy_and_Pauson_synthesis_of_ferrocene_v2.jpg/600px-Kealy_and_Pauson_synthesis_of_ferrocene_v2.jpg" decoding="async" width="600" height="239" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/2b/Kealy_and_Pauson_synthesis_of_ferrocene_v2.jpg/900px-Kealy_and_Pauson_synthesis_of_ferrocene_v2.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/2/2b/Kealy_and_Pauson_synthesis_of_ferrocene_v2.jpg 2x" data-file-width="1115" data-file-height="444" /></a></dd></dl> <figure class="mw-halign-left" typeof="mw:File/Thumb"><a href="/wiki/File:Miller_Ferrocen_Synthese.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/7c/Miller_Ferrocen_Synthese.svg/300px-Miller_Ferrocen_Synthese.svg.png" decoding="async" width="300" height="115" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/7c/Miller_Ferrocen_Synthese.svg/450px-Miller_Ferrocen_Synthese.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/7c/Miller_Ferrocen_Synthese.svg/600px-Miller_Ferrocen_Synthese.svg.png 2x" data-file-width="494" data-file-height="190" /></a><figcaption>The Miller et al.<a href="#cite_note-miller-9">[9]</a> approach to ferrocene</figcaption></figure> Another early synthesis of ferrocene was by Miller et al.,<a href="#cite_note-miller-9">[9]</a> who treated metallic iron with <a href="/wiki/Gas" title="Gas">gaseous</a> cyclopentadiene at elevated temperature.<a href="#cite_note-31">[31]</a> An approach using <a href="/wiki/Iron_pentacarbonyl" title="Iron pentacarbonyl">iron pentacarbonyl</a> was also reported.<a href="#cite_note-32">[32]</a> <dl><dd>Fe(CO)5 + 2 C5H6 → Fe(C5H5)2 + 5 CO + H2</dd></dl> <div class="mw-heading mw-heading3"><h3 id="Via_alkali_cyclopentadienide">Via alkali cyclopentadienide</h3>[<a href="/w/index.php?title=Ferrocene&action=edit&section=8" title="Edit section: Via alkali cyclopentadienide">edit</a>]</div> More efficient preparative methods are generally a modification of the original <a href="/wiki/Transmetalation" title="Transmetalation">transmetalation</a> sequence using either commercially available <a href="/wiki/Sodium_cyclopentadienide" title="Sodium cyclopentadienide">sodium cyclopentadienide</a><a href="#cite_note-orgsyn-33">[33]</a> or freshly <a href="/wiki/Dicyclopentadiene" title="Dicyclopentadiene">cracked</a> cyclopentadiene deprotonated with <a href="/wiki/Potassium_hydroxide" title="Potassium hydroxide">potassium hydroxide</a><a href="#cite_note-34">[34]</a> and reacted with anhydrous iron(II) chloride in ethereal solvents. Modern modifications of Pauson and Kealy's original Grignard approach are known: <ul><li>Using sodium cyclopentadienide:       2 NaC5H5   +   FeCl2   →   Fe(C5H5)2   +   2 NaCl</li> <li>Using freshly-cracked cyclopentadiene:     FeCl2·4H2O   +   2 C5H6   +   2 KOH   →   Fe(C5H5)2   +   2 KCl   +   6 H2O</li> <li>Using an iron(II) salt with a Grignard reagent:     2 C5H5MgBr   +   FeCl2   →   Fe(C5H5)2   +   2 MgBrCl</li></ul> Even some <a href="/wiki/Amine" title="Amine">amine</a> bases (such as <a href="/wiki/Diethylamine" title="Diethylamine">diethylamine</a>) can be used for the deprotonation, though the reaction proceeds more slowly than when using stronger bases:<a href="#cite_note-orgsyn-33">[33]</a> <dl><dd>2 C5H6   +   2 (CH3CH2)2NH   +   FeCl2   →   Fe(C5H5)2   +   2 (CH3CH2)2NH2Cl</dd></dl> Direct transmetalation can also be used to prepare ferrocene from some other metallocenes, such as <a href="/wiki/Manganocene" title="Manganocene">manganocene</a>:<a href="#cite_note-35">[35]</a> <dl><dd>FeCl2   +   Mn(C5H5)2   →   MnCl2   +   Fe(C5H5)2</dd></dl> <div class="mw-heading mw-heading2"><h2 id="Properties">Properties</h2>[<a href="/w/index.php?title=Ferrocene&action=edit&section=9" title="Edit section: Properties">edit</a>]</div> <figure class="mw-default-size mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Ferrocen.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/74/Ferrocen.jpg/220px-Ferrocen.jpg" decoding="async" width="220" height="165" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/74/Ferrocen.jpg/330px-Ferrocen.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/74/Ferrocen.jpg/440px-Ferrocen.jpg 2x" data-file-width="640" data-file-height="480" /></a><figcaption>Crystals of ferrocene after purification by vacuum sublimation</figcaption></figure> Ferrocene is an <a href="/wiki/Air" class="mw-redirect" title="Air">air</a>-stable orange solid with a camphor-like odor. As expected for a symmetric, uncharged species, ferrocene is soluble in normal organic solvents, such as benzene, but is insoluble in water. It is stable to temperatures as high as 400 °C.<a href="#cite_note-36">[36]</a> Ferrocene readily <a href="/wiki/Sublimation_(phase_transition)" title="Sublimation (phase transition)">sublimes</a>, especially upon heating in a vacuum. Its vapor pressure is about 1 <a href="/wiki/Pascal_(unit)" title="Pascal (unit)">Pa</a> at 25 °C, 10 Pa at 50 °C, 100 Pa at 80 °C, 1000 Pa at 116 °C, and 10,000 Pa (nearly 0.1 <a href="/wiki/Atmosphere_(unit)" class="mw-redirect" title="Atmosphere (unit)">atm</a>) at 162 °C.<a href="#cite_note-37">[37]</a><a href="#cite_note-fulem2013-38">[38]</a> <div class="mw-heading mw-heading2"><h2 id="Reactions">Reactions</h2>[<a href="/w/index.php?title=Ferrocene&action=edit&section=10" title="Edit section: Reactions">edit</a>]</div> <div class="mw-heading mw-heading3"><h3 id="With_electrophiles">With electrophiles</h3>[<a href="/w/index.php?title=Ferrocene&action=edit&section=11" title="Edit section: With electrophiles">edit</a>]</div> Ferrocene undergoes many reactions characteristic of aromatic compounds, enabling the preparation of substituted derivatives. A common undergraduate experiment is the <a href="/wiki/Friedel%E2%80%93Crafts_reaction" title="Friedel–Crafts reaction">Friedel–Crafts reaction</a> of ferrocene with <a href="/wiki/Acetic_anhydride" title="Acetic anhydride">acetic anhydride</a> (or <a href="/wiki/Acetyl_chloride" title="Acetyl chloride">acetyl chloride</a>) in the presence of <a href="/wiki/Phosphoric_acid" title="Phosphoric acid">phosphoric acid</a> as a catalyst. Under conditions for a <a href="/wiki/Mannich_reaction" title="Mannich reaction">Mannich reaction</a>, ferrocene gives <a href="/wiki/N,N-Dimethylaminomethylferrocene" title="N,N-Dimethylaminomethylferrocene">N,N-dimethylaminomethylferrocene</a>. <figure class="mw-halign-center" typeof="mw:File/Thumb"><a href="/wiki/File:FcGen%27l.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/2/25/FcGen%27l.png/400px-FcGen%27l.png" decoding="async" width="400" height="295" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/25/FcGen%27l.png/600px-FcGen%27l.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/25/FcGen%27l.png/800px-FcGen%27l.png 2x" data-file-width="1358" data-file-height="1001" /></a><figcaption>Important reactions of ferrocene with electrophiles and other reagents</figcaption></figure> Ferrocene can itself be oxidized to the ferrocenium cation (Fc+); the ferrocene/ferrocenium couple is often used as a reference in electrochemistry.