CINXE.COM

<!DOCTYPE html> <html class="client-nojs vector-feature-language-in-header-enabled vector-feature-language-in-main-page-header-disabled vector-feature-sticky-header-disabled vector-feature-page-tools-pinned-disabled vector-feature-toc-pinned-clientpref-1 vector-feature-main-menu-pinned-disabled vector-feature-limited-width-clientpref-1 vector-feature-limited-width-content-enabled vector-feature-custom-font-size-clientpref-1 vector-feature-appearance-pinned-clientpref-1 vector-feature-night-mode-enabled skin-theme-clientpref-day vector-toc-available" lang="en" dir="ltr"> <head> <meta charset="UTF-8"> <title>Haloalkane - Wikipedia</title> <script>(function(){var className="client-js vector-feature-language-in-header-enabled vector-feature-language-in-main-page-header-disabled vector-feature-sticky-header-disabled vector-feature-page-tools-pinned-disabled vector-feature-toc-pinned-clientpref-1 vector-feature-main-menu-pinned-disabled vector-feature-limited-width-clientpref-1 vector-feature-limited-width-content-enabled vector-feature-custom-font-size-clientpref-1 vector-feature-appearance-pinned-clientpref-1 vector-feature-night-mode-enabled skin-theme-clientpref-day vector-toc-available";var cookie=document.cookie.match(/(?:^|; )enwikimwclientpreferences=([^;]+)/);if(cookie){cookie[1].split('%2C').forEach(function(pref){className=className.replace(new RegExp('(^| )'+pref.replace(/-clientpref-\w+$|[^\w-]+/g,'')+'-clientpref-\\w+( |$)'),'$1'+pref+'$2');});}document.documentElement.className=className;}());RLCONF={"wgBreakFrames":false,"wgSeparatorTransformTable":["",""],"wgDigitTransformTable":["",""],"wgDefaultDateFormat":"dmy", "wgMonthNames":["","January","February","March","April","May","June","July","August","September","October","November","December"],"wgRequestId":"23e8fcd2-1d05-4033-a8a7-808e8705b669","wgCanonicalNamespace":"","wgCanonicalSpecialPageName":false,"wgNamespaceNumber":0,"wgPageName":"Haloalkane","wgTitle":"Haloalkane","wgCurRevisionId":1244629621,"wgRevisionId":1244629621,"wgArticleId":75075,"wgIsArticle":true,"wgIsRedirect":false,"wgAction":"view","wgUserName":null,"wgUserGroups":["*"],"wgCategories":["Articles with short description","Short description matches Wikidata","Commons category link is on Wikidata","Haloalkanes","Halogenated solvents","Refrigerants","Functional groups"],"wgPageViewLanguage":"en","wgPageContentLanguage":"en","wgPageContentModel":"wikitext","wgRelevantPageName":"Haloalkane","wgRelevantArticleId":75075,"wgIsProbablyEditable":true,"wgRelevantPageIsProbablyEditable":true,"wgRestrictionEdit":[],"wgRestrictionMove":[],"wgRedirectedFrom":"Alkyl_halide","wgNoticeProject" :"wikipedia","wgCiteReferencePreviewsActive":false,"wgFlaggedRevsParams":{"tags":{"status":{"levels":1}}},"wgMediaViewerOnClick":true,"wgMediaViewerEnabledByDefault":true,"wgPopupsFlags":0,"wgVisualEditor":{"pageLanguageCode":"en","pageLanguageDir":"ltr","pageVariantFallbacks":"en"},"wgMFDisplayWikibaseDescriptions":{"search":true,"watchlist":true,"tagline":false,"nearby":true},"wgWMESchemaEditAttemptStepOversample":false,"wgWMEPageLength":20000,"wgInternalRedirectTargetUrl":"/wiki/Haloalkane","wgRelatedArticlesCompat":[],"wgCentralAuthMobileDomain":false,"wgEditSubmitButtonLabelPublish":true,"wgULSPosition":"interlanguage","wgULSisCompactLinksEnabled":false,"wgVector2022LanguageInHeader":true,"wgULSisLanguageSelectorEmpty":false,"wgWikibaseItemId":"Q271026","wgCheckUserClientHintsHeadersJsApi":["brands","architecture","bitness","fullVersionList","mobile","model","platform","platformVersion"],"GEHomepageSuggestedEditsEnableTopics":true,"wgGETopicsMatchModeEnabled":false, "wgGEStructuredTaskRejectionReasonTextInputEnabled":false,"wgGELevelingUpEnabledForUser":false};RLSTATE={"ext.globalCssJs.user.styles":"ready","site.styles":"ready","user.styles":"ready","ext.globalCssJs.user":"ready","user":"ready","user.options":"loading","ext.cite.styles":"ready","skins.vector.search.codex.styles":"ready","skins.vector.styles":"ready","skins.vector.icons":"ready","jquery.makeCollapsible.styles":"ready","ext.wikimediamessages.styles":"ready","ext.visualEditor.desktopArticleTarget.noscript":"ready","ext.uls.interlanguage":"ready","wikibase.client.init":"ready","ext.wikimediaBadges":"ready"};RLPAGEMODULES=["mediawiki.action.view.redirect","ext.cite.ux-enhancements","mediawiki.page.media","site","mediawiki.page.ready","jquery.makeCollapsible","mediawiki.toc","skins.vector.js","ext.centralNotice.geoIP","ext.centralNotice.startUp","ext.gadget.ReferenceTooltips","ext.gadget.switcher","ext.urlShortener.toolbar","ext.centralauth.centralautologin","mmv.bootstrap","ext.popups" ,"ext.visualEditor.desktopArticleTarget.init","ext.visualEditor.targetLoader","ext.echo.centralauth","ext.eventLogging","ext.wikimediaEvents","ext.navigationTiming","ext.uls.interface","ext.cx.eventlogging.campaigns","ext.cx.uls.quick.actions","wikibase.client.vector-2022","ext.checkUser.clientHints","ext.growthExperiments.SuggestedEditSession","wikibase.sidebar.tracking"];</script> <script>(RLQ=window.RLQ||[]).push(function(){mw.loader.impl(function(){return["user.options@12s5i",function($,jQuery,require,module){mw.user.tokens.set({"patrolToken":"+\\","watchToken":"+\\","csrfToken":"+\\"}); }];});});</script> <link rel="stylesheet" href="/w/load.php?lang=en&modules=ext.cite.styles%7Cext.uls.interlanguage%7Cext.visualEditor.desktopArticleTarget.noscript%7Cext.wikimediaBadges%7Cext.wikimediamessages.styles%7Cjquery.makeCollapsible.styles%7Cskins.vector.icons%2Cstyles%7Cskins.vector.search.codex.styles%7Cwikibase.client.init&only=styles&skin=vector-2022"> <script async="" src="/w/load.php?lang=en&modules=startup&only=scripts&raw=1&skin=vector-2022"></script> <meta name="ResourceLoaderDynamicStyles" content=""> <link rel="stylesheet" href="/w/load.php?lang=en&modules=site.styles&only=styles&skin=vector-2022"> <meta name="generator" content="MediaWiki 1.44.0-wmf.4"> <meta name="referrer" content="origin"> <meta name="referrer" content="origin-when-cross-origin"> <meta name="robots" content="max-image-preview:standard"> <meta name="format-detection" content="telephone=no"> <meta property="og:image" content="https://upload.wikimedia.org/wikipedia/commons/b/bd/Tetrafluoroethane_liquid.jpg"> <meta property="og:image:width" content="1200"> <meta property="og:image:height" content="1794"> <meta property="og:image" content="https://upload.wikimedia.org/wikipedia/commons/thumb/b/bd/Tetrafluoroethane_liquid.jpg/800px-Tetrafluoroethane_liquid.jpg"> <meta property="og:image:width" content="800"> <meta property="og:image:height" content="1196"> <meta property="og:image" content="https://upload.wikimedia.org/wikipedia/commons/thumb/b/bd/Tetrafluoroethane_liquid.jpg/640px-Tetrafluoroethane_liquid.jpg"> <meta property="og:image:width" content="640"> <meta property="og:image:height" content="957"> <meta name="viewport" content="width=1120"> <meta property="og:title" content="Haloalkane - Wikipedia"> <meta property="og:type" content="website"> <link rel="preconnect" href="//upload.wikimedia.org"> <link rel="alternate" media="only screen and (max-width: 640px)" href="//en.m.wikipedia.org/wiki/Haloalkane"> <link rel="alternate" type="application/x-wiki" title="Edit this page" href="/w/index.php?title=Haloalkane&action=edit"> <link rel="apple-touch-icon" href="/static/apple-touch/wikipedia.png"> <link rel="icon" href="/static/favicon/wikipedia.ico"> <link rel="search" type="application/opensearchdescription+xml" href="/w/rest.php/v1/search" title="Wikipedia (en)"> <link rel="EditURI" type="application/rsd+xml" href="//en.wikipedia.org/w/api.php?action=rsd"> <link rel="canonical" href="https://en.wikipedia.org/wiki/Haloalkane"> <link rel="license" href="https://creativecommons.org/licenses/by-sa/4.0/deed.en"> <link rel="alternate" type="application/atom+xml" title="Wikipedia Atom feed" href="/w/index.php?title=Special:RecentChanges&feed=atom"> <link rel="dns-prefetch" href="//meta.wikimedia.org" /> <link rel="dns-prefetch" href="//login.wikimedia.org"> </head> <body class="skin--responsive skin-vector skin-vector-search-vue mediawiki ltr sitedir-ltr mw-hide-empty-elt ns-0 ns-subject mw-editable page-Haloalkane rootpage-Haloalkane skin-vector-2022 action-view"><a class="mw-jump-link" href="#bodyContent">Jump to content</a> <div class="vector-header-container"> <header class="vector-header mw-header"> <div class="vector-header-start"> <nav class="vector-main-menu-landmark" aria-label="Site"> <div id="vector-main-menu-dropdown" class="vector-dropdown vector-main-menu-dropdown vector-button-flush-left vector-button-flush-right" > <input type="checkbox" id="vector-main-menu-dropdown-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-main-menu-dropdown" class="vector-dropdown-checkbox " aria-label="Main menu" > <label id="vector-main-menu-dropdown-label" for="vector-main-menu-dropdown-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" ><span class="vector-icon mw-ui-icon-menu mw-ui-icon-wikimedia-menu"></span> <span class="vector-dropdown-label-text">Main menu</span> </label> <div class="vector-dropdown-content"> <div id="vector-main-menu-unpinned-container" class="vector-unpinned-container"> <div id="vector-main-menu" class="vector-main-menu vector-pinnable-element"> <div class="vector-pinnable-header vector-main-menu-pinnable-header vector-pinnable-header-unpinned" data-feature-name="main-menu-pinned" data-pinnable-element-id="vector-main-menu" data-pinned-container-id="vector-main-menu-pinned-container" data-unpinned-container-id="vector-main-menu-unpinned-container" > <div class="vector-pinnable-header-label">Main menu</div> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-pin-button" data-event-name="pinnable-header.vector-main-menu.pin">move to sidebar</button> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-unpin-button" data-event-name="pinnable-header.vector-main-menu.unpin">hide</button> </div> <div id="p-navigation" class="vector-menu mw-portlet mw-portlet-navigation" > <div class="vector-menu-heading"> Navigation </div> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="n-mainpage-description" class="mw-list-item"><a href="/wiki/Main_Page" title="Visit the main page [z]" accesskey="z"><span>Main page</span></a></li><li id="n-contents" class="mw-list-item"><a href="/wiki/Wikipedia:Contents" title="Guides to browsing Wikipedia"><span>Contents</span></a></li><li id="n-currentevents" class="mw-list-item"><a href="/wiki/Portal:Current_events" title="Articles related to current events"><span>Current events</span></a></li><li id="n-randompage" class="mw-list-item"><a href="/wiki/Special:Random" title="Visit a randomly selected article [x]" accesskey="x"><span>Random article</span></a></li><li id="n-aboutsite" class="mw-list-item"><a href="/wiki/Wikipedia:About" title="Learn about Wikipedia and how it works"><span>About Wikipedia</span></a></li><li id="n-contactpage" class="mw-list-item"><a href="//en.wikipedia.org/wiki/Wikipedia:Contact_us" title="How to contact Wikipedia"><span>Contact us</span></a></li> </ul> </div> </div> <div id="p-interaction" class="vector-menu mw-portlet mw-portlet-interaction" > <div class="vector-menu-heading"> Contribute </div> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="n-help" class="mw-list-item"><a href="/wiki/Help:Contents" title="Guidance on how to use and edit Wikipedia"><span>Help</span></a></li><li id="n-introduction" class="mw-list-item"><a href="/wiki/Help:Introduction" title="Learn how to edit Wikipedia"><span>Learn to edit</span></a></li><li id="n-portal" class="mw-list-item"><a href="/wiki/Wikipedia:Community_portal" title="The hub for editors"><span>Community portal</span></a></li><li id="n-recentchanges" class="mw-list-item"><a href="/wiki/Special:RecentChanges" title="A list of recent changes to Wikipedia [r]" accesskey="r"><span>Recent changes</span></a></li><li id="n-upload" class="mw-list-item"><a href="/wiki/Wikipedia:File_upload_wizard" title="Add images or other media for use on Wikipedia"><span>Upload file</span></a></li> </ul> </div> </div> </div> </div> </div> </div> </nav> <a href="/wiki/Main_Page" class="mw-logo"> <img class="mw-logo-icon" src="/static/images/icons/wikipedia.png" alt="" aria-hidden="true" height="50" width="50"> <span class="mw-logo-container skin-invert"> <img class="mw-logo-wordmark" alt="Wikipedia" src="/static/images/mobile/copyright/wikipedia-wordmark-en.svg" style="width: 7.5em; height: 1.125em;"> <img class="mw-logo-tagline" alt="The Free Encyclopedia" src="/static/images/mobile/copyright/wikipedia-tagline-en.svg" width="117" height="13" style="width: 7.3125em; height: 0.8125em;"> </span> </a> </div> <div class="vector-header-end"> <div id="p-search" role="search" class="vector-search-box-vue vector-search-box-collapses vector-search-box-show-thumbnail vector-search-box-auto-expand-width vector-search-box"> <a href="/wiki/Special:Search" class="cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only search-toggle" title="Search Wikipedia [f]" accesskey="f"><span class="vector-icon mw-ui-icon-search mw-ui-icon-wikimedia-search"></span> <span>Search</span> </a> <div class="vector-typeahead-search-container"> <div class="cdx-typeahead-search cdx-typeahead-search--show-thumbnail cdx-typeahead-search--auto-expand-width"> <form action="/w/index.php" id="searchform" class="cdx-search-input cdx-search-input--has-end-button"> <div id="simpleSearch" class="cdx-search-input__input-wrapper" data-search-loc="header-moved"> <div class="cdx-text-input cdx-text-input--has-start-icon"> <input class="cdx-text-input__input" type="search" name="search" placeholder="Search Wikipedia" aria-label="Search Wikipedia" autocapitalize="sentences" title="Search Wikipedia [f]" accesskey="f" id="searchInput" > <span class="cdx-text-input__icon cdx-text-input__start-icon"></span> </div> <input type="hidden" name="title" value="Special:Search"> </div> <button class="cdx-button cdx-search-input__end-button">Search</button> </form> </div> </div> </div> <nav class="vector-user-links vector-user-links-wide" aria-label="Personal tools"> <div class="vector-user-links-main"> <div id="p-vector-user-menu-preferences" class="vector-menu mw-portlet emptyPortlet" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> </ul> </div> </div> <div id="p-vector-user-menu-userpage" class="vector-menu mw-portlet emptyPortlet" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> </ul> </div> </div> <nav class="vector-appearance-landmark" aria-label="Appearance"> <div id="vector-appearance-dropdown" class="vector-dropdown " title="Change the appearance of the page's font size, width, and color" > <input type="checkbox" id="vector-appearance-dropdown-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-appearance-dropdown" class="vector-dropdown-checkbox " aria-label="Appearance" > <label id="vector-appearance-dropdown-label" for="vector-appearance-dropdown-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" ><span class="vector-icon mw-ui-icon-appearance mw-ui-icon-wikimedia-appearance"></span> <span class="vector-dropdown-label-text">Appearance</span> </label> <div