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class="vector-unpinned-container"> </div> </div> </div> </nav> <h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Halogenation</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 38 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-38" 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">38 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D9%87%D9%84%D8%AC%D9%86%D8%A9" title="هلجنة – Arabic" lang="ar" hreflang="ar" data-title="هلجنة" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-bn mw-list-item"><a href="https://bn.wikipedia.org/wiki/%E0%A6%B9%E0%A7%8D%E0%A6%AF%E0%A6%BE%E0%A6%B2%E0%A7%8B%E0%A6%9C%E0%A7%87%E0%A6%A8_%E0%A6%B8%E0%A6%82%E0%A6%AF%E0%A7%8B%E0%A6%97_%E0%A6%AC%E0%A6%BF%E0%A6%95%E0%A7%8D%E0%A6%B0%E0%A6%BF%E0%A6%AF%E0%A6%BC%E0%A6%BE" title="হ্যালোজেন সংযোগ বিক্রিয়া – Bangla" lang="bn" hreflang="bn" data-title="হ্যালোজেন সংযোগ বিক্রিয়া" data-language-autonym="বাংলা" data-language-local-name="Bangla" class="interlanguage-link-target"><span>বাংলা</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Halogenaci%C3%B3" title="Halogenació – Catalan" lang="ca" hreflang="ca" data-title="Halogenació" 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/Halogenace" title="Halogenace – Czech" lang="cs" hreflang="cs" data-title="Halogenace" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Halogenierung" title="Halogenierung – German" lang="de" hreflang="de" data-title="Halogenierung" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-et mw-list-item"><a href="https://et.wikipedia.org/wiki/Halogeenimine" title="Halogeenimine – Estonian" lang="et" hreflang="et" data-title="Halogeenimine" data-language-autonym="Eesti" data-language-local-name="Estonian" class="interlanguage-link-target"><span>Eesti</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Halogenaci%C3%B3n" title="Halogenación – Spanish" lang="es" hreflang="es" data-title="Halogenación" 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/Halogenazio" title="Halogenazio – Basque" lang="eu" hreflang="eu" data-title="Halogenazio" 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%DA%98%D9%86%E2%80%8C%D8%AF%D8%A7%D8%B1_%DA%A9%D8%B1%D8%AF%D9%86" title="هالوژن‌دار کردن – Persian" lang="fa" hreflang="fa" data-title="هالوژن‌دار کردن" 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%A9nation" title="Halogénation – French" lang="fr" hreflang="fr" data-title="Halogénation" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</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%9C%E0%A4%A8%E0%A4%A8" title="हैलोजनन – Hindi" lang="hi" hreflang="hi" data-title="हैलोजनन" data-language-autonym="हिन्दी" data-language-local-name="Hindi" class="interlanguage-link-target"><span>हिन्दी</span></a></li><li class="interlanguage-link interwiki-hr mw-list-item"><a href="https://hr.wikipedia.org/wiki/Halogeniranje" title="Halogeniranje – Croatian" lang="hr" hreflang="hr" data-title="Halogeniranje" data-language-autonym="Hrvatski" data-language-local-name="Croatian" class="interlanguage-link-target"><span>Hrvatski</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Halogenasi" title="Halogenasi – Indonesian" lang="id" hreflang="id" data-title="Halogenasi" 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/Alogenazione" title="Alogenazione – Italian" lang="it" hreflang="it" data-title="Alogenazione" 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%92%D7%A0%D7%A6%D7%99%D7%94" title="הלוגנציה – Hebrew" lang="he" hreflang="he" data-title="הלוגנציה" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-kk mw-list-item"><a href="https://kk.wikipedia.org/wiki/%D0%93%D0%B0%D0%BB%D0%BE%D0%B3%D0%B5%D0%BD%D0%B4%D0%B5%D1%83" title="Галогендеу – Kazakh" lang="kk" hreflang="kk" data-title="Галогендеу" data-language-autonym="Қазақша" data-language-local-name="Kazakh" class="interlanguage-link-target"><span>Қазақша</span></a></li><li class="interlanguage-link interwiki-lv mw-list-item"><a href="https://lv.wikipedia.org/wiki/Halogen%C4%93%C5%A1ana" title="Halogenēšana – Latvian" lang="lv" hreflang="lv" data-title="Halogenēšana" data-language-autonym="Latviešu" data-language-local-name="Latvian" class="interlanguage-link-target"><span>Latviešu</span></a></li><li class="interlanguage-link interwiki-lb mw-list-item"><a href="https://lb.wikipedia.org/wiki/Halogenatioun" title="Halogenatioun – Luxembourgish" lang="lb" hreflang="lb" data-title="Halogenatioun" data-language-autonym="Lëtzebuergesch" data-language-local-name="Luxembourgish" class="interlanguage-link-target"><span>Lëtzebuergesch</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Halog%C3%A9nez%C3%A9s" title="Halogénezés – Hungarian" lang="hu" hreflang="hu" data-title="Halogénezés" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-ms mw-list-item"><a href="https://ms.wikipedia.org/wiki/Penghalogenan" title="Penghalogenan – Malay" lang="ms" hreflang="ms" data-title="Penghalogenan" 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/Halogenering" title="Halogenering – Dutch" lang="nl" hreflang="nl" data-title="Halogenering" 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" title="ハロゲン化 – Japanese" lang="ja" hreflang="ja" data-title="ハロゲン化" 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/Halogenering" title="Halogenering – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Halogenering" 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-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Halogenowanie" title="Halogenowanie – Polish" lang="pl" hreflang="pl" data-title="Halogenowanie" 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/Halogena%C3%A7%C3%A3o" title="Halogenação – Portuguese" lang="pt" hreflang="pt" data-title="Halogenação" 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/Halogenare" title="Halogenare – Romanian" lang="ro" hreflang="ro" data-title="Halogenare" 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%B8%D1%80%D0%BE%D0%B2%D0%B0%D0%BD%D0%B8%D0%B5" title="Галогенирование – Russian" lang="ru" hreflang="ru" data-title="Галогенирование" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sk mw-list-item"><a href="https://sk.wikipedia.org/wiki/Halogen%C3%A1cia" title="Halogenácia – Slovak" lang="sk" hreflang="sk" data-title="Halogenácia" data-language-autonym="Slovenčina" data-language-local-name="Slovak" class="interlanguage-link-target"><span>Slovenčina</span></a></li><li class="interlanguage-link interwiki-sl mw-list-item"><a href="https://sl.wikipedia.org/wiki/Kloriranje" title="Kloriranje – Slovenian" lang="sl" hreflang="sl" data-title="Kloriranje" data-language-autonym="Slovenščina" data-language-local-name="Slovenian" class="interlanguage-link-target"><span>Slovenščina</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/%D0%A5%D0%B0%D0%BB%D0%BE%D0%B3%D0%B5%D0%BD%D0%B0%D1%86%D0%B8%D1%98%D0%B0" title="Халогенација – Serbian" lang="sr" hreflang="sr" data-title="Халогенација" 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/Halogenacija" title="Halogenacija – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Halogenacija" 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/Halogenointi" title="Halogenointi – Finnish" lang="fi" hreflang="fi" data-title="Halogenointi" 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/Halogenering" title="Halogenering – Swedish" lang="sv" hreflang="sv" data-title="Halogenering" 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%AE%9A%E0%AE%A9%E0%AF%87%E0%AE%B1%E0%AF%8D%E0%AE%B1%E0%AE%AE%E0%AF%8D" title="ஆலசனேற்றம் – Tamil" lang="ta" hreflang="ta" data-title="ஆலசனேற்றம்" data-language-autonym="தமிழ்" data-language-local-name="Tamil" class="interlanguage-link-target"><span>தமிழ்</span></a></li><li class="interlanguage-link interwiki-tg mw-list-item"><a href="https://tg.wikipedia.org/wiki/%D2%B2%D0%BE%D0%BB%D1%83%D0%B6%D0%B5%D0%BD%D0%B4%D0%BE%D1%80_%D0%BA%D0%B0%D1%80%D0%B4%D0%B0%D0%BD" title="Ҳолужендор кардан – Tajik" lang="tg" hreflang="tg" data-title="Ҳолужендор кардан" data-language-autonym="Тоҷикӣ" data-language-local-name="Tajik" class="interlanguage-link-target"><span>Тоҷикӣ</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Halojenleme" title="Halojenleme – Turkish" lang="tr" hreflang="tr" data-title="Halojenleme" 