<a href="#cite_note-federman-12">[12]</a> It is an <a href="/wiki/Aromaticity" title="Aromaticity">aromatic substance</a> and undergoes <a href="/wiki/Substitution_reaction" title="Substitution reaction">substitution reactions</a> rather than <a href="/wiki/Addition_reaction" title="Addition reaction">addition reactions</a> on the cyclopentadienyl ligands. For example, <a href="/wiki/Friedel-Crafts_reaction#Friedel-Crafts_acylation" class="mw-redirect" title="Friedel-Crafts reaction">Friedel-Crafts acylation</a> of ferrocene with <a href="/wiki/Acetic_anhydride" title="Acetic anhydride">acetic anhydride</a> yields <a href="/wiki/Acetylferrocene" title="Acetylferrocene">acetylferrocene</a><a href="#cite_note-39">[39]</a> just as acylation of benzene yields <a href="/wiki/Acetophenone" title="Acetophenone">acetophenone</a> under similar conditions. <a href="/wiki/Vilsmeier-Haack_reaction" class="mw-redirect" title="Vilsmeier-Haack reaction">Vilsmeier-Haack reaction</a> (formylation) using formylanilide and <a href="/wiki/Phosphorus_oxychloride" class="mw-redirect" title="Phosphorus oxychloride">phosphorus oxychloride</a> gives <a href="/wiki/Ferrocenecarboxaldehyde" title="Ferrocenecarboxaldehyde">ferrocenecarboxaldehyde</a>. Diformylation does not occur readily, showing the electronic communication between the two rings.<a href="#cite_note-Rausch-40">[40]</a> Protonation of ferrocene allows isolation of [Cp2FeH]PF6.<a href="#cite_note-41">[41]</a> In the presence of <a href="/wiki/Aluminium_chloride" title="Aluminium chloride">aluminium chloride</a>, Me2NPCl2 and ferrocene react to give ferrocenyl dichlorophosphine,<a href="#cite_note-42">[42]</a> whereas treatment with <a href="/wiki/Dichlorophenylphosphine" title="Dichlorophenylphosphine">phenyldichlorophosphine</a> under similar conditions forms P,P-diferrocenyl-P-phenyl phosphine.<a href="#cite_note-43">[43]</a> Ferrocene reacts with <a href="/wiki/Phosphorus_pentasulfide" title="Phosphorus pentasulfide">P4S10</a> forms a diferrocenyl-dithiadiphosphetane disulfide.<a href="#cite_note-44">[44]</a> <div class="mw-heading mw-heading3"><h3 id="Lithiation">Lithiation</h3>[<a href="/w/index.php?title=Ferrocene&action=edit&section=12" title="Edit section: Lithiation">edit</a>]</div> Ferrocene reacts with <a href="/wiki/Butyllithium" title="Butyllithium">butyllithium</a> to give <a href="/wiki/1,1%27-Dilithioferrocene" title="1,1'-Dilithioferrocene">1,1′-dilithioferrocene</a>, which is a versatile <a href="/wiki/Nucleophile" title="Nucleophile">nucleophile</a>. In combination with butyllithiium, <a href="/wiki/Tert-Butyllithium" title="Tert-Butyllithium">tert-butyllithium</a> produces monolithioferrocene.<a href="#cite_note-45">[45]</a> <div class="mw-heading mw-heading3"><h3 id="Redox_chemistry">Redox chemistry</h3>[<a href="/w/index.php?title=Ferrocene&action=edit&section=13" title="Edit section: Redox chemistry">edit</a>]</div> Ferrocene undergoes a one-electron oxidation at around 0.4 V versus a <a href="/wiki/Saturated_calomel_electrode" title="Saturated calomel electrode">saturated calomel electrode</a> (SCE), becoming ferrocenium. This reversible oxidation has been used as standard in electrochemistry as Fc+/Fc = 0.64 V versus the <a href="/wiki/Standard_hydrogen_electrode" title="Standard hydrogen electrode">standard hydrogen electrode</a>,<a href="#cite_note-46">[46]</a> however other values have been reported.<a href="#cite_note-47">[47]</a> <a href="/wiki/Ferrocenium_tetrafluoroborate" title="Ferrocenium tetrafluoroborate">Ferrocenium tetrafluoroborate</a> is a common reagent.<a href="#cite_note-48">[48]</a> The remarkably reversible oxidation-reduction behaviour has been extensively used to control electron-transfer processes in electrochemical<a href="#cite_note-49">[49]</a><a href="#cite_note-50">[50]</a> and photochemical<a href="#cite_note-51">[51]</a><a href="#cite_note-52">[52]</a> systems. <figure class="mw-halign-left" typeof="mw:File/Thumb"><a href="/wiki/File:Biferrocene.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/76/Biferrocene.svg/132px-Biferrocene.svg.png" decoding="async" width="132" height="112" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/76/Biferrocene.svg/198px-Biferrocene.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/76/Biferrocene.svg/264px-Biferrocene.svg.png 2x" data-file-width="1821" data-file-height="1546" /></a><figcaption>The one-electron oxidized derivative of <a href="/wiki/Biferrocene" title="Biferrocene">biferrocene</a> has attracted much research attention.</figcaption></figure> Substituents on the cyclopentadienyl ligands alters the redox potential in the expected way: electron-withdrawing groups such as a <a href="/wiki/Carboxylic_acid" title="Carboxylic acid">carboxylic acid</a> shift the potential in the <a href="/wiki/Anodic" class="mw-redirect" title="Anodic">anodic</a> direction (i.e. made more positive), whereas electron-releasing groups such as <a href="/wiki/Methyl" class="mw-redirect" title="Methyl">methyl</a> groups shift the potential in the <a href="/wiki/Cathode" title="Cathode">cathodic</a> direction (more negative). Thus, <a href="/wiki/Decamethylferrocene" title="Decamethylferrocene">decamethylferrocene</a> is much more easily oxidised than ferrocene and can even be oxidised to the corresponding dication.<a href="#cite_note-53">[53]</a> Ferrocene is often used as an <a href="/wiki/Internal_standard" title="Internal standard">internal standard</a> for calibrating redox potentials in non-aqueous <a href="/wiki/Electrochemistry" title="Electrochemistry">electrochemistry</a>. <div class="mw-heading mw-heading2"><h2 id="Stereochemistry_of_substituted_ferrocenes">Stereochemistry of substituted ferrocenes</h2>[<a href="/w/index.php?title=Ferrocene&action=edit&section=14" title="Edit section: Stereochemistry of substituted ferrocenes">edit</a>]</div> <figure class="mw-default-size mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Planar_chiral_ferrocene_derivative.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/5/53/Planar_chiral_ferrocene_derivative.svg/220px-Planar_chiral_ferrocene_derivative.svg.png" decoding="async" width="220" height="207" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/53/Planar_chiral_ferrocene_derivative.svg/330px-Planar_chiral_ferrocene_derivative.