class="vector-dropdown-content"> <div id="vector-appearance-unpinned-container" class="vector-unpinned-container"> </div> </div> </div> </nav> <div id="p-vector-user-menu-notifications" class="vector-menu mw-portlet emptyPortlet" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> </ul> </div> </div> <div id="p-vector-user-menu-overflow" class="vector-menu mw-portlet" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="pt-sitesupport-2" class="user-links-collapsible-item mw-list-item user-links-collapsible-item"><a data-mw="interface" href="https://donate.wikimedia.org/wiki/Special:FundraiserRedirector?utm_source=donate&utm_medium=sidebar&utm_campaign=C13_en.wikipedia.org&uselang=en" class=""><span>Donate</span></a> </li> <li id="pt-createaccount-2" class="user-links-collapsible-item mw-list-item user-links-collapsible-item"><a data-mw="interface" href="/w/index.php?title=Special:CreateAccount&returnto=Haloalkane" title="You are encouraged to create an account and log in; however, it is not mandatory" class=""><span>Create account</span></a> </li> <li id="pt-login-2" class="user-links-collapsible-item mw-list-item user-links-collapsible-item"><a data-mw="interface" href="/w/index.php?title=Special:UserLogin&returnto=Haloalkane" title="You're encouraged to log in; however, it's not mandatory. [o]" accesskey="o" class=""><span>Log in</span></a> </li> </ul> </div> </div> </div> <div id="vector-user-links-dropdown" class="vector-dropdown vector-user-menu vector-button-flush-right vector-user-menu-logged-out" title="Log in and more options" > <input type="checkbox" id="vector-user-links-dropdown-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-user-links-dropdown" class="vector-dropdown-checkbox " aria-label="Personal tools" > <label id="vector-user-links-dropdown-label" for="vector-user-links-dropdown-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" ><span class="vector-icon mw-ui-icon-ellipsis mw-ui-icon-wikimedia-ellipsis"></span> <span class="vector-dropdown-label-text">Personal tools</span> </label> <div class="vector-dropdown-content"> <div id="p-personal" class="vector-menu mw-portlet mw-portlet-personal user-links-collapsible-item" title="User menu" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="pt-sitesupport" class="user-links-collapsible-item mw-list-item"><a href="https://donate.wikimedia.org/wiki/Special:FundraiserRedirector?utm_source=donate&utm_medium=sidebar&utm_campaign=C13_en.wikipedia.org&uselang=en"><span>Donate</span></a></li><li id="pt-createaccount" class="user-links-collapsible-item mw-list-item"><a href="/w/index.php?title=Special:CreateAccount&returnto=Haloalkane" title="You are encouraged to create an account and log in; however, it is not mandatory"><span class="vector-icon mw-ui-icon-userAdd mw-ui-icon-wikimedia-userAdd"></span> <span>Create account</span></a></li><li id="pt-login" class="user-links-collapsible-item mw-list-item"><a href="/w/index.php?title=Special:UserLogin&returnto=Haloalkane" title="You're encouraged to log in; however, it's not mandatory. [o]" accesskey="o"><span class="vector-icon mw-ui-icon-logIn mw-ui-icon-wikimedia-logIn"></span> <span>Log in</span></a></li> </ul> </div> </div> <div id="p-user-menu-anon-editor" class="vector-menu mw-portlet mw-portlet-user-menu-anon-editor" > <div class="vector-menu-heading"> Pages for logged out editors <a href="/wiki/Help:Introduction" aria-label="Learn more about editing"><span>learn more</span></a> </div> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="pt-anoncontribs" class="mw-list-item"><a href="/wiki/Special:MyContributions" title="A list of edits made from this IP address [y]" accesskey="y"><span>Contributions</span></a></li><li id="pt-anontalk" class="mw-list-item"><a href="/wiki/Special:MyTalk" title="Discussion about edits from this IP address [n]" accesskey="n"><span>Talk</span></a></li> </ul> </div> </div> </div> </div> </nav> </div> </header> </div> <div class="mw-page-container"> <div class="mw-page-container-inner"> <div class="vector-sitenotice-container"> <div id="siteNotice"></div> </div> <div class="vector-column-start"> <div class="vector-main-menu-container"> <div id="mw-navigation"> <nav id="mw-panel" class="vector-main-menu-landmark" aria-label="Site"> <div id="vector-main-menu-pinned-container" class="vector-pinned-container"> </div> </nav> </div> </div> <div class="vector-sticky-pinned-container"> <nav id="mw-panel-toc" aria-label="Contents" data-event-name="ui.sidebar-toc" class="mw-table-of-contents-container vector-toc-landmark"> <div id="vector-toc-pinned-container" class="vector-pinned-container"> <div id="vector-toc" class="vector-toc vector-pinnable-element"> <div class="vector-pinnable-header vector-toc-pinnable-header vector-pinnable-header-pinned" data-feature-name="toc-pinned" data-pinnable-element-id="vector-toc" > <h2 class="vector-pinnable-header-label">Contents</h2> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-pin-button" data-event-name="pinnable-header.vector-toc.pin">move to sidebar</button> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-unpin-button" data-event-name="pinnable-header.vector-toc.unpin">hide</button> </div> <ul class="vector-toc-contents" id="mw-panel-toc-list"> <li id="toc-mw-content-text" class="vector-toc-list-item vector-toc-level-1"> <a href="#" class="vector-toc-link"> <div class="vector-toc-text">(Top)</div> </a> </li> <li id="toc-Classes" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Classes"> <div class="vector-toc-text"> <span class="vector-toc-numb">1</span> <span>Classes</span> </div> </a> <ul id="toc-Classes-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Properties" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Properties"> <div class="vector-toc-text"> <span class="vector-toc-numb">2</span> <span>Properties</span> </div> </a> <ul id="toc-Properties-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Natural_occurrence" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Natural_occurrence"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Natural occurrence</span> </div> </a> <ul id="toc-Natural_occurrence-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Nomenclature" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Nomenclature"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Nomenclature</span> </div> </a> <button aria-controls="toc-Nomenclature-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Nomenclature subsection</span> </button> <ul id="toc-Nomenclature-sublist" class="vector-toc-list"> <li id="toc-IUPAC" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#IUPAC"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.1</span> <span>IUPAC</span> </div> </a> <ul id="toc-IUPAC-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Production" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Production"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Production</span> </div> </a> <button aria-controls="toc-Production-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Production subsection</span> </button> <ul id="toc-Production-sublist" class="vector-toc-list"> <li id="toc-From_alkanes" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#From_alkanes"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.1</span> <span>From alkanes</span> </div> </a> <ul id="toc-From_alkanes-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-From_alkenes_and_alkynes" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#From_alkenes_and_alkynes"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.2</span> <span>From alkenes and alkynes</span> </div> </a> <ul id="toc-From_alkenes_and_alkynes-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-From_alcohols" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#From_alcohols"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.3</span> <span>From alcohols</span> </div> </a> <ul id="toc-From_alcohols-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-From_carboxylic_acids" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#From_carboxylic_acids"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.4</span> <span>From carboxylic acids</span> </div> </a> <ul id="toc-From_carboxylic_acids-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Biosynthesis" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Biosynthesis"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.5</span> <span>Biosynthesis</span> </div> </a> <ul id="toc-Biosynthesis-sublist" class="vector-toc-list"> <li id="toc-From_amines_by_Sandmeyer's_Method" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#From_amines_by_Sandmeyer's_Method"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.5.1</span> <span>From amines by Sandmeyer's Method</span> </div> </a> <ul id="toc-From_amines_by_Sandmeyer's_Method-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> </ul> </li> <li id="toc-Reactions" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Reactions"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>Reactions</span> </div> </a> <button aria-controls="toc-Reactions-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Reactions subsection</span> </button> <ul id="toc-Reactions-sublist" class="vector-toc-list"> <li id="toc-Substitution" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Substitution"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.1</span> <span>Substitution</span> </div> </a> <ul id="toc-Substitution-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Elimination" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Elimination"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.2</span> <span>Elimination</span> </div> </a> <ul id="toc-Elimination-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Other" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Other"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.3</span> <span>Other</span> </div> </a> <ul id="toc-Other-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Applications" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Applications"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>Applications</span> </div> </a> <ul id="toc-Applications-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Environmental_considerations" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Environmental_considerations"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</span> <span>Environmental considerations</span> </div> </a> <ul id="toc-Environmental_considerations-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Safety" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Safety"> <div class="vector-toc-text"> <span class="vector-toc-numb">9</span> <span>Safety</span> </div> </a> <ul id="toc-Safety-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">10</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-External_links" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#External_links"> <div class="vector-toc-text"> <span class="vector-toc-numb">11</span> <span>External links</span> </div> </a> <ul id="toc-External_links-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav aria-label="Contents" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" > <input type="checkbox" id="vector-page-titlebar-toc-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-titlebar-toc" class="vector-dropdown-checkbox " aria-label="Toggle the table of contents" > <label id="vector-page-titlebar-toc-label" for="vector-page-titlebar-toc-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" ><span class="vector-icon mw-ui-icon-listBullet mw-ui-icon-wikimedia-listBullet"></span> <span class="vector-dropdown-label-text">Toggle the table of contents</span> </label> <div class="vector-dropdown-content"> <div id="vector-page-titlebar-toc-unpinned-container" class="vector-unpinned-container"> </div> </div> </div> </nav> <h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Haloalkane</span></h1> <div id="p-lang-btn" class="vector-dropdown mw-portlet mw-portlet-lang" > <input type="checkbox" id="p-lang-btn-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-p-lang-btn" class="vector-dropdown-checkbox mw-interlanguage-selector" aria-label="Go to an article in another language. Available in 48 languages" > <label id="p-lang-btn-label" for="p-lang-btn-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--action-progressive mw-portlet-lang-heading-48" aria-hidden="true" ><span class="vector-icon mw-ui-icon-language-progressive mw-ui-icon-wikimedia-language-progressive"></span> <span class="vector-dropdown-label-text">48 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-af mw-list-item"><a href="https://af.wikipedia.org/wiki/Halogenoalkaan" title="Halogenoalkaan – Afrikaans" lang="af" hreflang="af" data-title="Halogenoalkaan" data-language-autonym="Afrikaans" data-language-local-name="Afrikaans" class="interlanguage-link-target"><span>Afrikaans</span></a></li><li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D9%87%D8%A7%D9%84%D9%8A%D8%AF_%D8%A7%D9%84%D8%A3%D9%84%D9%83%D9%8A%D9%84" title="هاليد الألكيل – Arabic" lang="ar" hreflang="ar" data-title="هاليد الألكيل" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-ast mw-list-item"><a href="https://ast.wikipedia.org/wiki/Haloalcano" title="Haloalcano – Asturian" lang="ast" hreflang="ast" data-title="Haloalcano" data-language-autonym="Asturianu" data-language-local-name="Asturian" class="interlanguage-link-target"><span>Asturianu</span></a></li><li class="interlanguage-link interwiki-bg mw-list-item"><a href="https://bg.wikipedia.org/wiki/%D0%A5%D0%B0%D0%BB%D0%BE%D0%B0%D0%BB%D0%BA%D0%B0%D0%BD" title="Халоалкан – Bulgarian" lang="bg" hreflang="bg" data-title="Халоалкан" 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/Haloalc%C3%A0" title="Haloalcà – Catalan" lang="ca" hreflang="ca" data-title="Haloalcà" 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/Halogenalkany" title="Halogenalkany – Czech" lang="cs" hreflang="cs" data-title="Halogenalkany" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-cy mw-list-item"><a href="https://cy.wikipedia.org/wiki/Halogenoalcan" title="Halogenoalcan – Welsh" lang="cy" hreflang="cy" data-title="Halogenoalcan" data-language-autonym="Cymraeg" data-language-local-name="Welsh" class="interlanguage-link-target"><span>Cymraeg</span></a></li><li class="interlanguage-link interwiki-da mw-list-item"><a href="https://da.wikipedia.org/wiki/Alkylhalid" title="Alkylhalid – Danish" lang="da" hreflang="da" data-title="Alkylhalid" data-language-autonym="Dansk" data-language-local-name="Danish" class="interlanguage-link-target"><span>Dansk</span></a></li><li class="interlanguage-link interwiki-et mw-list-item"><a href="https://et.wikipedia.org/wiki/Alk%C3%BC%C3%BClhaliidid" title="Alküülhaliidid – Estonian" lang="et" hreflang="et" data-title="Alküülhaliidid" data-language-autonym="Eesti" data-language-local-name="Estonian" class="interlanguage-link-target"><span>Eesti</span></a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/%CE%91%CE%BB%CE%BA%CF%85%CE%BB%CE%B1%CE%BB%CE%BF%CE%B3%CE%BF%CE%BD%CE%AF%CE%B4%CE%B9%CE%B1" title="Αλκυλαλογονίδια – Greek" lang="el" hreflang="el" data-title="Αλκυλαλογονίδια" 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/Haloalcano" title="Haloalcano – Spanish" lang="es" hreflang="es" data-title="Haloalcano" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-eu mw-list-item"><a href="https://eu.wikipedia.org/wiki/Haloalkano" title="Haloalkano – Basque" lang="eu" hreflang="eu" data-title="Haloalkano" 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%87%D8%A7%D9%84%D9%88%D8%A2%D9%84%DA%A9%D8%A7%D9%86" title="هالوآلکان – Persian" lang="fa" hreflang="fa" data-title="هالوآلکان" 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/Halog%C3%A9noalcane" title="Halogénoalcane – French" lang="fr" hreflang="fr" data-title="Halogénoalcane" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-ga mw-list-item"><a href="https://ga.wikipedia.org/wiki/Halaigionalc%C3%A1n" title="Halaigionalcán – Irish" lang="ga" hreflang="ga" data-title="Halaigionalcán" data-language-autonym="Gaeilge" data-language-local-name="Irish" class="interlanguage-link-target"><span>Gaeilge</span></a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/Haloalcano" title="Haloalcano – Galician" lang="gl" hreflang="gl" data-title="Haloalcano" data-language-autonym="Galego" data-language-local-name="Galician" class="interlanguage-link-target"><span>Galego</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%ED%95%A0%EB%A1%9C%EC%95%8C%EC%BC%80%EC%9D%B8" title="할로알케인 – Korean" lang="ko" hreflang="ko" data-title="할로알케인" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-hi mw-list-item"><a href="https://hi.wikipedia.org/wiki/%E0%A4%B9%E0%A5%88%E0%A4%B2%E0%A5%8B%E0%A4%8F%E0%A4%B2%E0%A5%8D%E0%A4%95%E0%A5%87%E0%A4%A8" title="हैलोएल्केन – Hindi" lang="hi" hreflang="hi" data-title="हैलोएल्केन" data-language-autonym="हिन्दी" data-language-local-name="Hindi" class="interlanguage-link-target"><span>हिन्दी</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Haloalkana" title="Haloalkana – Indonesian" lang="id" hreflang="id" data-title="Haloalkana" 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/Alogenuri_alchilici" title="Alogenuri alchilici – Italian" lang="it" hreflang="it" data-title="Alogenuri alchilici" 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%94%D7%9C%D7%95%D7%90%D7%9C%D7%A7%D7%90%D7%9F" title="הלואלקאן – Hebrew" lang="he" hreflang="he" data-title="הלואלקאן" 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%B0%E1%83%90%E1%83%9A%E1%83%9D%E1%83%92%E1%83%94%E1%83%9C%E1%83%90%E1%83%9A%E1%83%99%E1%83%90%E1%83%9C%E1%83%94%E1%83%91%E1%83%98" title="ჰალოგენალკანები – Georgian" lang="ka" hreflang="ka" data-title="ჰალოგენალკანები" 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/Halog%C4%93nog%C4%BC%C5%ABde%C5%86ra%C5%BEi" title="Halogēnogļūdeņraži – Latvian" lang="lv" hreflang="lv" data-title="Halogēnogļūdeņraži" data-language-autonym="Latviešu" data-language-local-name="Latvian" class="interlanguage-link-target"><span>Latviešu</span></a></li><li class="interlanguage-link interwiki-lt mw-list-item"><a href="https://lt.wikipedia.org/wiki/Alkilhalidai" title="Alkilhalidai – Lithuanian" lang="lt" hreflang="lt" data-title="Alkilhalidai" data-language-autonym="Lietuvių" data-language-local-name="Lithuanian" class="interlanguage-link-target"><span>Lietuvių</span></a></li><li class="interlanguage-link interwiki-mk mw-list-item"><a href="https://mk.wikipedia.org/wiki/%D0%A5%D0%B0%D0%BB%D0%BE%D0%B0%D0%BB%D0%BA%D0%B0%D0%BD" title="Халоалкан – Macedonian" lang="mk" hreflang="mk" data-title="Халоалкан" data-language-autonym="Македонски" data-language-local-name="Macedonian" class="interlanguage-link-target"><span>Македонски</span></a></li><li class="interlanguage-link interwiki-ms mw-list-item"><a href="https://ms.wikipedia.org/wiki/Haloalkana" title="Haloalkana – Malay" lang="ms" hreflang="ms" data-title="Haloalkana" data-language-autonym="Bahasa Melayu" data-language-local-name="Malay" class="interlanguage-link-target"><span>Bahasa Melayu</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Halogeenalkaan" title="Halogeenalkaan – Dutch" lang="nl" hreflang="nl" data-title="Halogeenalkaan" 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%8F%E3%83%AD%E3%82%B2%E3%83%B3%E5%8C%96%E3%82%A2%E3%83%AB%E3%82%AD%E3%83%AB" title="ハロゲン化アルキル – Japanese" lang="ja" hreflang="ja" data-title="ハロゲン化アルキル" 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/Hydroklorfluorkarbon" title="Hydroklorfluorkarbon – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Hydroklorfluorkarbon" 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-pnb mw-list-item"><a href="https://pnb.wikipedia.org/wiki/%DB%81%DB%8C%D9%84%D9%88%D8%A7%D9%84%DA%A9%DB%8C%D9%86" title="ہیلوالکین – Western Punjabi" lang="pnb" hreflang="pnb" data-title="ہیلوالکین" data-language-autonym="پنجابی" data-language-local-name="Western Punjabi" class="interlanguage-link-target"><span>پنجابی</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Halogenki_alkilowe" title="Halogenki alkilowe – Polish" lang="pl" hreflang="pl" data-title="Halogenki alkilowe" 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/Haloalcano" title="Haloalcano – Portuguese" lang="pt" hreflang="pt" data-title="Haloalcano" 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/Compu%C8%99i_halogena%C8%9Bi" title="Compuși halogenați – Romanian" lang="ro" hreflang="ro" data-title="Compuși halogenați" 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%93%D0%B0%D0%BB%D0%BE%D0%B3%D0%B5%D0%BD%D0%B0%D0%BB%D0%BA%D0%B0%D0%BD%D1%8B" title="Галогеналканы – Russian" lang="ru" hreflang="ru" data-title="Галогеналканы" 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/Haloalkane" title="Haloalkane – Simple English" lang="en-simple" hreflang="en-simple" data-title="Haloalkane" 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/Haloalkan" title="Haloalkan – Serbian" lang="sr" hreflang="sr" data-title="Haloalkan" 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/Haloalkan" title="Haloalkan – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Haloalkan" 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/Alkyylihalidit" title="Alkyylihalidit – Finnish" lang="fi" hreflang="fi" data-title="Alkyylihalidit" 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/Halogenalkan" title="Halogenalkan – Swedish" lang="sv" hreflang="sv" data-title="Halogenalkan" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-ta mw-list-item"><a href="https://ta.wikipedia.org/wiki/%E0%AE%86%E0%AE%B2%E0%AF%8B%E0%AE%85%E0%AE%B2%E0%AF%8D%E0%AE%95%E0%AF%87%E0%AE%A9%E0%AF%8D" title="ஆலோஅல்கேன் – Tamil" lang="ta" hreflang="ta" data-title="ஆலோஅல்கேன்" data-language-autonym="தமிழ்" data-language-local-name="Tamil" class="interlanguage-link-target"><span>தமிழ்</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Haloalkan" title="Haloalkan – Turkish" lang="tr" hreflang="tr" data-title="Haloalkan" 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%93%D0%B0%D0%BB%D0%BE%D0%B3%D0%B5%D0%BD%D0%BE%D0%B0%D0%BB%D0%BA%D0%B0%D0%BD%D0%B8" title="Галогеноалкани – Ukrainian" lang="uk" hreflang="uk" data-title="Галогеноалкани" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-ur mw-list-item"><a href="https://ur.wikipedia.org/wiki/%DB%81%DB%8C%D9%84%D9%88_%D8%A7%D9%84%DA%A9%DB%8C%D9%86" title="ہیلو الکین – Urdu" lang="ur" hreflang="ur" data-title="ہیلو الکین" data-language-autonym="اردو" data-language-local-name="Urdu" class="interlanguage-link-target"><span>اردو</span></a></li><li class="interlanguage-link interwiki-vi mw-list-item"><a href="https://vi.wikipedia.org/wiki/Haloalkan" title="Haloalkan – Vietnamese" lang="vi" hreflang="vi" data-title="Haloalkan" 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-classical mw-list-item"><a href="https://zh-classical.wikipedia.org/wiki/%E9%B9%B5%E4%BB%A3%E7%83%B7" title="鹵代烷 – Literary Chinese" lang="lzh" hreflang="lzh" data-title="鹵代烷" data-language-autonym="文言" data-language-local-name="Literary Chinese" class="interlanguage-link-target"><span>文言</span></a></li><li class="interlanguage-link interwiki-war mw-list-item"><a href="https://war.wikipedia.org/wiki/Haloalkane" title="Haloalkane – Waray" lang="war" hreflang="war" data-title="Haloalkane" data-language-autonym="Winaray" data-language-local-name="Waray" class="interlanguage-link-target"><span>Winaray</span></a></li><li class="interlanguage-link interwiki-zh-yue mw-list-item"><a href="https://zh-yue.wikipedia.org/wiki/%E9%B9%B5%E7%83%B7" title="鹵烷 – Cantonese" lang="yue" hreflang="yue" data-title="鹵烷" 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/%E5%8D%A4%E4%BB%A3%E7%83%B7%E7%83%83" title="卤代烷烃 – Chinese" lang="zh" hreflang="zh" data-title="卤代烷烃" 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/Q271026#sitelinks-wikipedia" title="Edit interlanguage links" class="wbc-editpage">Edit links</a></span></div> </div> </div> </div> </header> <div class="vector-page-toolbar"> <div class="vector-page-toolbar-container"> <div id="left-navigation"> <nav aria-label="Namespaces"> <div id="p-associated-pages" class="vector-menu vector-menu-tabs mw-portlet mw-portlet-associated-pages" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="ca-nstab-main" class="selected vector-tab-noicon mw-list-item"><a href="/wiki/Haloalkane" title="View the content page [c]" accesskey="c"><span>Article</span></a></li><li id="ca-talk" class="vector-tab-noicon mw-list-item"><a href="/wiki/Talk:Haloalkane" rel="discussion" title="Discuss improvements to the content page [t]" accesskey="t"><span>Talk</span></a></li> </ul> </div> </div> <div id="vector-variants-dropdown" class="vector-dropdown emptyPortlet" > <input type="checkbox" id="vector-variants-dropdown-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-variants-dropdown" class="vector-dropdown-checkbox " aria-label="Change language variant" > <label id="vector-variants-dropdown-label" for="vector-variants-dropdown-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet" aria-hidden="true" ><span class="vector-dropdown-label-text">English</span> </label> <div class="vector-dropdown-content"> <div id="p-variants" class="vector-menu mw-portlet mw-portlet-variants emptyPortlet" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> </ul> </div> </div> </div> </div> </nav> </div> <div id="right-navigation" class="vector-collapsible"> <nav aria-label="Views"> <div id="p-views" class="vector-menu vector-menu-tabs mw-portlet mw-portlet-views" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="ca-view" class="selected vector-tab-noicon mw-list-item"><a href="/wiki/Haloalkane"><span>Read</span></a></li><li id="ca-edit" class="vector-tab-noicon mw-list-item"><a href="/w/index.php?title=Haloalkane&action=edit" title="Edit this page [e]" accesskey="e"><span>Edit</span></a></li><li id="ca-history" class="vector-tab-noicon mw-list-item"><a href="/w/index.php?title=Haloalkane&action=history" title="Past revisions of this page [h]" accesskey="h"><span>View history</span></a></li> </ul> </div> </div> </nav> <nav class="vector-page-tools-landmark" aria-label="Page tools"> <div id="vector-page-tools-dropdown" class="vector-dropdown vector-page-tools-dropdown" > <input type="checkbox" id="vector-page-tools-dropdown-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-tools-dropdown" class="vector-dropdown-checkbox " aria-label="Tools" > <label id="vector-page-tools-dropdown-label" for="vector-page-tools-dropdown-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet" aria-hidden="true" ><span class="vector-dropdown-label-text">Tools</span> </label> <div class="vector-dropdown-content"> <div id="vector-page-tools-unpinned-container" class="vector-unpinned-container"> <div id="vector-page-tools" class="vector-page-tools vector-pinnable-element"> <div class="vector-pinnable-header vector-page-tools-pinnable-header vector-pinnable-header-unpinned" data-feature-name="page-tools-pinned" data-pinnable-element-id="vector-page-tools" data-pinned-container-id="vector-page-tools-pinned-container" data-unpinned-container-id="vector-page-tools-unpinned-container" > <div class="vector-pinnable-header-label">Tools</div> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-pin-button" data-event-name="pinnable-header.vector-page-tools.pin">move to sidebar</button> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-unpin-button" data-event-name="pinnable-header.vector-page-tools.unpin">hide</button> </div> <div id="p-cactions" class="vector-menu mw-portlet mw-portlet-cactions emptyPortlet vector-has-collapsible-items" title="More options" > <div class="vector-menu-heading"> Actions </div> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="ca-more-view" class="selected vector-more-collapsible-item mw-list-item"><a href="/wiki/Haloalkane"><span>Read</span></a></li><li id="ca-more-edit" class="vector-more-collapsible-item mw-list-item"><a href="/w/index.php?title=Haloalkane&action=edit" title="Edit this page [e]" accesskey="e"><span>Edit</span></a></li><li id="ca-more-history" class="vector-more-collapsible-item mw-list-item"><a href="/w/index.php?title=Haloalkane&action=history"><span>View history</span></a></li> </ul> </div> </div> <div id="p-tb" class="vector-menu mw-portlet mw-portlet-tb" > <div class="vector-menu-heading"> General </div> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="t-whatlinkshere" class="mw-list-item"><a href="/wiki/Special:WhatLinksHere/Haloalkane" title="List of all English Wikipedia pages containing links to this page [j]" accesskey="j"><span>What links here</span></a></li><li id="t-recentchangeslinked" class="mw-list-item"><a href="/wiki/Special:RecentChangesLinked/Haloalkane" rel="nofollow" title="Recent changes in pages linked from this page [k]" accesskey="k"><span>Related changes</span></a></li><li id="t-upload" class="mw-list-item"><a href="/wiki/Wikipedia:File_Upload_Wizard" title="Upload files [u]" accesskey="u"><span>Upload file</span></a></li><li id="t-specialpages" class="mw-list-item"><a href="/wiki/Special:SpecialPages" title="A list of all special pages [q]" accesskey="q"><span>Special pages</span></a></li><li id="t-permalink" class="mw-list-item"><a href="/w/index.php?title=Haloalkane&oldid=1244629621" title="Permanent link to this revision of this page"><span>Permanent link</span></a></li><li id="t-info" class="mw-list-item"><a href="/w/index.php?title=Haloalkane&action=info" title="More information about this page"><span>Page information</span></a></li><li id="t-cite" class="mw-list-item"><a href="/w/index.php?title=Special:CiteThisPage&page=Haloalkane&id=1244629621&wpFormIdentifier=titleform" title="Information on how to cite this page"><span>Cite this page</span></a></li><li id="t-urlshortener" class="mw-list-item"><a href="/w/index.php?title=Special:UrlShortener&url=https%3A%2F%2Fen.wikipedia.org%2Fwiki%2FHaloalkane"><span>Get shortened URL</span></a></li><li id="t-urlshortener-qrcode" class="mw-list-item"><a href="/w/index.php?title=Special:QrCode&url=https%3A%2F%2Fen.wikipedia.org%2Fwiki%2FHaloalkane"><span>Download QR code</span></a></li> </ul> </div> </div> <div