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class="vector-unpinned-container"> </div> </div> </div> </nav> <h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Cyclopentane</span></h1> <div id="p-lang-btn" class="vector-dropdown mw-portlet mw-portlet-lang" > <input type="checkbox" id="p-lang-btn-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-p-lang-btn" class="vector-dropdown-checkbox mw-interlanguage-selector" aria-label="Go to an article in another language. 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href="https://ar.wikipedia.org/wiki/%D8%AD%D9%84%D9%82%D9%8A_%D8%A7%D9%84%D8%A8%D9%86%D8%AA%D8%A7%D9%86" title="حلقي البنتان – Arabic" lang="ar" hreflang="ar" data-title="حلقي البنتان" 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/Siklopentan" title="Siklopentan – Azerbaijani" lang="az" hreflang="az" data-title="Siklopentan" 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/%D8%B3%DB%8C%DA%A9%D9%84%D9%88%D9%BE%D9%86%D8%AA%D8%A7%D9%86" title="سیکلوپنتان – South Azerbaijani" lang="azb" hreflang="azb" data-title="سیکلوپنتان" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-be mw-list-item"><a href="https://be.wikipedia.org/wiki/%D0%A6%D1%8B%D0%BA%D0%BB%D0%B0%D0%BF%D0%B5%D0%BD%D1%82%D0%B0%D0%BD" title="Цыклапентан – Belarusian" lang="be" hreflang="be" data-title="Цыклапентан" data-language-autonym="Беларуская" data-language-local-name="Belarusian" class="interlanguage-link-target"><span>Беларуская</span></a></li><li class="interlanguage-link interwiki-bg mw-list-item"><a href="https://bg.wikipedia.org/wiki/%D0%A6%D0%B8%D0%BA%D0%BB%D0%BE%D0%BF%D0%B5%D0%BD%D1%82%D0%B0%D0%BD" title="Циклопентан – Bulgarian" lang="bg" hreflang="bg" data-title="Циклопентан" data-language-autonym="Български" data-language-local-name="Bulgarian" class="interlanguage-link-target"><span>Български</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Ciclopent%C3%A0" title="Ciclopentà – Catalan" lang="ca" hreflang="ca" data-title="Ciclopentà" 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/Cyklopentan" title="Cyklopentan – Czech" lang="cs" hreflang="cs" data-title="Cyklopentan" 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/Cyclopentan" title="Cyclopentan – German" lang="de" hreflang="de" data-title="Cyclopentan" 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%9A%CF%85%CE%BA%CE%BB%CE%BF%CF%80%CE%B5%CE%BD%CF%84%CE%AC%CE%BD%CE%B9%CE%BF" title="Κυκλοπεντάνιο – Greek" lang="el" hreflang="el" data-title="Κυκλοπεντάνιο" 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/Ciclopentano" title="Ciclopentano – Spanish" lang="es" hreflang="es" data-title="Ciclopentano" 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/Ciklopentano" title="Ciklopentano – Esperanto" lang="eo" hreflang="eo" data-title="Ciklopentano" data-language-autonym="Esperanto" data-language-local-name="Esperanto" class="interlanguage-link-target"><span>Esperanto</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%B3%DB%8C%DA%A9%D9%84%D9%88%D9%BE%D9%86%D8%AA%D8%A7%D9%86" title="سیکلوپنتان – Persian" lang="fa" hreflang="fa" data-title="سیکلوپنتان" 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/Cyclopentane" title="Cyclopentane – French" lang="fr" hreflang="fr" data-title="Cyclopentane" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/Ciclopentano" title="Ciclopentano – Galician" lang="gl" hreflang="gl" data-title="Ciclopentano" data-language-autonym="Galego" data-language-local-name="Galician" class="interlanguage-link-target"><span>Galego</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EC%82%AC%EC%9D%B4%ED%81%B4%EB%A1%9C%ED%8E%9C%ED%85%8C%EC%9D%B8" title="사이클로펜테인 – Korean" lang="ko" hreflang="ko" data-title="사이클로펜테인" 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%91%D5%AB%D5%AF%D5%AC%D5%B8%D5%BA%D5%A5%D5%B6%D5%BF%D5%A1%D5%B6" title="Ցիկլոպենտան – Armenian" lang="hy" hreflang="hy" data-title="Ցիկլոպենտան" data-language-autonym="Հայերեն" data-language-local-name="Armenian" class="interlanguage-link-target"><span>Հայերեն</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Siklopentana" title="Siklopentana – Indonesian" lang="id" hreflang="id" data-title="Siklopentana" 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/Ciclopentano" title="Ciclopentano – Italian" lang="it" hreflang="it" data-title="Ciclopentano" 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%A6%D7%99%D7%A7%D7%9C%D7%95%D7%A4%D7%A0%D7%98%D7%90%D7%9F" title="ציקלופנטאן – Hebrew" lang="he" hreflang="he" data-title="ציקלופנטאן" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-ka mw-list-item"><a href="https://ka.wikipedia.org/wiki/%E1%83%AA%E1%83%98%E1%83%99%E1%83%9A%E1%83%9D%E1%83%9E%E1%83%94%E1%83%9C%E1%83%A2%E1%83%90%E1%83%9C%E1%83%98" title="ციკლოპენტანი – Georgian" lang="ka" hreflang="ka" data-title="ციკლოპენტანი" data-language-autonym="ქართული" data-language-local-name="Georgian" class="interlanguage-link-target"><span>ქართული</span></a></li><li class="interlanguage-link interwiki-lv mw-list-item"><a href="https://lv.wikipedia.org/wiki/Ciklopent%C4%81ns" title="Ciklopentāns – Latvian" lang="lv" hreflang="lv" data-title="Ciklopentāns" data-language-autonym="Latviešu" data-language-local-name="Latvian" class="interlanguage-link-target"><span>Latviešu</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Ciklopent%C3%A1n" title="Ciklopentán – Hungarian" lang="hu" hreflang="hu" data-title="Ciklopentán" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-mk mw-list-item"><a href="https://mk.wikipedia.org/wiki/%D0%A6%D0%B8%D0%BA%D0%BB%D0%BE%D0%BF%D0%B5%D0%BD%D1%82%D0%B0%D0%BD" title="Циклопентан – Macedonian" lang="mk" hreflang="mk" data-title="Циклопентан" data-language-autonym="Македонски" data-language-local-name="Macedonian" class="interlanguage-link-target"><span>Македонски</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Cyclopentaan" title="Cyclopentaan – Dutch" lang="nl" hreflang="nl" data-title="Cyclopentaan" 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%82%B7%E3%82%AF%E3%83%AD%E3%83%9A%E3%83%B3%E3%82%BF%E3%83%B3" title="シクロペンタン – Japanese" lang="ja" hreflang="ja" data-title="シクロペンタン" 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-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Cyklopentan" title="Cyklopentan – Polish" lang="pl" hreflang="pl" data-title="Cyklopentan" 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/Ciclopentano" title="Ciclopentano – Portuguese" lang="pt" hreflang="pt" data-title="Ciclopentano" 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/Ciclopentan" title="Ciclopentan – Romanian" lang="ro" hreflang="ro" data-title="Ciclopentan" 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%A6%D0%B8%D0%BA%D0%BB%D0%BE%D0%BF%D0%B5%D0%BD%D1%82%D0%B0%D0%BD" title="Циклопентан – Russian" lang="ru" hreflang="ru" data-title="Циклопентан" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-simple mw-list-item"><a href="https://simple.wikipedia.org/wiki/Cyclopentane" title="Cyclopentane – Simple English" lang="en-simple" hreflang="en-simple" data-title="Cyclopentane" data-language-autonym="Simple English" data-language-local-name="Simple English" class="interlanguage-link-target"><span>Simple English</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Ciklopentan" title="Ciklopentan – Serbian" lang="sr" hreflang="sr" data-title="Ciklopentan" 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/Ciklopentan" title="Ciklopentan – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Ciklopentan" 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/Syklopentaani" title="Syklopentaani – Finnish" lang="fi" hreflang="fi" data-title="Syklopentaani" 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/Cyklopentan" title="Cyklopentan – Swedish" lang="sv" hreflang="sv" data-title="Cyklopentan" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Siklopentan" title="Siklopentan – Turkish" lang="tr" hreflang="tr" data-title="Siklopentan" data-language-autonym="Türkçe" data-language-local-name="Turkish" class="interlanguage-link-target"><span>Türkçe</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%A6%D0%B8%D0%BA%D0%BB%D0%BE%D0%BF%D0%B5%D0%BD%D1%82%D0%B0%D0%BD" title="Циклопентан – Ukrainian" lang="uk" hreflang="uk" data-title="Циклопентан" 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/Cyclopentan" title="Cyclopentan – Vietnamese" lang="vi" hreflang="vi" data-title="Cyclopentan" 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-zh-yue