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/53/Planar_chiral_ferrocene_derivative.svg/440px-Planar_chiral_ferrocene_derivative.svg.png 2x" data-file-width="254" data-file-height="239" /></a><figcaption>A planar chiral ferrocene derivative</figcaption></figure> Disubstituted ferrocenes can exist as either 1,2-, 1,3- or 1,1′- isomers, none of which are interconvertible. Ferrocenes that are asymmetrically disubstituted on one ring are chiral – for example [CpFe(EtC5H3Me)]. This <a href="/wiki/Planar_chirality" title="Planar chirality">planar chirality</a> arises despite no single atom being a <a href="/wiki/Stereocenter" title="Stereocenter">stereogenic centre</a>. The substituted ferrocene shown at right (a 4-(dimethylamino)pyridine derivative) has been shown to be effective when used for the <a href="/wiki/Kinetic_resolution" title="Kinetic resolution">kinetic resolution</a> of <a href="/wiki/Racemic" class="mw-redirect" title="Racemic">racemic</a> secondary <a href="/wiki/Alcohol_(chemistry)" title="Alcohol (chemistry)">alcohols</a>.<a href="#cite_note-54">[54]</a> Several approaches have been developed to asymmetrically 1,1′-functionalise the ferrocene.<a href="#cite_note-55">[55]</a> <div class="mw-heading mw-heading2"><h2 id="Applications_of_ferrocene_and_its_derivatives">Applications of ferrocene and its derivatives</h2>[<a href="/w/index.php?title=Ferrocene&action=edit&section=15" title="Edit section: Applications of ferrocene and its derivatives">edit</a>]</div> Ferrocene and its numerous derivatives have no large-scale applications, but have many niche uses that exploit the unusual structure (<a href="/wiki/Ligand" title="Ligand">ligand</a> scaffolds, <a href="/wiki/Pharmaceutical_drug" class="mw-redirect" title="Pharmaceutical drug">pharmaceutical candidates</a>), <a href="/wiki/Robustness" title="Robustness">robustness</a> (<a href="/wiki/Anti-knock" class="mw-redirect" title="Anti-knock">anti-knock formulations</a>, <a href="/wiki/Precursor_(chemistry)" title="Precursor (chemistry)">precursors</a> to materials), and redox (reagents and redox standards). <div class="mw-heading mw-heading3"><h3 id="Ligand_scaffolds">Ligand scaffolds</h3>[<a href="/w/index.php?title=Ferrocene&action=edit&section=16" title="Edit section: Ligand scaffolds">edit</a>]</div> Chiral ferrocenyl <a href="/wiki/Phosphine" title="Phosphine">phosphines</a> are employed as ligands for transition-metal catalyzed reactions. Some of them have found industrial applications in the synthesis of pharmaceuticals and agrochemicals. For example, the <a href="/wiki/Diphosphines" class="mw-redirect" title="Diphosphines">diphosphine</a> <a href="/wiki/1,1%27-bis(diphenylphosphino)ferrocene" class="mw-redirect" title="1,1'-bis(diphenylphosphino)ferrocene">1,1′-bis(diphenylphosphino)ferrocene</a> (dppf) is a valued ligand for <a href="/wiki/Palladium" title="Palladium">palladium</a>-<a href="/wiki/Coupling_reaction" title="Coupling reaction">coupling reactions</a> and <a href="/wiki/Josiphos_ligand" class="mw-redirect" title="Josiphos ligand">Josiphos ligand</a> is useful for hydrogenation catalysis.<a href="#cite_note-H-U._Blaser_2002-56">[56]</a> They are named after the technician who made the first one, Josi Puleo.<a href="#cite_note-57">[57]</a><a href="#cite_note-Stepnicka-58">[58]</a> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Josiphos.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/63/Josiphos.png/220px-Josiphos.png" decoding="async" width="220" height="195" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/6/63/Josiphos.png 1.5x" data-file-width="258" data-file-height="229" /></a><figcaption>Josiphos ligand.<a href="#cite_note-H-U._Blaser_2002-56">[56]</a></figcaption></figure> <div class="mw-heading mw-heading3"><h3 id="Fuel_additives">Fuel additives</h3>[<a href="/w/index.php?title=Ferrocene&action=edit&section=17" title="Edit section: Fuel additives">edit</a>]</div> Ferrocene and its derivatives are <a href="/wiki/Antiknock_agent" title="Antiknock agent">antiknock agents</a> used in the fuel for <a href="/wiki/Petrol_engine" title="Petrol engine">petrol engines</a>. They are safer than previously used <a href="/wiki/Tetraethyllead" title="Tetraethyllead">tetraethyllead</a>.<a href="#cite_note-59">[59]</a> Petrol additive solutions containing ferrocene can be added to unleaded petrol to enable its use in vintage cars designed to run on leaded petrol.<a href="#cite_note-60">[60]</a> The <a href="/wiki/Iron" title="Iron">iron</a>-containing deposits formed from ferrocene can form a <a href="/wiki/Conductive" class="mw-redirect" title="Conductive">conductive</a> coating on <a href="/wiki/Spark_plug" title="Spark plug">spark plug</a> surfaces. Ferrocene polyglycol copolymers, prepared by effecting a polycondensation reaction between a ferrocene derivative and a substituted dihydroxy alcohol, has promise as a component of rocket propellants. These copolymers provide rocket propellants with heat stability, serving as a propellant binder and controlling propellant burn rate.<a href="#cite_note-61">[61]</a> Ferrocene has been found to be effective at reducing smoke and sulfur trioxide produced when burning coal. The addition by any practical means, impregnating the coal or adding ferrocene to the combustion chamber, can significantly reduce the amount of these undesirable byproducts, even with a small amount of the metal cyclopentadienyl compound.<a href="#cite_note-62">[62]</a> <div class="mw-heading mw-heading3"><h3 id="Pharmaceuticals">Pharmaceuticals</h3>[<a href="/w/index.php?title=Ferrocene&action=edit&section=18" title="Edit section: Pharmaceuticals">edit</a>]</div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Ferroceron.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/71/Ferroceron.svg/220px-Ferroceron.svg.png" decoding="async" width="220" height="216" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/71/Ferroceron.svg/330px-Ferroceron.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/71/Ferroceron.svg/440px-Ferroceron.svg.png 2x" data-file-width="148" data-file-height="145" /></a><figcaption>Ferrocerone</figcaption></figure> Ferrocene derivatives have been investigated as drugs,<a href="#cite_note-63">[63]</a> with one compound <a href="/w/index.php?title=Ferrocerone&action=edit&redlink=1" class="new" title="Ferrocerone (page does not exist)">ferrocerone</a> [<a href="https://ru.wikipedia.org/wiki/%D0%A4%D0%B5%D1%80%D1%80%D0%BE%D1%86%D0%B5%D1%80%D0%BE%D0%BD" class="extiw" title="ru:Ферроцерон">ru</a>] approved for use in the USSR in the 1970s as an <a href="/wiki/Iron_supplement" title="Iron supplement">iron supplement</a>, though it is no longer marketed today.<a href="#cite_note-64">[64]</a> Only one drug has entered clinical trials in recent years, <a href="/wiki/Ferroquine" title="Ferroquine">Ferroquine</a> (7-chloro-N-(2-((dimethylamino)methyl)ferrocenyl)quinolin-4-amine), an <a href="/wiki/Antimalarial" class="mw-redirect" title="Antimalarial">antimalarial</a>,<a href="#cite_note-BiotNosten2011-65">[65]</a><a href="#cite_note-66">[66]</a><a href="#cite_note-67">[67]</a> which has reached Phase IIb trials.<a href="#cite_note-68">[68]</a> Ferrocene-containing polymer-based drug delivery systems have been investigated.<a href="#cite_note-69">[69]</a> <figure typeof="mw:File/Thumb"><a href="/wiki/File:Ferroquine.