id="p-coll-print_export" class="vector-menu mw-portlet mw-portlet-coll-print_export" > <div class="vector-menu-heading"> Print/export </div> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="coll-download-as-rl" class="mw-list-item"><a href="/w/index.php?title=Special:DownloadAsPdf&page=Haloalkane&action=show-download-screen" title="Download this page as a PDF file"><span>Download as PDF</span></a></li><li id="t-print" class="mw-list-item"><a href="/w/index.php?title=Haloalkane&printable=yes" title="Printable version of this page [p]" accesskey="p"><span>Printable version</span></a></li> </ul> </div> </div> <div id="p-wikibase-otherprojects" class="vector-menu mw-portlet mw-portlet-wikibase-otherprojects" > <div class="vector-menu-heading"> In other projects </div> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="wb-otherproject-link wb-otherproject-commons mw-list-item"><a href="https://commons.wikimedia.org/wiki/Category:Haloalkanes" hreflang="en"><span>Wikimedia Commons</span></a></li><li class="wb-otherproject-link wb-otherproject-wikiquote mw-list-item"><a href="https://en.wikiquote.org/wiki/Haloalkane" hreflang="en"><span>Wikiquote</span></a></li><li id="t-wikibase" class="wb-otherproject-link wb-otherproject-wikibase-dataitem mw-list-item"><a href="https://www.wikidata.org/wiki/Special:EntityPage/Q271026" title="Structured data on this page hosted by Wikidata [g]" accesskey="g"><span>Wikidata item</span></a></li> </ul> </div> </div> </div> </div> </div> </div> </nav> </div> </div> </div> <div class="vector-column-end"> <div class="vector-sticky-pinned-container"> <nav class="vector-page-tools-landmark" aria-label="Page tools"> <div id="vector-page-tools-pinned-container" class="vector-pinned-container"> </div> </nav> <nav class="vector-appearance-landmark" aria-label="Appearance"> <div id="vector-appearance-pinned-container" class="vector-pinned-container"> <div id="vector-appearance" class="vector-appearance vector-pinnable-element"> <div class="vector-pinnable-header vector-appearance-pinnable-header vector-pinnable-header-pinned" data-feature-name="appearance-pinned" data-pinnable-element-id="vector-appearance" data-pinned-container-id="vector-appearance-pinned-container" data-unpinned-container-id="vector-appearance-unpinned-container" > <div class="vector-pinnable-header-label">Appearance</div> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-pin-button" data-event-name="pinnable-header.vector-appearance.pin">move to sidebar</button> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-unpin-button" data-event-name="pinnable-header.vector-appearance.unpin">hide</button> </div> </div> </div> </nav> </div> </div> <div id="bodyContent" class="vector-body" aria-labelledby="firstHeading" data-mw-ve-target-container> <div class="vector-body-before-content"> <div class="mw-indicators"> </div> <div id="siteSub" class="noprint">From Wikipedia, the free encyclopedia</div> </div> <div id="contentSub"><div id="mw-content-subtitle"><span class="mw-redirectedfrom">(Redirected from <a href="/w/index.php?title=Alkyl_halide&redirect=no" class="mw-redirect" title="Alkyl halide">Alkyl halide</a>)</span></div></div> <div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Group of chemical compounds derived from alkanes containing one or more halogens</div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Tetrafluoroethane_liquid.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/bd/Tetrafluoroethane_liquid.jpg/170px-Tetrafluoroethane_liquid.jpg" decoding="async" width="170" height="254" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/bd/Tetrafluoroethane_liquid.jpg/255px-Tetrafluoroethane_liquid.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/bd/Tetrafluoroethane_liquid.jpg/340px-Tetrafluoroethane_liquid.jpg 2x" data-file-width="943" data-file-height="1410" /></a><figcaption><a href="/wiki/Tetrafluoroethane" title="Tetrafluoroethane">Tetrafluoroethane</a> (a haloalkane) is a colorless liquid that boils well below room temperature (as seen here) and can be extracted from common <a href="/wiki/Canned_air" class="mw-redirect" title="Canned air">canned air</a> canisters by simply inverting them during use.</figcaption></figure> <p>The <b>haloalkanes</b> (also known as <b>halogenoalkanes</b> or <b>alkyl halides</b>) are <a href="/wiki/Alkane" title="Alkane">alkanes</a> containing one or more <a href="/wiki/Halogen" title="Halogen">halogen</a> substituents.<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> They are a subset of the general class of <a href="/wiki/Halocarbon" title="Halocarbon">halocarbons</a>, although the distinction is not often made. Haloalkanes are widely used commercially. They are used as <a href="/wiki/Flame_retardant" title="Flame retardant">flame retardants</a>, <a href="/wiki/Fire_extinguisher" title="Fire extinguisher">fire extinguishants</a>, <a href="/wiki/Refrigerant" title="Refrigerant">refrigerants</a>, <a href="/wiki/Propellant" title="Propellant">propellants</a>, <a href="/wiki/Solvent" title="Solvent">solvents</a>, and <a href="/wiki/Pharmaceutical" class="mw-redirect" title="Pharmaceutical">pharmaceuticals</a>. Subsequent to the widespread use in commerce, many halocarbons have also been shown to be serious <a href="/wiki/Pollutant" title="Pollutant">pollutants</a> and toxins. For example, the <a href="/wiki/Chlorofluorocarbon" title="Chlorofluorocarbon">chlorofluorocarbons</a> have been shown to lead to <a href="/wiki/Ozone_depletion" title="Ozone depletion">ozone depletion</a>. <a href="/wiki/Methyl_bromide" class="mw-redirect" title="Methyl bromide">Methyl bromide</a> is a controversial fumigant. Only haloalkanes that contain chlorine, bromine, and iodine are a threat to the <a href="/wiki/Ozone_layer" title="Ozone layer">ozone layer</a>, but fluorinated volatile haloalkanes in theory may have activity as <a href="/wiki/Greenhouse_gas" title="Greenhouse gas">greenhouse gases</a>. <a href="/wiki/Methyl_iodide" class="mw-redirect" title="Methyl iodide">Methyl iodide</a>, a naturally occurring substance, however, does not have ozone-depleting properties and the United States Environmental Protection Agency has designated the compound a non-ozone layer depleter. For more information, see <a href="/wiki/Halomethane" title="Halomethane">Halomethane</a>. Haloalkane or alkyl halides are the compounds which have the general formula "RX" where R is an alkyl or substituted alkyl group and X is a halogen (F, Cl, Br, I). </p><p>Haloalkanes have been known for centuries. <a href="/wiki/Chloroethane" title="Chloroethane">Chloroethane</a> was produced in the 15th century. The systematic synthesis of such compounds developed in the 19th century in step with the development of organic chemistry and the understanding of the structure of alkanes. Methods were developed for the selective formation of C-halogen bonds. Especially versatile methods included the addition of halogens to alkenes, <a href="/wiki/Hydrohalogenation" title="Hydrohalogenation">hydrohalogenation</a> of alkenes, and the conversion of <a href="/wiki/Alcohol_(chemistry)" title="Alcohol (chemistry)">alcohols</a> to alkyl halides. These methods are so reliable and so easily implemented that haloalkanes became cheaply available for use in industrial chemistry because the halide could be further replaced by other functional groups. </p><p>While many haloalkanes are human-produced, substantial amounts are biogenic. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Classes">Classes</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Haloalkane&action=edit&section=1" title="Edit section: Classes"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>From the structural perspective, haloalkanes can be classified according to the connectivity of the carbon atom to which the halogen is attached. In primary (1°) haloalkanes, the <a href="/wiki/Carbon" title="Carbon">carbon</a> that carries the halogen atom is only attached to one other alkyl group. An example is <a href="/wiki/Chloroethane" title="Chloroethane">chloroethane</a> (<span class="chemf nowrap">CH<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">3</sub></span></span>CH<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">2</sub></span></span>Cl</span>). In secondary (2°) haloalkanes, the carbon that carries the halogen atom has two C–C bonds. In tertiary (3°) haloalkanes, the carbon that carries the halogen atom has three C–C bonds. </p><p>Haloalkanes can also be classified according to the type of halogen on group 17 responding to a specific halogenoalkane. Haloalkanes containing carbon bonded to <a href="/wiki/Fluorine" title="Fluorine">fluorine</a>, <a href="/wiki/Chlorine" title="Chlorine">chlorine</a>, <a href="/wiki/Bromine" title="Bromine">bromine</a>, and <a href="/wiki/Iodine" title="Iodine">iodine</a> results in <a href="/wiki/Organofluorine_chemistry" title="Organofluorine chemistry">organofluorine</a>, <a href="/wiki/Organochloride" class="mw-redirect" title="Organochloride">organochlorine</a>, <a href="/wiki/Organobromine_compound" class="mw-redirect" title="Organobromine compound">organobromine</a> and <a href="/wiki/Organoiodine_compound" class="mw-redirect" title="Organoiodine compound">organoiodine</a> compounds, respectively. Compounds containing more than one kind of halogen are also possible. Several classes of widely used haloalkanes are classified in this way <a href="/wiki/Chlorofluorocarbons" class="mw-redirect" title="Chlorofluorocarbons">chlorofluorocarbons</a> (CFCs), <a href="/wiki/Hydrochlorofluorocarbons" class="mw-redirect" title="Hydrochlorofluorocarbons">hydrochlorofluorocarbons</a> (HCFCs) and <a href="/wiki/Hydrofluorocarbons" class="mw-redirect" title="Hydrofluorocarbons">hydrofluorocarbons</a> (HFCs). These abbreviations are particularly common in discussions of the environmental impact of haloalkanes. </p> <div class="mw-heading mw-heading2"><h2 id="Properties">Properties</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Haloalkane&action=edit&section=2" title="Edit section: Properties"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Haloalkanes generally resemble the parent alkanes in being colorless, relatively odorless, and hydrophobic. The melting and boiling points of chloro-, bromo-, and iodoalkanes are higher than the analogous alkanes, scaling with the atomic weight and number of halides. This effect is due to the increased strength of the <a href="/wiki/Intermolecular_force" title="Intermolecular force">intermolecular forces</a>—from <a href="/wiki/London_dispersion_force" title="London dispersion force">London dispersion</a> to dipole-dipole interaction because of the increased polarizability. Thus <a href="/wiki/Tetraiodomethane" class="mw-redirect" title="Tetraiodomethane">tetraiodomethane</a> (<span class="chemf nowrap">CI<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">4</sub></span></span></span>) is a solid whereas <a href="/wiki/Tetrachloromethane" class="mw-redirect" title="Tetrachloromethane">tetrachloromethane</a> (<span class="chemf nowrap">CCl<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">4</sub></span></span></span>) is a liquid. Many fluoroalkanes, however, go against this trend and have lower melting and boiling points than their nonfluorinated analogues due to the decreased polarizability of fluorine. For example, <a href="/wiki/Methane" title="Methane">methane</a> (<span class="chemf nowrap">CH<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">4</sub></span></span></span>) has a melting point of −182.5 °C whereas <a href="/wiki/Tetrafluoromethane" class="mw-redirect" title="Tetrafluoromethane">tetrafluoromethane</a> (<span class="chemf nowrap">CF<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">4</sub></span></span></span>) has a melting point of −183.6 °C. </p><p>As they contain fewer C–H bonds, haloalkanes are less flammable than alkanes, and some are used in fire extinguishers. Haloalkanes are better <a href="/wiki/Solvent" title="Solvent">solvents</a> than the corresponding alkanes because of their increased polarity. Haloalkanes containing halogens other than fluorine are more reactive than the parent alkanes—it is this reactivity that is the basis of most controversies. Many are <a href="/wiki/Alkylating_agent" class="mw-redirect" title="Alkylating agent">alkylating agents</a>, with primary haloalkanes and those containing heavier halogens being the most active (fluoroalkanes do not act as alkylating agents under normal conditions). The ozone-depleting abilities of the CFCs arises from the <a href="/wiki/Photochemical_reaction" class="mw-redirect" title="Photochemical reaction">photolability</a> of the C–Cl bond. </p> <div class="mw-heading mw-heading2"><h2 id="Natural_occurrence">Natural occurrence</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Haloalkane&action=edit&section=3" title="Edit section: Natural occurrence"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>An estimated 4,100,000,000 kg of <a href="/wiki/Chloromethane" title="Chloromethane">chloromethane</a> are produced annually by natural sources.<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> The oceans are estimated to release 1 to 2 million tons of <a href="/wiki/Bromomethane" title="Bromomethane">bromomethane</a> annually.