mw-list-item"><a href="https://zh-yue.wikipedia.org/wiki/%E7%92%B0%E6%88%8A%E7%83%B7" title="環戊烷 – Cantonese" lang="yue" hreflang="yue" data-title="環戊烷" 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/%E7%8E%AF%E6%88%8A%E7%83%B7" title="环戊烷 – Chinese" lang="zh" hreflang="zh" data-title="环戊烷" 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/Q80260#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 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figure:not(.skin-invert-image):not(.skin-invert):not(.bg-transparent){background:var(--background-color-inverted,#f8f9fa)}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .ib-chembox figure:not(.skin-invert-image):not(.skin-invert):not(.bg-transparent){background:var(--background-color-inverted,#f8f9fa)}}</style> <table class="infobox ib-chembox"> <caption>Cyclopentane </caption> <tbody><tr> <td colspan="2" class="borderless" style="text-align:center"> <table border="0" style="width:100%;display:inline-table;"> <tbody><tr> <td style="border-right:1px solid #aaa; width:50%;"><figure class="mw-halign-center skin-invert-image" typeof="mw:File"><a href="/wiki/File:Cyclopentane_v2.svg" class="mw-file-description"><img alt="Skeletal formula" src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e1/Cyclopentane_v2.svg/100px-Cyclopentane_v2.svg.png" decoding="async" width="100" height="96" class="mw-file-element" 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</td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; 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;">Cyclopentane</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;">pentamethylene</div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; 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=287-92-3">287-92-3</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=C1CCCC1">Interactive image</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChEBI" title="ChEBI">ChEBI</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=23492">CHEBI:23492</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChemSpider" title="ChemSpider">ChemSpider</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.chemspider.com"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.8896.html">8896</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ECHA_InfoCard" class="mw-redirect" title="ECHA InfoCard"><span title="echa.europa.eu">ECHA InfoCard</span></a> </td> <td><a rel="nofollow" class="external text" href="https://echa.europa.eu/substance-information/-/substanceinfo/100.005.470">100.005.470</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q80260#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>206-016-6</li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/PubChem" title="PubChem">PubChem</a> <abbr title="Compound ID">CID</abbr></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/9253">9253</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/RTECS" class="mw-redirect" title="RTECS">RTECS number</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li>GY2390000</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/T86PB90RNU">T86PB90RNU</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/DTXSID6024886">DTXSID6024886</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q80260#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;"><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/C5H10/c1-2-4-5-3-1/h1-5H2<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: RGSFGYAAUTVSQA-UHFFFAOYSA-N<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div></div></li><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1/C5H10/c1-2-4-5-3-1/h1-5H2</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: RGSFGYAAUTVSQA-UHFFFAOYAL</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;"><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%;">C1CCCC1</div></li></ul> </div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; 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>C<sub>5</sub>H<sub>10</sub>  </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td>70.1 g/mol    </td></tr> <tr> <td>Appearance </td> <td>clear, colorless liquid </td></tr> <tr> <td><a