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a9/Ferroquine.png/220px-Ferroquine.png" decoding="async" width="220" height="87" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/a/a9/Ferroquine.png 1.5x" data-file-width="300" data-file-height="118" /></a><figcaption>Ferroquine</figcaption></figure> The anticancer activity of ferrocene derivatives was first investigated in the late 1970s, when derivatives bearing <a href="/wiki/Amine" title="Amine">amine</a> or <a href="/wiki/Amide" title="Amide">amide</a> groups were tested against lymphocytic <a href="/wiki/Leukemia" title="Leukemia">leukemia</a>.<a href="#cite_note-:0-70">[70]</a> Some ferrocenium salts exhibit anticancer activity, but no compound has seen evaluation in the clinic.<a href="#cite_note-Babin-71">[71]</a> Ferrocene derivatives have strong inhibitory activity against human lung cancer cell line A549, colorectal cancer cell line HCT116, and breast cancer cell line MCF-7.<a href="#cite_note-72">[72]</a> An experimental drug was reported which is a ferrocenyl version of <a href="/wiki/Tamoxifen" title="Tamoxifen">tamoxifen</a>.<a href="#cite_note-top2003-73">[73]</a> The idea is that the tamoxifen will bind to the <a href="/wiki/Estrogen" title="Estrogen">estrogen</a> binding sites, resulting in cytotoxicity.<a href="#cite_note-top2003-73">[73]</a><a href="#cite_note-74">[74]</a> Ferrocifens are exploited for cancer applications by a French biotech, Feroscan, founded by Pr. Gerard Jaouen. <div class="mw-heading mw-heading3"><h3 id="Solid_rocket_propellant">Solid rocket propellant</h3>[<a href="/w/index.php?title=Ferrocene&action=edit&section=19" title="Edit section: Solid rocket propellant">edit</a>]</div> Ferrocene and related derivatives are used as powerful burn rate catalysts in <a href="/wiki/Ammonium_perchlorate_composite_propellant" title="Ammonium perchlorate composite propellant">ammonium perchlorate composite propellant</a>.<a href="#cite_note-75">[75]</a> <div class="mw-heading mw-heading2"><h2 id="Derivatives_and_variations">Derivatives and variations</h2>[<a href="/w/index.php?title=Ferrocene&action=edit&section=20" title="Edit section: Derivatives and variations">edit</a>]</div> Ferrocene analogues can be prepared with variants of cyclopentadienyl. For example, bis<a href="/wiki/Indene" title="Indene">indenyliron</a> and bisfluorenyliron.<a href="#cite_note-Stepnicka-58">[58]</a> <figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:FcVarietyPack.png" class="mw-file-description" title="Various ferrocene derivatives where cyclopentadienyl has been replaced by related ligands"><img alt="Various ferrocene derivatives where cyclopentadienyl has been replaced by related ligands" src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c2/FcVarietyPack.png/400px-FcVarietyPack.png" decoding="async" width="400" height="83" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c2/FcVarietyPack.png/600px-FcVarietyPack.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c2/FcVarietyPack.png/800px-FcVarietyPack.png 2x" data-file-width="1294" data-file-height="270" /></a><figcaption>Various ferrocene derivatives where cyclopentadienyl has been replaced by related ligands</figcaption></figure> Carbon atoms can be replaced by heteroatoms as illustrated by Fe(η5-C5Me5)(η5-P5) and Fe(η5-C5H5)(η5-C4H4N) ("<a href="/w/index.php?title=Azaferrocene&action=edit&redlink=1" class="new" title="Azaferrocene (page does not exist)">azaferrocene</a>"). Azaferrocene arises from decarbonylation of Fe(η5-C5H5)(CO)2(η1-pyrrole) in <a href="/wiki/Cyclohexane" title="Cyclohexane">cyclohexane</a>.<a href="#cite_note-76">[76]</a> This compound on boiling under <a href="/wiki/Reflux" title="Reflux">reflux</a> in <a href="/wiki/Benzene" title="Benzene">benzene</a> is converted to ferrocene.<a href="#cite_note-77">[77]</a> Because of the ease of substitution, many structurally unusual ferrocene derivatives have been prepared. For example, the penta(ferrocenyl)cyclopentadienyl ligand,<a href="#cite_note-78">[78]</a> features a cyclopentadienyl anion derivatized with five ferrocene substituents. <figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Penta(ferrocenyl)cyclopentadienyl.png" class="mw-file-description" title="Penta(ferrocenyl)cyclopentadienyl ligand"><img alt="Penta(ferrocenyl)cyclopentadienyl ligand" src="//upload.wikimedia.org/wikipedia/commons/thumb/1/18/Penta%28ferrocenyl%29cyclopentadienyl.png/500px-Penta%28ferrocenyl%29cyclopentadienyl.png" decoding="async" width="500" height="128" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/18/Penta%28ferrocenyl%29cyclopentadienyl.png/750px-Penta%28ferrocenyl%29cyclopentadienyl.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/18/Penta%28ferrocenyl%29cyclopentadienyl.png/1000px-Penta%28ferrocenyl%29cyclopentadienyl.png 2x" data-file-width="15238" data-file-height="3890" /></a><figcaption>Penta(ferrocenyl)cyclopentadienyl ligand</figcaption></figure> <figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Hexaferrocenylbenzene-3D-sticks.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/07/Hexaferrocenylbenzene-3D-sticks.png/200px-Hexaferrocenylbenzene-3D-sticks.png" decoding="async" width="200" height="192" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/07/Hexaferrocenylbenzene-3D-sticks.png/300px-Hexaferrocenylbenzene-3D-sticks.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/07/Hexaferrocenylbenzene-3D-sticks.png/400px-Hexaferrocenylbenzene-3D-sticks.png 2x" data-file-width="1100" data-file-height="1058" /></a><figcaption>Structure of hexaferrocenylbenzene</figcaption></figure> In hexaferrocenylbenzene, C6[(η5-C5H4)Fe(η5-C5H5)]6, all six positions on a <a href="/wiki/Benzene" title="Benzene">benzene</a> molecule have ferrocenyl substituents (R).<a href="#cite_note-hexaferrocenylbenzene-79">[79]</a> <a href="/wiki/X-ray_diffraction" title="X-ray diffraction">X-ray diffraction</a> analysis of this compound confirms that the cyclopentadienyl ligands are not co-planar with the benzene core but have alternating <a href="/wiki/Dihedral_angle" title="Dihedral angle">dihedral angles</a> of +30° and −80°. Due to steric crowding the ferrocenyls are slightly bent with angles of 177° and have elongated C-Fe bonds. The quaternary cyclopentadienyl carbon atoms are also <a href="/wiki/Pyramidalization" class="mw-redirect" title="Pyramidalization">pyramidalized</a>. Also, the benzene core has a <a href="/wiki/Chair_conformation" class="mw-redirect" title="Chair conformation">chair conformation</a> with dihedral angles of 14° and displays <a href="/wiki/Bond_length" title="Bond length">bond length</a> alternation between 142.7 <a href="/wiki/Picometer" class="mw-redirect" title="Picometer">pm</a> and 141.1 pm, both indications of steric crowding of the substituents. The synthesis of hexaferrocenylbenzene has been reported using <a href="/wiki/Negishi_coupling" title="Negishi coupling">Negishi coupling</a> of hexaiodidobenzene and diferrocenylzinc, using <a href="/wiki/Tris(dibenzylideneacetone)dipalladium(0)" title="Tris(dibenzylideneacetone)dipalladium(0)">tris(dibenzylideneacetone)dipalladium(0)</a> as <a href="/wiki/Catalyst" class="mw-redirect" title="Catalyst">catalyst</a>, in <a href="/wiki/Tetrahydrofuran" title="Tetrahydrofuran">tetrahydrofuran</a>:<a href="#cite_note-hexaferrocenylbenzene-79">[79]</a> <dl><dd><a href="/wiki/File:Hexaferrocenylbenzene.png" class="mw-file-description" title="Hexaferrocenylbenzene synthesis by Negishi coupling"><img alt="Hexaferrocenylbenzene synthesis by Negishi coupling" src="//upload.wikimedia.org/wikipedia/commons/thumb/8/83/Hexaferrocenylbenzene.png/400px-Hexaferrocenylbenzene.png" decoding="async" width="400" height="138" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/83/Hexaferrocenylbenzene.png/600px-Hexaferrocenylbenzene.