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%D1%83%D0%B2%D0%B0%D0%BD%D0%BD%D1%8F" title="Галогенування – Ukrainian" lang="uk" hreflang="uk" data-title="Галогенування" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E9%B9%B5%E5%8C%96" title="鹵化 – Chinese" lang="zh" hreflang="zh" data-title="鹵化" data-language-autonym="中文" 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</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"></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">Chemical reaction which adds one or more halogen elements to a compound</div> <style data-mw-deduplicate="TemplateStyles:r1236090951">.mw-parser-output .hatnote{font-style:italic}.mw-parser-output div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">"Fluorination" redirects here. For the addition of fluoride to drinking water, see <a href="/wiki/Water_fluoridation" title="Water fluoridation">Water fluoridation</a>.</div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">For the addition of chlorine, hypochlorite, etc. to drinking water, see <a href="/wiki/Water_chlorination" title="Water chlorination">Water chlorination</a>.</div> <p>In <a href="/wiki/Chemistry" title="Chemistry">chemistry</a>, <b>halogenation</b> is a <a href="/wiki/Chemical_reaction" title="Chemical reaction">chemical reaction</a> which introduces one or more <a href="/wiki/Halogen" title="Halogen">halogens</a> into a <a href="/wiki/Chemical_compound" title="Chemical compound">chemical compound</a>. <a href="/wiki/Halide" title="Halide">Halide</a>-containing compounds are pervasive, making this type of transformation important, e.g. in the production of <a href="/wiki/Polymers" class="mw-redirect" title="Polymers">polymers</a>, <a href="/wiki/Drugs" class="mw-redirect" title="Drugs">drugs</a>.<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> This kind of conversion is in fact so common that a comprehensive overview is challenging. This article mainly deals with halogenation using elemental halogens (<style data-mw-deduplicate="TemplateStyles:r1123817410">.mw-parser-output .template-chem2-su{display:inline-block;font-size:80%;line-height:1;vertical-align:-0.35em}.mw-parser-output .template-chem2-su>span{display:block;text-align:left}.mw-parser-output sub.template-chem2-sub{font-size:80%;vertical-align:-0.35em}.mw-parser-output sup.template-chem2-sup{font-size:80%;vertical-align:0.65em}</style><span class="chemf nowrap"><a href="/wiki/Fluorine" title="Fluorine">F<sub class="template-chem2-sub">2</sub></a>, <a href="/wiki/Chlorine" title="Chlorine">Cl<sub class="template-chem2-sub">2</sub></a>, <a href="/wiki/Bromine" title="Bromine">Br<sub class="template-chem2-sub">2</sub></a>, <a href="/wiki/Iodine" title="Iodine">I<sub class="template-chem2-sub">2</sub></a></span>). Halides are also commonly introduced using salts of the halides and halogen acids.<sup class="noprint Inline-Template" style="margin-left:0.1em; white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Please_clarify" title="Wikipedia:Please clarify"><span title="What on this Earth is "halogen acids"??? (July 2023)">clarification needed</span></a></i>]</sup> Many specialized <a href="/wiki/Reagent" title="Reagent">reagents</a> exist for and introducing halogens into diverse <a href="/wiki/Substrate_(chemistry)" title="Substrate (chemistry)">substrates</a>, e.g. <a href="/wiki/Thionyl_chloride" title="Thionyl chloride">thionyl chloride</a>. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Organic_chemistry">Organic chemistry</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Halogenation&action=edit&section=1" title="Edit section: Organic chemistry"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Several pathways exist for the halogenation of organic compounds, including <a href="/wiki/Free_radical_halogenation" class="mw-redirect" title="Free radical halogenation">free radical halogenation</a>, <a href="/wiki/Ketone_halogenation" title="Ketone halogenation">ketone halogenation</a>, <a href="/wiki/Electrophilic_halogenation" title="Electrophilic halogenation">electrophilic halogenation</a>, and <a