href="/wiki/Odor" title="Odor">Odor</a> </td> <td>mild, sweet </td></tr> <tr> <td><a href="/wiki/Density" title="Density">Density</a> </td> <td>0.751 g/cm<sup>3</sup> </td></tr> <tr> <td><a href="/wiki/Melting_point" title="Melting point">Melting point</a> </td> <td>−93.9 °C (−137.0 °F; 179.2 K) </td></tr> <tr> <td><a href="/wiki/Boiling_point" title="Boiling point">Boiling point</a> </td> <td>49.2 °C (120.6 °F; 322.3 K) </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Aqueous_solution" title="Aqueous solution">Solubility in water</a></div> </td> <td>156 mg·l<sup>−1</sup> (25 °C)<sup id="cite_ref-1" class="reference"><a href="#cite_note-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Solubility" title="Solubility">Solubility</a> </td> <td>soluble in <a href="/wiki/Ethanol" title="Ethanol">ethanol</a>, <a href="/wiki/Acetone" title="Acetone">acetone</a>, <a href="/wiki/Diethyl_ether" title="Diethyl ether">ether</a> </td></tr> <tr> <td><a href="/wiki/Vapor_pressure" title="Vapor pressure">Vapor pressure</a> </td> <td>45 <a href="/wiki/KPa" class="mw-redirect" title="KPa">kPa</a> (20 °C) <sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Acid_dissociation_constant" title="Acid dissociation constant">Acidity</a> (p<i>K</i><sub>a</sub>) </td> <td>~45 </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Magnetic_susceptibility" title="Magnetic susceptibility">Magnetic susceptibility</a> (χ)</div> </td> <td>-59.18·10<sup>−6</sup> cm<sup>3</sup>/mol </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Refractive_index" title="Refractive index">Refractive index</a> (<i>n</i><sub>D</sub>)</div> </td> <td>1.4065 </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Hazards </th></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;color:inherit;"><b><a href="/wiki/Occupational_safety_and_health" title="Occupational safety and health">Occupational safety and health</a></b> (OHS/OSH): </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Main hazards</div> </td> <td>Flammable<sup id="cite_ref-PGCH_3-0" class="reference"><a href="#cite_note-PGCH-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/NFPA_704" title="NFPA 704"><b>NFPA 704</b></a> (fire diamond) </td> <td><style data-mw-deduplicate="TemplateStyles:r1170367383">.mw-parser-output .nfpa-704-diamond-ref{float:right;padding:1px;text-align:right}.mw-parser-output .nfpa-704-diamond-container{width:82px;font-family:sans-serif;margin:0 auto}.mw-parser-output .nfpa-704-diamond-container-ref{float:left;margin-left:1em}.mw-parser-output .nfpa-704-diamond-images{float:left;font-size:20px;text-align:center;position:relative;height:80px;width:80px;padding:1px}.mw-parser-output .nfpa-704-diamond-map{position:absolute;height:80px;width:80px}.mw-parser-output .nfpa-704-diamond .noresize{margin:0 auto}.mw-parser-output .nfpa-704-diamond-code{line-height:1em;text-align:center;position:absolute}.mw-parser-output .nfpa-704-diamond-code>a{color:black}.mw-parser-output .nfpa-704-diamond-blue{width:13px;top:31px;left:15px}.mw-parser-output .nfpa-704-diamond-red{width:12px;top:12px;left:35px}.mw-parser-output .nfpa-704-diamond-yellow{width:13px;top:31px;left:54px}.mw-parser-output .nfpa-704-diamond-white-image{position:relative;top:51px;left:0}.mw-parser-output .nfpa-704-diamond-white-text{vertical-align:middle;text-align:center;line-height:80%;position:absolute;top:52px}.mw-parser-output .nfpa-704-diamond-white-text a>span{position:absolute;color:black}.mw-parser-output .nfpa-704-diamond-white-wors{font-size:15px;width:23px;left:29px}.mw-parser-output .nfpa-704-diamond-white-wox{font-size:15px;font-stretch:condensed;width:21px;line-height:80%;top:-4px;left:29px}.mw-parser-output .nfpa-704-diamond-white-abcp{font-size:13.5px;font-stretch:condensed;width:28px;left:26px}.mw-parser-output .nfpa-704-diamond-white-ac{font-size:10px;width:30px;left:25px}.mw-parser-output .nfpa-704-diamond-white-strike{text-decoration:line-through}</style><div class="nfpa-704-diamond notheme"><div class="nfpa-704-diamond-container"><div class="nfpa-704-diamond-images nounderlines"> <div class="nfpa-704-diamond-map"><figure class="noresize" typeof="mw:File"><span><img alt="NFPA 704 four-colored diamond" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/80px-NFPA_704.svg.png" decoding="async" width="80" height="80" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/120px-NFPA_704.