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vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Organic_chemistry"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Organic chemistry</span> </div> </a> <ul id="toc-Organic_chemistry-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Notes" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Notes"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Notes</span> </div> </a> <ul id="toc-Notes-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-External_links" class="vector-toc-list-item vector-toc-level-1 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Available in 39 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-39" aria-hidden="true" ><span class="vector-icon mw-ui-icon-language-progressive mw-ui-icon-wikimedia-language-progressive"></span> <span class="vector-dropdown-label-text">39 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-af mw-list-item"><a href="https://af.wikipedia.org/wiki/Propyn" title="Propyn – Afrikaans" lang="af" hreflang="af" data-title="Propyn" data-language-autonym="Afrikaans" data-language-local-name="Afrikaans" class="interlanguage-link-target"><span>Afrikaans</span></a></li><li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D8%A8%D8%B1%D9%88%D8%A8%D8%A7%D9%8A%D9%86" title="بروباين – Arabic" lang="ar" hreflang="ar" data-title="بروباين" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-az mw-list-item"><a href="https://az.wikipedia.org/wiki/Propin" title="Propin – Azerbaijani" lang="az" hreflang="az" data-title="Propin" data-language-autonym="Azərbaycanca" data-language-local-name="Azerbaijani" class="interlanguage-link-target"><span>Azərbaycanca</span></a></li><li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%D9%85%D8%AA%DB%8C%D9%84_%D8%A7%D8%B3%D8%AA%DB%8C%D9%84%D9%86" title="متیل استیلن – South Azerbaijani" lang="azb" hreflang="azb" data-title="متیل استیلن" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-bn mw-list-item"><a href="https://bn.wikipedia.org/wiki/%E0%A6%AA%E0%A7%8D%E0%A6%B0%E0%A7%8B%E0%A6%AA%E0%A6%BE%E0%A6%87%E0%A6%A8" title="প্রোপাইন – Bangla" lang="bn" hreflang="bn" data-title="প্রোপাইন" data-language-autonym="বাংলা" data-language-local-name="Bangla" class="interlanguage-link-target"><span>বাংলা</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Metilacetil%C3%A8" title="Metilacetilè – Catalan" lang="ca" hreflang="ca" data-title="Metilacetilè" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target"><span>Català</span></a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Propyn" title="Propyn – Czech" lang="cs" hreflang="cs" data-title="Propyn" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Propin" title="Propin – German" lang="de" hreflang="de" data-title="Propin" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/%CE%A0%CF%81%CE%BF%CF%80%CE%AF%CE%BD%CE%B9%CE%BF" title="Προπίνιο – Greek" lang="el" hreflang="el" data-title="Προπίνιο" data-language-autonym="Ελληνικά" data-language-local-name="Greek" class="interlanguage-link-target"><span>Ελληνικά</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Propino" title="Propino – Spanish" lang="es" hreflang="es" data-title="Propino" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-eo mw-list-item"><a href="https://eo.wikipedia.org/wiki/Propino" title="Propino – Esperanto" lang="eo" hreflang="eo" data-title="Propino" data-language-autonym="Esperanto" data-language-local-name="Esperanto" class="interlanguage-link-target"><span>Esperanto</span></a></li><li class="interlanguage-link interwiki-eu mw-list-item"><a href="https://eu.wikipedia.org/wiki/Propino" title="Propino – Basque" lang="eu" hreflang="eu" data-title="Propino" data-language-autonym="Euskara" data-language-local-name="Basque" class="interlanguage-link-target"><span>Euskara</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D9%BE%D8%B1%D9%88%D9%BE%DB%8C%D9%86" title="پروپین – Persian" lang="fa" hreflang="fa" data-title="پروپین" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Propyne" title="Propyne – French" lang="fr" hreflang="fr" data-title="Propyne" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%ED%94%84%EB%A1%9C%ED%8C%8C%EC%9D%B8" title="프로파인 – Korean" lang="ko" hreflang="ko" data-title="프로파인" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-hy mw-list-item"><a href="https://hy.wikipedia.org/wiki/%D5%8A%D6%80%D5%B8%D5%BA%D5%AB%D5%B6" title="Պրոպին – Armenian" lang="hy" hreflang="hy" data-title="Պրոպին" data-language-autonym="Հայերեն" data-language-local-name="Armenian" class="interlanguage-link-target"><span>Հայերեն</span></a></li><li class="interlanguage-link interwiki-hr mw-list-item"><a href="https://hr.wikipedia.org/wiki/Propin" title="Propin – Croatian" lang="hr" hreflang="hr" data-title="Propin" data-language-autonym="Hrvatski" data-language-local-name="Croatian" class="interlanguage-link-target"><span>Hrvatski</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Propuna" title="Propuna – Indonesian" lang="id" hreflang="id" data-title="Propuna" data-language-autonym="Bahasa Indonesia" data-language-local-name="Indonesian" class="interlanguage-link-target"><span>Bahasa Indonesia</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Propino" title="Propino – Italian" lang="it" hreflang="it" data-title="Propino" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-he mw-list-item"><a href="https://he.wikipedia.org/wiki/%D7%A4%D7%A8%D7%95%D7%A4%D7%99%D7%9F" title="פרופין – Hebrew" lang="he" hreflang="he" data-title="פרופין" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-kn mw-list-item"><a href="https://kn.wikipedia.org/wiki/%E0%B2%AA%E0%B3%8D%E0%B2%B0%E0%B3%8A%E0%B2%AA%E0%B3%88%E0%B2%A8%E0%B3%8D" title="ಪ್ರೊಪೈನ್ – Kannada" lang="kn" hreflang="kn" data-title="ಪ್ರೊಪೈನ್" data-language-autonym="ಕನ್ನಡ" data-language-local-name="Kannada" class="interlanguage-link-target"><span>ಕನ್ನಡ</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Propin" title="Propin – Hungarian" lang="hu" hreflang="hu" data-title="Propin" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Propyn" title="Propyn – Dutch" lang="nl" hreflang="nl" data-title="Propyn" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%83%97%E3%83%AD%E3%83%94%E3%83%B3" title="プロピン – Japanese" lang="ja" hreflang="ja" data-title="プロピン" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-no mw-list-item"><a href="https://no.wikipedia.org/wiki/Metylacetylen" title="Metylacetylen – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Metylacetylen" data-language-autonym="Norsk bokmål" data-language-local-name="Norwegian Bokmål" class="interlanguage-link-target"><span>Norsk bokmål</span></a></li><li class="interlanguage-link interwiki-nn mw-list-item"><a href="https://nn.wikipedia.org/wiki/Metylacetylen" title="Metylacetylen – Norwegian Nynorsk" lang="nn" hreflang="nn" data-title="Metylacetylen" data-language-autonym="Norsk nynorsk" data-language-local-name="Norwegian Nynorsk" class="interlanguage-link-target"><span>Norsk nynorsk</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Propyn" title="Propyn – Polish" lang="pl" hreflang="pl" data-title="Propyn" data-language-autonym="Polski" data-language-local-name="Polish" class="interlanguage-link-target"><span>Polski</span></a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/Metilacetileno" title="Metilacetileno – Portuguese" lang="pt" hreflang="pt" data-title="Metilacetileno" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target"><span>Português</span></a></li><li class="interlanguage-link interwiki-ro mw-list-item"><a href="https://ro.wikipedia.org/wiki/Propin%C4%83" title="Propină – Romanian" lang="ro" hreflang="ro" data-title="Propină" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%9F%D1%80%D0%BE%D0%BF%D0%B8%D0%BD" title="Пропин – Russian" lang="ru" hreflang="ru" data-title="Пропин" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Metilacetilen" title="Metilacetilen – Serbian" lang="sr" hreflang="sr" data-title="Metilacetilen" data-language-autonym="Српски / srpski" data-language-local-name="Serbian" class="interlanguage-link-target"><span>Српски / srpski</span></a></li><li class="interlanguage-link interwiki-sh mw-list-item"><a href="https://sh.wikipedia.org/wiki/Metilacetilen" title="Metilacetilen – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Metilacetilen" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Propyyni" title="Propyyni – Finnish" lang="fi" hreflang="fi" data-title="Propyyni" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-sv mw-list-item"><a href="https://sv.wikipedia.org/wiki/Propyn" title="Propyn – Swedish" lang="sv" hreflang="sv" data-title="Propyn" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%9F%D1%80%D0%BE%D0%BF%D1%96%D0%BD" title="Пропін – Ukrainian" lang="uk" hreflang="uk" data-title="Пропін" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-vi mw-list-item"><a href="https://vi.wikipedia.org/wiki/Propyn" title="Propyn – Vietnamese" lang="vi" hreflang="vi" data-title="Propyn" data-language-autonym="Tiếng Việt" data-language-local-name="Vietnamese" class="interlanguage-link-target"><span>Tiếng Việt</span></a></li><li class="interlanguage-link interwiki-wuu mw-list-item"><a href="https://wuu.wikipedia.org/wiki/%E4%B8%99%E7%82%94" title="丙炔 – Wu" lang="wuu" hreflang="wuu" data-title="丙炔" data-language-autonym="吴语" data-language-local-name="Wu" class="interlanguage-link-target"><span>吴语</span></a></li><li class="interlanguage-link interwiki-zh-yue mw-list-item"><a href="https://zh-yue.wikipedia.org/wiki/%E4%B8%99%E7%82%94" title="丙炔 – Cantonese" lang="yue" hreflang="yue" data-title="丙炔" data-language-autonym="粵語" data-language-local-name="Cantonese" class="interlanguage-link-target"><span>粵語</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E4%B8%99%E7%82%94" title="丙炔 – Chinese" lang="zh" hreflang="zh" data-title="丙炔" data-language-autonym="中文" data-language-local-name="Chinese" class="interlanguage-link-target"><span>中文</span></a></li> </ul> <div class="after-portlet after-portlet-lang"><span class="wb-langlinks-edit wb-langlinks-link"><a href="https://www.wikidata.org/wiki/Special:EntityPage/Q151446#sitelinks-wikipedia" title="Edit interlanguage links" class="wbc-editpage">Edit links</a></span></div> </div> </div> </div> </header> <div class="vector-page-toolbar"> <div class="vector-page-toolbar-container"> <div id="left-navigation"> <nav aria-label="Namespaces"> <div 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.hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">Not to be confused with <a href="/wiki/Propane" title="Propane">propane</a> or <a href="/wiki/Propene" class="mw-redirect" title="Propene">propene</a>.</div> <style data-mw-deduplicate="TemplateStyles:r1084375498">.mw-parser-output .ib-chembox{border-collapse:collapse;text-align:left}.mw-parser-output .ib-chembox td,.mw-parser-output .ib-chembox th{border:1px solid #a2a9b1;width:40%}.mw-parser-output .ib-chembox td+td{width:60%}</style> <table class="infobox ib-chembox"> <caption>Propyne </caption> <tbody><tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:PROPYNE.png" class="mw-file-description" title="Methylacetylene"><img alt="Methylacetylene" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/af/PROPYNE.png/120px-PROPYNE.png" decoding="async" width="120" height="72" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/af/PROPYNE.png/180px-PROPYNE.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/af/PROPYNE.png/240px-PROPYNE.png 2x" data-file-width="330" data-file-height="199" /></a></span> </td></tr> <tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:Propyne-3D-vdW.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/66/Propyne-3D-vdW.png/180px-Propyne-3D-vdW.png" decoding="async" width="180" height="117" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/66/Propyne-3D-vdW.png/270px-Propyne-3D-vdW.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/66/Propyne-3D-vdW.png/360px-Propyne-3D-vdW.png 2x" data-file-width="1100" data-file-height="713" /></a></span> </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;">Propyne<sup id="cite_ref-iupac2013_1-0" class="reference"><a href="#cite_note-iupac2013-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">[</span>note 1<span class="cite-bracket">]</span></a></sup></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;">Methylacetylene<br />Methyl acetylene<br />Allylene</div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Identifiers </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></div> </td> <td><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style><div class="plainlist"><ul><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=74-99-7">74-99-7</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=CC%23C">Interactive image</a></span></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Beilstein_database" title="Beilstein database">Beilstein Reference</a></div> </td> <td>878138 </td></tr> <tr> <td><a href="/wiki/ChEBI" title="ChEBI">ChEBI</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=48086">CHEBI:48086</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChEMBL" title="ChEMBL">ChEMBL</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembldb/index.php/compound/inspect/ChEMBL116902">ChEMBL116902</a></span><sup> <span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChemSpider" title="ChemSpider">ChemSpider</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.chemspider.com"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.6095.html">6095</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ECHA_InfoCard" class="mw-redirect" title="ECHA InfoCard"><span title="echa.europa.eu">ECHA InfoCard</span></a> </td> <td><a rel="nofollow" class="external text" href="https://echa.europa.eu/substance-information/-/substanceinfo/100.000.754">100.000.754</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q151446#P2566" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span> </td></tr> <tr> <td><a href="/wiki/European_Community_number" title="European Community number"><span title="European Community number (chemical identifier)">EC Number</span></a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li>200-828-4</li></ul></div> </td></tr> <tr> <td><a href="/wiki/Medical_Subject_Headings" title="Medical Subject Headings">MeSH</a> </td> <td><span title="www.