<sup id="cite_ref-Gribble_3-0" class="reference"><a href="#cite_note-Gribble-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Nomenclature">Nomenclature</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Haloalkane&action=edit&section=4" title="Edit section: Nomenclature"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="IUPAC">IUPAC</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Haloalkane&action=edit&section=5" title="Edit section: IUPAC"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The formal naming of haloalkanes should follow <a href="/wiki/IUPAC_nomenclature" class="mw-redirect" title="IUPAC nomenclature">IUPAC nomenclature</a>, which put the halogen as a <a href="/wiki/Prefix_(linguistics)" class="mw-redirect" title="Prefix (linguistics)">prefix</a> to the alkane. For example, <a href="/wiki/Ethane" title="Ethane">ethane</a> with <a href="/wiki/Bromine" title="Bromine">bromine</a> becomes <a href="/wiki/Bromoethane" title="Bromoethane">bromoethane</a>, <a href="/wiki/Methane" title="Methane">methane</a> with four <a href="/wiki/Chlorine" title="Chlorine">chlorine</a> groups becomes <a href="/wiki/Carbon_tetrachloride" title="Carbon tetrachloride">tetrachloromethane</a>. However, many of these compounds have already an established trivial name, which is endorsed by the IUPAC nomenclature, for example <a href="/wiki/Chloroform" title="Chloroform">chloroform</a> (trichloromethane) and methylene chloride (<a href="/wiki/Dichloromethane" title="Dichloromethane">dichloromethane</a>). But nowadays, IUPAC nomenclature is used. To reduce confusion this article follows the systematic naming scheme throughout. </p> <div class="mw-heading mw-heading2"><h2 id="Production">Production</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Haloalkane&action=edit&section=6" title="Edit section: Production"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Haloalkanes can be produced from virtually all organic precursors. From the perspective of industry, the most important ones are alkanes and alkenes. </p> <div class="mw-heading mw-heading3"><h3 id="From_alkanes">From alkanes</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Haloalkane&action=edit&section=7" title="Edit section: From alkanes"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1236090951">.mw-parser-output .hatnote{font-style:italic}.mw-parser-output div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Free_radical_halogenation" class="mw-redirect" title="Free radical halogenation">Free radical halogenation</a></div> <p>Alkanes react with halogens by <a href="/wiki/Free_radical_halogenation" class="mw-redirect" title="Free radical halogenation">free radical halogenation</a>. In this reaction a hydrogen atom is removed from the alkane, then replaced by a halogen atom by reaction with a diatomic halogen molecule. Free radical halogenation typically produces a mixture of compounds mono- or multihalogenated at various positions. </p> <div class="mw-heading mw-heading3"><h3 id="From_alkenes_and_alkynes">From alkenes and alkynes</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Haloalkane&action=edit&section=8" title="Edit section: From alkenes and alkynes"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In <a href="/wiki/Hydrohalogenation" title="Hydrohalogenation">hydrohalogenation</a>, an <a href="/wiki/Alkene" title="Alkene">alkene</a> reacts with a dry hydrogen halide (HX) <a href="/wiki/Electrophile" title="Electrophile">electrophile</a> like <a href="/wiki/Hydrogen_chloride" title="Hydrogen chloride">hydrogen chloride</a> (<span class="chemf nowrap">HCl</span>) or <a href="/wiki/Hydrogen_bromide" title="Hydrogen bromide">hydrogen bromide</a> (<span class="chemf nowrap">HBr</span>) to form a mono-haloalkane. The double bond of the alkene is replaced by two new bonds, one with the halogen and one with the hydrogen atom of the hydrohalic acid. <a href="/wiki/Markovnikov%27s_rule" title="Markovnikov's rule">Markovnikov's rule</a> states that under normal conditions, hydrogen is attached to the unsaturated carbon with the most hydrogen substituents. The rule is violated when neighboring functional groups <a href="/wiki/Polarizability" title="Polarizability">polarize</a> the multiple bond, or in certain additions of hydrogen bromide (addition in the presence of <a href="/wiki/Peroxides" class="mw-redirect" title="Peroxides">peroxides</a> and the <a href="/wiki/Wohl-Ziegler_reaction" class="mw-redirect" title="Wohl-Ziegler reaction">Wohl-Ziegler reaction</a>) which occur by a free-radical mechanism. </p><p>Alkenes also react with halogens (X<sub>2</sub>) to form haloalkanes with two neighboring halogen atoms in a <a href="/wiki/Halogen_addition_reaction" title="Halogen addition reaction">halogen addition reaction</a>. Alkynes react similarly, forming the tetrahalo compounds. This is sometimes known as "decolorizing" the halogen, since the reagent X<sub>2</sub> is colored and the product is usually colorless and odorless. </p> <div class="mw-heading mw-heading3"><h3 id="From_alcohols">From alcohols</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Haloalkane&action=edit&section=9" title="Edit section: From alcohols"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Alcohol_(chemistry)" title="Alcohol (chemistry)">Alcohol</a> can be converted to haloalkanes. Direct reaction with a <a href="/wiki/Hydrohalic_acid" class="mw-redirect" title="Hydrohalic acid">hydrohalic acid</a> rarely gives a pure product, instead generating <a href="/wiki/Ether" title="Ether">ethers</a>. However, some exceptions are known: ionic liquids suppress the formation or promote the cleavage of ethers,<sup id="cite_ref-UllmannIL_4-0" class="reference"><a href="#cite_note-UllmannIL-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Hydrochloric_acid" title="Hydrochloric acid">hydrochloric acid</a> converts tertiary alcohols to choloroalkanes, and primary and <a href="/wiki/Secondary_alcohol" class="mw-redirect" title="Secondary alcohol">secondary alcohols</a> convert similarly in the presence of a <a href="/wiki/Lewis_acid" class="mw-redirect" title="Lewis acid">Lewis acid</a> activator, such as <a href="/wiki/Zinc_chloride" title="Zinc chloride">zinc chloride</a>. The latter is exploited in the <a href="/wiki/Lucas%27_reagent" title="Lucas' reagent">Lucas test</a>. </p><p>In the laboratory, more active deoxygenating and halogenating agents combine with base to effect the conversion. In the "<a href="/wiki/Darzens_halogenation" title="Darzens halogenation">Darzens halogenation</a>", <a href="/wiki/Thionyl_chloride" title="Thionyl chloride">thionyl chloride</a> (<span class="chemf nowrap">SOCl<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">2</sub></span></span></span>) with <a href="/wiki/Pyridine" title="Pyridine">pyridine</a> converts less reactive alcohols to chlorides. Both <a href="/wiki/Phosphorus_pentachloride" title="Phosphorus pentachloride">phosphorus pentachloride</a> (<span class="chemf nowrap">PCl<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">5</sub></span></span></span>) and <a href="/wiki/Phosphorus_trichloride" title="Phosphorus trichloride">phosphorus trichloride</a> (<span class="chemf nowrap">PCl<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">3</sub></span></span></span>) function similarly, and alcohols convert to bromoalkanes under <a href="/wiki/Hydrobromic_acid" title="Hydrobromic acid">hydrobromic acid</a> or <a href="/wiki/Phosphorus_tribromide" title="Phosphorus tribromide">phosphorus tribromide</a> (PBr<sub>3</sub>). The heavier halogens do not require preformed reagents: A catalytic amount of <span class="chemf nowrap">PBr<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">3</sub></span></span></span> may be used for the transformation using phosphorus and bromine; <span class="chemf nowrap">PBr<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">3</sub></span></span></span> is formed <i>in situ</i>.<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> Iodoalkanes may similarly be prepared using red <a href="/wiki/Phosphorus" title="Phosphorus">phosphorus</a> and <a href="/wiki/Iodine" title="Iodine">iodine</a> (equivalent to <a href="/wiki/Phosphorus_triiodide" title="Phosphorus triiodide">phosphorus triiodide</a>). </p><p>One family of <a href="/wiki/Named_reaction" class="mw-redirect" title="Named reaction">named reactions</a> relies on the <a href="/wiki/Oxophilicity" title="Oxophilicity">deoxygenating</a> effect of <a href="/wiki/Triphenylphosphine" title="Triphenylphosphine">triphenylphosphine</a>. In the <a href="/wiki/Appel_reaction" title="Appel reaction">Appel reaction</a>, the reagent is tetrahalomethane and <a href="/wiki/Triphenylphosphine" title="Triphenylphosphine">triphenylphosphine</a>; the co-products are <a href="/wiki/Haloform" class="mw-redirect" title="Haloform">haloform</a> and <a href="/wiki/Triphenylphosphine_oxide" title="Triphenylphosphine oxide">triphenylphosphine oxide</a>. In the <a href="/wiki/Mitsunobu_reaction" title="Mitsunobu reaction">Mitsunobu reaction</a>, the reagents are any <a href="/wiki/Nucleophile" title="Nucleophile">nucleophile</a>, triphenylphosphine, and a <a href="/w/index.php?title=Diazodicarboxylate&action=edit&redlink=1" class="new" title="Diazodicarboxylate (page does not exist)">diazodicarboxylate</a>; the coproducts are triphenylphosphine oxide and a <a href="/w/index.php?title=Hydrazodiamide&action=edit&redlink=1" class="new" title="Hydrazodiamide (page does not exist)">hydrazodiamide</a>. </p> <div class="mw-heading mw-heading3"><h3 id="From_carboxylic_acids">From carboxylic acids</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Haloalkane&action=edit&section=10" title="Edit section: From carboxylic acids"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Two methods for the synthesis of haloalkanes from <a href="/wiki/Carboxylic_acid" title="Carboxylic acid">carboxylic acids</a> are <a href="/wiki/Hunsdiecker_reaction" title="Hunsdiecker reaction">Hunsdiecker reaction</a> and <a href="/wiki/Kochi_reaction" title="Kochi reaction">Kochi reaction</a>. </p> <div class="mw-heading mw-heading3"><h3 id="Biosynthesis">Biosynthesis</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Haloalkane&action=edit&section=11" title="Edit section: Biosynthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Many chloro and bromoalkanes are formed naturally. The principal pathways involve the enzymes <a href="/wiki/Chloroperoxidase" class="mw-redirect" title="Chloroperoxidase">chloroperoxidase</a> and <a href="/wiki/Bromoperoxidase" class="mw-redirect" title="Bromoperoxidase">bromoperoxidase</a>. </p> <div class="mw-heading mw-heading4"><h4 id="From_amines_by_Sandmeyer's_Method"><span id="From_amines_by_Sandmeyer.27s_Method"></span>From amines by <a href="/wiki/Sandmeyer_reaction" title="Sandmeyer reaction">Sandmeyer's Method</a></h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Haloalkane&action=edit&section=12" title="Edit section: From amines by Sandmeyer's Method"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Primary aromatic <a href="/wiki/Amine" title="Amine">amines</a> yield <a href="/wiki/Diazonium_compound" title="Diazonium compound">diazonium</a> ions in a solution of <a href="/wiki/Sodium_nitrite" title="Sodium nitrite">sodium nitrite</a>. Upon heating this solution with copper(I) chloride, the diazonium group is replaced by -Cl. This is a comparatively easy method to make aryl halides as the gaseous product can be separated easily from aryl halide. </p><p>When an iodide is to be made, copper chloride is not needed. Addition of <a href="/wiki/Potassium_iodide" title="Potassium iodide">potassium iodide</a> with gentle shaking produces the haloalkane. </p> <div class="mw-heading mw-heading2"><h2 id="Reactions">Reactions</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Haloalkane&action=edit&section=13" title="Edit section: Reactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Haloalkanes are reactive towards <a href="/wiki/Nucleophile" title="Nucleophile">nucleophiles</a>. They are <a href="/wiki/Chemical_polarity" title="Chemical polarity">polar</a> molecules: the carbon to which the halogen is attached is slightly <a href="/wiki/Electropositive" class="mw-redirect" title="Electropositive">electropositive</a> where the halogen is slightly <a href="/wiki/Electronegative" class="mw-redirect" title="Electronegative">electronegative</a>. This results in an <a href="/wiki/Electron_deficiency" title="Electron deficiency">electron deficient</a> (electrophilic) carbon which, inevitably, attracts <a href="/wiki/Nucleophile" title="Nucleophile">nucleophiles</a>. </p> <div class="mw-heading mw-heading3"><h3 id="Substitution">Substitution</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Haloalkane&action=edit&section=14" title="Edit section: Substitution"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Substitution_reaction" title="Substitution reaction">Substitution reactions</a> involve the replacement of the halogen with another molecule—thus leaving <a href="/wiki/Saturated_hydrocarbons" class="mw-redirect" title="Saturated hydrocarbons">saturated hydrocarbons</a>, as well as the halogenated product. Haloalkanes behave as the R<sup>+</sup> <a href="/wiki/Synthon" title="Synthon">synthon</a>, and readily react with nucleophiles. </p><p><a href="/wiki/Hydrolysis" title="Hydrolysis">Hydrolysis</a>, a reaction in which <a href="/wiki/Water_(molecule)" class="mw-redirect" title="Water (molecule)">water</a> breaks a bond, is a good example of the nucleophilic nature of haloalkanes. The polar bond attracts a <a href="/wiki/Hydroxide" title="Hydroxide">hydroxide</a> ion, OH<sup>−</sup> (NaOH<sub>(aq)</sub> being a common source of this ion). This OH<sup>−</sup> is a nucleophile with a clearly negative charge, as it has excess electrons it donates them to the carbon, which results in a <a href="/wiki/Covalent" class="mw-redirect" title="Covalent">covalent</a> bond between the two. Thus C–X is broken by <a href="/wiki/Heterolytic_fission" class="mw-redirect" title="Heterolytic fission">heterolytic fission</a> resulting in a halide ion, X<sup>−</sup>. As can be seen, the OH is now attached to the alkyl group, creating an <a href="/wiki/Alcohol_(chemistry)" title="Alcohol (chemistry)">alcohol</a>. (Hydrolysis of bromoethane, for example, yields <a href="/wiki/Ethanol" title="Ethanol">ethanol</a>). Reactions with ammonia give primary amines. </p><p>Chloro- and bromoalkanes are readily substituted by iodide in the <a href="/wiki/Finkelstein_reaction" title="Finkelstein reaction">Finkelstein reaction</a>. The iodoalkanes produced easily undergo further reaction. <a href="/wiki/Sodium_iodide" title="Sodium iodide">Sodium iodide</a> is used as a <a href="/wiki/Catalyst" class="mw-redirect" title="Catalyst">catalyst</a>. </p><p>Haloalkanes react with ionic nucleophiles (e.g. <a href="/wiki/Cyanide" title="Cyanide">cyanide</a>, <a href="/wiki/Thiocyanate" title="Thiocyanate">thiocyanate</a>, <a href="/wiki/Azide" title="Azide">azide</a>); the halogen is replaced by the respective group. This is of great synthetic utility: chloroalkanes are often inexpensively available. For example, after undergoing substitution reactions, cyanoalkanes may be hydrolyzed to carboxylic acids, or reduced to primary amines using <a href="/wiki/Lithium_aluminium_hydride" title="Lithium aluminium hydride">lithium aluminium hydride</a>. Azoalkanes may be reduced to primary amines by <a href="/wiki/Staudinger_reduction" class="mw-redirect" title="Staudinger reduction">Staudinger reduction</a> or <a href="/wiki/Lithium_aluminium_hydride" title="Lithium aluminium hydride">lithium aluminium hydride</a>. Amines may also be prepared from alkyl halides in <a href="/wiki/Amine_alkylation" title="Amine alkylation">amine alkylation</a>, <a href="/wiki/Gabriel_synthesis" title="Gabriel synthesis">Gabriel synthesis</a> and <a href="/wiki/Delepine_reaction" class="mw-redirect" title="Delepine reaction">Delepine reaction</a>, by undergoing nucleophilic substitution with <a href="/wiki/Potassium_phthalimide" title="Potassium phthalimide">potassium phthalimide</a> or <a href="/wiki/Hexamine" class="mw-redirect" title="Hexamine">hexamine</a> respectively, followed by hydrolysis. </p><p>In the presence of a base, haloalkanes <a href="/wiki/Alkylation" title="Alkylation">alkylate</a> alcohols, amines, and thiols to obtain <a href="/wiki/Ether" title="Ether">ethers</a>, <i>N</i>-substituted amines, and thioethers respectively. They are substituted by <a href="/wiki/Grignard_reagent" title="Grignard reagent">Grignard reagent</a> to give magnesium salts and an extended alkyl compound. </p> <div class="mw-heading mw-heading3"><h3 id="Elimination">Elimination</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Haloalkane&action=edit&section=15" title="Edit