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/160px-NFPA_704.svg.png 2x" data-file-width="512" data-file-height="512" usemap="#ImageMap_dc8789d9d8c839e4" /></span><map name="ImageMap_dc8789d9d8c839e4"><area href="/wiki/NFPA_704#Blue" shape="poly" coords="23,23,47,47,23,70,0,47" alt="Health 1: Exposure would cause irritation but only minor residual injury. E.g. turpentine" title="Health 1: Exposure would cause irritation but only minor residual injury. E.g. turpentine" /><area href="/wiki/NFPA_704#Red" shape="poly" coords="47,0,70,23,47,47,23,23" alt="Flammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasoline" title="Flammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasoline" /><area href="/wiki/NFPA_704#Yellow" shape="poly" coords="70,23,94,47,70,70,47,47" alt="Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen" title="Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen" /><area href="/wiki/NFPA_704#White" shape="poly" coords="47,47,70,70,47,94,23,70" alt="Special hazards (white): no code" title="Special hazards (white): no code" /></map><figcaption></figcaption></figure></div><div class="nfpa-704-diamond-code nfpa-704-diamond-blue"> <a href="/wiki/NFPA_704#Blue" title="NFPA 704"><span title="Health 1: Exposure would cause irritation but only minor residual injury. E.g. turpentine" class="notheme mw-no-invert">1</span></a></div><div class="nfpa-704-diamond-code nfpa-704-diamond-red"> <a href="/wiki/NFPA_704#Red" title="NFPA 704"><span title="Flammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasoline" class="notheme mw-no-invert">3</span></a></div><div class="nfpa-704-diamond-code nfpa-704-diamond-yellow"> <a href="/wiki/NFPA_704#Yellow" title="NFPA 704"><span title="Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen" class="notheme mw-no-invert">0</span></a></div></div></div></div> </td></tr> <tr> <td><a href="/wiki/Flash_point" title="Flash point">Flash point</a> </td> <td>−37.2 °C (−35.0 °F; 236.0 K) </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Autoignition_temperature" title="Autoignition temperature">Autoignition<br />temperature</a></div> </td> <td>361 °C (682 °F; 634 K) </td></tr> <tr> <td><a href="/wiki/Explosive_limit" class="mw-redirect" title="Explosive limit">Explosive limits</a> </td> <td>1.1%-8.7%<sup id="cite_ref-PGCH_3-1" class="reference"><a href="#cite_note-PGCH-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;color:inherit;"><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>none<sup id="cite_ref-PGCH_3-2" class="reference"><a href="#cite_note-PGCH-3"><span class="cite-bracket">[</span>3<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 600 ppm (1720 mg/m<sup>3</sup>)<sup id="cite_ref-PGCH_3-3" class="reference"><a href="#cite_note-PGCH-3"><span class="cite-bracket">[</span>3<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>N.D.<sup id="cite_ref-PGCH_3-4" class="reference"><a href="#cite_note-PGCH-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Related compounds </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Related compounds</div> </td> <td><a href="/wiki/Cyclopropane" title="Cyclopropane">cyclopropane</a>, <a href="/wiki/Cyclobutane" title="Cyclobutane">cyclobutane</a>, <a href="/wiki/Cyclohexane" title="Cyclohexane">cyclohexane</a> </td></tr> <tr> <td colspan="2" style="text-align:left; background:#f8eaba; color:inherit; border:1px solid #a2a9b1;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Except where otherwise noted, data are given for materials in their <a href="/wiki/Standard_state" title="Standard state">standard state</a> (at 25 °C [77 °F], 100 kPa).