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://www.nlm.nih.gov/cgi/mesh/2014/MB_cgi?mode=&term=C022030">C022030</a></span> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/PubChem" title="PubChem">PubChem</a> <abbr title="Compound ID">CID</abbr></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/6335">6335</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/Unique_Ingredient_Identifier" title="Unique Ingredient Identifier">UNII</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="precision.fda.gov"><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/086L40ET1B">086L40ET1B</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CompTox_Chemicals_Dashboard" title="CompTox Chemicals Dashboard">CompTox Dashboard</a> <span style="font-weight:normal">(<abbr title="U.S. Environmental Protection Agency">EPA</abbr>)</span></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="comptox.epa.gov"><a rel="nofollow" class="external text" href="https://comptox.epa.gov/dashboard/chemical/details/DTXSID0026387">DTXSID0026387</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q151446#P3117" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span></span></li></ul></div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal; background:transparent;"><div><a href="/wiki/International_Chemical_Identifier" title="International Chemical Identifier">InChI</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1S/C3H4/c1-3-2/h1H,2H3</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: MWWATHDPGQKSAR-UHFFFAOYSA-N</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/C3H4/c1-3-2/h1H,2H3</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: MWWATHDPGQKSAR-UHFFFAOYAI</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%;">CC#C</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><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><span class="chemf nowrap">C<sub class="template-chem2-sub">3</sub>H<sub class="template-chem2-sub">4</sub></span>  </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td>40.0639 g/mol    </td></tr> <tr> <td>Appearance </td> <td>Colorless gas<sup id="cite_ref-NIOSH_3-0" class="reference"><a href="#cite_note-NIOSH-3"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Odor" title="Odor">Odor</a> </td> <td>Sweet<sup id="cite_ref-NIOSH_3-1" class="reference"><a href="#cite_note-NIOSH-3"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Density" title="Density">Density</a> </td> <td>0.53 g/cm<sup>3</sup> </td></tr> <tr> <td><a href="/wiki/Melting_point" title="Melting point">Melting point</a> </td> <td>−102.7 °C (−152.9 °F; 170.5 K) </td></tr> <tr> <td><a href="/wiki/Boiling_point" title="Boiling point">Boiling point</a> </td> <td>−23.2 °C (−9.8 °F; 250.0 K) </td></tr> <tr> <td><a href="/wiki/Vapor_pressure" title="Vapor pressure">Vapor pressure</a> </td> <td>5.2 atm (20°C)<sup id="cite_ref-NIOSH_3-2" class="reference"><a href="#cite_note-NIOSH-3"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Hazards </th></tr> <tr> <td><a href="/wiki/Explosive_limit" class="mw-redirect" title="Explosive limit">Explosive limits</a> </td> <td>1.7%-?<sup id="cite_ref-NIOSH_3-3" class="reference"><a href="#cite_note-NIOSH-3"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </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"><b>NIOSH</b></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 1000 ppm (1650 mg/m<sup>3</sup>)<sup id="cite_ref-NIOSH_3-4" class="reference"><a href="#cite_note-NIOSH-3"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </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 1000 ppm (1650 mg/m<sup>3</sup>)<sup id="cite_ref-NIOSH_3-5" class="reference"><a href="#cite_note-NIOSH-3"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </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>1700 ppm<sup id="cite_ref-NIOSH_3-6" class="reference"><a href="#cite_note-NIOSH-3"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td colspan="2" style="text-align:left; background:#f8eaba; border:1px solid #a2a9b1;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Except where otherwise noted, data are given for materials in their <a href="/wiki/Standard_state" title="Standard state">standard state</a> (at 25 °C [77 °F], 100 kPa).</div> <div style="margin-top: 0.3em;"><div style="text-align:center;"><span typeof="mw:File"><span><img alt="☒" 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" /></span></span><span style="display:none">N</span> <span class="reflink plainlinks nourlexpansion"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=406858995&page2=Propyne">verify</a></span> (<a href="/wiki/Wikipedia:WikiProject_Chemicals/Chembox_validation" title="Wikipedia:WikiProject Chemicals/Chembox validation">what is</a> <sup><span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span><span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span></sup> ?) </div></div> <div style="margin-top: 0.3em; text-align: center;"><a href="/wiki/Wikipedia:Chemical_infobox#References" title="Wikipedia:Chemical infobox">Infobox references</a></div> </td></tr> </tbody></table><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Chemical compound</div> <p><b>Propyne</b> (<b>methylacetylene</b>) is an <a href="/wiki/Alkyne" title="Alkyne">alkyne</a> with the <a href="/wiki/Chemical_formula" title="Chemical formula">chemical formula</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>C≡CH</span>. It is a component of <a href="/wiki/MAPP_gas" title="MAPP gas">MAPD gas</a>—along with its <a href="/wiki/Isomer" title="Isomer">isomer</a> <a href="/wiki/Propadiene" title="Propadiene">propadiene</a> (allene), which was commonly used in <a href="/wiki/Gas_welding" class="mw-redirect" title="Gas welding">gas welding</a>. Unlike <a href="/wiki/Acetylene" title="Acetylene">acetylene</a>, propyne can be safely <a href="/wiki/Condensation" title="Condensation">condensed</a>.<sup id="cite_ref-Ullmann_4-0" class="reference"><a href="#cite_note-Ullmann-4"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Production_and_equilibrium_with_propadiene">Production and equilibrium with propadiene</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Propyne&action=edit&section=1" title="Edit section: Production and equilibrium with propadiene"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Propyne exists in equilibrium with <a href="/wiki/Propadiene" title="Propadiene">propadiene</a>, the mixture of propyne and propadiene being called MAPD: </p> <dl><dd><span class="mwe-math-element"><span class="mwe-math-mathml-inline mwe-math-mathml-a11y" style="display: none;"><math xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle {\ce {H3CC#CH <=> H2C=C=CH2}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <msubsup> <mtext>H</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>3</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mtext>CC</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>≡</mo> </mrow> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-REL"> <mover> <mrow class="MJX-TeXAtom-OP MJX-fixedlimits"> <mrow class="MJX-TeXAtom-ORD"> <mpadded height="0" depth="0"> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">↽</mo> </mrow> <mspace width="negativethinmathspace" /> <mspace width="negativethinmathspace" /> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> </mpadded> </mrow> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="false" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> <mspace width="negativethinmathspace" /> <mspace width="negativethinmathspace" /> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">⇀</mo> </mrow> </mrow> </mstyle> </mrow> </mover> </mrow> <msubsup> <mtext>H</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mtext>C</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>=</mo> </mrow> <mtext>C</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>=</mo> </mrow> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\ce {H3CC#CH <=> H2C=C=CH2}}}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/819ca886d51e0802ef0c73426455f0621078c949" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -1.005ex; width:30.276ex; height:3.343ex;" alt="{\displaystyle {\ce {H3CC#CH <=> H2C=C=CH2}}}"></span></dd></dl> <p>The coefficient of equilibrium <i>K</i><sub>eq</sub> is 0.22 at 270 °C or 0.1 at 5 °C. MAPD is produced as a side product, often an undesirable one, by <a href="/wiki/Cracking_(chemistry)" title="Cracking (chemistry)">cracking</a> <a href="/wiki/Propane" title="Propane">propane</a> to produce <a href="/wiki/Propene" class="mw-redirect" title="Propene">propene</a>, an important <a href="/wiki/Feedstock" class="mw-redirect" title="Feedstock">feedstock</a> in the <a href="/wiki/Chemical_industry" title="Chemical industry">chemical industry</a>.<sup id="cite_ref-Ullmann_4-1" class="reference"><a href="#cite_note-Ullmann-4"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> MAPD interferes with the <a href="/wiki/Ziegler%E2%80%93Natta_catalyst" title="Ziegler–Natta catalyst">catalytic</a> <a href="/wiki/Polymerization" title="Polymerization">polymerization</a> of propene. </p> <div class="mw-heading mw-heading3"><h3 id="Laboratory_methods">Laboratory methods</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Propyne&action=edit&section=2" title="Edit section: Laboratory methods"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Propyne can also be synthesized on laboratory scale by reducing <a href="/wiki/1-propanol" class="mw-redirect" title="1-propanol">1-propanol</a>,<sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Allyl_alcohol" title="Allyl alcohol">allyl alcohol</a> or <a href="/wiki/Acetone" title="Acetone">acetone</a><sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> vapors over magnesium. </p> <div class="mw-heading mw-heading2"><h2 id="Use_as_a_rocket_fuel">Use as a rocket fuel</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Propyne&action=edit&section=3" title="Edit section: Use as a rocket fuel"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>European space companies have researched using light <a href="/wiki/Hydrocarbons" class="mw-redirect" title="Hydrocarbons">hydrocarbons</a> with <a href="/wiki/Liquid_oxygen" title="Liquid oxygen">liquid oxygen</a>, a relatively high performing <a href="/wiki/Liquid_rocket_propellant" title="Liquid rocket propellant">liquid rocket propellant</a> combination that would also be less toxic than the commonly used MMH/NTO (<a href="/wiki/Monomethylhydrazine" title="Monomethylhydrazine">monomethylhydrazine</a>/<a href="/wiki/Nitrogen_tetroxide" class="mw-redirect" title="Nitrogen tetroxide">nitrogen tetroxide</a>). Their research showed<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (September 2013)">citation needed</span></a></i>]</sup> that propyne would be highly advantageous as a <a href="/wiki/Rocket_fuel" class="mw-redirect" title="Rocket fuel">rocket fuel</a> for craft intended for <a href="/wiki/Low_Earth_orbit" title="Low Earth orbit">low Earth orbital</a> operations. They reached this conclusion based upon a <a href="/wiki/Specific_impulse" title="Specific impulse">specific impulse</a> expected to reach 370 <a href="/wiki/Second" title="Second">s</a> with oxygen as the oxidizer, a high <a href="/wiki/Density" title="Density">density</a> and <a href="/wiki/Power_density" title="Power density">power density</a>—and the moderate <a href="/wiki/Boiling_point" title="Boiling point">boiling point</a>, which makes the chemical easier to store than <a href="/wiki/Cryogenic_fuel" title="Cryogenic fuel">cryogenic fuels</a> that must be kept at extremely low temperatures.<sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Organic_chemistry">Organic chemistry</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Propyne&action=edit&section=4" title="Edit section: Organic chemistry"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Propyne is a convenient three-carbon building block for <a href="/wiki/Organic_synthesis" title="Organic synthesis">organic synthesis</a>. Deprotonation with <a href="/wiki/N-Butyllithium" title="N-Butyllithium"><i>n</i>-butyllithium</a> gives <a href="/wiki/Propynyllithium" title="Propynyllithium">propynyllithium</a>. This <a href="/wiki/Nucleophilic" class="mw-redirect" title="Nucleophilic">nucleophilic</a> reagent adds to <a href="/wiki/Carbonyl" class="mw-redirect" title="Carbonyl">carbonyl</a> groups, producing <a href="/wiki/Alcohol_(chemistry)" title="Alcohol (chemistry)">alcohols</a> and <a href="/wiki/Ester" title="Ester">esters</a>.