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/83/Hexaferrocenylbenzene.png/800px-Hexaferrocenylbenzene.png 2x" data-file-width="997" data-file-height="345" /></a></dd></dl> The <a href="/wiki/Yield_(chemistry)" title="Yield (chemistry)">yield</a> is only 4%, which is further evidence consistent with substantial <a href="/wiki/Steric_strain" class="mw-redirect" title="Steric strain">steric</a> crowding around the arene core. <div style="clear:both;" class=""></div> <div class="mw-heading mw-heading3"><h3 id="Materials_chemistry">Materials chemistry</h3>[<a href="/w/index.php?title=Ferrocene&action=edit&section=21" title="Edit section: Materials chemistry">edit</a>]</div> <figure class="mw-halign-left" typeof="mw:File/Thumb"><a href="/wiki/File:Wettability_of_a_silica_surface_with_a_bound_ferrocene-substituted_polymer.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/4/4c/Wettability_of_a_silica_surface_with_a_bound_ferrocene-substituted_polymer.jpg/500px-Wettability_of_a_silica_surface_with_a_bound_ferrocene-substituted_polymer.jpg" decoding="async" width="500" height="196" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/4c/Wettability_of_a_silica_surface_with_a_bound_ferrocene-substituted_polymer.jpg/750px-Wettability_of_a_silica_surface_with_a_bound_ferrocene-substituted_polymer.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/4c/Wettability_of_a_silica_surface_with_a_bound_ferrocene-substituted_polymer.jpg/1000px-Wettability_of_a_silica_surface_with_a_bound_ferrocene-substituted_polymer.jpg 2x" data-file-width="1302" data-file-height="511" /></a><figcaption>Strands of an uncharged ferrocene-substituted polymer are tethered to a <a href="/wiki/Hydrophobic" class="mw-redirect" title="Hydrophobic">hydrophobic</a> <a href="/wiki/Silica" class="mw-redirect" title="Silica">silica</a> surface. Oxidation of the ferrocenyl groups produces a <a href="/wiki/Hydrophilic" class="mw-redirect" title="Hydrophilic">hydrophilic</a> surface due to electrostatic attractions between the resulting charges and the polar solvent.<a href="#cite_note-Pietschnig-80">[80]</a></figcaption></figure> Ferrocene, a precursor to iron nanoparticles, can be used as a catalyst for the production of carbon nanotubes.<a href="#cite_note-81">[81]</a> <a href="/wiki/Vinylferrocene" title="Vinylferrocene">Vinylferrocene</a> can be converted to (polyvinylferrocene, PVFc), a ferrocenyl version of <a href="/wiki/Polystyrene" title="Polystyrene">polystyrene</a> (the phenyl groups are replaced with ferrocenyl groups). Another <a href="/wiki/Polyferrocenes" title="Polyferrocenes">polyferrocene</a> which can be formed is poly(2-(methacryloyloxy)ethyl ferrocenecarboxylate), PFcMA. In addition to using organic polymer backbones, these pendant ferrocene units have been attached to inorganic backbones such as <a href="/wiki/Polysiloxane" class="mw-redirect" title="Polysiloxane">polysiloxanes</a>, <a href="/wiki/Polyphosphazene" title="Polyphosphazene">polyphosphazenes</a>, and poly<a href="/w/index.php?title=Phosphinoborane&action=edit&redlink=1" class="new" title="Phosphinoborane (page does not exist)">phosphinoboranes</a>, (–PH(R)–BH2–)n, and the resulting materials exhibit unusual physical and electronic properties relating to the ferrocene / ferrocinium redox couple.<a href="#cite_note-Pietschnig-80">[80]</a> Both PVFc and PFcMA have been tethered onto <a href="/wiki/Silica" class="mw-redirect" title="Silica">silica</a> wafers and the <a href="/wiki/Wettability" class="mw-redirect" title="Wettability">wettability</a> measured when the polymer chains are uncharged and when the ferrocene moieties are oxidised to produce positively charged groups. The <a href="/wiki/Contact_angle" title="Contact angle">contact angle</a> with water on the PFcMA-coated wafers was 70° smaller following oxidation, while in the case of PVFc the decrease was 30°, and the switching of wettability is reversible. In the PFcMA case, the effect of lengthening the chains and hence introducing more ferrocene groups is significantly larger reductions in the contact angle upon oxidation.<a href="#cite_note-Pietschnig-80">[80]</a><a href="#cite_note-82">[82]</a> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2>[<a href="/w/index.php?title=Ferrocene&action=edit&section=22" title="Edit section: See also">edit</a>]</div> <ul><li><a href="/wiki/Josiphos_ligands" title="Josiphos ligands">Josiphos ligands</a></li></ul> <div class="mw-heading mw-heading2"><h2 id="References">References</h2>[<a href="/w/index.php?title=Ferrocene&action=edit&section=23" title="Edit section: References">edit</a>]</div> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-1"><a href="#cite_ref-1">^</a> <style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite id="CITEREFInternational_Union_of_Pure_and_Applied_Chemistry2014" class="citation book cs1"><a href="/wiki/International_Union_of_Pure_and_Applied_Chemistry" title="International Union of Pure and Applied Chemistry">International Union of Pure and Applied Chemistry</a> (2014). 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Chemical Communications (24): 2572–2574. <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%2Fb604844g">10.1039/b604844g</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/16779481">16779481</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Chemical+Communications&rft.atitle=Hexaferrocenylbenzene&rft.issue=24&rft.pages=2572-2574&rft.date=2006-06&rft_id=info%3Adoi%2F10.1039%2Fb604844g&rft_id=info%3Apmid%2F16779481&rft.aulast=Yu&rft.aufirst=Y&rft.au=Bond%2C+AD&rft.au=Leonard%2C+PW&rft.au=Lorenz%2C+UJ&rft.au=Timofeeva%2C+TV&rft.au=Vollhardt%2C+KP&rft.au=Whitener%2C+GD&rft.au=Yakovenko%2C+AA&rft_id=https%3A%2F%2Fzenodo.org%2Frecord%2F896672&rfr_id=info%3Asid%2Fen.wikipedia.org%3AFerrocene" class="Z3988"> </li> <li id="cite_note-Pietschnig-80">^ <a href="#cite_ref-Pietschnig_80-0">a</a> <a href="#cite_ref-Pietschnig_80-1">b</a> <a href="#cite_ref-Pietschnig_80-2">c</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFPietschnig2016" class="citation journal cs1">Pietschnig R (October 2016). <a rel="nofollow" class="external text" href="https://doi.org/10.1039%2FC6CS00196C">"Polymers with pendant ferrocenes"</a>. Chemical Society Reviews. 