section: Elimination"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Dehydrohalogenation" title="Dehydrohalogenation">Dehydrohalogenation</a></div> <p>In <a href="/wiki/Dehydrohalogenation" title="Dehydrohalogenation">dehydrohalogenation</a> reactions, the halogen and an adjacent proton are removed from halocarbons, thus forming an <a href="/wiki/Alkene" title="Alkene">alkene</a>. For example, with <a href="/wiki/Bromoethane" title="Bromoethane">bromoethane</a> and sodium hydroxide (NaOH) in <a href="/wiki/Ethanol" title="Ethanol">ethanol</a>, the hydroxide ion HO<sup>−</sup> abstracts a hydrogen atom. A <a href="/wiki/Bromide" title="Bromide">Bromide</a> ion is then lost, resulting in <a href="/wiki/Ethene" class="mw-redirect" title="Ethene">ethene</a>, H<sub>2</sub>O and NaBr. Thus, haloalkanes can be converted to alkenes. Similarly, dihaloalkanes can be converted to <a href="/wiki/Alkyne" title="Alkyne">alkynes</a>. </p><p>In related reactions, 1,2-dibromocompounds are debrominated by <a href="/wiki/Zinc" title="Zinc">zinc</a> dust to give alkenes and <a href="/wiki/Geminal" title="Geminal">geminal</a> dihalides can react with strong bases to give <a href="/wiki/Carbene" title="Carbene">carbenes</a>. </p> <div class="mw-heading mw-heading3"><h3 id="Other">Other</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Haloalkane&action=edit&section=16" title="Edit section: Other"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Haloalkanes undergo free-radical reactions with elemental magnesium to give alkyl-magnesium compound: <a href="/wiki/Grignard_reagent" title="Grignard reagent">Grignard reagent</a>. Haloalkanes also react with <a href="/wiki/Lithium" title="Lithium">lithium</a> metal to give <a href="/wiki/Organolithium_compound" class="mw-redirect" title="Organolithium compound">organolithium compounds</a>. Both Grignard reagents and organolithium compounds behave as the R<sup>−</sup> synthon. Alkali metals such as <a href="/wiki/Sodium" title="Sodium">sodium</a> and <a href="/wiki/Lithium" title="Lithium">lithium</a> are able to cause haloalkanes to couple in <a href="/wiki/Wurtz_reaction" title="Wurtz reaction">Wurtz reaction</a>, giving symmetrical alkanes. Haloalkanes, especially iodoalkanes, also undergo <a href="/wiki/Oxidative_addition" title="Oxidative addition">oxidative addition</a> reactions to give <a href="/wiki/Organometallic_compound" class="mw-redirect" title="Organometallic compound">organometallic compounds</a>. </p> <div class="mw-heading mw-heading2"><h2 id="Applications">Applications</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Haloalkane&action=edit&section=17" title="Edit section: Applications"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Polytetrafluoroethylene.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e0/Polytetrafluoroethylene.svg/110px-Polytetrafluoroethylene.svg.png" decoding="async" width="110" height="96" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e0/Polytetrafluoroethylene.svg/165px-Polytetrafluoroethylene.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e0/Polytetrafluoroethylene.svg/220px-Polytetrafluoroethylene.svg.png 2x" data-file-width="168" data-file-height="147" /></a><figcaption>Teflon structure</figcaption></figure> <p>Chlorinated or fluorinated alkenes undergo polymerization. Important halogenated polymers include <a href="/wiki/Polyvinyl_chloride" title="Polyvinyl chloride">polyvinyl chloride</a> (PVC), and <a href="/wiki/Polytetrafluoroethene" class="mw-redirect" title="Polytetrafluoroethene">polytetrafluoroethene</a> (PTFE, or teflon). </p> <dl><dt>Alkyl fluorides</dt> <dd>An estimated one fifth of pharmaceuticals contain fluorine, including several of the top drugs. Most of these compounds are alkyl fluorides.<sup id="cite_ref-fab_6-0" class="reference"><a href="#cite_note-fab-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> Examples include <a href="/wiki/5-fluorouracil" class="mw-redirect" title="5-fluorouracil">5-fluorouracil</a>, <a href="/wiki/Flunitrazepam" title="Flunitrazepam">flunitrazepam</a> (Rohypnol), <a href="/wiki/Fluoxetine" title="Fluoxetine">fluoxetine</a> (Prozac), <a href="/wiki/Paroxetine" title="Paroxetine">paroxetine</a> (Paxil), <a href="/wiki/Ciprofloxacin" title="Ciprofloxacin">ciprofloxacin</a> (Cipro), <a href="/wiki/Mefloquine" title="Mefloquine">mefloquine</a> and <a href="/wiki/Fluconazole" title="Fluconazole">fluconazole</a>. Fluorine-substituted <a href="/wiki/Ethers" class="mw-redirect" title="Ethers">ethers</a> are <a href="/wiki/Volatile_anesthetic" class="mw-redirect" title="Volatile anesthetic">volatile anesthetics</a>, including the commercial products <a href="/wiki/Methoxyflurane" title="Methoxyflurane">methoxyflurane</a>, <a href="/wiki/Enflurane" title="Enflurane">enflurane</a>, <a href="/wiki/Isoflurane" title="Isoflurane">isoflurane</a>, <a href="/wiki/Sevoflurane" title="Sevoflurane">sevoflurane</a> and <a href="/wiki/Desflurane" title="Desflurane">desflurane</a>.</dd></dl> <dl><dt>Alkyl chlorides</dt> <dd>Some low molecular weight chlorinated hydrocarbons such as <a href="/wiki/Chloroform" title="Chloroform">chloroform</a>, <a href="/wiki/Dichloromethane" title="Dichloromethane">dichloromethane</a>, <a href="/wiki/Dichloroethene" title="Dichloroethene">dichloroethene</a>, and <a href="/wiki/Trichloroethane" title="Trichloroethane">trichloroethane</a> are useful solvents. Several million tons of chlorinated methanes are produced annually. Chloromethane is a precursor to <a href="/wiki/Chlorosilane" title="Chlorosilane">chlorosilanes</a> and <a href="/wiki/Silicone" title="Silicone">silicones</a>. <a href="/wiki/Chlorodifluoromethane" title="Chlorodifluoromethane">Chlorodifluoromethane</a> (CHClF<sub>2</sub>) is used to make teflon.<sup id="cite_ref-Ullmann_7-0" class="reference"><a href="#cite_note-Ullmann-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup></dd></dl> <dl><dt>Alkyl bromides</dt> <dd>Large scale applications of alkyl bromides exploit their toxicity, which also limits their usefulness. <a href="/wiki/Methyl_bromide" class="mw-redirect" title="Methyl bromide">Methyl bromide</a> is also an effective fumigant, but its production and use are controversial.</dd></dl> <dl><dt>Alkyl iodides</dt> <dd>No large scale applications are known for alkyl iodides. <a href="/wiki/Methyl_iodide" class="mw-redirect" title="Methyl iodide">Methyl iodide</a> is a popular methylating agent in <a href="/wiki/Organic_synthesis" title="Organic synthesis">organic synthesis</a>.</dd></dl> <dl><dt>Chlorofluorocarbons</dt> <dd><a href="/wiki/Chlorofluorocarbons" class="mw-redirect" title="Chlorofluorocarbons">Chlorofluorocarbons</a> were used almost universally as <a href="/wiki/Refrigerants" class="mw-redirect" title="Refrigerants">refrigerants</a> and <a href="/wiki/Propellants" class="mw-redirect" title="Propellants">propellants</a> due to their relatively low toxicity and high <a href="/wiki/Heat_of_vaporization" class="mw-redirect" title="Heat of vaporization">heat of vaporization</a>. Starting in the 1980s, as their contribution to <a href="/wiki/Ozone_depletion" title="Ozone depletion">ozone depletion</a> became known, their use was increasingly restricted, and they have now largely been replaced by HFCs.</dd></dl> <div class="mw-heading mw-heading2"><h2 id="Environmental_considerations">Environmental considerations</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Haloalkane&action=edit&section=18" title="Edit section: Environmental considerations"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Nature produces massive amounts of chloromethane and bromomethane. Most concern focuses on anthropogenic sources, which are potential toxins, even carcinogens. Similarly, great interest has been shown in remediation of man made halocarbons such as those produced on large scale, such as dry cleaning fluids. Volatile halocarbons degrade photochemically because the carbon-halogen bond can be labile. Some microorganisms dehalogenate halocarbons. While this behavior is intriguing, the rates of remediation are generally very slow.<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> </p> <div class="mw-heading mw-heading2"><h2 id="Safety">Safety</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Haloalkane&action=edit&section=19" title="Edit section: Safety"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>As <a href="/wiki/Alkylating_agent" class="mw-redirect" title="Alkylating agent">alkylating agents</a>, haloalkanes are potential carcinogens. The more reactive members of this large class of compounds generally pose greater risk, e.g. <a href="/wiki/Carbon_tetrachloride" title="Carbon tetrachloride">carbon tetrachloride</a>.<sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p> <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=Haloalkane&action=edit&section=20" 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"><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"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite id="CITEREFPatai1973" class="citation book cs1">Patai, Saul, ed. (1973). <a rel="nofollow" class="external text" href="https://www.worldcat.org/oclc/520990502"><i>The chemistry of the carbon-halogen bond</i></a>. Saul Patai. London: John Wiley & Sons. <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%2F9780470771280">10.1002/9780470771280</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-470-77128-0" title="Special:BookSources/978-0-470-77128-0"><bdi>978-0-470-77128-0</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/520990502">520990502</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=The+chemistry+of+the+carbon-halogen+bond&rft.place=London&rft.pub=John+Wiley+%26+Sons&rft.date=1973&rft_id=info%3Aoclcnum%2F520990502&rft_id=info%3Adoi%2F10.1002%2F9780470771280&rft.isbn=978-0-470-77128-0&rft_id=https%3A%2F%2Fwww.worldcat.org%2Foclc%2F520990502&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHaloalkane" class="Z3988"></span></span> </li> <li id="cite_note-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-2">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFGribble,_Gordon2023" class="citation book cs1">Gribble, Gordon (2023). Kinghorn, A. Douglas; Falk, Heinz; Gibbons, Simon; Asakawa, Yoshinori; Liu, Ji-Kai; Dirsch, Verena M. Cham (eds.). <i>Naturally Occurring Organohalogen Compounds</i>. Progress in the Chemistry of Organic Natural Products. Switzerland: Springer Nature. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/3-031-26629-3" title="Special:BookSources/3-031-26629-3"><bdi>3-031-26629-3</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Naturally+Occurring+Organohalogen+Compounds&rft.place=Switzerland&rft.series=Progress+in+the+Chemistry+of+Organic+Natural+Products&rft.pub=Springer+Nature&rft.date=2023&rft.isbn=3-031-26629-3&rft.au=Gribble%2C+Gordon&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHaloalkane" class="Z3988"></span></span> </li> <li id="cite_note-Gribble-3"><span class="mw-cite-backlink"><b><a href="#cite_ref-Gribble_3-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFGordon_W._Gribble1998" class="citation journal cs1">Gordon W. Gribble (1998). "Naturally Occurring Organohalogen Compounds". <i><a href="/wiki/Acc._Chem._Res." class="mw-redirect" title="Acc. Chem. Res.">Acc. Chem. Res.</a></i> <b>31</b> (3): 141–152. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Far9701777">10.1021/ar9701777</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Acc.+Chem.+Res.&rft.atitle=Naturally+Occurring+Organohalogen+Compounds&rft.volume=31&rft.issue=3&rft.pages=141-152&rft.date=1998&rft_id=info%3Adoi%2F10.1021%2Far9701777&rft.au=Gordon+W.+Gribble&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHaloalkane" class="Z3988"></span></span> </li> <li id="cite_note-UllmannIL-4"><span class="mw-cite-backlink"><b><a href="#cite_ref-UllmannIL_4-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation encyclopaedia cs1">"Ionic liquids". <i><a href="/wiki/Ullmann%27s_Encyclopedia_of_Industrial_Chemistry" title="Ullmann's Encyclopedia of Industrial Chemistry">Ullmann's Encyclopedia of Industrial Chemistry</a></i>. Weinheim: Wiley-VCH. p. 557. <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.l14_l01">10.1002/14356007.l14_l01</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3527306732" title="Special:BookSources/978-3527306732"><bdi>978-3527306732</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Ionic+liquids&rft.btitle=Ullmann%27s+Encyclopedia+of+Industrial+Chemistry&rft.place=Weinheim&rft.pages=557&rft.pub=Wiley-VCH&rft_id=info%3Adoi%2F10.1002%2F14356007.l14_l01&rft.isbn=978-3527306732&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHaloalkane" class="Z3988"></span></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 class="citation web cs1"><a rel="nofollow" class="external text" href="https://www.iswori.com.np/2023/02/haloalkanes-and-chloroform-class-12-chemistry-notes.html">"Haloalkanes & Chloroform: Class 12 Organic Chemistry Notes"</a>. <i>NEB Notes: SEE, Class 11, Class 12 Notes Exercise Questions</i><span class="reference-accessdate">. Retrieved <span class="nowrap">2023-01-07</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=NEB+Notes%3A+SEE%2C+Class+11%2C+Class+12+Notes+Exercise+Questions&rft.atitle=Haloalkanes+%26+Chloroform%3A+Class+12+Organic+Chemistry+Notes&rft_id=https%3A%2F%2Fwww.iswori.com.np%2F2023%2F02%2Fhaloalkanes-and-chloroform-class-12-chemistry-notes.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHaloalkane" class="Z3988"></span></span> </li> <li id="cite_note-fab-6"><span class="mw-cite-backlink"><b><a href="#cite_ref-fab_6-0">^</a></b></span> <span class="reference-text">Ann M. Thayer "Fabulous Fluorine" Chemical and Engineering News, June 5, 2006, Volume 84, pp. 15-24. <a rel="nofollow" class="external free" href="http://pubs.acs.org/cen/coverstory/84/8423cover1.html">http://pubs.acs.org/cen/coverstory/84/8423cover1.html</a></span> </li> <li id="cite_note-Ullmann-7"><span class="mw-cite-backlink"><b><a href="#cite_ref-Ullmann_7-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFRossbergLendlePfleidererTögel2006" class="citation encyclopaedia cs1">Rossberg, Manfred; Lendle, Wilhelm; Pfleiderer, Gerhard; Tögel, Adolf; Dreher, Eberhard-Ludwig; Langer, Ernst; Rassaerts, Heinz; Kleinschmidt, Peter; Strack, Heinz; Cook, Richard; Beck, Uwe; Lipper, Karl-August; Torkelson, Theodore R.; Löser, Eckhard; Beutel, Klaus K.; Mann, Trevor (2006). "Chlorinated Hydrocarbons". <i><a href="/wiki/Ullmann%27s_Encyclopedia_of_Industrial_Chemistry" title="Ullmann's Encyclopedia of Industrial Chemistry">Ullmann's Encyclopedia of Industrial Chemistry</a></i>. Weinheim: Wiley-VCH. <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.a06_233.pub2">10.1002/14356007.a06_233.pub2</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/3527306730" title="Special:BookSources/3527306730"><bdi>3527306730</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Chlorinated+Hydrocarbons&rft.btitle=Ullmann%27s+Encyclopedia+of+Industrial+Chemistry&rft.place=Weinheim&rft.pub=Wiley-VCH&rft.date=2006&rft_id=info%3Adoi%2F10.1002%2F14356007.a06_233.pub2&rft.isbn=3527306730&rft.aulast=Rossberg&rft.aufirst=Manfred&rft.au=Lendle%2C+Wilhelm&rft.au=Pfleiderer%2C+Gerhard&rft.au=T%C3%B6gel%2C+Adolf&rft.au=Dreher%2C+Eberhard-Ludwig&rft.au=Langer%2C+Ernst&rft.au=Rassaerts%2C+Heinz&rft.au=Kleinschmidt%2C+Peter&rft.au=Strack%2C+Heinz&rft.au=Cook%2C+Richard&rft.au=Beck%2C+Uwe&rft.au=Lipper%2C+Karl-August&rft.au=Torkelson%2C+Theodore+R.