<sup id="cite_ref-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> Whereas purified propyne is expensive, MAPP gas could be used to cheaply generate large amounts of the reagent.<sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p><p>Propyne, along with <a href="/wiki/2-butyne" class="mw-redirect" title="2-butyne">2-butyne</a>, is also used to synthesize <a href="/wiki/Alkylated" class="mw-redirect" title="Alkylated">alkylated</a> <a href="/wiki/Hydroquinone" title="Hydroquinone">hydroquinones</a> in the <a href="/wiki/Total_synthesis" title="Total synthesis">total synthesis</a> of <a href="/wiki/Vitamin_E" title="Vitamin E">vitamin E</a>.<sup id="cite_ref-Cyclization_10-0" class="reference"><a href="#cite_note-Cyclization-10"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p><p>The chemical shift of an alkynyl proton and propargylic proton generally occur in the same region of the <a href="/wiki/Proton_nuclear_magnetic_resonance" title="Proton nuclear magnetic resonance"><sup>1</sup>H NMR</a> spectrum. In propyne, these two signals have almost exactly the same chemical shifts, leading to overlap of the signals, and the <sup>1</sup>H NMR spectrum of propyne, when recorded in deuteriochloroform on a 300 MHz instrument, consists of a single signal, a sharp singlet resonating at 1.8 ppm.<sup id="cite_ref-11" class="reference"><a href="#cite_note-11"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Notes">Notes</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Propyne&action=edit&section=5" title="Edit section: Notes"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-references-wrap"><ol class="references"> <li id="cite_note-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-2">^</a></b></span> <span class="reference-text">"Prop-1-yne" mistake fixed in the <a rel="nofollow" class="external text" href="https://www.qmul.ac.uk/sbcs/iupac/bibliog/BBerrors.html">errata</a> <a rel="nofollow" class="external text" href="https://web.archive.org/web/20190801093648/https://www.qmul.ac.uk/sbcs/iupac/bibliog/BBerrors.html">Archived</a> 2019-08-01 at the <a href="/wiki/Wayback_Machine" title="Wayback Machine">Wayback Machine</a>. The locant is omitted according to P-14.3.4.2 (d), p. 31 for propene and P-31.1.1.1, Examples, p. 374 for propyne.</span> </li> </ol></div> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Propyne&action=edit&section=6" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-references-wrap"><ol class="references"> <li id="cite_note-iupac2013-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-iupac2013_1-0">^</a></b></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite class="citation book cs1">"Characteristic (Functional) and Substituent Groups". <i>Nomenclature of Organic Chemistry. IUPAC Recommendations and Preferred Names 2013 (Blue Book)</i>. Cambridge: <a href="/wiki/Royal_Society_of_Chemistry" title="Royal Society of Chemistry">The Royal Society of Chemistry</a>. 2014. p. 374. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1039%2F9781849733069-00372">10.1039/9781849733069-00372</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-85404-182-4" title="Special:BookSources/978-0-85404-182-4"><bdi>978-0-85404-182-4</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Characteristic+%28Functional%29+and+Substituent+Groups&rft.btitle=Nomenclature+of+Organic+Chemistry.+IUPAC+Recommendations+and+Preferred+Names+2013+%28Blue+Book%29&rft.place=Cambridge&rft.pages=374&rft.pub=The+Royal+Society+of+Chemistry&rft.date=2014&rft_id=info%3Adoi%2F10.1039%2F9781849733069-00372&rft.isbn=978-0-85404-182-4&rfr_id=info%3Asid%2Fen.wikipedia.org%3APropyne" class="Z3988"></span></span> </li> <li id="cite_note-NIOSH-3"><span class="mw-cite-backlink">^ <a href="#cite_ref-NIOSH_3-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-NIOSH_3-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-NIOSH_3-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-NIOSH_3-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-NIOSH_3-4"><sup><i><b>e</b></i></sup></a> <a href="#cite_ref-NIOSH_3-5"><sup><i><b>f</b></i></sup></a> <a href="#cite_ref-NIOSH_3-6"><sup><i><b>g</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFNIOSH_Pocket_Guide_to_Chemical_Hazards" class="citation web cs1">NIOSH Pocket Guide to Chemical Hazards. <a rel="nofollow" class="external text" href="https://www.cdc.gov/niosh/npg/npgd0392.html">"#0392"</a>. <a href="/wiki/National_Institute_for_Occupational_Safety_and_Health" title="National Institute for Occupational Safety and Health">National Institute for Occupational Safety and Health</a> (NIOSH).</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=%230392&rft.pub=National+Institute+for+Occupational+Safety+and+Health+%28NIOSH%29&rft.au=NIOSH+Pocket+Guide+to+Chemical+Hazards&rft_id=https%3A%2F%2Fwww.cdc.gov%2Fniosh%2Fnpg%2Fnpgd0392.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3APropyne" class="Z3988"></span></span> </li> <li id="cite_note-Ullmann-4"><span class="mw-cite-backlink">^ <a href="#cite_ref-Ullmann_4-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Ullmann_4-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text">Peter Pässler, Werner Hefner, Klaus Buckl, Helmut Meinass, Andreas Meiswinkel, Hans-Jürgen Wernicke, Günter Ebersberg, Richard Müller, Jürgen Bässler, Hartmut Behringer, Dieter Mayer, "Acetylene" in Ullmann's Encyclopedia of Industrial Chemistry Wiley-VCH, Weinheim 2007 (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2F14356007.a01_097.pub2">10.1002/14356007.a01_097.pub2</a>).</span> </li> <li id="cite_note-5"><span class="mw-cite-backlink"><b><a href="#cite_ref-5">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFKeiser,_EdwardBreed,_Mary1895" class="citation journal cs1">Keiser, Edward & Breed, Mary (1895). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=jn-VkwcIt5QC&q=allylene+franklin+magnesium&pg=PA309">"The Action of Magnesium Upon the Vapors of the Alcohols and a New Method of Preparing Allylene"</a>. <i>Journal of the Franklin Institute</i>. <b>CXXXIX</b> (4): 304–309. <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%2F0016-0032%2885%2990206-6">10.1016/0016-0032(85)90206-6</a><span class="reference-accessdate">. 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Heathcock (1990). <a rel="nofollow" class="external text" href="http://www.orgsyn.org/demo.aspx?prep=CV7P0226">"Ethyl Isocrotonate"</a>. <i><a href="/wiki/Organic_Syntheses" title="Organic Syntheses">Organic Syntheses</a></i></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Organic+Syntheses&rft.atitle=Ethyl+Isocrotonate&rft.date=1990&rft.au=Michael+J.+Taschner&rft.au=Terry+Rosen&rft.au=Clayton+H.+Heathcock&rft_id=http%3A%2F%2Fwww.orgsyn.org%2Fdemo.aspx%3Fprep%3DCV7P0226&rfr_id=info%3Asid%2Fen.wikipedia.org%3APropyne" class="Z3988"></span>; <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation cs2"><i>Collected Volumes</i>, vol. 7, p. 226</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Collected+Volumes&rft.pages=226&rfr_id=info%3Asid%2Fen.wikipedia.org%3APropyne" class="Z3988"></span>.</span> </li> <li id="cite_note-9"><span class="mw-cite-backlink"><b><a href="#cite_ref-9">^</a></b></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1041539562">.mw-parser-output .citation{word-wrap:break-word}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}</style><span class="citation patent" id="harv"><a rel="nofollow" class="external text" href="https://worldwide.espacenet.com/textdoc?DB=EPODOC&IDX=US5744071">US patent 5744071</a>, Philip Franklin Sims, Anne Pautard-Cooper, "Processes for preparing alkynyl ketones and precursors thereof", issued 1996-11-19</span><span class="Z3988" title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Apatent&rft.number=5744071&rft.cc=US&rft.title=Processes+for+preparing+alkynyl+ketones+and+precursors+thereof&rft.inventor=Philip+Franklin+Sims%2C+Anne+Pautard-Cooper&rft.date=1996-11-19"><span style="display: none;"> </span></span></span> </li> <li id="cite_note-Cyclization-10"><span class="mw-cite-backlink"><b><a href="#cite_ref-Cyclization_10-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFReppe,_WalterKutepow,_NMagin,_A1969" class="citation journal cs1">Reppe, Walter; Kutepow, N & Magin, A (1969). 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Freeman. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9781936221349" title="Special:BookSources/9781936221349"><bdi>9781936221349</bdi></a>. <a href="/wiki/OCLC_(identifier)" class="mw-redirect" title="OCLC (identifier)">OCLC</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/oclc/907161629">907161629</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Organic+chemistry&rft.place=Greenwood+Village%2C+Colorado&rft.edition=Sixth&rft.pub=W.+H.+Freeman&rft.date=2015-08-26&rft_id=info%3Aoclcnum%2F907161629&rft.isbn=9781936221349&rft.aulast=Loudon&rft.aufirst=Marc&rft.au=Parise%2C+Jim&rfr_id=info%3Asid%2Fen.wikipedia.org%3APropyne" class="Z3988"></span></span> </li> </ol></div> <div class="mw-heading mw-heading2"><h2 id="External_links">External links</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Propyne&action=edit&section=7" title="Edit section: External links"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a rel="nofollow" class="external text" href="http://webbook.nist.gov/cgi/cbook.cgi?ID=C74997">NIST Chemistry WebBook page for propyne</a></li> <li><a rel="nofollow" class="external text" href="https://web.archive.org/web/20060110171612/http://www.la.dlr.de/ra/sart/publications/pdf/esa02-2004.pdf">German Aerospace Center</a></li> <li><a rel="nofollow" class="external text" href="https://web.archive.org/web/20070928144135/http://www.novachem.com/ProductServices/docs/CrudePropylene_MSDS_EN.pdf">Nova Chemicals</a></li> <li><a rel="nofollow" class="external text" href="https://www.cdc.gov/niosh/npg/npgd0392.html">CDC - NIOSH Pocket Guide to Chemical Hazards</a></li></ul> <div class="navbox-styles"><style data-mw-deduplicate="TemplateStyles:r1129693374">.mw-parser-output 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.navbar-brackets::before{margin-right:-0.125em;content:"[ "}.mw-parser-output .navbar-brackets::after{margin-left:-0.125em;content:" ]"}.mw-parser-output .navbar li{word-spacing:-0.125em}.mw-parser-output .navbar a>span,.mw-parser-output .navbar a>abbr{text-decoration:inherit}.mw-parser-output .navbar-mini abbr{font-variant:small-caps;border-bottom:none;text-decoration:none;cursor:inherit}.mw-parser-output .navbar-ct-full{font-size:114%;margin:0 7em}.mw-parser-output .navbar-ct-mini{font-size:114%;margin:0 4em}html.skin-theme-clientpref-night .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}@media(prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}}@media print{.mw-parser-output .navbar{display:none!important}}</style><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Alkynes" title="Template:Alkynes"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Alkynes" title="Template talk:Alkynes"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Alkynes" title="Special:EditPage/Template:Alkynes"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Alkynes" style="font-size:114%;margin:0 4em"><a href="/wiki/Alkyne" title="Alkyne">Alkynes</a></div></th></tr><tr><td colspan="2" class="navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acetylene" title="Acetylene">Ethyne</a> (<span class="chemf nowrap">C<sub class="template-chem2-sub">2</sub>H<sub class="template-chem2-sub">2</sub></span>)</li> <li><a class="mw-selflink selflink">Propyne</a> (<span class="chemf nowrap">C<sub class="template-chem2-sub">3</sub>H<sub class="template-chem2-sub">4</sub></span>)</li> <li><a href="/wiki/Butyne" title="Butyne">Butyne</a> (<span class="chemf nowrap">C<sub class="template-chem2-sub">4</sub>H<sub class="template-chem2-sub">6</sub></span>) <ul><li><a href="/wiki/1-Butyne" title="1-Butyne">1</a></li> <li><a href="/wiki/2-Butyne" title="2-Butyne">2</a></li></ul></li> <li><a href="/wiki/Pentyne" title="Pentyne">Pentyne</a> (<span class="chemf nowrap">C<sub class="template-chem2-sub">5</sub>H<sub class="template-chem2-sub">8</sub></span>) <ul><li><a href="/wiki/1-Pentyne" title="1-Pentyne">1</a></li> <li><a href="/wiki/2-Pentyne" title="2-Pentyne">2</a></li></ul></li> <li><a href="/wiki/Hexyne" title="Hexyne">Hexyne</a> (<span class="chemf nowrap">C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">10</sub></span>) <ul><li><a href="/wiki/1-Hexyne" title="1-Hexyne">1</a></li> <li><a href="/wiki/2-Hexyne" title="2-Hexyne">2</a></li> <li><a href="/wiki/3-Hexyne" title="3-Hexyne">3</a></li></ul></li> <li><a href="/wiki/Heptyne" title="Heptyne">Heptyne</a> (<span class="chemf nowrap">C<sub class="template-chem2-sub">7</sub>H<sub class="template-chem2-sub">12</sub></span>)</li> <li><a href="/wiki/Octyne" title="Octyne">Octyne</a> (<span class="chemf nowrap">C<sub class="template-chem2-sub">8</sub>H<sub class="template-chem2-sub">14</sub></span>) <ul><li><a href="/wiki/2-Octyne" title="2-Octyne">2</a></li> <li><a href="/wiki/4-Octyne" title="4-Octyne">4</a></li></ul></li> <li><a href="/wiki/Nonyne" title="Nonyne">Nonyne</a> (<span class="chemf nowrap">C<sub class="template-chem2-sub">9</sub>H<sub class="template-chem2-sub">16</sub></span>)</li> <li><a href="/wiki/Decyne" title="Decyne">Decyne</a> (<span class="chemf nowrap">C<sub class="template-chem2-sub">10</sub>H<sub class="template-chem2-sub">18</sub></span>) <ul><li><a href="/wiki/1-Decyne" title="1-Decyne">1</a></li> <li><a