45 (19): 5216–5231. <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%2FC6CS00196C">10.1039/C6CS00196C</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/27156979">27156979</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Chemical+Society+Reviews&rft.atitle=Polymers+with+pendant+ferrocenes&rft.volume=45&rft.issue=19&rft.pages=5216-5231&rft.date=2016-10&rft_id=info%3Adoi%2F10.1039%2FC6CS00196C&rft_id=info%3Apmid%2F27156979&rft.aulast=Pietschnig&rft.aufirst=R&rft_id=https%3A%2F%2Fdoi.org%2F10.1039%252FC6CS00196C&rfr_id=info%3Asid%2Fen.wikipedia.org%3AFerrocene" class="Z3988"> </li> <li id="cite_note-81"><a href="#cite_ref-81">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFConroyMoisalaCardosoWindle2010" class="citation journal cs1">Conroy D, Moisala A, Cardoso S, Windle A, Davidson J (2010). "Carbon nanotube reactor: Ferrocene decomposition, iron particle growth, nanotube aggregation and scale-up". <a href="/wiki/Chemical_Engineering_Science" title="Chemical Engineering Science">Chem. Eng. Sci.</a> 65 (10): 2965–2977. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.ces.2010.01.019">10.1016/j.ces.2010.01.019</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Chem.+Eng.+Sci.&rft.atitle=Carbon+nanotube+reactor%3A+Ferrocene+decomposition%2C+iron+particle+growth%2C+nanotube+aggregation+and+scale-up&rft.volume=65&rft.issue=10&rft.pages=2965-2977&rft.date=2010&rft_id=info%3Adoi%2F10.1016%2Fj.ces.2010.01.019&rft.aulast=Conroy&rft.aufirst=D&rft.au=Moisala%2C+A&rft.au=Cardoso%2C+S&rft.au=Windle%2C+A&rft.au=Davidson%2C+J&rfr_id=info%3Asid%2Fen.wikipedia.org%3AFerrocene" class="Z3988"> </li> <li id="cite_note-82"><a href="#cite_ref-82">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFElbertGalleiRüttigerBrunsen2013" class="citation journal cs1">Elbert J, Gallei M, Rüttiger C, Brunsen A, Didzoleit H, Stühn B, Rehahn M (2013). "Ferrocene Polymers for Switchable Surface Wettability". <a href="/wiki/Organometallics" title="Organometallics">Organometallics</a>. 32 (20): 5873–5878. <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%2Fom400468p">10.1021/om400468p</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Organometallics&rft.atitle=Ferrocene+Polymers+for+Switchable+Surface+Wettability&rft.volume=32&rft.issue=20&rft.pages=5873-5878&rft.date=2013&rft_id=info%3Adoi%2F10.1021%2Fom400468p&rft.aulast=Elbert&rft.aufirst=J&rft.au=Gallei%2C+M&rft.au=R%C3%BCttiger%2C+C&rft.au=Brunsen%2C+A&rft.au=Didzoleit%2C+H&rft.au=St%C3%BChn%2C+B&rft.au=Rehahn%2C+M&rfr_id=info%3Asid%2Fen.wikipedia.org%3AFerrocene" class="Z3988"> </li> </ol></div> <div class="mw-heading mw-heading2"><h2 id="External_links">External links</h2>[<a 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pentacarbonyl">Fe(CO)5</a></li> <li><a href="/wiki/Diiron_nonacarbonyl" title="Diiron nonacarbonyl">Fe2(CO)9</a></li> <li><a href="/wiki/Triiron_dodecacarbonyl" title="Triiron dodecacarbonyl">Fe3(CO)12</a></li> <li><a href="/wiki/(Benzylideneacetone)iron_tricarbonyl" title="(Benzylideneacetone)iron tricarbonyl">Fe(CO)3CH3COC2H2C6H6</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Fe(I)</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Iron(I)_hydride" title="Iron(I) hydride">FeH</a></li></ul></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Organoiron(I)_compounds" scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Organoiron_chemistry" title="Organoiron chemistry">Organoiron</a>(I) compounds</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <li><a href="/wiki/Cyclopentadienyliron_dicarbonyl_dimer" title="Cyclopentadienyliron dicarbonyl dimer">(C5H5FeCO)2(CO)2</a></li> </div></td></tr></tbody></table><div> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Fe(0,II)</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Iron_carbide" class="mw-redirect" title="Iron carbide">Fe3C</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Fe(II)</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Iron(II)_hydride" title="Iron(II) hydride">FeH2</a></li> <li><a href="/wiki/Magnesium_iron_hexahydride" title="Magnesium iron hexahydride">Mg2FeH6</a></li> <li><a href="/wiki/Iron(II)_fluoride" title="Iron(II) fluoride">FeF2</a></li> <li><a href="/wiki/Iron(II)_chloride" title="Iron(II) chloride">FeCl2</a></li> <li><a href="/wiki/Iron(II)_perchlorate" title="Iron(II) perchlorate">Fe(ClO4)2</a></li> <li><a href="/wiki/Iron(II)_bromide" title="Iron(II) bromide">FeBr2</a></li> <li><a href="/wiki/Iron(II)_iodide" title="Iron(II) iodide">FeI2</a></li> <li><a href="/wiki/Iron(II)_oxide" title="Iron(II) oxide">FeO</a></li> <li><a href="/wiki/Iron(II)_hydroxide" title="Iron(II) hydroxide">Fe(OH)2</a></li> <li><a href="/wiki/Iron(II)_sulfide" title="Iron(II) sulfide">FeS</a></li> <li><a href="/wiki/Iron(II)_sulfate" title="Iron(II) sulfate">FeSO4</a></li> <li><a href="/wiki/Ammonium_iron(II)_sulfate" title="Ammonium iron(II) sulfate">(NH4)2Fe(SO4)2·6H2O</a></li> <li><a href="/wiki/Iron(II)_selenide" title="Iron(II) selenide">FeSe</a></li> <li><a href="/wiki/Iron(II)_selenate" title="Iron(II) selenate">FeSeO4</a></li> <li><a href="/wiki/Iron(II)_nitrate" title="Iron(II) nitrate">Fe(NO3)2</a></li> <li><a href="/wiki/Iron(II)_phosphate" title="Iron(II) phosphate">Fe3(PO4)2</a></li> <li><a href="/wiki/Iron_disilicide" title="Iron disilicide">FeSi2</a></li> <li><a href="/wiki/Iron(II)_tetrafluoroborate" title="Iron(II) tetrafluoroborate">Fe(BF4)2</a></li> <li><a href="/wiki/Iron(II)_chromite" title="Iron(II) chromite">FeCr2O4</a></li> <li><a href="/wiki/Iron(II)_molybdate" title="Iron(II) molybdate">FeMoO4</a></li> <li><a href="/wiki/Iron(II)_titanate" class="mw-redirect" title="Iron(II) titanate">FeTiO3</a></li> <li><a href="/wiki/Iron(II)_carbonate" title="Iron(II) carbonate">FeCO3</a></li> <li><a href="/wiki/Iron(II)_oxalate" title="Iron(II) oxalate">FeC2O4</a></li> <li><a href="/wiki/Iron(II)_acetate" title="Iron(II) acetate">Fe(C2H3O2)2</a></li> <li><a href="/wiki/Iron(II)_lactate" title="Iron(II) lactate">Fe(C3H5O3)2</a></li> <li><a href="/wiki/Iron(II)_citrate" title="Iron(II) citrate">FeC6H6O7</a></li> <li><a href="/wiki/Iron(II)_gluconate" title="Iron(II) gluconate">FeC12H22O14</a></li> <li><a href="/wiki/Iron_tetracarbonyl_diiodide" title="Iron tetracarbonyl diiodide">FeI2(CO)4</a></li></ul> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Organoiron(II)_compounds" scope="row" class="navbox-group" style="width:1%">Organoiron(II) compounds</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 class="mw-selflink selflink">Fe(C5H5)2</a></li> <li><a href="/wiki/Cyclopentadienyliron_dicarbonyl_iodide" title="Cyclopentadienyliron dicarbonyl iodide">Fe(C5H5)(CO)2I</a></li> <li><a