</div> <div style="margin-top: 0.3em;"><div style="text-align:center;"><span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/12px-Yes_check.svg.png" decoding="async" width="12" height="12" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/18px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/24px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span> <span class="reflink plainlinks nourlexpansion"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=444653737&page2=Cyclopentane">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>Cyclopentane</b> (also called <b>C pentane</b>)<sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> is a highly <a href="/wiki/Flammable" class="mw-redirect" title="Flammable">flammable</a> <a href="/wiki/Alicyclic_compound" title="Alicyclic compound">alicyclic</a> <a href="/wiki/Hydrocarbon" title="Hydrocarbon">hydrocarbon</a> with <a href="/wiki/Chemical_formula" title="Chemical formula">chemical formula</a> <a href="/wiki/C5H10" title="C5H10">C<sub>5</sub>H<sub>10</sub></a> and <a href="/wiki/CAS_number" class="mw-redirect" title="CAS number">CAS number</a> 287-92-3, consisting of a ring of five <a href="/wiki/Carbon" title="Carbon">carbon</a> atoms each bonded with two <a href="/wiki/Hydrogen" title="Hydrogen">hydrogen</a> atoms above and below the plane. It is a colorless <a href="/wiki/Liquid" title="Liquid">liquid</a> with a <a href="/wiki/Petrol" class="mw-redirect" title="Petrol">petrol</a>-like <a href="/wiki/Odor" title="Odor">odor</a>. Its <a href="/wiki/Freezing_point" class="mw-redirect" title="Freezing point">freezing point</a> is −94 °C and its <a href="/wiki/Boiling_point" title="Boiling point">boiling point</a> is 49 °C. Cyclopentane is in the class of <a href="/wiki/Cycloalkane" title="Cycloalkane">cycloalkanes</a>, being <a href="/wiki/Alkane" title="Alkane">alkanes</a> that have one or more <a href="/wiki/Carbon_ring" class="mw-redirect" title="Carbon ring">carbon rings</a>. It is formed by <a href="/wiki/Cracking_(chemistry)" title="Cracking (chemistry)">cracking</a> <a href="/wiki/Cyclohexane" title="Cyclohexane">cyclohexane</a> in the presence of <a href="/wiki/Alumina" class="mw-redirect" title="Alumina">alumina</a> at a high temperature and pressure. </p><p>It was first prepared in 1893 by the German chemist <a href="/wiki/Johannes_Wislicenus" title="Johannes Wislicenus">Johannes Wislicenus</a>.<sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Production,_occurrence_and_use"><span id="Production.2C_occurrence_and_use"></span>Production, occurrence and use</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cyclopentane&action=edit&section=1" title="Edit section: Production, occurrence and use"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Cycloalkanes are formed by <a href="/wiki/Catalytic_reforming" title="Catalytic reforming">catalytic reforming</a>. For example, when passed over a hot platinum surface, <a href="/wiki/2-Methylbutane" class="mw-redirect" title="2-Methylbutane">2-methylbutane</a> converts into cyclopentane. </p> <figure class="mw-default-size mw-halign-left" typeof="mw:File/Thumb"><a href="/wiki/File:Cyclopentane_warning_on_refrigerator.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a0/Cyclopentane_warning_on_refrigerator.jpg/220px-Cyclopentane_warning_on_refrigerator.jpg" decoding="async" width="220" height="165" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a0/Cyclopentane_warning_on_refrigerator.jpg/330px-Cyclopentane_warning_on_refrigerator.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a0/Cyclopentane_warning_on_refrigerator.jpg/440px-Cyclopentane_warning_on_refrigerator.jpg 2x" data-file-width="2133" data-file-height="1600" /></a><figcaption>This prominent sign on the back of a refrigerator marks it as containing cyclopentane-based insulation</figcaption></figure> <p>Cyclopentane is principally used as a <a href="/wiki/Blowing_agent" title="Blowing agent">blowing agent</a> in the manufacture of <a href="/wiki/Polyurethane_foam" title="Polyurethane foam">polyurethane insulating foam</a>, replacing ozone-depleting agents such as <a href="/wiki/Trichlorofluoromethane" title="Trichlorofluoromethane">CFC-11</a> and <a href="/wiki/1,1-Dichloro-1-fluoroethane" title="1,1-Dichloro-1-fluoroethane">HCFC-141b</a>.