href="/wiki/5-Decyne" title="5-Decyne">5</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Preparations</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/Cracking_(chemistry)" title="Cracking (chemistry)">Cracking</a></li> <li><a href="/wiki/Dehydrogenation" title="Dehydrogenation">Dehydrogenation</a> of <a href="/wiki/Alkane" title="Alkane">alkane</a>, <a href="/wiki/Alkene" title="Alkene">alkene</a></li> <li><a href="/wiki/Alkylation" title="Alkylation">Alkylation</a> of <a href="/wiki/Acetylide" title="Acetylide">alkynyl anion</a></li> <li><a href="/wiki/Dehydrohalogenation" title="Dehydrohalogenation">Dehydrohalogenation</a> of <a href="/wiki/Dihaloalkane" class="mw-redirect" title="Dihaloalkane">dihaloalkane</a></li> <li><a href="/wiki/Fritsch%E2%80%93Buttenberg%E2%80%93Wiechell_rearrangement" title="Fritsch–Buttenberg–Wiechell rearrangement">Fritsch–Buttenberg–Wiechell rearrangement</a></li> <li><a href="/wiki/Corey%E2%80%93Fuchs_reaction" title="Corey–Fuchs reaction">Corey–Fuchs reaction</a></li> <li><a href="/wiki/Seyferth%E2%80%93Gilbert_homologation" title="Seyferth–Gilbert homologation">Seyferth–Gilbert homologation</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Reactions</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/Acetylide" title="Acetylide">Deprotonation</a></li> <li><a href="/wiki/Hydrogenation" title="Hydrogenation">Hydrogenation</a></li> <li><a href="/wiki/Halogenation" title="Halogenation">Halogenation</a></li> <li><a href="/wiki/Hydration_reaction" title="Hydration reaction">Hydration</a></li> <li><a href="/wiki/Hydroboration" title="Hydroboration">Hydroboration</a></li> <li><a href="/wiki/Hydrohalogenation" title="Hydrohalogenation">Hydrohalogenation</a></li> <li><a href="/wiki/Alkynylation" title="Alkynylation">Alkynylation</a></li> <li><a href="/wiki/Thiol-yne_reaction" title="Thiol-yne reaction">Thiol-yne reaction</a></li> <li><a href="/wiki/Alkyne_trimerisation" title="Alkyne trimerisation">Alkyne trimerisation</a></li> <li><a href="/wiki/Diels%E2%80%93Alder_reaction" title="Diels–Alder reaction">Diels–Alder reaction</a></li> <li><a href="/wiki/Pauson%E2%80%93Khand_reaction" title="Pauson–Khand reaction">Pauson–Khand reaction</a></li> <li><a href="/wiki/Azide-alkyne_Huisgen_cycloaddition" title="Azide-alkyne Huisgen cycloaddition">Azide-alkyne Huisgen cycloaddition</a></li> <li><a href="/wiki/Sonogashira_coupling" title="Sonogashira coupling">Sonogashira coupling</a></li> <li><a href="/wiki/Cadiot%E2%80%93Chodkiewicz_coupling" title="Cadiot–Chodkiewicz coupling">Cadiot–Chodkiewicz coupling</a></li> <li><a href="/wiki/Glaser_coupling" title="Glaser coupling">Glaser coupling</a></li> <li><a href="/wiki/Favorskii_reaction" title="Favorskii reaction">Favorskii reaction</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="Molecules_detected_in_outer_space" style="padding:3px"><table class="nowraplinks hlist mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><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:Molecules_detected_in_outer_space" title="Template:Molecules detected in outer space"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Molecules_detected_in_outer_space" title="Template talk:Molecules detected in outer space"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Molecules_detected_in_outer_space" title="Special:EditPage/Template:Molecules detected in outer space"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Molecules_detected_in_outer_space" style="font-size:114%;margin:0 4em"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules" title="List of interstellar and circumstellar molecules">Molecules detected in outer space</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Molecule" title="Molecule">Molecules</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Diatomic_molecule" title="Diatomic molecule">Diatomic</a></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/Aluminium_monochloride" title="Aluminium monochloride">Aluminium monochloride</a></li> <li><a href="/wiki/Aluminium_monofluoride" title="Aluminium monofluoride">Aluminium monofluoride</a></li> <li><a href="/wiki/Aluminium(II)_oxide" title="Aluminium(II) oxide">Aluminium(II) oxide</a></li> <li><a href="/wiki/Argonium" title="Argonium">Argonium</a></li> <li><a href="/wiki/Carbon_cation" class="mw-redirect" title="Carbon cation">Carbon cation</a></li> <li><a href="/wiki/Carbon_monophosphide" title="Carbon monophosphide">Carbon monophosphide</a></li> <li><a href="/wiki/Carbon_monosulfide" title="Carbon monosulfide">Carbon monosulfide</a></li> <li><a href="/wiki/Carbon_monoxide" title="Carbon monoxide">Carbon monoxide</a></li> <li><a href="/wiki/Cyano_radical" title="Cyano radical">Cyano radical</a></li> <li><a href="/wiki/Diatomic_carbon" title="Diatomic carbon">Diatomic carbon</a></li> <li><a href="/w/index.php?title=Fluoromethylidynium&action=edit&redlink=1" class="new" title="Fluoromethylidynium (page does not exist)">Fluoromethylidynium</a></li> <li><a href="/wiki/Helium_hydride_ion" title="Helium hydride ion">Helium hydride ion</a></li> <li><a href="/wiki/Hydrogen_chloride" title="Hydrogen chloride">Hydrogen chloride</a></li> <li><a href="/wiki/Hydrogen_fluoride" title="Hydrogen fluoride">Hydrogen fluoride</a></li> <li><a href="/wiki/Hydrogen" title="Hydrogen">Hydrogen</a> (molecular)</li> <li><a href="/wiki/Hydroxyl_radical" title="Hydroxyl radical">Hydroxyl radical</a></li> <li><a href="/wiki/Iron(II)_oxide" title="Iron(II) oxide">Iron(II) oxide</a></li> <li><a href="/wiki/Magnesium_monohydride" title="Magnesium monohydride">Magnesium monohydride</a></li> <li><a href="/wiki/Methylidyne_radical" title="Methylidyne radical">Methylidyne radical</a></li> <li><a href="/wiki/Nitric_oxide" title="Nitric oxide">Nitric oxide</a></li> <li><a href="/wiki/Nitrogen" title="Nitrogen">Nitrogen</a> (molecular)</li> <li><a href="/wiki/Imidogen" title="Imidogen">Imidogen</a></li> <li><a href="/wiki/Sulfur_mononitride" title="Sulfur mononitride">Sulfur mononitride</a></li> <li><a href="/wiki/Oxygen" title="Oxygen">Oxygen</a> (molecular)</li> <li><a href="/wiki/Phosphorus_monoxide" title="Phosphorus monoxide">Phosphorus monoxide</a></li> <li><a href="/wiki/Phosphorus_mononitride" title="Phosphorus mononitride">Phosphorus mononitride</a></li> <li><a href="/wiki/Potassium_chloride" title="Potassium chloride">Potassium chloride</a></li> <li><a href="/wiki/Silicon_carbide" title="Silicon carbide">Silicon carbide</a></li> <li><a href="/wiki/Silicon_monoxide" title="Silicon monoxide">Silicon monoxide</a></li> <li><a href="/wiki/Silicon_monosulfide" title="Silicon monosulfide">Silicon monosulfide</a></li> <li><a href="/wiki/Sodium_chloride" title="Sodium chloride">Sodium chloride</a></li> <li><a href="/wiki/Sodium_iodide" title="Sodium iodide">Sodium iodide</a></li> <li><a href="/wiki/Sulfanyl" title="Sulfanyl">Sulfanyl</a></li> <li><a href="/wiki/Sulfur_monoxide" title="Sulfur monoxide">Sulfur monoxide</a></li> <li><a href="/wiki/Titanium(II)_oxide" title="Titanium(II) oxide">Titanium(II) oxide</a></li></ul> </div></td><td class="noviewer navbox-image" rowspan="9" style="width:1px;padding:0 0 0 2px"><div><span typeof="mw:File"><a href="/wiki/Nitrous_oxide" title="Nitrous oxide"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/93/Nitrous-oxide-3D-balls.png/60px-Nitrous-oxide-3D-balls.png" decoding="async" width="60" height="24" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/93/Nitrous-oxide-3D-balls.png/90px-Nitrous-oxide-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/93/Nitrous-oxide-3D-balls.png/120px-Nitrous-oxide-3D-balls.png 2x" data-file-width="1100" data-file-height="441" /></a></span> <br /><br /><br /><br /> <span typeof="mw:File"><a href="/wiki/Ethanol" title="Ethanol"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b0/Ethanol-3D-balls.png/60px-Ethanol-3D-balls.png" decoding="async" width="60" height="41" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b0/Ethanol-3D-balls.png/90px-Ethanol-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b0/Ethanol-3D-balls.png/120px-Ethanol-3D-balls.png 2x" data-file-width="1100" data-file-height="754" /></a></span> <br /><br /><br /><br /> <span typeof="mw:File"><a href="/wiki/Buckminsterfullerene" title="Buckminsterfullerene"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/0f/Buckminsterfullerene-perspective-3D-balls.png/60px-Buckminsterfullerene-perspective-3D-balls.png" decoding="async" width="60" height="63" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/0f/Buckminsterfullerene-perspective-3D-balls.png/90px-Buckminsterfullerene-perspective-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/0f/Buckminsterfullerene-perspective-3D-balls.png/120px-Buckminsterfullerene-perspective-3D-balls.png 2x" data-file-width="1056" data-file-height="1100" /></a></span></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Triatomic_molecule" title="Triatomic molecule">Triatomic</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Aluminium(I)_hydroxide" class="mw-redirect" title="Aluminium(I) hydroxide">Aluminium(I) hydroxide</a></li> <li><a href="/w/index.php?title=Aluminium_isocyanide&action=edit&redlink=1" class="new" title="Aluminium isocyanide (page does not exist)">Aluminium isocyanide</a></li> <li><a href="/wiki/Amino_radical" title="Amino radical">Amino radical</a></li> <li><a href="/wiki/Carbon_dioxide" title="Carbon dioxide">Carbon dioxide</a></li> <li><a href="/wiki/Carbonyl_sulfide" title="Carbonyl sulfide">Carbonyl sulfide</a></li> <li><a href="/w/index.php?title=CCP_radical&action=edit&redlink=1" class="new" title="CCP radical (page does not exist)">CCP radical</a></li> <li><a href="/wiki/Halonium_ion" title="Halonium ion">Chloronium</a></li> <li><a href="/wiki/Diazenylium" title="Diazenylium">Diazenylium</a></li> <li><a href="/wiki/Dicarbon_monoxide" title="Dicarbon monoxide">Dicarbon monoxide</a></li> <li><a href="/w/index.php?title=Disilicon_carbide&action=edit&redlink=1" class="new" title="Disilicon carbide (page does not exist)">Disilicon carbide</a></li> <li><a href="/wiki/Ethynyl_radical" title="Ethynyl radical">Ethynyl radical</a></li> <li><a href="/w/index.php?title=Formyl_radical&action=edit&redlink=1" class="new" title="Formyl radical (page does not exist)">Formyl radical</a></li> <li><a href="/wiki/Hydrogen_cyanide" title="Hydrogen cyanide">Hydrogen cyanide</a> (HCN)</li> <li><a href="/wiki/Hydrogen_isocyanide" title="Hydrogen isocyanide">Hydrogen isocyanide</a> (HNC)</li> <li><a href="/wiki/Hydrogen_sulfide" title="Hydrogen sulfide">Hydrogen sulfide</a></li> <li><a href="/wiki/Hydroperoxyl" title="Hydroperoxyl">Hydroperoxyl</a></li> <li><a href="/w/index.php?title=Iron_cyanide&action=edit&redlink=1" class="new" title="Iron cyanide (page does not exist)">Iron cyanide</a></li> <li><a href="/w/index.php?title=Isoformyl&action=edit&redlink=1" class="new" title="Isoformyl (page does not exist)">Isoformyl</a></li> <li><a href="/wiki/Magnesium_cyanide" title="Magnesium cyanide">Magnesium cyanide</a></li> <li><a href="/w/index.php?title=Magnesium_isocyanide&action=edit&redlink=1" class="new" title="Magnesium isocyanide (page does not exist)">Magnesium isocyanide</a></li> <li><a href="/wiki/Methylene_(compound)" title="Methylene (compound)">Methylene</a></li> <li><a href="/wiki/Diazenylium" title="Diazenylium">N<sub>2</sub>H<sup>+</sup></a></li> <li><a href="/wiki/Nitrous_oxide" title="Nitrous oxide">Nitrous oxide</a></li> <li><a href="/wiki/Nitroxyl" title="Nitroxyl">Nitroxyl</a></li> <li><a href="/wiki/Ozone" title="Ozone">Ozone</a></li> <li><a href="/wiki/Methylidynephosphane" title="Methylidynephosphane">Methylidynephosphane</a></li> <li><a href="/wiki/Potassium_cyanide" title="Potassium cyanide">Potassium cyanide</a></li> <li><a href="/wiki/Trihydrogen_cation" title="Trihydrogen cation">Trihydrogen cation</a></li> <li><a href="/wiki/Sodium_cyanide" title="Sodium cyanide">Sodium cyanide</a></li> <li><a href="/wiki/Sodium_hydroxide" title="Sodium hydroxide">Sodium hydroxide</a></li> <li><a href="/w/index.php?title=Silicon_carbonitride&action=edit&redlink=1" class="new" title="Silicon carbonitride (page does not exist)">Silicon carbonitride</a></li> <li><a href="/w/index.php?title=C-Silicon_dicarbide&action=edit&redlink=1" class="new" title="C-Silicon dicarbide (page does not exist)">c-Silicon dicarbide</a></li> <li><a href="/w/index.php?title=SiNC&action=edit&redlink=1" class="new" title="SiNC (page does not exist)">SiNC</a></li> <li><a href="/wiki/Sulfur_dioxide" title="Sulfur dioxide">Sulfur dioxide</a></li> <li><a href="/w/index.php?title=Thioformyl&action=edit&redlink=1" class="new" title="Thioformyl (page does not exist)">Thioformyl</a></li> <li><a href="/wiki/Thioxoethenylidene" title="Thioxoethenylidene">Thioxoethenylidene</a></li> <li><a href="/wiki/Titanium_dioxide" title="Titanium dioxide">Titanium dioxide</a></li> <li><a href="/wiki/Tricarbon" title="Tricarbon">Tricarbon</a></li> <li><a href="/wiki/Water" title="Water">Water</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules#Molecules" title="List of interstellar and circumstellar molecules">Four<br />atoms</a></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/Acetylene" title="Acetylene">Acetylene</a></li> <li><a href="/wiki/Ammonia" title="Ammonia">Ammonia</a></li> <li><a href="/wiki/Isocyanic_acid" title="Isocyanic acid">Isocyanic acid</a></li> <li><a href="/wiki/Polyyne" title="Polyyne">Cyanoethynyl</a></li> <li><a