href="/wiki/1,1%27-Bis(diphenylphosphino)ferrocene" title="1,1'-Bis(diphenylphosphino)ferrocene">Fe(C5H4P(C6H5)2)2</a></li> <li><a href="/wiki/Cyclobutadieneiron_tricarbonyl" title="Cyclobutadieneiron tricarbonyl">C4H4Fe(CO)3</a></li> <li><a href="/wiki/(Butadiene)iron_tricarbonyl" title="(Butadiene)iron tricarbonyl">C4H6Fe(CO)3</a></li></ul> </div></td></tr></tbody></table><div> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Fe(0,III)</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Iron_monosilicide" title="Iron monosilicide">FeSi</a></li> <li><a href="/wiki/Iron_germanide" title="Iron germanide">FeGe</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Fe(II,III)</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Iron(II,III)_oxide" title="Iron(II,III) oxide">Fe3O4</a></li> <li><a href="/wiki/Iron(II,III)_sulfide" title="Iron(II,III) sulfide">Fe3S4</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Fe(III)</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Iron(III)_iodide" title="Iron(III) iodide">FeI3</a></li> <li><a href="/wiki/Iron(III)_bromide" title="Iron(III) bromide">FeBr3</a></li> <li><a href="/wiki/Iron(III)_chloride" title="Iron(III) chloride">FeCl3</a></li> <li><a href="/wiki/Iron(III)_fluoride" title="Iron(III) fluoride">FeF3</a></li> <li><a href="/wiki/Iron_phosphide" title="Iron phosphide">FeP</a></li> <li><a href="/wiki/Iron(III)_nitrate" title="Iron(III) nitrate">Fe(NO3)3</a></li> <li><a href="/wiki/Tris(acetylacetonato)iron(III)" title="Tris(acetylacetonato)iron(III)">Fe(acac)3</a></li> <li><a href="/wiki/Iron_oxychloride" title="Iron oxychloride">FeOCl</a></li> <li><a href="/wiki/Tetraethylammonium_diiron_oxyhexachloride" title="Tetraethylammonium diiron oxyhexachloride">[(C2H5)4N][O(FeCl3)2]</a></li> <li><a href="/wiki/Iron(III)_oxide-hydroxide" title="Iron(III) oxide-hydroxide">FeO(OH)</a></li> <li><a href="/wiki/Iron(III)_phosphate" title="Iron(III) phosphate">FePO4</a></li> <li><a href="/wiki/Iron(III)_pyrophosphate" title="Iron(III) pyrophosphate">Fe4(P2O7)3</a></li> <li><a href="/wiki/Iron(III)_chromate" title="Iron(III) chromate">Fe2(CrO4)3</a></li> <li><a href="/wiki/Ferric_oxalate" title="Ferric oxalate">Fe2(C2O4)3</a></li> <li><a href="/wiki/Iron(III)_oxide" title="Iron(III) oxide">Fe2O3</a></li> <li><a href="/wiki/Iron(III)_selenite" title="Iron(III) selenite">Fe2(SeO3)3</a></li> <li><a href="/wiki/Iron(III)_sulfide" title="Iron(III) sulfide">Fe2S3</a></li> <li><a href="/wiki/Iron(III)_sulfate" title="Iron(III) sulfate">Fe2(SO4)3</a></li> <li><a href="/wiki/Iron(III)_azide" title="Iron(III) azide">Fe(N3)3</a></li> <li><a href="/wiki/Ammonium_iron(III)_sulfate" title="Ammonium iron(III) sulfate">NH4Fe(SO4)2·12H2O</a></li></ul> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Organoiron(III)_compounds" scope="row" class="navbox-group" style="width:1%">Organoiron(III) compounds</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/Ferrocenium_tetrafluoroborate" title="Ferrocenium tetrafluoroborate">Fe(C5H5)2BF4</a></li> <li><a href="/wiki/Ammonium_ferric_citrate" title="Ammonium ferric citrate">C6H8O7·xFe3+·yNH3</a></li> <li><a href="/wiki/Ferric_stearate" title="Ferric stearate">C 54H 105FeO 6</a></li></ul> </div></td></tr></tbody></table><div> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Fe(IV)</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Iron_tetrafluoride" title="Iron tetrafluoride">FeF4</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Fe(VI)</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Potassium_ferrate" title="Potassium ferrate">K2FeO4</a></li> <li><a href="/wiki/Barium_ferrate" title="Barium ferrate">BaFeO4</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Purported</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Hemolithin" title="Hemolithin">Hemolithin (protein)</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">sort</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Potassium_ferricyanide" title="Potassium ferricyanide">K3Fe(CN)6</a></li> <li><a href="/wiki/Potassium_ferrocyanide" title="Potassium ferrocyanide">K4Fe(CN)6</a></li> <li><a href="/wiki/Potassium_ferrioxalate" title="Potassium ferrioxalate">K3Fe(C2O4)3</a></li> <li><a href="/wiki/Potassium_ferrooxalate" title="Potassium ferrooxalate">K2Fe(C2O4)2</a></li> <li><a href="/wiki/Sodium_ferrioxalate" title="Sodium ferrioxalate">Na3Fe(C2O4)3</a></li> <li><a href="/wiki/Prussian_blue" title="Prussian blue">Prussian blue</a></li></ul> </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"></div><div role="navigation" class="navbox" aria-labelledby="Salts_and_covalent_derivatives_of_the_cyclopentadienide_ion" style="display:table;;padding:3px"><table class="nowraplinks mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit;table-layout:fixed;"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Cyclopentadienide_complexes" title="Template:Cyclopentadienide complexes"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Cyclopentadienide_complexes" title="Template talk:Cyclopentadienide complexes"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Cyclopentadienide_complexes" title="Special:EditPage/Template:Cyclopentadienide complexes"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Salts_and_covalent_derivatives_of_the_cyclopentadienide_ion" style="font-size:114%;margin:0 4em">Salts and covalent derivatives of the <a href="/wiki/Cyclopentadienide" class="mw-redirect" title="Cyclopentadienide">cyclopentadienide</a> ion</div></th></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0;border-width:0;"><div style="padding:0"><div class="mw-collapsible-content" style="overflow-x:auto"> <table class="center"> <tbody><tr style="background-color:mistyrose"> <td><a href="/wiki/Cyclopentadiene" title="Cyclopentadiene">CpH</a> </td> <td style="background-color:white;border:none"> </td> <td style="background-color:white;border:none" colspan="11" rowspan="3"> </td> <td style="background-color:white;border:none" colspan="5"> </td> <td>He </td></tr> <tr style="background-color:mistyrose"> <td><a href="/wiki/Lithium_cyclopentadienide" title="Lithium cyclopentadienide">LiCp</a> </td> <td>Be </td> <td>B </td> <td><a href="/wiki/Methylcyclopentadiene" title="Methylcyclopentadiene">CpMe</a> </td> <td>N </td> <td><a href="/wiki/Cyclopentadienone" title="Cyclopentadienone">C5H4O</a> </td> <td>F </td> <td>Ne </td></tr> <tr style="background-color:mistyrose"> <td><a href="/wiki/Sodium_cyclopentadienide" title="Sodium cyclopentadienide">NaCp</a> </td> <td><a href="/wiki/Magnesocene" title="Magnesocene">MgCp2</a> <a href="/wiki/Cyclopentadienyl_magnesium_bromide" title="Cyclopentadienyl magnesium bromide">MgCpBr</a> </td> <td>Al </td> <td>Si </td> <td>P </td> <td>S </td> <td>Cl </td> <td>Ar </td></tr> <tr style="background-color:mistyrose"> <td>K </td> <td><a href="/wiki/Calcium_cyclopentadienylide" class="mw-redirect" title="Calcium cyclopentadienylide">CaCp2</a> </td> <td