&rft.au=L%C3%B6ser%2C+Eckhard&rft.au=Beutel%2C+Klaus+K.&rft.au=Mann%2C+Trevor&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHaloalkane" class="Z3988"></span></span> </li> <li id="cite_note-8"><span class="mw-cite-backlink"><b><a href="#cite_ref-8">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFFetznerLingens1994" class="citation journal cs1">Fetzner, S.; Lingens, F. (1994). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC372986">"Bacterial dehalogenases: Biochemistry, genetics, and biotechnological applications"</a>. <i>Microbiological Reviews</i>. <b>58</b> (4): 641–685. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1128%2Fmmbr.58.4.641-685.1994">10.1128/mmbr.58.4.641-685.1994</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC372986">372986</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/7854251">7854251</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Microbiological+Reviews&rft.atitle=Bacterial+dehalogenases%3A+Biochemistry%2C+genetics%2C+and+biotechnological+applications&rft.volume=58&rft.issue=4&rft.pages=641-685&rft.date=1994&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC372986%23id-name%3DPMC&rft_id=info%3Apmid%2F7854251&rft_id=info%3Adoi%2F10.1128%2Fmmbr.58.4.641-685.1994&rft.aulast=Fetzner&rft.aufirst=S.&rft.au=Lingens%2C+F.&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC372986&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHaloalkane" 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"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFWeberBollStampfl2003" class="citation journal cs1">Weber, Lutz W. D.; Boll, Meinrad; Stampfl, Andreas (2003). "Hepatotoxicity and Mechanism of Action of Haloalkanes: Carbon Tetrachloride as a Toxicological Model". <i>Critical Reviews in Toxicology</i>. <b>33</b> (2): 105–136. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1080%2F713611034">10.1080/713611034</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/12708612">12708612</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:435416">435416</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Critical+Reviews+in+Toxicology&rft.atitle=Hepatotoxicity+and+Mechanism+of+Action+of+Haloalkanes%3A+Carbon+Tetrachloride+as+a+Toxicological+Model&rft.volume=33&rft.issue=2&rft.pages=105-136&rft.date=2003&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A435416%23id-name%3DS2CID&rft_id=info%3Apmid%2F12708612&rft_id=info%3Adoi%2F10.1080%2F713611034&rft.aulast=Weber&rft.aufirst=Lutz+W.+D.&rft.au=Boll%2C+Meinrad&rft.au=Stampfl%2C+Andreas&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHaloalkane" class="Z3988"></span></span> </li> </ol></div></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=Haloalkane&action=edit&section=21" title="Edit section: External links"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><span class="noviewer" typeof="mw:File"><a href="/wiki/File:Commons-logo.svg" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/12px-Commons-logo.svg.png" decoding="async" width="12" height="16" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/18px-Commons-logo.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/24px-Commons-logo.svg.png 2x" data-file-width="1024" data-file-height="1376" /></a></span> Media related to <a href="https://commons.wikimedia.org/wiki/Category:Haloalkanes" class="extiw" title="commons:Category:Haloalkanes">Haloalkanes</a> at Wikimedia Commons</li></ul> <div class="navbox-styles"><style data-mw-deduplicate="TemplateStyles:r1129693374">.mw-parser-output .hlist dl,.mw-parser-output .hlist ol,.mw-parser-output .hlist ul{margin:0;padding:0}.mw-parser-output .hlist dd,.mw-parser-output .hlist dt,.mw-parser-output .hlist li{margin:0;display:inline}.mw-parser-output .hlist.inline,.mw-parser-output .hlist.inline dl,.mw-parser-output .hlist.inline ol,.mw-parser-output .hlist.inline ul,.mw-parser-output .hlist dl dl,.mw-parser-output .hlist dl ol,.mw-parser-output .hlist dl ul,.mw-parser-output .hlist ol dl,.mw-parser-output .hlist ol ol,.mw-parser-output .hlist ol ul,.mw-parser-output .hlist ul dl,.mw-parser-output .hlist ul ol,.mw-parser-output .hlist ul ul{display:inline}.mw-parser-output .hlist .mw-empty-li{display:none}.mw-parser-output .hlist dt::after{content:": "}.mw-parser-output .hlist dd::after,.mw-parser-output .hlist li::after{content:" · ";font-weight:bold}.mw-parser-output .hlist dd:last-child::after,.mw-parser-output .hlist dt:last-child::after,.mw-parser-output .hlist li:last-child::after{content:none}.mw-parser-output .hlist dd dd:first-child::before,.mw-parser-output .hlist dd dt:first-child::before,.mw-parser-output .hlist dd li:first-child::before,.mw-parser-output .hlist dt dd:first-child::before,.mw-parser-output .hlist dt dt:first-child::before,.mw-parser-output .hlist dt li:first-child::before,.mw-parser-output .hlist li dd:first-child::before,.mw-parser-output .hlist li dt:first-child::before,.mw-parser-output .hlist li li:first-child::before{content:" (";font-weight:normal}.mw-parser-output .hlist dd dd:last-child::after,.mw-parser-output .hlist dd dt:last-child::after,.mw-parser-output .hlist dd li:last-child::after,.mw-parser-output .hlist dt dd:last-child::after,.mw-parser-output .hlist dt dt:last-child::after,.mw-parser-output .hlist dt li:last-child::after,.mw-parser-output .hlist li dd:last-child::after,.mw-parser-output .hlist li dt:last-child::after,.mw-parser-output .hlist li li:last-child::after{content:")";font-weight:normal}.mw-parser-output .hlist ol{counter-reset:listitem}.mw-parser-output .hlist ol>li{counter-increment:listitem}.mw-parser-output .hlist ol>li::before{content:" "counter(listitem)"\a0 "}.mw-parser-output .hlist dd ol>li:first-child::before,.mw-parser-output .hlist dt ol>li:first-child::before,.mw-parser-output .hlist li ol>li:first-child::before{content:" ("counter(listitem)"\a0 "}</style><style data-mw-deduplicate="TemplateStyles:r1236075235">.mw-parser-output .navbox{box-sizing:border-box;border:1px solid #a2a9b1;width:100%;clear:both;font-size:88%;text-align:center;padding:1px;margin:1em auto 0}.mw-parser-output .navbox .navbox{margin-top:0}.mw-parser-output .navbox+.navbox,.mw-parser-output .navbox+.navbox-styles+.navbox{margin-top:-1px}.mw-parser-output .navbox-inner,.mw-parser-output .navbox-subgroup{width:100%}.mw-parser-output .navbox-group,.mw-parser-output .navbox-title,.mw-parser-output .navbox-abovebelow{padding:0.25em 1em;line-height:1.5em;text-align:center}.mw-parser-output .navbox-group{white-space:nowrap;text-align:right}.mw-parser-output .navbox,.mw-parser-output .navbox-subgroup{background-color:#fdfdfd}.mw-parser-output .navbox-list{line-height:1.5em;border-color:#fdfdfd}.mw-parser-output .navbox-list-with-group{text-align:left;border-left-width:2px;border-left-style:solid}.mw-parser-output tr+tr>.navbox-abovebelow,.mw-parser-output tr+tr>.navbox-group,.mw-parser-output tr+tr>.navbox-image,.mw-parser-output tr+tr>.navbox-list{border-top:2px solid #fdfdfd}.mw-parser-output .navbox-title{background-color:#ccf}.mw-parser-output .navbox-abovebelow,.mw-parser-output .navbox-group,.mw-parser-output .navbox-subgroup .navbox-title{background-color:#ddf}.mw-parser-output .navbox-subgroup .navbox-group,.mw-parser-output .navbox-subgroup .navbox-abovebelow{background-color:#e6e6ff}.mw-parser-output .navbox-even{background-color:#f7f7f7}.mw-parser-output .navbox-odd{background-color:transparent}.mw-parser-output .navbox .hlist td dl,.mw-parser-output .navbox .hlist td ol,.mw-parser-output .navbox .hlist td ul,.mw-parser-output .navbox td.hlist dl,.mw-parser-output .navbox td.hlist ol,.mw-parser-output .navbox td.hlist ul{padding:0.125em 0}.mw-parser-output .navbox .navbar{display:block;font-size:100%}.mw-parser-output .navbox-title .navbar{float:left;text-align:left;margin-right:0.5em}body.skin--responsive .mw-parser-output .navbox-image img{max-width:none!important}@media print{body.ns-0 .mw-parser-output .navbox{display:none!important}}</style><style data-mw-deduplicate="TemplateStyles:r886047488">.mw-parser-output .nobold{font-weight:normal}</style><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r886047488"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r886047488"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r886047488"></div><div role="navigation" class="navbox" aria-labelledby="Functional_groups" 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"><style data-mw-deduplicate="TemplateStyles:r1239400231">.mw-parser-output .navbar{display:inline;font-size:88%;font-weight:normal}.mw-parser-output .navbar-collapse{float:left;text-align:left}.mw-parser-output .navbar-boxtext{word-spacing:0}.mw-parser-output .navbar ul{display:inline-block;white-space:nowrap;line-height:inherit}.mw-parser-output .navbar-brackets::before{margin-right:-0.125em;content:"[ "}.mw-parser-output .navbar-brackets::after{margin-left:-0.125em;content:" ]"}.mw-parser-output .navbar li{word-spacing:-0.125em}.mw-parser-output .navbar a>span,.mw-parser-output .navbar a>abbr{text-decoration:inherit}.mw-parser-output .navbar-mini abbr{font-variant:small-caps;border-bottom:none;text-decoration:none;cursor:inherit}.mw-parser-output .navbar-ct-full{font-size:114%;margin:0 7em}.mw-parser-output .navbar-ct-mini{font-size:114%;margin:0 4em}html.skin-theme-clientpref-night .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}@media(prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}}@media print{.mw-parser-output .navbar{display:none!important}}</style><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Functional_groups" title="Template:Functional groups"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Functional_groups" title="Template talk:Functional groups"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Functional_groups" title="Special:EditPage/Template:Functional groups"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Functional_groups" style="font-size:114%;margin:0 4em"><a href="/wiki/Functional_group" title="Functional group">Functional groups</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Hydrocarbon" title="Hydrocarbon">Hydrocarbons</a> <br /><span class="nobold">(only C and H)</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Alkyl" class="mw-redirect" title="Alkyl">Alkyl</a> <ul><li><a href="/wiki/Methyl_group" title="Methyl group">Methyl</a></li> <li><a href="/wiki/Ethyl_group" title="Ethyl group">Ethyl</a></li> <li><a href="/wiki/Propyl_group" title="Propyl group">Propyl</a></li> <li><a href="/wiki/Cyclopropyl" class="mw-redirect" title="Cyclopropyl">Cyclopropyl</a></li> <li><a href="/wiki/Butyl_group" title="Butyl group">Butyl</a></li> <li><a href="/wiki/Pentyl_group" title="Pentyl group">Pentyl</a></li></ul></li> <li><a href="/wiki/Methylene_group" title="Methylene group">Methylene</a> <ul><li><a href="/wiki/Methylene_bridge" title="Methylene bridge">Bridge</a></li> <li><a href="/wiki/Methine_group" title="Methine group">Methine</a></li></ul></li> <li><a href="/wiki/Alkene" title="Alkene">Alkene</a> <ul><li><a href="/wiki/Vinyl_group" title="Vinyl group">Vinyl</a></li> <li><a href="/wiki/Allyl_group" title="Allyl group">Allyl</a></li> <li><a href="/wiki/Propenyl" title="Propenyl">1-Propenyl</a></li> <li><a href="/wiki/Crotyl_group" title="Crotyl group">Crotyl</a></li> <li><a href="/wiki/Allenes" title="Allenes">Allene</a></li> <li><a href="/wiki/Cumulene" title="Cumulene">Cumulene</a></li></ul></li> <li><a href="/wiki/Aryl" class="mw-redirect" title="Aryl">Aryl</a> <ul><li><a href="/wiki/Phenyl_group" title="Phenyl group">Phenyl</a></li> <li><a href="/wiki/Benzyl_group" title="Benzyl group">Benzyl</a></li></ul></li> <li><a href="/wiki/Alkyne" title="Alkyne">Alkyne</a></li> <li><a href="/wiki/Carbene" title="Carbene">Carbene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Only <a href="/wiki/Carbon" title="Carbon">carbon</a>, <br /><a href="/wiki/Hydrogen" title="Hydrogen">hydrogen</a>, <br />and <a href="/wiki/Oxygen" title="Oxygen">oxygen</a> <br /><span class="nobold">(only C, H and O)</span></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%">R-O-R</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/Acetal" title="Acetal">Acetal</a></li> <li><a href="/wiki/Alcohol_(chemistry)" title="Alcohol (chemistry)">Alcohol</a></li> <li><a href="/wiki/Alkoxy_group" title="Alkoxy group">Alkoxy</a> <ul><li><a href="/wiki/Methoxy_group" title="Methoxy group">Methoxy</a></li></ul></li> <li><a href="/wiki/Ether" title="Ether">Ether</a> <ul><li><a href="/wiki/Enol_ether" title="Enol ether">Enol ether</a></li> <li><a href="/wiki/Epoxide" title="Epoxide">Epoxide</a></li></ul></li> <li><a href="/wiki/Organic_peroxides" title="Organic peroxides">Peroxy</a> <ul><li><a href="/wiki/Hydroperoxide" title="Hydroperoxide">Hydroperoxy</a></li> <li><a href="/wiki/Dioxirane" title="Dioxirane">Dioxiranes</a></li></ul></li> <li><a href="/wiki/Ethylenedioxy" title="Ethylenedioxy">Ethylenedioxy</a></li> <li><a href="/wiki/Methylenedioxy" title="Methylenedioxy">Methylenedioxy</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Carbonyl_group" title="Carbonyl group">carbonyl</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/Acyl_group" title="Acyl group">Acyl</a> <ul><li><a href="/wiki/Acetyl_group" title="Acetyl group">Acetyl</a></li> <li><a href="/wiki/Acryloyl_group" class="mw-redirect" title="Acryloyl group">Acryloyl</a></li> <li><a href="/wiki/Benzoyl_group" title="Benzoyl group">Benzoyl</a></li></ul></li> <li><a href="/wiki/Aldehyde" title="Aldehyde">Aldehyde</a> <ul><li><a href="/wiki/Ketene" title="Ketene">Ketene</a></li></ul></li> <li><a href="/wiki/Ketone" title="Ketone">Ketone</a></li> <li><a href="/wiki/Ynone" title="Ynone">Ynone</a></li> <li><a href="/wiki/Reductone" title="Reductone">Reductone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">carboxy</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/Carboxylic_acid" title="Carboxylic acid">Carboxyl</a> <ul><li><a href="/wiki/Acetoxy_group" title="Acetoxy group">Acetoxy</a></li> <li><a href="/wiki/Carboxylic_anhydride" class="mw-redirect" title="Carboxylic anhydride">Anhydride</a></li></ul></li> <li><a href="/wiki/Ester" title="Ester">Ester</a> <ul><li><a href="/wiki/Orthoester" class="mw-redirect" title="Orthoester">Orthoester</a></li></ul></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Only one <br />element, <br />not being <br />carbon, <br />hydrogen, <br />or oxygen <br /><span class="nobold">(one element, <br />not C, H or O)</span></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/Nitrogen" title="Nitrogen">Nitrogen</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/Amine" title="Amine">Amine</a> <ul><li><a