href="/wiki/Interstellar_formaldehyde" title="Interstellar formaldehyde">Formaldehyde</a></li> <li><a href="/wiki/Fulminic_acid" title="Fulminic acid">Fulminic acid</a></li> <li><a href="/w/index.php?title=HCCN&action=edit&redlink=1" class="new" title="HCCN (page does not exist)">HCCN</a></li> <li><a href="/wiki/Hydrogen_peroxide" title="Hydrogen peroxide">Hydrogen peroxide</a></li> <li><a href="/w/index.php?title=Hydromagnesium_isocyanide&action=edit&redlink=1" class="new" title="Hydromagnesium isocyanide (page does not exist)">Hydromagnesium isocyanide</a></li> <li><a href="/wiki/Isocyanic_acid" title="Isocyanic acid">Isocyanic acid</a></li> <li><a href="/wiki/Thiocyanic_acid" title="Thiocyanic acid">Isothiocyanic acid</a></li> <li><a href="/w/index.php?title=Ketenyl&action=edit&redlink=1" class="new" title="Ketenyl (page does not exist)">Ketenyl</a></li> <li><a href="/w/index.php?title=Methylene_amidogen&action=edit&redlink=1" class="new" title="Methylene amidogen (page does not exist)">Methylene amidogen</a></li> <li><a href="/wiki/Methyl_cation" class="mw-redirect" title="Methyl cation">Methyl cation</a></li> <li><a href="/wiki/Methyl_radical" title="Methyl radical">Methyl radical</a></li> <li><a href="/wiki/Propynylidyne" title="Propynylidyne">Propynylidyne</a></li> <li><a href="/w/index.php?title=Protonated_carbon_dioxide&action=edit&redlink=1" class="new" title="Protonated carbon dioxide (page does not exist)">Protonated carbon dioxide</a></li> <li><a href="/wiki/Protonated_hydrogen_cyanide" title="Protonated hydrogen cyanide">Protonated hydrogen cyanide</a></li> <li><a href="/w/index.php?title=Silicon_tricarbide&action=edit&redlink=1" class="new" title="Silicon tricarbide (page does not exist)">Silicon tricarbide</a></li> <li><a href="/wiki/Thioformaldehyde" title="Thioformaldehyde">Thioformaldehyde</a></li> <li><a href="/wiki/Tricarbon_monoxide" title="Tricarbon monoxide">Tricarbon monoxide</a></li> <li><a href="/wiki/Tricarbon_monosulfide" title="Tricarbon monosulfide">Tricarbon monosulfide</a></li> <li><a href="/wiki/Thiocyanic_acid" title="Thiocyanic acid">Thiocyanic acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules#Molecules" title="List of interstellar and circumstellar molecules">Five<br />atoms</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Ammonium" title="Ammonium">Ammonium</a> ion</li> <li><a href="/wiki/Polyyne" title="Polyyne">Butadiynyl</a></li> <li><a href="/wiki/Carbodiimide" title="Carbodiimide">Carbodiimide</a></li> <li><a href="/wiki/Cyanamide" title="Cyanamide">Cyanamide</a></li> <li><a href="/wiki/Cyanoacetylene" title="Cyanoacetylene">Cyanoacetylene</a></li> <li><a href="/w/index.php?title=Cyanoformaldehyde&action=edit&redlink=1" class="new" title="Cyanoformaldehyde (page does not exist)">Cyanoformaldehyde</a></li> <li><a href="/wiki/Cyanomethyl" title="Cyanomethyl">Cyanomethyl</a></li> <li><a href="/wiki/Cyclopropenylidene" title="Cyclopropenylidene">Cyclopropenylidene</a></li> <li><a href="/wiki/Formic_acid" title="Formic acid">Formic acid</a></li> <li><a href="/w/index.php?title=Isocyanoacetylene&action=edit&redlink=1" class="new" title="Isocyanoacetylene (page does not exist)">Isocyanoacetylene</a></li> <li><a href="/wiki/Ketene" title="Ketene">Ketene</a></li> <li><a href="/wiki/Methane" title="Methane">Methane</a></li> <li><a href="/wiki/Methoxy" class="mw-redirect" title="Methoxy">Methoxy radical</a></li> <li><a href="/w/index.php?title=Methylenimine&action=edit&redlink=1" class="new" title="Methylenimine (page does not exist)">Methylenimine</a></li> <li><a href="/w/index.php?title=Propadienylidene&action=edit&redlink=1" class="new" title="Propadienylidene (page does not exist)">Propadienylidene</a></li> <li><a href="/w/index.php?title=Protonated_formaldehyde&action=edit&redlink=1" class="new" title="Protonated formaldehyde (page does not exist)">Protonated formaldehyde</a></li> <li><a href="/wiki/Silane" title="Silane">Silane</a></li> <li><a href="/w/index.php?title=Silicon-carbide_cluster&action=edit&redlink=1" class="new" title="Silicon-carbide cluster (page does not exist)">Silicon-carbide cluster</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules#Molecules" title="List of interstellar and circumstellar molecules">Six<br />atoms</a></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/Acetonitrile" title="Acetonitrile">Acetonitrile</a></li> <li><a href="/w/index.php?title=Cyanobutadiynyl_radical&action=edit&redlink=1" class="new" title="Cyanobutadiynyl radical (page does not exist)">Cyanobutadiynyl radical</a></li> <li><a href="/w/index.php?title=E-Cyanomethanimine&action=edit&redlink=1" class="new" title="E-Cyanomethanimine (page does not exist)">E-Cyanomethanimine</a></li> <li><a href="/wiki/Cyclopropenone" title="Cyclopropenone">Cyclopropenone</a></li> <li><a href="/wiki/Diacetylene" title="Diacetylene">Diacetylene</a></li> <li><a href="/wiki/Ethylene" title="Ethylene">Ethylene</a></li> <li><a href="/wiki/Formamide" title="Formamide">Formamide</a></li> <li><a href="/w/index.php?title=HC4N&action=edit&redlink=1" class="new" title="HC4N (page does not exist)">HC<sub>4</sub>N</a></li> <li><a href="/wiki/Ketenimine" class="mw-redirect" title="Ketenimine">Ketenimine</a></li> <li><a href="/wiki/Methanethiol" title="Methanethiol">Methanethiol</a></li> <li><a href="/wiki/Methanol" title="Methanol">Methanol</a></li> <li><a href="/wiki/Methyl_isocyanide" title="Methyl isocyanide">Methyl isocyanide</a></li> <li><a href="/wiki/Polyyne" title="Polyyne">Pentynylidyne</a></li> <li><a href="/wiki/Propynal" class="mw-redirect" title="Propynal">Propynal</a></li> <li><a href="/w/index.php?title=Protonated_cyanoacetylene&action=edit&redlink=1" class="new" title="Protonated cyanoacetylene (page does not exist)">Protonated cyanoacetylene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules#Molecules" title="List of interstellar and circumstellar molecules">Seven<br />atoms</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acetaldehyde" title="Acetaldehyde">Acetaldehyde</a></li> <li><a href="/wiki/Acrylonitrile" title="Acrylonitrile">Acrylonitrile</a> <ul><li><a href="/wiki/Vinyl_cyanide" class="mw-redirect" title="Vinyl cyanide">Vinyl cyanide</a></li></ul></li> <li><a href="/wiki/Cyanopolyyne" title="Cyanopolyyne">Cyanodiacetylene</a></li> <li><a href="/wiki/Ethylene_oxide" title="Ethylene oxide">Ethylene oxide</a></li> <li><a href="/wiki/Glycolonitrile" title="Glycolonitrile">Glycolonitrile</a></li> <li><a href="/wiki/Hexatriynyl_radical" title="Hexatriynyl radical">Hexatriynyl radical</a></li> <li><a class="mw-selflink selflink">Propyne</a></li> <li><a href="/wiki/Methylamine" title="Methylamine">Methylamine</a></li> <li><a href="/wiki/Methyl_isocyanate" title="Methyl isocyanate">Methyl isocyanate</a></li> <li><a href="/wiki/Vinyl_alcohol" title="Vinyl alcohol">Vinyl alcohol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules#Molecules" title="List of interstellar and circumstellar molecules">Eight<br />atoms</a></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/Acetic_acid" title="Acetic acid">Acetic acid</a></li> <li><a href="/wiki/Aminoacetonitrile" title="Aminoacetonitrile">Aminoacetonitrile</a></li> <li><a href="/w/index.php?title=Cyanoallene&action=edit&redlink=1" class="new" title="Cyanoallene (page does not exist)">Cyanoallene</a></li> <li><a href="/wiki/Ethanimine" title="Ethanimine">Ethanimine</a></li> <li><a href="/wiki/Glycolaldehyde" title="Glycolaldehyde">Glycolaldehyde</a></li> <li><a href="/wiki/Polyyne" title="Polyyne">Hexapentaenylidene</a></li> <li><a href="/wiki/Polyyne" title="Polyyne">Methylcyanoacetylene</a></li> <li><a href="/wiki/Methyl_formate" title="Methyl formate">Methyl formate</a></li> <li><a href="/wiki/Acrolein" title="Acrolein">Acrolein</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules#Molecules" title="List of interstellar and circumstellar molecules">Nine<br />atoms</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acetamide" title="Acetamide">Acetamide</a></li> <li><a href="/wiki/Cyanopolyyne" title="Cyanopolyyne">Cyanohexatriyne</a></li> <li><a href="/wiki/Dimethyl_ether" title="Dimethyl ether">Dimethyl ether</a></li> <li><a href="/wiki/Ethanol" title="Ethanol">Ethanol</a></li> <li><a href="/wiki/Polyyne" title="Polyyne">Methyldiacetylene</a></li> <li><a href="/wiki/Octatetraynyl_radical" title="Octatetraynyl radical">Octatetraynyl radical</a></li> <li><a href="/wiki/Propene" class="mw-redirect" title="Propene">Propene</a></li> <li><a href="/wiki/Ethanethiol" title="Ethanethiol">Ethanethiol</a></li> <li><a href="/wiki/Propionitrile" title="Propionitrile">Propionitrile</a></li> <li><a href="/wiki/N-Methylformamide" title="N-Methylformamide">N-Methylformamide</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules#Molecules" title="List of interstellar and circumstellar molecules">Ten<br />atoms<br />or more</a></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/Acetone" title="Acetone">Acetone</a></li> <li><a href="/wiki/Benzene" title="Benzene">Benzene</a></li> <li><a href="/wiki/Benzonitrile" title="Benzonitrile">Benzonitrile</a></li> <li><a href="/wiki/Buckminsterfullerene" title="Buckminsterfullerene">Buckminsterfullerene</a> (C<sub>60</sub>, C<sub>60</sub><sup>+</sup>, fullerene, buckyball)</li> <li><a href="/wiki/C70_fullerene" title="C70 fullerene">C<sub>70</sub> fullerene</a></li> <li><a href="/wiki/Cyanopolyyne" title="Cyanopolyyne">Cyanodecapentayne</a></li> <li><a href="/wiki/Ethylene_glycol" title="Ethylene glycol">Ethylene glycol</a></li> <li><a href="/wiki/Ethyl_formate" title="Ethyl formate">Ethyl formate</a></li> <li><a href="/wiki/Methyl_acetate" title="Methyl acetate">Methyl acetate</a></li> <li><a href="/wiki/Cyanopolyyne" title="Cyanopolyyne">Methyl-cyano-diacetylene</a></li> <li><a href="/wiki/Polyyne" title="Polyyne">Methyltriacetylene</a></li> <li><a href="/wiki/Propionaldehyde" title="Propionaldehyde">Propionaldehyde</a></li> <li><a href="/wiki/Butyronitrile" title="Butyronitrile">Butyronitrile</a></li> <li><a href="/wiki/Pyrimidine" title="Pyrimidine">Pyrimidine</a></li> <li><a href="/w/index.php?title=Heptatrienyl_radical&action=edit&redlink=1" class="new" title="Heptatrienyl radical (page does not exist)">Heptatrienyl radical</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Deuterium" title="Deuterium">Deuterated</a><br />molecules</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Ammonia" title="Ammonia">Ammonia</a></li> <li><a href="/wiki/Ammonium" title="Ammonium">Ammonium</a> ion</li> <li><a href="/wiki/Formaldehyde" title="Formaldehyde">Formaldehyde</a></li> <li><a href="/wiki/Interstellar_formaldehyde#Interstellar_reactions" title="Interstellar formaldehyde">Formyl radical</a></li> <li><a href="/wiki/Heavy_water" title="Heavy water">Heavy water</a></li> <li><a href="/wiki/Hydrogen_cyanide" title="Hydrogen cyanide">Hydrogen cyanide</a></li> <li><a href="/wiki/Hydrogen_deuteride" title="Hydrogen deuteride">Hydrogen deuteride</a></li> <li><a href="/wiki/Hydrogen_isocyanide" title="Hydrogen isocyanide">Hydrogen isocyanide</a></li> <li><a class="mw-selflink selflink">Propyne</a></li> <li><a href="/wiki/Diazenylium" title="Diazenylium">N<sub>2</sub>D<sup>+</sup></a></li> <li><a href="/wiki/Trihydrogen_cation" title="Trihydrogen cation">Trihydrogen cation</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules#Molecules" title="List of interstellar and circumstellar molecules">Unconfirmed</a></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/Anthracene" title="Anthracene">Anthracene</a></li> <li><a href="/wiki/Dihydroxyacetone" title="Dihydroxyacetone">Dihydroxyacetone</a></li> <li><a href="/wiki/Methoxyethane" title="Methoxyethane">Methoxyethane</a></li> <li><a href="/wiki/Glycine" title="Glycine">Glycine</a></li> <li><a href="/wiki/Graphene" title="Graphene">Graphene</a></li> <li><a href="/wiki/Hemolithin" title="Hemolithin">Hemolithin</a></li> <li><a href="/w/index.php?title=H2NCO%2B&action=edit&redlink=1" class="new" title="H2NCO+ (page does not exist)">H<sub>2</sub>NCO<sup>+</sup></a></li> <li><a href="/wiki/Carbon" title="Carbon">Linear C<sub>5</sub></a></li> <li><a href="/wiki/Naphthalene" title="Naphthalene">Naphthalene cation</a></li> <li><a href="/wiki/Phosphine" title="Phosphine">Phosphine</a></li> <li><a href="/wiki/Pyrene" title="Pyrene">Pyrene</a></li> <li><a href="/wiki/Silylidyne" title="Silylidyne">Silylidyne</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules#See_also" title="List of interstellar and circumstellar molecules">Related</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Abiogenesis" title="Abiogenesis">Abiogenesis</a></li> <li><a href="/wiki/Astrobiology" title="Astrobiology">Astrobiology</a></li> <li><a href="/wiki/Astrochemistry" title="Astrochemistry">Astrochemistry</a></li> <li><a href="/wiki/Atomic_and_molecular_astrophysics" title="Atomic and molecular astrophysics">Atomic and molecular astrophysics</a></li> <li><a href="/wiki/Chemical_formula" title="Chemical formula">Chemical formula</a></li> <li><a href="/wiki/Circumstellar_dust" title="Circumstellar dust">Circumstellar dust</a></li> <li><a href="/wiki/Circumstellar_envelope" title="Circumstellar envelope">Circumstellar envelope</a></li> <li><a href="/wiki/Cosmic_dust" title="Cosmic dust">Cosmic dust</a></li> <li><a href="/wiki/Cosmic_ray" title="Cosmic ray">Cosmic ray</a></li> <li><a href="/wiki/Cosmochemistry" title="Cosmochemistry">Cosmochemistry</a></li> <li><a