style="background-color:white;border:none"> </td> <td><a href="/wiki/Scandocene" title="Scandocene">ScCp3</a> </td> <td><a href="/wiki/Titanocene_dichloride" title="Titanocene dichloride">TiCp2Cl2</a> <a href="/wiki/Nugent-RajanBabu_reagent" class="mw-redirect" title="Nugent-RajanBabu reagent">(TiCp2Cl)2</a> <a href="/wiki/(Cyclopentadienyl)titanium_trichloride" title="(Cyclopentadienyl)titanium trichloride">TiCpCl3</a> <a href="/wiki/Titanocene_pentasulfide" title="Titanocene pentasulfide">TiCp2S5</a> <a href="/wiki/Titanocene_dicarbonyl" title="Titanocene dicarbonyl">TiCp2(CO)2</a> <a href="/wiki/Petasis_reagent" title="Petasis reagent">TiCp2Me2</a> </td> <td><a href="/wiki/Vanadocene" title="Vanadocene">VCp2</a> <a href="/wiki/(Cycloheptatrienyl)(cyclopentadienyl)vanadium" title="(Cycloheptatrienyl)(cyclopentadienyl)vanadium">VCpCh</a> <a href="/wiki/Vanadocene_dichloride" title="Vanadocene dichloride">VCp2Cl2</a> <a href="/wiki/Cyclopentadienylvanadium_tetracarbonyl" title="Cyclopentadienylvanadium tetracarbonyl">VCp(CO)4</a> </td> <td><a href="/wiki/Chromocene" title="Chromocene">CrCp2</a> <a href="/wiki/Cyclopentadienylchromium_tricarbonyl_dimer" title="Cyclopentadienylchromium tricarbonyl dimer">(CrCp(CO)3)2</a> </td> <td><a href="/wiki/Manganocene" title="Manganocene">MnCp2</a> </td> <td><a class="mw-selflink selflink">FeCp2</a> <a href="/wiki/1,1%27-Dilithioferrocene" title="1,1'-Dilithioferrocene">Fe(η5-C5H4Li)2</a> <a href="/wiki/Biferrocene" title="Biferrocene">((C5H5)Fe(C5H4))2</a> <a href="/wiki/Bis(fulvalene)diiron" title="Bis(fulvalene)diiron">(C5H4-C5H4)2Fe2</a> <a href="/wiki/Ferrocenium_hexafluorophosphate" title="Ferrocenium hexafluorophosphate">FeCp2PF6</a> <a href="/wiki/Cyclopentadienyliron_dicarbonyl_iodide" title="Cyclopentadienyliron dicarbonyl iodide">FeCp(CO)2I</a> </td> <td><a href="/wiki/Cobaltocene" title="Cobaltocene">CoCp2</a> <a href="/wiki/Cyclopentadienylcobalt_dicarbonyl" title="Cyclopentadienylcobalt dicarbonyl">CoCp(CO)2</a> </td> <td><a href="/wiki/Nickelocene" title="Nickelocene">NiCp2</a> <a href="/wiki/Cyclopentadienyl_nickel_nitrosyl" title="Cyclopentadienyl nickel nitrosyl">NiCpNO</a> </td> <td>Cu </td> <td>Zn </td> <td>Ga </td> <td>Ge </td> <td>As </td> <td>Se </td> <td>Br </td> <td>Kr </td></tr> <tr style="background-color:mistyrose"> <td>Rb </td> <td>Sr </td> <td style="background-color:white;border:none"> </td> <td><a href="/wiki/Yttrocene" title="Yttrocene">Y(C5H5)3</a> </td> <td><a href="/wiki/Zirconocene_dichloride" title="Zirconocene dichloride">ZrCp2Cl2</a> <a href="/wiki/Schwartz%27s_reagent" title="Schwartz's reagent">ZrCp2ClH</a> </td> <td><a href="/wiki/Niobocene_dichloride" title="Niobocene dichloride">NbCp2Cl2</a> </td> <td><a href="/wiki/Molybdocene_dihydride" title="Molybdocene dihydride">MoCp2H2</a> <a href="/wiki/Molybdocene_dichloride" title="Molybdocene dichloride">MoCp2Cl2</a> <a href="/wiki/Cyclopentadienylmolybdenum_tricarbonyl_dimer" title="Cyclopentadienylmolybdenum tricarbonyl dimer">(MoCp(CO)3)2</a> </td> <td>Tc </td> <td><a href="/wiki/Ruthenocene" title="Ruthenocene">RuCp2</a> <a href="/wiki/Chloro(cyclopentadienyl)bis(triphenylphosphine)ruthenium" title="Chloro(cyclopentadienyl)bis(triphenylphosphine)ruthenium">RuCp(PPh3)2Cl</a> <a href="/wiki/Tris(acetonitrile)cyclopentadienylruthenium_hexafluorophosphate" title="Tris(acetonitrile)cyclopentadienylruthenium hexafluorophosphate">RuCp(MeCN)3PF6</a> </td> <td><a href="/wiki/Rhodocene" title="Rhodocene">RhCp2</a> </td> <td><a href="/wiki/Cyclopentadienyl_allyl_palladium" title="Cyclopentadienyl allyl palladium">PdCp(C3H5)</a> </td> <td>Ag </td> <td>Cd </td> <td><a href="/wiki/Cyclopentadienylindium(I)" title="Cyclopentadienylindium(I)">InCp</a> </td> <td><a href="/wiki/Stannocene" title="Stannocene">SnCp2</a> </td> <td>Sb </td> <td>Te </td> <td>I </td> <td>Xe </td></tr> <tr style="background-color:mistyrose"> <td>Cs </td> <td>Ba </td> <td style="background-color:white;border:none">* </td> <td><a href="/wiki/Lanthanocene" title="Lanthanocene">LuCp3</a> </td> <td><a href="/wiki/Hafnocene_dichloride" title="Hafnocene dichloride">HfCp2Cl2</a> </td> <td>Ta </td> <td><a href="/wiki/Cyclopentadienyltungsten_tricarbonyl_dimer" title="Cyclopentadienyltungsten tricarbonyl dimer">(WCp(CO)3)2</a> </td> <td><a href="/wiki/Rhenocene" class="mw-redirect" title="Rhenocene">ReCp2H</a> </td> <td><a href="/wiki/Osmocene" title="Osmocene">OsCp2</a> </td> <td><a href="/wiki/Iridocene" class="mw-redirect" title="Iridocene">IrCp2</a> </td> <td>Pt </td> <td>Au </td> <td>Hg </td> <td><a href="/wiki/Cyclopentadienylthallium" title="Cyclopentadienylthallium">TlCp</a> </td> <td><a href="/wiki/Plumbocene" title="Plumbocene">PbCp2</a> </td> <td>Bi </td> <td>Po </td> <td>At </td> <td>Rn </td></tr> <tr style="background-color:mistyrose"> <td>Fr </td> <td>Ra </td> <td style="background-color:white;border:none">** </td> <td>Lr </td> <td>Rf </td> <td>Db </td> <td>Sg </td> <td>Bh </td> <td><a href="/wiki/Hassocene" class="mw-redirect" title="Hassocene">HsCp2</a> </td> <td>Mt </td> <td>Ds </td> <td>Rg </td> <td>Cn </td> <td>Nh </td> <td>Fl </td> <td>Mc </td> <td>Lv </td> <td>Ts </td> <td>Og </td></tr> <tr> <td style="background-color:white;border:none" colspan="2" rowspan="3"> </td> <td style="background-color:white;border:none" colspan="20">  </td></tr> <tr style="background-color:mistyrose"> <td style="background-color:white;border:none">* </td> <td><a href="/wiki/Lanthanocene" title="Lanthanocene">LaCp3</a> </td> <td><a href="/wiki/Cerocene" title="Cerocene">CeCp3</a> </td> <td><a href="/wiki/Lanthanocene" title="Lanthanocene">PrCp3</a> </td> <td><a href="/wiki/Lanthanocene" title="Lanthanocene">NdCp3</a> </td> <td><a href="/wiki/Promethocene" title="Promethocene">PmCp3</a> </td> <td><a href="/wiki/Lanthanocene" title="Lanthanocene">SmCp3</a> </td> <td>Eu </td> <td>Gd </td> <td>Tb </td> <td><a href="/wiki/Lanthanocene" title="Lanthanocene">DyCp3</a> </td> <td>Ho </td> <td><a href="/wiki/Lanthanocene" title="Lanthanocene">ErCp3</a> </td> <td><a href="/wiki/Lanthanocene" title="Lanthanocene">TmCp3</a> </td> <td><a href="/wiki/Lanthanocene" title="Lanthanocene">YbCp3</a> </td></tr> <tr style="background-color:mistyrose"> <td style="background-color:white;border:none">** </td> <td>Ac </td> <td><a href="/wiki/Thorium#Organothorium_compounds" title="Thorium">ThCp3 ThCp4</a> </td> <td>Pa </td> <td><a href="/wiki/Tetrakis(cyclopentadienyl)uranium(IV)" title="Tetrakis(cyclopentadienyl)uranium(IV)">UCp4</a> </td> <td>Np </td> <td>Pu </td> <td>Am </td> <td>Cm </td> <td>Bk </td> <td>Cf </td> <td>Es </td> <td>Fm </td> <td>Md </td> <td>No </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></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 <a href="https://www.wikidata.org/wiki/Q211972#identifiers" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" 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