href="/wiki/Enamine" title="Enamine">Enamine</a></li> <li><a href="/wiki/Quaternary_ammonium_cation" title="Quaternary ammonium cation">Ammonium</a></li></ul></li> <li><a href="/wiki/Hydrazines" title="Hydrazines">Hydrazo</a></li> <li><a href="/wiki/Nitrene" title="Nitrene">Nitrene</a></li> <li><a href="/wiki/Imine" title="Imine">Imine</a></li> <li><a href="/wiki/Oxime" title="Oxime">Oxime</a></li> <li><a href="/wiki/Hydrazone" title="Hydrazone">Hydrazone</a></li> <li><a href="/wiki/Azo_compound" title="Azo compound">Azo</a></li> <li><a href="/wiki/Amide_(functional_group)" title="Amide (functional group)">Amide</a></li> <li><a href="/wiki/Imidate" class="mw-redirect" title="Imidate">Imidate</a></li> <li><a href="/wiki/Amidine" title="Amidine">Amidine</a></li> <li><a href="/wiki/Carbamate" title="Carbamate">Carbamate</a></li> <li><a href="/wiki/Imide" title="Imide">Imide</a></li> <li><a href="/wiki/Nitrile" title="Nitrile">Nitrile</a></li> <li><a href="/wiki/Isocyanide" title="Isocyanide">Isonitrile</a></li> <li><a href="/wiki/Cyanate_ester" title="Cyanate ester">Cyanate</a></li> <li><a href="/wiki/Isocyanate" title="Isocyanate">Isocyanate</a></li> <li><a href="/wiki/Nitrate_ester" title="Nitrate ester">Nitrate</a></li> <li><a href="/wiki/Nitrite_ester" class="mw-redirect" title="Nitrite ester">Nitrite</a></li> <li><a href="/wiki/Nitro_compound" title="Nitro compound">Nitro</a></li> <li><a href="/wiki/Nitroso" title="Nitroso">Nitroso</a></li> <li><a href="/wiki/NONOate" title="NONOate">NONOate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Phosphorus" title="Phosphorus">Phosphorus</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/Organophosphate" title="Organophosphate">Phosphate</a> <ul><li><a href="/wiki/Phosphodiester" class="mw-redirect" title="Phosphodiester">Phosphodiester</a></li></ul></li> <li><a href="/wiki/Phosphonate" title="Phosphonate">Phosphonate</a> <ul><li><a href="/wiki/Phosphite_ester" title="Phosphite ester">Phosphite</a></li></ul></li> <li><a href="/wiki/Phosphonite" title="Phosphonite">Phosphonous</a></li> <li><a href="/wiki/Phosphinate" title="Phosphinate">Phosphinate</a></li> <li><a href="/wiki/Phosphine_oxide" title="Phosphine oxide">Phosphine oxide</a></li> <li><a href="/wiki/Organophosphine" title="Organophosphine">Phosphine</a> <ul><li><a href="/wiki/Phosphonium" title="Phosphonium">Phosphonium</a></li></ul></li> <li><a href="/wiki/Phosphaalkene" title="Phosphaalkene">Phosphaalkene</a></li> <li><a href="/wiki/Phosphaalkyne" title="Phosphaalkyne">Phosphaalkyne</a></li> <li><a href="/wiki/1-Phosphaallenes" title="1-Phosphaallenes">Phosphaallene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Sulfur" title="Sulfur">Sulfur</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/Thiol" title="Thiol">Thiol</a></li> <li><a href="/wiki/Sulfide_(organic)" class="mw-redirect" title="Sulfide (organic)">Sulfide</a> <ul><li><a href="/wiki/Sulfonium" title="Sulfonium">Sulfonium</a></li></ul></li> <li><a href="/wiki/Persulfide" title="Persulfide">Persulfide</a></li> <li><a href="/wiki/Disulfide" title="Disulfide">Disulfide</a></li> <li><a href="/wiki/Sulfenic_acid" title="Sulfenic acid">Sulfenic acid</a></li> <li><a href="/wiki/Thiosulfinate" title="Thiosulfinate">Thiosulfinate</a></li> <li><a href="/wiki/Sulfoxide" title="Sulfoxide">Sulfoxide</a></li> <li><a href="/wiki/Thiosulfonate" title="Thiosulfonate">Thiosulfonate</a></li> <li><a href="/wiki/Sulfinic_acid" title="Sulfinic acid">Sulfinic acid</a></li> <li><a href="/wiki/Sulfone" title="Sulfone">Sulfone</a></li> <li><a href="/wiki/Sulfonic_acid" title="Sulfonic acid">Sulfonic acid</a></li> <li><a href="/wiki/Thioketone" title="Thioketone">Thioketone</a></li> <li><a href="/wiki/Thial" title="Thial">Thial</a></li> <li><a href="/wiki/Thioester" title="Thioester">Thioester</a></li> <li><a href="/wiki/Thionoester" class="mw-redirect" title="Thionoester">Thionoester</a></li> <li><a href="/wiki/Thioxanthate" title="Thioxanthate">Thioxanthate</a></li> <li><a href="/wiki/Xanthate" title="Xanthate">Xanthate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Boron" title="Boron">Boron</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/Boronic_acid" title="Boronic acid">Boronic acid</a></li> <li><a href="/wiki/Borinic_acid" title="Borinic acid">Borinic acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Selenium" title="Selenium">Selenium</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/Selenol" title="Selenol">Selenol</a></li> <li><a href="/wiki/Selenonic_acid" title="Selenonic acid">Selenonic acid</a></li> <li><a href="/wiki/Seleninic_acid" title="Seleninic acid">Seleninic acid</a></li> <li><a href="/wiki/Selenenic_acid" title="Selenenic acid">Selenenic acid</a></li> <li><a href="/wiki/Selone" title="Selone">Selone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Tellurium" title="Tellurium">Tellurium</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/Tellurol" title="Tellurol">Tellurol</a></li> <li><a href="/wiki/Telluroketone" title="Telluroketone">Telluroketone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><i><a href="/wiki/Halocarbon" title="Halocarbon">Halo</a></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><a class="mw-selflink selflink">Haloalkane</a> <ul><li><a href="/wiki/Fluoroethyl" title="Fluoroethyl">Fluoroethyl</a></li> <li><a href="/wiki/Trifluoromethyl" class="mw-redirect" title="Trifluoromethyl">Trifluoromethyl</a></li> <li><a href="/wiki/Trichloromethyl_group" title="Trichloromethyl group">Trichloromethyl</a></li> <li><a href="/wiki/Trifluoromethoxy_group" title="Trifluoromethoxy group">Trifluoromethoxy</a></li> <li><a href="/wiki/Iodane" class="mw-redirect" title="Iodane">Hypervalent iodine</a></li></ul></li> <li><a href="/wiki/Vinyl_halide" title="Vinyl halide">Vinyl halide</a> <ul><li><a href="/wiki/Vinyl_iodide_functional_group" title="Vinyl iodide functional group">Iodide</a></li></ul></li> <li><a href="/wiki/Acyl_halide" title="Acyl halide">Acyl halide</a> <ul><li><a href="/wiki/Acyl_chloride" title="Acyl chloride">Chloride</a></li></ul></li> <li><a href="/wiki/Perchlorate_ester" class="mw-redirect" title="Perchlorate ester">Perchlorate</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other</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/Isothiocyanate" title="Isothiocyanate">Isothiocyanate</a></li> <li><a href="/wiki/Phosphoramides" title="Phosphoramides">Phosphoramides</a></li> <li><a href="/wiki/Sulfenyl_chloride" title="Sulfenyl chloride">Sulfenyl chloride</a></li> <li><a href="/wiki/Sulfonamide" title="Sulfonamide">Sulfonamide</a></li> <li><a href="/wiki/Organic_thiocyanates" title="Organic thiocyanates">Thiocyanate</a></li> <li><a href="/wiki/Sulfinylamine" title="Sulfinylamine">Sulfinylamines</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <dl><dt><span class="nobold">See also</span></dt> <dd><i><a href="/wiki/Chemical_classification" class="mw-redirect" title="Chemical classification">chemical classification</a></i></dd> <dd><i><a href="/wiki/Chemical_nomenclature" title="Chemical nomenclature">chemical nomenclature</a></i> <dl><dd><a href="/wiki/IUPAC_nomenclature_of_inorganic_chemistry" title="IUPAC nomenclature of inorganic chemistry">inorganic</a></dd> <dd><a href="/wiki/IUPAC_nomenclature_of_organic_chemistry" title="IUPAC nomenclature of organic chemistry">organic</a></dd></dl></dd></dl> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"><style data-mw-deduplicate="TemplateStyles:r1038841319">.mw-parser-output .tooltip-dotted{border-bottom:1px dotted;cursor:help}</style></div><div role="navigation" class="navbox authority-control" aria-label="Navbox" style="padding:3px"><table class="nowraplinks hlist navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Help:Authority_control" title="Help:Authority control">Authority control databases</a>: National <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q271026#identifiers" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"><ul><li><span class="uid"><span class="rt-commentedText tooltip tooltip-dotted" title="organohalogeny"><a rel="nofollow" class="external text" href="https://aleph.nkp.cz/F/?func=find-c&local_base=aut&ccl_term=ica=ph241658&CON_LNG=ENG">Czech Republic</a></span></span></li></ul></div></td></tr></tbody></table></div>    </div><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?type=1x1" alt="" width="1" height="1" style="border: none; position: absolute;"></noscript> <div class="printfooter" data-nosnippet="">Retrieved from "<a dir="ltr" href="https://en.wikipedia.org/w/index.php?title=Haloalkane&oldid=1244629621">https://en.wikipedia.org/w/index.php?title=Haloalkane&oldid=1244629621</a>"</div></div> <div id="catlinks" class="catlinks" data-mw="interface"><div id="mw-normal-catlinks" class="mw-normal-catlinks"><a href="/wiki/Help:Category" title="Help:Category">Categories</a>: <ul><li><a href="/wiki/Category:Haloalkanes" title="Category:Haloalkanes">Haloalkanes</a></li><li><a href="/wiki/Category:Halogenated_solvents" title="Category:Halogenated solvents">Halogenated solvents</a></li><li><a href="/wiki/Category:Refrigerants" title="Category:Refrigerants">Refrigerants</a></li><li><a href="/wiki/Category:Functional_groups" title="Category:Functional groups">Functional groups</a></li></ul></div><div id="mw-hidden-catlinks" class="mw-hidden-catlinks mw-hidden-cats-hidden">Hidden categories: <ul><li><a href="/wiki/Category:Articles_with_short_description" title="Category:Articles with short description">Articles with short description</a></li><li><a href="/wiki/Category:Short_description_matches_Wikidata" title="Category:Short description matches Wikidata">Short description matches Wikidata</a></li><li><a href="/wiki/Category:Commons_category_link_is_on_Wikidata" title="Category:Commons category link is on Wikidata">Commons category link is on Wikidata</a></li></ul></div></div> </div> </main> </div> <div class="mw-footer-container"> <footer id="footer" class="mw-footer" > <ul id="footer-info"> <li id="footer-info-lastmod"> This page was last edited on 8 September 2024, at 06:14<span class="anonymous-show"> (UTC)</span>.</li> <li id="footer-info-copyright">Text is available under the <a href="/wiki/Wikipedia:Text_of_the_Creative_Commons_Attribution-ShareAlike_4.0_International_License" title="Wikipedia:Text of the Creative Commons Attribution-ShareAlike 4.0 International License">Creative Commons Attribution-ShareAlike 4.0 License</a>; additional terms may apply. By using this site, you agree to the <a href="https://foundation.wikimedia.org/wiki/Special:MyLanguage/Policy:Terms_of_Use" class="extiw" title="foundation:Special:MyLanguage/Policy:Terms of Use">Terms of Use</a> and <a href="https://foundation.wikimedia.org/wiki/Special:MyLanguage/Policy:Privacy_policy" class="extiw" title="foundation:Special:MyLanguage/Policy:Privacy policy">Privacy Policy</a>. Wikipedia® is a registered trademark of the <a rel="nofollow" class="external text" href="https://wikimediafoundation.org/">Wikimedia Foundation, Inc.</a>, a non-profit organization.</li> </ul> <ul id="footer-places"> <li id="footer-places-privacy"><a href="https://foundation.wikimedia.org/wiki/Special:MyLanguage/Policy:Privacy_policy">Privacy policy</a></li> <li id="footer-places-about"><a href="/wiki/Wikipedia:About">About Wikipedia</a></li> <li id="footer-places-disclaimers"><a href="/wiki/Wikipedia:General_disclaimer">Disclaimers</a></li> <li id="footer-places-contact"><a href="//en.wikipedia.org/wiki/Wikipedia:Contact_us">Contact Wikipedia</a></li> <li id="footer-places-wm-codeofconduct"><a href="https://foundation.wikimedia.org/wiki/Special:MyLanguage/Policy:Universal_Code_of_Conduct">Code of Conduct</a></li> <li id="footer-places-developers"><a href="https://developer.wikimedia.org">Developers</a></li> <li id="footer-places-statslink"><a href="https://stats.wikimedia.org/#/en.wikipedia.org">Statistics</a></li> <li id="footer-places-cookiestatement"><a href="https://foundation.wikimedia.org/wiki/Special:MyLanguage/Policy:Cookie_statement">Cookie statement</a></li> <li id="footer-places-mobileview"><a href="//en.m.wikipedia.org/w/index.php?title=Haloalkane&mobileaction=toggle_view_mobile" class="noprint stopMobileRedirectToggle">Mobile view</a></li> </ul> <ul id="footer-icons" class="noprint"> <li id="footer-copyrightico"><a href="https://wikimediafoundation.org/" class="cdx-button cdx-button--fake-button cdx-button--size-large cdx-button--fake-button--enabled"><img src="/static/images/footer/wikimedia-button.svg" width="84" height="29" alt="Wikimedia Foundation" loading="lazy"></a></li> <li id="footer-poweredbyico"><a href="https://www.mediawiki.org/" class="cdx-button cdx-button--fake-button cdx-button--size-large cdx-button--fake-button--enabled"><img src="/w/resources/assets/poweredby_mediawiki.svg" alt="Powered by MediaWiki" width="88" height="31" loading="lazy"></a></li> </ul> </footer> </div> </div> </div> <div class="vector-settings" id="p-dock-bottom"> <ul></ul> </div><script>(RLQ=window.RLQ||[]).push(function(){mw.config.set({"wgHostname":"mw-web.codfw.main-f69cdc8f6-tggkq","wgBackendResponseTime":178,"wgPageParseReport":{"limitreport":{"cputime":"0.451","walltime":"0.590","ppvisitednodes":{"value":2823,"limit":1000000},"postexpandincludesize":{"value":97542,"limit":2097152},"templateargumentsize":{"value":5330,"limit":2097152},"expansiondepth":{"value":15,"limit":100},"expensivefunctioncount":{"value":3,"limit":500},"unstrip-depth":{"value":1,"limit":20},"unstrip-size":{"value":45522,"limit":5000000},"entityaccesscount":{"value":1,"limit":400},"timingprofile":["100.00% 466.913 1 -total"," 33.88% 158.206 1 Template:Reflist"," 23.27% 108.673 3 Template:Navbox"," 22.04% 102.899 1 Template:Functional_group"," 19.80% 92.471 2 Template:Cite_book"," 17.56% 81.968 1 Template:Short_description"," 11.85% 55.351 2 Template:Pagetype"," 6.98% 32.604 12 Template:Chem"," 6.45% 30.109 1 Template:Authority_control"," 5.88% 27.471 2 Template:Main_article"]},"scribunto":{"limitreport-timeusage":{"value":"0.262","limit":"10.000"},"limitreport-memusage":{"value":5000043,"limit":52428800}},"cachereport":{"origin":"mw-api-int.codfw.main-849f99967d-fm4ck","timestamp":"20241123045141","ttl":2592000,"transientcontent":false}}});});</script> <script type="application/ld+json">{"@context":"https:\/\/schema.org","@type":"Article","name":"Haloalkane","url":"https:\/\/en.wikipedia.org\/wiki\/Haloalkane","sameAs":"http:\/\/www.wikidata.org\/entity\/Q271026","mainEntity":"http:\/\/www.wikidata.org\/entity\/Q271026","author":{"@type":"Organization","name":"Contributors to Wikimedia projects"},"publisher":{"@type":"Organization","name":"Wikimedia Foundation, Inc.","logo":{"@type":"ImageObject","url":"https:\/\/www.wikimedia.org\/static\/images\/wmf-hor-googpub.png"}},"datePublished":"2002-08-23T06:13:23Z","dateModified":"2024-09-08T06:14:36Z","image":"https:\/\/upload.wikimedia.org\/wikipedia\/commons\/b\/bd\/Tetrafluoroethane_liquid.jpg","headline":"group of chemical compounds derived from alkanes containing one or more halogens"}</script> </body> </html>