href="/wiki/Diffuse_interstellar_band" class="mw-redirect" title="Diffuse interstellar band">Diffuse interstellar band</a></li> <li><a href="/wiki/Earliest_known_life_forms" title="Earliest known life forms">Earliest known life forms</a></li> <li><a href="/wiki/Extraterrestrial_life" title="Extraterrestrial life">Extraterrestrial life</a></li> <li><a href="/wiki/Extraterrestrial_liquid_water" title="Extraterrestrial liquid water">Extraterrestrial liquid water</a></li> <li><a href="/wiki/Forbidden_mechanism" title="Forbidden mechanism">Forbidden mechanism</a></li> <li><a href="/wiki/Homochirality" title="Homochirality">Homochirality</a></li> <li><a href="/wiki/Intergalactic_dust" title="Intergalactic dust">Intergalactic dust</a></li> <li><a href="/wiki/Interplanetary_medium" title="Interplanetary medium">Interplanetary medium</a></li> <li><a href="/wiki/Interstellar_medium" title="Interstellar medium">Interstellar medium</a></li> <li><a href="/wiki/Photodissociation_region" title="Photodissociation region">Photodissociation region</a></li> <li><a href="/wiki/Iron%E2%80%93sulfur_world_theory" class="mw-redirect" title="Iron–sulfur world theory">Iron–sulfur world theory</a></li> <li><a href="/wiki/Kerogen" title="Kerogen">Kerogen</a></li> <li><a href="/wiki/Molecules_in_stars" title="Molecules in stars">Molecules in stars</a></li> <li><a href="/wiki/Nexus_for_Exoplanet_System_Science" title="Nexus for Exoplanet System Science">Nexus for Exoplanet System Science</a></li> <li><a href="/wiki/Organic_compound" title="Organic compound">Organic compound</a></li> <li><a href="/wiki/Outer_space" title="Outer space">Outer space</a></li> <li><a href="/wiki/PAH_world_hypothesis" title="PAH world hypothesis">PAH world hypothesis</a></li> <li><a href="/wiki/Pseudo-panspermia" title="Pseudo-panspermia">Pseudo-panspermia</a></li> <li><a href="/wiki/Polycyclic_aromatic_hydrocarbon" title="Polycyclic aromatic hydrocarbon">Polycyclic aromatic hydrocarbon</a> (PAH)</li> <li><a href="/wiki/RNA_world_hypothesis" class="mw-redirect" title="RNA world hypothesis">RNA world hypothesis</a></li> <li><a href="/wiki/Spectroscopy" title="Spectroscopy">Spectroscopy</a></li> <li><a href="/wiki/Tholin" title="Tholin">Tholin</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2" style="font-weight: bold;"><div> <ul><li><b><span class="noviewer" typeof="mw:File"><span title="Category"><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/16px-Symbol_category_class.svg.png" decoding="async" width="16" height="16" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/23px-Symbol_category_class.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/31px-Symbol_category_class.svg.png 2x" data-file-width="180" data-file-height="185" /></span></span> <a href="/wiki/Category:Astrochemistry" title="Category:Astrochemistry">Category:Astrochemistry</a></b></li> <li><span class="nowrap"><span class="noviewer" typeof="mw:File"><span><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/5/5c/Earth-moon.jpg/16px-Earth-moon.jpg" decoding="async" width="16" height="13" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/5c/Earth-moon.jpg/24px-Earth-moon.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/5c/Earth-moon.jpg/32px-Earth-moon.jpg 2x" data-file-width="3000" data-file-height="2400" /></span></span> </span><a href="/wiki/Portal:Outer_space" title="Portal:Outer space">Outer space portal</a></li> <li><span class="nowrap"><span class="noviewer" typeof="mw:File"><span><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/0/00/Crab_Nebula.jpg/16px-Crab_Nebula.jpg" decoding="async" width="16" height="16" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/00/Crab_Nebula.jpg/24px-Crab_Nebula.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/00/Crab_Nebula.jpg/32px-Crab_Nebula.jpg 2x" data-file-width="3864" data-file-height="3864" /></span></span> </span><a href="/wiki/Portal:Astronomy" title="Portal:Astronomy">Astronomy portal</a></li> <li><span class="nowrap"><span class="noviewer" typeof="mw:File"><span><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/e/ed/Papapishu-Lab-icon-6.svg/16px-Papapishu-Lab-icon-6.svg.png" decoding="async" width="16" height="16" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/ed/Papapishu-Lab-icon-6.svg/24px-Papapishu-Lab-icon-6.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/ed/Papapishu-Lab-icon-6.svg/32px-Papapishu-Lab-icon-6.svg.png 2x" data-file-width="512" data-file-height="512" /></span></span> </span><a href="/wiki/Portal:Chemistry" title="Portal:Chemistry">Chemistry portal</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="Binary_compounds_of_hydrogen" style="padding:3px"><table class="nowraplinks mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><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:Hydrides_by_group" title="Template:Hydrides by group"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Hydrides_by_group" title="Template talk:Hydrides by group"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Hydrides_by_group" title="Special:EditPage/Template:Hydrides by group"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Binary_compounds_of_hydrogen" style="font-size:114%;margin:0 4em"><a href="/wiki/Binary_compounds_of_hydrogen" title="Binary compounds of hydrogen">Binary compounds of hydrogen</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Hydride#Ionic_hydrides" title="Hydride">Alkali metal <br />(Group 1) hydrides</a></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/Lithium_hydride" title="Lithium hydride">LiH</a></li> <li><a href="/wiki/Sodium_hydride" title="Sodium hydride">NaH</a></li> <li><a href="/wiki/Potassium_hydride" title="Potassium hydride">KH</a></li> <li><a href="/wiki/Rubidium_hydride" title="Rubidium hydride">RbH</a></li> <li><a href="/wiki/Caesium_hydride" title="Caesium hydride">CsH</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Hydride#Ionic_hydrides" title="Hydride">Alkaline <br />(Group 2) <br />earth hydrides</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Monohydrides" scope="row" class="navbox-group" style="width:1%">Monohydrides</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Beryllium_monohydride" title="Beryllium monohydride">BeH</a></li> <li><a href="/wiki/Magnesium_monohydride" title="Magnesium monohydride">MgH</a></li> <li><a href="/wiki/Calcium_monohydride" title="Calcium monohydride">CaH</a></li> <li><a href="/w/index.php?title=Strontium_monohydride&action=edit&redlink=1" class="new" title="Strontium monohydride (page does not exist)">SrH</a></li> <li><a href="/w/index.php?title=Barium_monohydride&action=edit&redlink=1" class="new" title="Barium monohydride (page does not exist)">BaH</a></li></ul> </div></td></tr></tbody></table><div> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Dihydrides" scope="row" class="navbox-group" style="width:1%">Dihydrides</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/Beryllium_hydride" title="Beryllium hydride">BeH<sub>2</sub></a></li> <li><a href="/wiki/Magnesium_hydride" title="Magnesium hydride">MgH<sub>2</sub></a></li> <li><a href="/wiki/Calcium_hydride" title="Calcium hydride">CaH<sub>2</sub></a></li> <li><a href="/wiki/Strontium_hydride" title="Strontium hydride">SrH<sub>2</sub></a></li> <li><a href="/wiki/Barium_hydride" title="Barium hydride">BaH<sub>2</sub></a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Group_13_hydride" title="Group 13 hydride">Group 13 <br />hydrides</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Boranes" scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Boranes" title="Boranes">Boranes</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Borane" title="Borane">BH<sub>3</sub></a></li> <li><a href="/wiki/Boron_monohydride" title="Boron monohydride">BH</a></li> <li><a href="/wiki/Diborane" title="Diborane">B<sub>2</sub>H<sub>6</sub></a></li> <li><a href="/wiki/Diborane(2)" title="Diborane(2)">B<sub>2</sub>H<sub>2</sub></a></li> <li><a href="/wiki/Diborane(4)" title="Diborane(4)">B<sub>2</sub>H<sub>4</sub></a></li> <li><a href="/wiki/Tetraborane" title="Tetraborane">B<sub>4</sub>H<sub>10</sub></a></li> <li><a href="/wiki/Pentaborane(9)" title="Pentaborane(9)">B<sub>5</sub>H<sub>9</sub></a></li> <li><a href="/wiki/Pentaborane(11)" title="Pentaborane(11)">B<sub>5</sub>H<sub>11</sub></a></li> <li><a href="/wiki/Hexaborane(10)" title="Hexaborane(10)">B<sub>6</sub>H<sub>10</sub></a></li> <li><a href="/wiki/Hexaborane(12)" title="Hexaborane(12)">B<sub>6</sub>H<sub>12</sub></a></li> <li><a href="/wiki/Decaborane" title="Decaborane">B<sub>10</sub>H<sub>14</sub></a></li> <li><a href="/wiki/Octadecaborane" title="Octadecaborane">B<sub>18</sub>H<sub>22</sub></a></li></ul> </div></td></tr></tbody></table><div> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Alanes" scope="row" class="navbox-group" style="width:1%">Alanes</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/Aluminium_hydride" title="Aluminium hydride">AlH<sub>3</sub></a></li> <li><a href="/wiki/Dialane" title="Dialane">Al<sub>2</sub>H<sub>6</sub></a></li></ul> </div></td></tr></tbody></table><div> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Gallanes" scope="row" class="navbox-group" style="width:1%">Gallanes</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Gallane" title="Gallane">GaH<sub>3</sub></a></li> <li><a href="/wiki/Digallane" title="Digallane">Ga<sub>2</sub>H<sub>6</sub></a></li></ul> </div></td></tr></tbody></table><div> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Indiganes" scope="row" class="navbox-group" style="width:1%">Indiganes</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/Indium_trihydride" title="Indium trihydride">InH<sub>3</sub></a></li> <li><a href="/w/index.php?title=Diindigane&action=edit&redlink=1" class="new" title="Diindigane (page does not exist)">In<sub>2</sub>H<sub>6</sub></a></li></ul> </div></td></tr></tbody></table><div> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Thallanes" scope="row" class="navbox-group" style="width:1%">Thallanes</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Thallane" title="Thallane">TlH<sub>3</sub></a></li> <li><a href="/w/index.php?title=Dithallane&action=edit&redlink=1" class="new" title="Dithallane (page does not exist)">Tl<sub>2</sub>H<sub>6</sub></a></li></ul> </div></td></tr></tbody></table><div> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Nihonanes_(predicted)" scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Nihonium" title="Nihonium">Nihonanes</a> (<i>predicted</i>)</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>NhH</i></li> <li><i>NhH<sub>3</sub></i></li> <li><i>Nh<sub>2</sub>H<sub>6</sub></i></li> <li><i>NhH<sub>5</sub></i></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Group_14_hydride" title="Group 14 hydride">Group 14 hydrides</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Hydrocarbons" scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Hydrocarbon" title="Hydrocarbon">Hydrocarbons</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Alkane" title="Alkane">alkanes</a></li> <li><a href="/wiki/Alkene" title="Alkene">alkenes</a></li> <li><a href="/wiki/Alkyne" title="Alkyne">alkynes</a></li> <li><a href="/wiki/Cycloalkane" title="Cycloalkane">Cycloalkanes</a></li> <li><a href="/wiki/Cycloalkene" title="Cycloalkene">Cycloalkenes</a></li> <li><a href="/wiki/Cycloalkyne" title="Cycloalkyne">Cycloalkynes</a></li> <li><a href="/wiki/Annulenes" class="mw-redirect" title="Annulenes">Annulenes</a></li></ul> </div></td></tr></tbody></table><div> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Methylidyne_radical" title="Methylidyne radical">CH</a></li> <li><a href="/wiki/Methylene_(compound)" title="Methylene (compound)">CH<sub>2</sub></a></li> <li><a href="/wiki/Methyl_radical" title="Methyl radical">CH<sub>3</sub></a></li> <li><a href="/wiki/Ethynyl_radical" title="Ethynyl radical">C<sub>2</sub>H</a></li></ul> </div></td></tr></tbody></table><div> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Silanes" scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Silanes" title="Silanes">Silanes</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Silane" title="Silane">SiH<sub>4</sub></a></li> <li><a href="/wiki/Disilane" title="Disilane">Si<sub>2</sub>H<sub>6</sub></a></li> <li><a href="/wiki/Trisilane" title="Trisilane">Si<sub>3</sub>H<sub>8</sub></a></li> <li><a href="/wiki/Tetrasilane" title="Tetrasilane">Si<sub>4</sub>H<sub>10</sub></a></li> <li><a href="/wiki/Pentasilane" class="mw-redirect" title="Pentasilane">Si<sub>5</sub>H<sub>12</sub></a></li> <li><a href="/wiki/Hexasilane" class="mw-redirect" title="Hexasilane">Si<sub>6</sub>H<sub>14</sub></a></li> <li><a href="/w/index.php?title=Heptasilane&action=edit&redlink=1" class="new" title="Heptasilane (page does not exist)">Si<sub>7</sub>H<sub>16</sub></a></li> <li><a href="/w/index.php?title=Octasilane&action=edit&redlink=1" class="new" title="Octasilane (page does not exist)">Si<sub>8</sub>H<sub>18</sub></a></li> <li><a href="/w/index.php?title=Nonasilane&action=edit&redlink=1" class="new" title="Nonasilane (page does not exist)">Si<sub>9</sub>H<sub>20</sub></a></li> <li><a href="/w/index.php?title=Decasilane&action=edit&redlink=1" class="new" title="Decasilane (page does not exist)">Si<sub>10</sub>H<sub>22</sub></a></li> <li><a href="/wiki/Silanes" title="Silanes">more...