<sup id="cite_ref-Schilling2000_6-0" class="reference"><a href="#cite_note-Schilling2000-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-greenpeace_7-0" class="reference"><a href="#cite_note-greenpeace-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> While cyclopentane is not typically used as a <a href="/wiki/Refrigerant" title="Refrigerant">refrigerant</a>, it is common for domestic appliances that are insulated with cyclopentane-based foam, such as <a href="/wiki/Refrigerator" title="Refrigerator">refrigerators</a> and <a href="/wiki/Freezer" class="mw-redirect" title="Freezer">freezers</a>, to be marked with cyclopentane warning labels due to its flammability. Cyclopentane is also used in the manufacture of <a href="/wiki/Chemical_synthesis" title="Chemical synthesis">synthetic</a> <a href="/wiki/Resin" title="Resin">resins</a> and <a href="/wiki/Rubber" class="mw-redirect" title="Rubber">rubber</a> <a href="/wiki/Adhesive" title="Adhesive">adhesives</a>.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (June 2024)">citation needed</span></a></i>]</sup> </p><p>Cyclopentane is a minor component of automobile fuel, with its share in US <a href="/wiki/Gasoline" title="Gasoline">gasoline</a> varying between 0.2 and 1.6% in early 1990s<sup id="cite_ref-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> and 0.1 to 1.7% in 2011.<sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> Its research and motor <a href="/wiki/Octane_rating" title="Octane rating">octane numbers</a> are reported as 101 or 103 and 85 or 86 respectively.<sup id="cite_ref-10" class="reference"><a href="#cite_note-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-11" class="reference"><a href="#cite_note-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> </p><p>Multiple alkylated cyclopentane (MAC) lubricants, such as 1,3,4-tri-(2-octyldodecyl) cyclopentane, have low volatility and are used by NASA in space applications.<sup id="cite_ref-NASA_12-0" class="reference"><a href="#cite_note-NASA-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-13" class="reference"><a href="#cite_note-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> </p><p>Cyclopentane requires safety precautions to prevent leakage and ignition as it is both highly flammable and can also cause respiratory arrest when inhaled.<sup id="cite_ref-14" class="reference"><a href="#cite_note-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> </p><p>Cyclopentane can be fluorinated to give compounds ranging from <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">5</sub>H<sub class="template-chem2-sub">9</sub>F</span> to <a href="/w/index.php?title=Perfluorocyclopentane&action=edit&redlink=1" class="new" title="Perfluorocyclopentane (page does not exist)">perfluorocyclopentane</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C<sub class="template-chem2-sub">5</sub>F<sub class="template-chem2-sub">10</sub></span>. Such species are conceivable refrigerants and specialty solvents.<sup id="cite_ref-Tatlow_1995_15-0" class="reference"><a href="#cite_note-Tatlow_1995-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-16" class="reference"><a href="#cite_note-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> </p><p>The cyclopentane ring is pervasive in <a href="/wiki/Natural_product" title="Natural product">natural products</a> including many useful drugs. Examples include most <a href="/wiki/Steroid" title="Steroid">steroids</a>, <a href="/wiki/Prostaglandin" title="Prostaglandin">prostaglandins</a>, and some <a href="/wiki/Lipid" title="Lipid">lipids</a>. </p> <div class="mw-heading mw-heading2"><h2 id="Conformations">Conformations</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cyclopentane&action=edit&section=2" title="Edit section: Conformations"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In a <a href="/wiki/Regular_pentagon" class="mw-redirect" title="Regular pentagon">regular pentagon</a>, the angles at the vertices are all 108°, slightly less than the bond angle in perfectly tetrahedrally bonded carbon, which is about 109.47°. However, cyclopentane is not planar in its normal <a href="/wiki/Conformational_isomerism" class="mw-redirect" title="Conformational isomerism">conformations</a>. It puckers in order to increase the distances between the hydrogen atoms (something which does not happen in the planar <a href="/wiki/Cyclopentadienyl_anion" title="Cyclopentadienyl anion">cyclopentadienyl anion</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C<sub