</a></li></ul> </div></td></tr></tbody></table><div> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Silenes" scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Silenes" title="Silenes">Silenes</a></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/Disilene" title="Disilene">Si<sub>2</sub>H<sub>4</sub></a></li></ul> </div></td></tr></tbody></table><div> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Silynes" scope="row" class="navbox-group" style="width:1%"><a href="/w/index.php?title=Silynes&action=edit&redlink=1" class="new" title="Silynes (page does not exist)">Silynes</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Disilyne" title="Disilyne">Si<sub>2</sub>H<sub>2</sub></a></li> <li><a href="/wiki/Silicon_monohydride" class="mw-redirect" title="Silicon monohydride">SiH</a></li></ul> </div></td></tr></tbody></table><div> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Germanes" scope="row" class="navbox-group" style="width:1%"><a href="/w/index.php?title=Germanes&action=edit&redlink=1" class="new" title="Germanes (page does not exist)">Germanes</a></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/Germane" title="Germane">GeH<sub>4</sub></a></li> <li><a href="/wiki/Digermane" title="Digermane">Ge<sub>2</sub>H<sub>6</sub></a></li> <li><a href="/w/index.php?title=Trigermane&action=edit&redlink=1" class="new" title="Trigermane (page does not exist)">Ge<sub>3</sub>H<sub>8</sub></a></li> <li><a href="/w/index.php?title=Tetragermane&action=edit&redlink=1" class="new" title="Tetragermane (page does not exist)">Ge<sub>4</sub>H<sub>10</sub></a></li> <li><a href="/w/index.php?title=Pentagermane&action=edit&redlink=1" class="new" title="Pentagermane (page does not exist)">Ge<sub>5</sub>H<sub>12</sub></a></li></ul> </div></td></tr></tbody></table><div></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Stannanes" scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Stannanes" class="mw-redirect" title="Stannanes">Stannanes</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Stannane" title="Stannane">SnH<sub>4</sub></a></li> <li><a href="/w/index.php?title=Distannane&action=edit&redlink=1" class="new" title="Distannane (page does not exist)">Sn<sub>2</sub>H<sub>6</sub></a></li></ul> </div></td></tr></tbody></table><div></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Plumbanes" scope="row" class="navbox-group" style="width:1%">Plumbanes</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/Plumbane" title="Plumbane">PbH<sub>4</sub></a></li></ul> </div></td></tr></tbody></table><div></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Flerovanes_(predicted)" scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Flerovium" title="Flerovium">Flerovanes</a> (<i>predicted</i>)</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>FlH</i></li> <li><i>FlH<sub>2</sub></i></li> <li><i>FlH<sub>4</sub></i></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Pnictogen_hydride" title="Pnictogen hydride">Pnictogen <br />(Group 15) hydrides</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Azanes" scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Azane" title="Azane">Azanes</a></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/Ammonia" title="Ammonia">NH<sub>3</sub></a></li> <li><a href="/wiki/Hydrazine" title="Hydrazine">N<sub>2</sub>H<sub>4</sub></a></li> <li><a href="/wiki/Triazane" title="Triazane">N<sub>3</sub>H<sub>5</sub></a></li> <li><a href="/w/index.php?title=Tetrazane&action=edit&redlink=1" class="new" title="Tetrazane (page does not exist)">N<sub>4</sub>H<sub>6</sub></a></li> <li><a href="/w/index.php?title=Pentazane&action=edit&redlink=1" class="new" title="Pentazane (page does not exist)">N<sub>5</sub>H<sub>7</sub></a></li> <li><a href="/w/index.php?title=Hexazane&action=edit&redlink=1" class="new" title="Hexazane (page does not exist)">N<sub>6</sub>H<sub>8</sub></a></li> <li><a href="/w/index.php?title=Heptazane&action=edit&redlink=1" class="new" title="Heptazane (page does not exist)">N<sub>7</sub>H<sub>9</sub></a></li> <li><a href="/w/index.php?title=Octazane&action=edit&redlink=1" class="new" title="Octazane (page does not exist)">N<sub>8</sub>H<sub>10</sub></a></li> <li><a href="/w/index.php?title=Nonazane&action=edit&redlink=1" class="new" title="Nonazane (page does not exist)">N<sub>9</sub>H<sub>11</sub></a></li> <li><a href="/w/index.php?title=Decazane&action=edit&redlink=1" class="new" title="Decazane (page does not exist)">N<sub>10</sub>H<sub>12</sub></a></li> <li><a href="/wiki/Azane" title="Azane">more...</a></li></ul> </div></td></tr></tbody></table><div> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Azenes" scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Azo_compound" title="Azo compound">Azenes</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Diazene" class="mw-redirect" title="Diazene">N<sub>2</sub>H<sub>2</sub></a></li> <li><a href="/wiki/Triazene" title="Triazene">N<sub>3</sub>H<sub>3</sub></a></li> <li><a href="/wiki/Tetrazene" title="Tetrazene">N<sub>4</sub>H<sub>4</sub></a></li></ul> </div></td></tr></tbody></table><div> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Phosphanes" scope="row" class="navbox-group" style="width:1%"><a href="/w/index.php?title=Phosphanes&action=edit&redlink=1" class="new" title="Phosphanes (page does not exist)">Phosphanes</a></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/Phosphine" title="Phosphine">PH<sub>3</sub></a></li> <li><a href="/wiki/Diphosphane" title="Diphosphane">P<sub>2</sub>H<sub>4</sub></a></li> <li><a href="/wiki/Triphosphane" title="Triphosphane">P<sub>3</sub>H<sub>5</sub></a></li> <li><a href="/w/index.php?title=Tetraphosphane&action=edit&redlink=1" class="new" title="Tetraphosphane (page does not exist)">P<sub>4</sub>H<sub>6</sub></a></li> <li><a href="/w/index.php?title=Pentaphosphane&action=edit&redlink=1" class="new" title="Pentaphosphane (page does not exist)">P<sub>5</sub>H<sub>7</sub></a></li> <li><a href="/w/index.php?title=Hexaphosphane&action=edit&redlink=1" class="new" title="Hexaphosphane (page does not exist)">P<sub>6</sub>H<sub>8</sub></a></li> <li><a href="/w/index.php?title=Heptaphosphane&action=edit&redlink=1" class="new" title="Heptaphosphane (page does not exist)">P<sub>7</sub>H<sub>9</sub></a></li> <li><a href="/w/index.php?title=Octaphosphane&action=edit&redlink=1" class="new" title="Octaphosphane (page does not exist)">P<sub>8</sub>H<sub>10</sub></a></li> <li><a href="/w/index.php?title=Nonaphosphane&action=edit&redlink=1" class="new" title="Nonaphosphane (page does not exist)">P<sub>9</sub>H<sub>11</sub></a></li> <li><a href="/w/index.php?title=Decaphosphane&action=edit&redlink=1" class="new" title="Decaphosphane (page does not exist)">P<sub>10</sub>H<sub>12</sub></a></li> <li><a href="/w/index.php?title=Phosphanes&action=edit&redlink=1" class="new" title="Phosphanes (page does not exist)">more...</a></li></ul> </div></td></tr></tbody></table><div> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Phosphenes" scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Diphosphenes" title="Diphosphenes">Phosphenes</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Diphosphene" title="Diphosphene">P<sub>2</sub>H<sub>2</sub></a></li> <li><a href="/w/index.php?title=Triphosphene&action=edit&redlink=1" class="new" title="Triphosphene (page does not exist)">P<sub>3</sub>H<sub>3</sub></a></li> <li><a href="/w/index.php?title=Tetraphosphene&action=edit&redlink=1" class="new" title="Tetraphosphene (page does not exist)">P<sub>4</sub>H<sub>4</sub></a></li></ul> </div></td></tr></tbody></table><div> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Arsanes" scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Arsane" class="mw-redirect" title="Arsane">Arsanes</a></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/Arsine" title="Arsine">AsH<sub>3</sub></a></li> <li><a href="/wiki/Diarsine" class="mw-redirect" title="Diarsine">As<sub>2</sub>H<sub>4</sub></a></li></ul> </div></td></tr></tbody></table><div> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Stibanes" scope="row" class="navbox-group" style="width:1%">Stibanes</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Stibine" title="Stibine">SbH<sub>3</sub></a></li></ul> </div></td></tr></tbody></table><div> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Bismuthanes" scope="row" class="navbox-group" style="width:1%">Bismuthanes</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/Bismuthine" title="Bismuthine">BiH<sub>3</sub></a></li></ul> </div></td></tr></tbody></table><div> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Moscovanes" scope="row" class="navbox-group" style="width:1%">Moscovanes</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i><a href="/wiki/Moscovium" title="Moscovium">McH<sub>3</sub></a></i> (<i>predicted</i>)</li></ul> </div></td></tr></tbody></table><div> <ul><li><a href="/wiki/Hydrazoic_acid" title="Hydrazoic acid">HN<sub>3</sub></a></li> <li><a href="/wiki/Imidogen" title="Imidogen">NH</a></li> <li><a href="/wiki/Pentazole" title="Pentazole">HN<sub>5</sub></a></li> <li><a href="/wiki/Nitrogen_pentahydride" title="Nitrogen pentahydride">NH<sub>5</sub></a> <i>(hypothetical)</i></li></ul></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Hydrogen_chalcogenide" title="Hydrogen chalcogenide">Hydrogen <br />chalcogenides <br />(Group 16 hydrides)</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Polyoxidanes" scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Hydrogen_polyoxide" title="Hydrogen polyoxide">Polyoxidanes</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <li><a href="/wiki/Properties_of_water" title="Properties of water">H<sub>2</sub>O</a></li> <li><a href="/wiki/Hydrogen_peroxide" title="Hydrogen peroxide">H<sub>2</sub>O<sub>2</sub></a></li> <li><a href="/wiki/Trioxidane" title="Trioxidane">H<sub>2</sub>O<sub>3</sub></a></li> <li><a href="/wiki/Tetraoxidane" title="Tetraoxidane">H<sub>2</sub>O<sub>4</sub></a></li> <li><a href="/wiki/Pentaoxidane" title="Pentaoxidane">H<sub>2</sub>O<sub>5</sub></a></li> <li><a href="/wiki/Hydrogen_polyoxide" title="Hydrogen polyoxide">more...</a></li> </div></td></tr></tbody></table><div> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Polysulfanes" scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Polysulfane" title="Polysulfane">Polysulfanes</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Hydrogen_sulfide" title="Hydrogen sulfide">H<sub>2</sub>S</a></li> <li><a href="/wiki/Hydrogen_disulfide" title="Hydrogen disulfide">H<sub>2</sub>S<sub>2</sub></a></li> <li><a href="/wiki/Trisulfane" title="Trisulfane">H<sub>2</sub>S<sub>3</sub></a></li> <li><a href="/w/index.php?title=Hydrogen_tetrasulfide&action=edit&redlink=1" class="new" title="Hydrogen tetrasulfide (page does not exist)">H<sub>2</sub>S<sub>4</sub></a></li> <li><a href="/w/index.php?title=Hydrogen_pentasulfide&action=edit&redlink=1" class="new" title="Hydrogen pentasulfide (page does not exist)">H<sub>2</sub>S<sub>5</sub></a></li> <li><a href="/w/index.php?title=Hydrogen_hexasulfide&action=edit&redlink=1" class="new" title="Hydrogen hexasulfide (page does not exist)">H<sub>2</sub>S<sub>6</sub></a></li> <li><a href="/w/index.php?title=Hydrogen_heptasulfide&action=edit&redlink=1" class="new" title="Hydrogen heptasulfide (page does not exist)">H<sub>2</sub>S<sub>7</sub></a></li> <li><a href="/w/index.php?title=Hydrogen_octasulfide&action=edit&redlink=1" class="new" title="Hydrogen octasulfide (page does not exist)">H<sub>2</sub>S<sub>8</sub></a></li> <li><a href="/w/index.php?title=Hydrogen_nonasulfide&action=edit&redlink=1" class="new" title="Hydrogen nonasulfide (page does not exist)">H<sub>2</sub>S<sub>9</sub></a></li> <li><a href="/w/index.php?title=Hydrogen_decasulfide&action=edit&redlink=1" class="new" title="Hydrogen decasulfide (page does not exist)">H<sub>2</sub>S<sub>10</sub></a></li> <li><a href="/wiki/Polysulfane" title="Polysulfane">more...</a></li></ul> </div></td></tr></tbody></table><div> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Selanes" scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Selanes" class="mw-redirect" title="Selanes">Selanes</a></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/Hydrogen_selenide" title="Hydrogen selenide">H<sub>2</sub>Se</a></li> <li><a href="/wiki/Hydrogen_diselenide" title="Hydrogen diselenide">H<sub>2</sub>Se<sub>2</sub></a></li></ul> </div></td></tr></tbody></table><div> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Tellanes" scope="row" class="navbox-group" style="width:1%">Tellanes</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Hydrogen_telluride" title="Hydrogen telluride">H<sub>2</sub>Te</a></li> <li><a href="/wiki/Hydrogen_ditelluride" title="Hydrogen ditelluride">H<sub>2</sub>Te<sub>2</sub></a></li></ul> </div></td></tr></tbody></table><div> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Polanes" scope="row" class="navbox-group" style="width:1%">Polanes</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/Polonium_hydride" title="Polonium hydride">PoH<sub>2</sub></a></li></ul> </div></td></tr></tbody></table><div> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Livermoranes" scope="row" class="navbox-group" style="width:1%">Livermoranes</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i><a href="/wiki/Livermorium" title="Livermorium">LvH<sub>2</sub></a></i> (<i>predicted</i>)</li></ul> </div></td></tr></tbody></table><div> <ul><li><a href="/wiki/Hydroxyl_radical" title="Hydroxyl radical">HO</a></li> <li><a href="/wiki/Hydroperoxyl" title="Hydroperoxyl">HO<sub>2</sub></a></li> <li><a href="/wiki/Hydrogen_ozonide" title="Hydrogen ozonide">HO<sub>3</sub></a></li> <li><a href="/w/index.php?title=Oxywater&action=edit&redlink=1" class="new" title="Oxywater (page does not exist)">H<sub>2</sub>O<sup>+</sup>–O<sup>–</sup></a> <i>(hypothetical)</i></li> <li><a href="/wiki/Sulfanyl" title="Sulfanyl">HS</a></li> <li><a href="/wiki/Semiheavy_water" title="Semiheavy water">HDO</a></li> <li><a href="/wiki/Heavy_water" title="Heavy water">D<sub>2</sub>O</a></li> <li><a href="/wiki/Tritiated_water" title="Tritiated water">T<sub>2</sub>O</a></li></ul></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Hydrogen_halide" title="Hydrogen halide">Hydrogen halides <br />(Group 17 hydrides)</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <li><a href="/wiki/Hydrogen_fluoride" title="Hydrogen fluoride">HF</a></li> <li><a href="/wiki/Hydrogen_chloride" title="Hydrogen chloride">HCl</a></li> <li><a href="/wiki/Hydrogen_bromide" title="Hydrogen bromide">HBr</a></li> <li><a href="/wiki/Hydrogen_iodide" title="Hydrogen iodide">HI</a></li> <li><a href="/wiki/Hydrogen_astatide" title="Hydrogen astatide">HAt</a></li> <li><i><a href="/wiki/Tennessine" title="Tennessine">HTs</a></i> (<i>predicted</i>)</li> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Transition_metal_hydrides" class="mw-redirect" title="Transition metal hydrides">Transition metal hydrides</a></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/Scandium_hydride" title="Scandium hydride">ScH<sub>2</sub></a></li> <li><a href="/wiki/Yttrium_hydride" title="Yttrium hydride">YH<sub>2</sub></a></li> <li><a href="/w/index.php?title=Yttrium_trihydride&action=edit&redlink=1" class="new" title="Yttrium trihydride (page does not exist)">YH<sub>3</sub></a></li> <li><a href="/w/index.php?title=Yttrium_hexahydride&action=edit&redlink=1" class="new" title="Yttrium hexahydride (page does not exist)">YH<sub>6</sub></a></li> <li><a href="/w/index.php?title=Yttrium_nonahydride&action=edit&redlink=1" class="new" title="Yttrium nonahydride (page does not exist)">YH<sub>9</sub></a></li> <li><a href="/w/index.php?title=Lutetium_dihydride&action=edit&redlink=1" class="new" title="Lutetium dihydride (page does not exist)">LuH<sub>2</sub></a></li> <li><a href="/w/index.php?title=Lutetium_trihydride&action=edit&redlink=1" class="new" title="Lutetium trihydride (page does not exist)">LuH<sub>3</sub></a></li> <li><a href="/wiki/Titanium_hydride" title="Titanium hydride">TiH<sub>2</sub></a></li> <li><a href="/wiki/Titanium(IV)_hydride" title="Titanium(IV) hydride">TiH<sub>4</sub></a></li> <li><a href="/wiki/Zirconium(II)_hydride" title="Zirconium(II) hydride">ZrH<sub>2</sub></a></li> <li><a href="/wiki/Zirconium_hydride" title="Zirconium hydride">ZrH<sub>4</sub></a></li> <li><a href="/w/index.php?title=Hafnium(II)_hydride&action=edit&redlink=1" class="new" title="Hafnium(II) hydride (page does not exist)">HfH<sub>2</sub></a></li> <li><a href="/w/index.php?title=Hafnium_hydride&action=edit&redlink=1" class="new" title="Hafnium hydride (page does not exist)">HfH<sub>4</sub></a></li> <li><a href="/w/index.php?title=Vanadium(I)_hydride&action=edit&redlink=1" class="new" title="Vanadium(I) hydride (page does not exist)">VH</a></li> <li><a href="/w/index.php?title=Vanadium(II)_hydride&action=edit&redlink=1" class="new" title="Vanadium(II) hydride (page does not exist)">VH<sub>2</sub></a></li> <li><a href="/w/index.php?title=Niobium_monohydride&action=edit&redlink=1" class="new" title="Niobium monohydride (page does not exist)">NbH</a></li> <li><a href="/w/index.php?title=Niobium_dihydride&action=edit&redlink=1" class="new" title="Niobium dihydride (page does not exist)">NbH<sub>2</sub></a></li> <li><a href="/w/index.php?title=Tantalum_monohydride&action=edit&redlink=1" class="new" title="Tantalum monohydride (page does not exist)">TaH</a></li> <li><a href="/w/index.php?title=Tantalum_dihydride&action=edit&redlink=1" class="new" title="Tantalum dihydride (page does not exist)">TaH<sub>2</sub></a></li> <li><a href="/wiki/Chromium(I)_hydride" title="Chromium(I) hydride">CrH</a></li> <li><a href="/wiki/Chromium(II)_hydride" title="Chromium(II) hydride">CrH<sub>2</sub></a></li> <li><a href="/wiki/Chromium_hydride" title="Chromium hydride">CrH<sub>x</sub></a></li> <li><a href="/wiki/Iron(I)_hydride" title="Iron(I) hydride">FeH</a></li> <li><a href="/wiki/Iron(II)_hydride" title="Iron(II) hydride">FeH<sub>2</sub></a></li> <li><a href="/wiki/Iron_pentahydride" title="Iron pentahydride">FeH<sub>5</sub></a></li> <li><a href="/wiki/Cobalt(II)_hydride" title="Cobalt(II) hydride">CoH<sub>2</sub></a></li> <li><a href="/w/index.php?title=Rhodium_hydride&action=edit&redlink=1" class="new" title="Rhodium hydride (page does not exist)">RhH<sub>2</sub></a></li> <li><a href="/wiki/Iridium_trihydride" title="Iridium trihydride">IrH<sub>3</sub></a></li> <li><a href="/wiki/Nickel_hydride" title="Nickel hydride">NiH</a></li> <li><a href="/wiki/Palladium_hydride" title="Palladium hydride">PdH<sub><i>x</i></sub> (<i>x</i> < 1)</a></li> <li><a href="/w/index.php?title=Platinum_hydride&action=edit&redlink=1" class="new" title="Platinum hydride (page does not exist)">PtH<sub><i>x</i></sub> (<i>x</i>< 1) </a></li> <li><i><a href="/wiki/Darmstadtium" title="Darmstadtium">DsH<sub>2</sub></a></i> (<i>predicted</i>)</li> <li><a href="/wiki/Copper_hydride" title="Copper hydride">CuH</a></li> <li><i><a href="/wiki/Roentgenium" title="Roentgenium">RgH</a></i> (<i>predicted</i>)</li> <li><a href="/wiki/Zinc_hydride" title="Zinc hydride">ZnH<sub>2</sub></a></li> <li><a href="/wiki/Cadmium_hydride" title="Cadmium hydride">CdH<sub>2</sub></a></li> <li><a href="/wiki/Mercury(I)_hydride" title="Mercury(I) hydride">HgH</a></li> <li><a href="/wiki/Mercury(I)_hydride" title="Mercury(I) hydride">Hg<sub>2</sub>H<sub>2</sub></a></li> <li><a href="/wiki/Mercury(II)_hydride" title="Mercury(II) hydride">HgH<sub>2</sub></a></li> <li><i><a href="/wiki/Copernicium" title="Copernicium">CnH<sub>2</sub></a></i> (<i>predicted</i>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/w/index.php?title=Lanthanide_hydrides&action=edit&redlink=1" class="new" title="Lanthanide hydrides (page does not exist)">Lanthanide hydrides</a></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="/w/index.php?title=Lanthanum_dihydride&action=edit&redlink=1" class="new" title="Lanthanum dihydride (page does not exist)">LaH<sub>2</sub></a></li> <li><a href="/w/index.php?title=Lanthanum_trihydride&action=edit&redlink=1" class="new" title="Lanthanum trihydride (page does not exist)">LaH<sub>3</sub></a></li> <li><a href="/wiki/Lanthanum_decahydride" title="Lanthanum decahydride">LaH<sub>10</sub></a></li> <li><a href="/w/index.php?title=Cerium_dihydride&action=edit&redlink=1" class="new" title="Cerium dihydride (page does not exist)">CeH<sub>2</sub></a></li> <li><a href="/w/index.php?title=Cerium_trihydride&action=edit&redlink=1" class="new" title="Cerium trihydride (page does not exist)">CeH<sub>3</sub></a></li> <li><a href="/w/index.php?title=Praseodymium_dihydride&action=edit&redlink=1" class="new" title="Praseodymium dihydride (page does not exist)">PrH<sub>2</sub></a></li> <li><a href="/w/index.php?title=Praseodymium_hydride&action=edit&redlink=1" class="new" title="Praseodymium hydride (page does not exist)">PrH<sub>3</sub></a></li> <li><a href="/wiki/Neodymium(II)_hydride" title="Neodymium(II) hydride">NdH<sub>2</sub></a></li> <li><a href="/wiki/Neodymium(III)_hydride" title="Neodymium(III) hydride">NdH<sub>3</sub></a></li> <li><a href="/w/index.php?title=Samarium_dihydride&action=edit&redlink=1" class="new" title="Samarium dihydride (page does not exist)">SmH<sub>2</sub></a></li> <li><a href="/w/index.php?title=Samarium_trihydride&action=edit&redlink=1" class="new" title="Samarium trihydride (page does not exist)">SmH<sub>3</sub></a></li> <li><a href="/wiki/Europium_hydride" title="Europium hydride">EuH<sub>2</sub></a></li> <li><a href="/w/index.php?title=Gadolinium_dihydride&action=edit&redlink=1" class="new" title="Gadolinium dihydride (page does not exist)">GdH<sub>2</sub></a></li> <li><a href="/w/index.php?title=Gadolinium_trihydride&action=edit&redlink=1" class="new" title="Gadolinium trihydride (page does not exist)">GdH<sub>3</sub></a></li> <li><a href="/w/index.php?title=Terbium_dihydride&action=edit&redlink=1" class="new" title="Terbium dihydride (page does not exist)">TbH<sub>2</sub></a></li> <li><a href="/w/index.php?title=Terbium_trihydride&action=edit&redlink=1" class="new" title="Terbium trihydride (page does not exist)">TbH<sub>3</sub></a></li> <li><a href="/w/index.php?title=Dysprosium_dihydride&action=edit&redlink=1" class="new" title="Dysprosium dihydride (page does not exist)">DyH<sub>2</sub></a></li> <li><a href="/w/index.php?title=Dysprosium_trihydride&action=edit&redlink=1" class="new" title="Dysprosium trihydride (page does not exist)">DyH<sub>3</sub></a></li> <li><a href="/w/index.php?title=Holmium_dihydride&action=edit&redlink=1" class="new" title="Holmium dihydride (page does not exist)">HoH<sub>2</sub></a></li> <li><a href="/w/index.php?title=Holmium_trihydride&action=edit&redlink=1" class="new" title="Holmium trihydride (page does not exist)">HoH<sub>3</sub></a></li> <li><a href="/w/index.php?title=Erbium_dihydride&action=edit&redlink=1" class="new" title="Erbium dihydride (page does not exist)">ErH<sub>2</sub></a></li> <li><a href="/w/index.php?title=Erbium_trihydride&action=edit&redlink=1" class="new" title="Erbium trihydride (page does not exist)">ErH<sub>3</sub></a></li> <li><a href="/w/index.php?title=Thulium_dihydride&action=edit&redlink=1" class="new" title="Thulium dihydride (page does not exist)">TmH<sub>2</sub></a></li> <li><a href="/w/index.php?title=Thulium_trihydride&action=edit&redlink=1" class="new" title="Thulium trihydride (page does not exist)">TmH<sub>3</sub></a></li> <li><a href="/wiki/Ytterbium(II)_hydride" title="Ytterbium(II) hydride">YbH<sub>2</sub></a></li> <li><a href="/w/index.php?title=Lutetium_dihydride&action=edit&redlink=1" class="new" title="Lutetium dihydride (page does not exist)">LuH<sub>2</sub></a></li> <li><a href="/w/index.php?title=Lutetium_trihydride&action=edit&redlink=1" class="new" title="Lutetium trihydride (page does not exist)">LuH<sub>3</sub></a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/w/index.php?title=Actinide_hydrides&action=edit&redlink=1" class="new" title="Actinide hydrides (page does not exist)">Actinide hydrides</a></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="/w/index.php?title=Actinium_dihydride&action=edit&redlink=1" class="new" title="Actinium dihydride (page does not exist)">AcH<sub>2</sub></a></li> <li><a href="/w/index.php?title=Thorium_hydride&action=edit&redlink=1" class="new" title="Thorium hydride (page does not exist)">ThH<sub>2</sub></a></li> <li><a href="/w/index.php?title=Thorium(IV)_hydride&action=edit&redlink=1" class="new" title="Thorium(IV) hydride (page does not exist)">ThH<sub>4</sub></a></li> <li>Th<sub>4</sub>H<sub>15</sub></li> <li><a href="/wiki/Protactinium_trihydride" title="Protactinium trihydride">PaH<sub>3</sub></a></li> <li><a href="/wiki/Uranium(III)_hydride" title="Uranium(III) hydride">UH<sub>3</sub></a></li> <li><a href="/wiki/Uranium(IV)_hydride" title="Uranium(IV) hydride">UH<sub>4</sub></a></li> <li><a href="/w/index.php?title=Neptunium_dihydride&action=edit&redlink=1" class="new" title="Neptunium dihydride (page does not exist)">NpH<sub>2</sub></a></li> <li><a href="/w/index.php?title=Neptunium_trihydride&action=edit&redlink=1" class="new" title="Neptunium trihydride (page does not exist)">NpH<sub>3</sub></a></li> <li><a href="/wiki/Plutonium_hydride" title="Plutonium hydride">PuH<sub>2</sub></a></li> <li><a href="/wiki/Plutonium_hydride" title="Plutonium hydride">PuH<sub>3</sub></a></li> <li><a href="/w/index.php?title=Americium_dihydride&action=edit&redlink=1" class="new" title="Americium dihydride (page does not exist)">AmH<sub>2</sub></a></li> <li><a href="/wiki/Americium_trihydride" title="Americium trihydride">AmH<sub>3</sub></a></li> <li><a href="/w/index.php?title=Curium_hydride&action=edit&redlink=1" class="new" title="Curium hydride (page does not exist)">CmH<sub>2</sub></a></li> <li><a href="/w/index.php?title=Berkelium_dihydride&action=edit&redlink=1" class="new" title="Berkelium dihydride (page does not exist)">BkH<sub>2</sub></a></li> <li><a href="/w/index.php?title=Berkelium_trihydride&action=edit&redlink=1" class="new" title="Berkelium trihydride (page does not exist)">BkH<sub>3</sub></a></li> <li><a href="/w/index.php?title=Californium_dihydride&action=edit&redlink=1" class="new" title="Californium dihydride (page does not exist)">CfH<sub>2</sub></a></li> <li><a href="/w/index.php?title=Californium_trihydride&action=edit&redlink=1" class="new" title="Californium trihydride (page does not exist)">CfH<sub>3</sub></a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Exotic_atoms" class="mw-redirect" title="Exotic atoms">Exotic matter hydrides</a></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/Positronium_hydride" title="Positronium hydride">PsH</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 authority-control" aria-label="Navbox" style="padding:3px"><table class="nowraplinks hlist navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Help:Authority_control" title="Help:Authority control">Authority control databases</a>: National <span 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