class="template-chem2-sub">5</sub>H<span class="template-chem2-su"><span>−</span><span>5</span></span></span> because it doesn't have as many hydrogen atoms). This means that the average C-C-C angle is less than 108°. There are two conformations that give local minima of the energy, the "envelope" and the "half-chair". The envelope has mirror symmetry (<a href="/wiki/Point_groups_in_three_dimensions" title="Point groups in three dimensions">C<sub>s</sub></a>), while the half chair has two-fold rotational symmetry (<a href="/wiki/Point_groups_in_three_dimensions" title="Point groups in three dimensions">C<sub>2</sub></a>). In both cases the symmetry implies that there are two pairs of equal C-C-C angles and one C-C-C angle that has no pair. In fact for cyclopentane, unlike for <a href="/wiki/Cyclohexane" title="Cyclohexane">cyclohexane</a> (C<sub>6</sub>H<sub>12</sub>, see <a href="/wiki/Cyclohexane_conformation" title="Cyclohexane conformation">cyclohexane conformation</a>) and higher <a href="/wiki/Cycloalkane" title="Cycloalkane">cycloalkanes</a>, it is not possible geometrically for all the angles and bond lengths to be equal except if it is in the form of a flat regular pentagon. </p> <ul class="gallery mw-gallery-traditional"> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Cyclopentane_envelope_conformation.svg" class="mw-file-description" title="Envelope"><img alt="Envelope" src="//upload.wikimedia.org/wikipedia/commons/thumb/1/1f/Cyclopentane_envelope_conformation.svg/120px-Cyclopentane_envelope_conformation.svg.png" decoding="async" width="120" height="70" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/1f/Cyclopentane_envelope_conformation.svg/180px-Cyclopentane_envelope_conformation.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/1f/Cyclopentane_envelope_conformation.svg/240px-Cyclopentane_envelope_conformation.svg.png 2x" data-file-width="512" data-file-height="297" /></a></span></div> <div class="gallerytext">Envelope</div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Cyclopentane3D.png" class="mw-file-description" title="3D envelope"><img alt="3D envelope" src="//upload.wikimedia.org/wikipedia/commons/thumb/9/9e/Cyclopentane3D.png/120px-Cyclopentane3D.png" decoding="async" width="120" height="89" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/9e/Cyclopentane3D.png/180px-Cyclopentane3D.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/9e/Cyclopentane3D.png/240px-Cyclopentane3D.png 2x" data-file-width="1000" data-file-height="740" /></a></span></div> <div class="gallerytext">3D envelope</div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Cyclopentane_halfchair.svg" class="mw-file-description" title="Half-chair"><img alt="Half-chair" src="//upload.wikimedia.org/wikipedia/commons/thumb/8/80/Cyclopentane_halfchair.svg/120px-Cyclopentane_halfchair.svg.png" decoding="async" width="120" height="75" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/80/Cyclopentane_halfchair.svg/180px-Cyclopentane_halfchair.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/80/Cyclopentane_halfchair.svg/240px-Cyclopentane_halfchair.svg.png 2x" data-file-width="307" data-file-height="192" /></a></span></div> <div class="gallerytext">Half-chair</div> </li> </ul> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cyclopentane&action=edit&section=3" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-1">^</a></b></span> <span class="reference-text"><a rel="nofollow" class="external text" href="https://gestis.dguv.de/data?name=027960&lang=en">Record of <i>cyclopentane</i></a> in the <a href="/wiki/GESTIS_Substance_Database" title="GESTIS Substance Database">GESTIS Substance Database</a> of the <a href="/wiki/Institute_for_Occupational_Safety_and_Health_of_the_German_Social_Accident_Insurance" title="Institute for Occupational Safety and Health of the German Social Accident Insurance">Institute for Occupational Safety and Health</a>, accessed on 28 February 2015. </span> </li> <li id="cite_note-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-2">^</a></b></span> <span class="reference-text"><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 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