href="/wiki/Halogen_addition_reaction" title="Halogen addition reaction">halogen addition reaction</a>. The nature of the <a href="/wiki/Substrate_(chemistry)" title="Substrate (chemistry)">substrate</a> determines the pathway. The facility of halogenation is influenced by the halogen. <a href="/wiki/Fluorine" title="Fluorine">Fluorine</a> and <a href="/wiki/Chlorine" title="Chlorine">chlorine</a> are more <a href="/wiki/Electrophilic" class="mw-redirect" title="Electrophilic">electrophilic</a> and are more aggressive halogenating agents. <a href="/wiki/Bromine" title="Bromine">Bromine</a> is a weaker halogenating agent than both fluorine and chlorine, while <a href="/wiki/Iodine" title="Iodine">iodine</a> is the least reactive of them all. The facility of <a href="/wiki/Dehydrohalogenation" title="Dehydrohalogenation">dehydrohalogenation</a> follows the reverse trend: iodine is most easily removed from organic compounds, and <a href="/wiki/Organofluorine" class="mw-redirect" title="Organofluorine">organofluorine</a> compounds are highly stable. </p> <div class="mw-heading mw-heading3"><h3 id="Free_radical_halogenation">Free radical halogenation</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Halogenation&action=edit&section=2" title="Edit section: Free radical halogenation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Halogenation of <a href="/wiki/Saturated_hydrocarbon" class="mw-redirect" title="Saturated hydrocarbon">saturated hydrocarbons</a> is a <a href="/wiki/Substitution_reaction" title="Substitution reaction">substitution reaction</a>. The reaction typically involves <a href="/wiki/Free_radical" class="mw-redirect" title="Free radical">free radical</a> pathways. The <a href="/wiki/Regiochemistry" class="mw-redirect" title="Regiochemistry">regiochemistry</a> of the halogenation of <a href="/wiki/Alkanes" class="mw-redirect" title="Alkanes">alkanes</a> is largely determined by the relative weakness of the <a href="/wiki/Carbon%E2%80%93hydrogen_bond" title="Carbon–hydrogen bond">C–H bonds</a>. This trend is reflected by the faster reaction at <a href="/wiki/Tertiary_(chemistry)" title="Tertiary (chemistry)">tertiary</a> and <a href="/wiki/Secondary_(chemistry)" title="Secondary (chemistry)">secondary</a> positions. </p><p>Free radical chlorination is used for the industrial production of some <a href="/wiki/Solvents" class="mw-redirect" title="Solvents">solvents</a>:<sup id="cite_ref-Ullmann_2-0" class="reference"><a href="#cite_note-Ullmann-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">4</sub> + Cl<sub class="template-chem2-sub">2</sub> → CH<sub class="template-chem2-sub">3</sub>Cl + HCl</span></dd></dl> <p>Naturally-occurring <a href="/wiki/Organobromine_compound" class="mw-redirect" title="Organobromine compound">organobromine compounds</a> are usually produced by free radical pathway <a href="/wiki/Catalyzed" class="mw-redirect" title="Catalyzed">catalyzed</a> by the <a href="/wiki/Enzyme" title="Enzyme">enzyme</a> <a href="/wiki/Bromoperoxidase" class="mw-redirect" title="Bromoperoxidase">bromoperoxidase</a>. The reaction requires <a href="/wiki/Bromide" title="Bromide">bromide</a> in combination with <a href="/wiki/Oxygen" title="Oxygen">oxygen</a> as an <a href="/wiki/Oxidant" class="mw-redirect" title="Oxidant">oxidant</a>. The <a href="/wiki/Oceans" class="mw-redirect" title="Oceans">oceans</a> are estimated to release 1–2 <a href="/wiki/Million" class="mw-redirect" title="Million">million</a> tons of <a href="/wiki/Bromoform" title="Bromoform">bromoform</a> and 56,000 tons of <a href="/wiki/Bromomethane" title="Bromomethane">bromomethane</a> annually.<sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup class="noprint Inline-Template" style="margin-left:0.1em; white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Please_clarify" title="Wikipedia:Please clarify"><span title="Which ton??? Short ton, long ton or metric ton??? (July 2023)">clarification needed</span></a></i>]</sup> </p><p>The <a href="/wiki/Iodoform_reaction" class="mw-redirect" title="Iodoform reaction">iodoform reaction</a>, which involves degradation of <a href="/wiki/Methyl_ketone" class="mw-redirect" title="Methyl ketone">methyl ketones</a>, proceeds by the free radical iodination. </p> <div class="mw-heading mw-heading3"><h3 id="Fluorination">Fluorination</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Halogenation&action=edit&section=3" title="Edit section: Fluorination"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Because of its extreme reactivity, fluorine (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">F<sub class="template-chem2-sub">2</sub></span>) represents a special category with respect to halogenation. Most organic compounds, saturated or otherwise, burn upon contact with <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">F<sub class="template-chem2-sub">2</sub></span>, ultimately yielding <a href="/wiki/Carbon_tetrafluoride" title="Carbon tetrafluoride">carbon tetrafluoride</a>. By contrast, the heavier halogens are far less reactive toward saturated hydrocarbons. </p><p>Highly specialised conditions and apparatus are required for fluorinations with elemental <a href="/wiki/Fluorine" title="Fluorine">fluorine</a>. Commonly, fluorination reagents are employed instead of <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">F<sub class="template-chem2-sub">2</sub></span>. Such reagents include <a href="/wiki/Cobalt_trifluoride" class="mw-redirect" title="Cobalt trifluoride">cobalt trifluoride</a>, <a href="/wiki/Chlorine_trifluoride" title="Chlorine trifluoride">chlorine trifluoride</a>, and <a href="/wiki/Iodine_pentafluoride" title="Iodine pentafluoride">iodine pentafluoride</a>.<sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p><p>The method <a href="/wiki/Electrochemical_fluorination" title="Electrochemical fluorination">electrochemical fluorination</a> is used commercially for the production of <a href="/wiki/Perfluorinated_compound" title="Perfluorinated compound">perfluorinated compounds</a>. It generates small amounts of elemental fluorine <a href="/wiki/In_situ" title="In situ">in situ</a> from <a href="/wiki/Hydrogen_fluoride" title="Hydrogen fluoride">hydrogen fluoride</a>. The method avoids the hazards of handling fluorine gas. Many commercially important <a href="/wiki/Organic_compounds" class="mw-redirect" title="Organic compounds">organic compounds</a> are fluorinated using this technology. </p> <div class="mw-heading mw-heading3"><h3 id="Addition_of_halogens_to_alkenes_and_alkynes">Addition of halogens to alkenes and alkynes</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Halogenation&action=edit&section=4" title="Edit section: Addition of halogens to alkenes and alkynes"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size mw-halign-right" typeof="mw:File/Thumb"><span><video id="mwe_player_0" poster="//upload.wikimedia.org/wikipedia/commons/thumb/5/51/96._%D0%90%D0%B4%D0%B8%D1%86%D0%B8%D1%98%D0%B0_%D0%BD%D0%B0_%D1%85%D0%BB%D0%BE%D1%80_%D0%BD%D0%B0_%D0%B5%D1%82%D0%B8%D0%BD.ogg/220px--96._%D0%90%D0%B4%D0%B8%D1%86%D0%B8%D1%98%D0%B0_%D0%BD%D0%B0_%D1%85%D0%BB%D0%BE%D1%80_%D0%BD%D0%B0_%D0%B5%D1%82%D0%B8%D0%BD.ogg.jpg" controls="" preload="none" data-mw-tmh="" class="mw-file-element" width="220" height="124" data-durationhint="97" data-mwtitle="96._Адиција_на_хлор_на_етин.ogg" data-mwprovider="wikimediacommons" resource="/wiki/File:96._%D0%90%D0%B4%D0%B8%D1%86%D0%B8%D1%98%D0%B0_%D0%BD%D0%B0_%D1%85%D0%BB%D0%BE%D1%80_%D0%BD%D0%B0_%D0%B5%D1%82%D0%B8%D0%BD.ogg"><source src="//upload.wikimedia.org/wikipedia/commons/transcoded/5/51/96._%D0%90%D0%B4%D0%B8%D1%86%D0%B8%D1%98%D0%B0_%D0%BD%D0%B0_%D1%85%D0%BB%D0%BE%D1%80_%D0%BD%D0%B0_%D0%B5%D1%82%D0%B8%D0%BD.ogg/96._%D0%90%D0%B4%D0%B8%D1%86%D0%B8%D1%98%D0%B0_%D0%BD%D0%B0_%D1%85%D0%BB%D0%BE%D1%80_%D0%BD%D0%B0_%D0%B5%D1%82%D0%B8%D0%BD.ogg.480p.vp9.webm" type="video/webm; 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codecs="theora, vorbis"" data-width="1920" data-height="1080" /><source src="//upload.wikimedia.org/wikipedia/commons/transcoded/5/51/96._%D0%90%D0%B4%D0%B8%D1%86%D0%B8%D1%98%D0%B0_%D0%BD%D0%B0_%D1%85%D0%BB%D0%BE%D1%80_%D0%BD%D0%B0_%D0%B5%D1%82%D0%B8%D0%BD.ogg/96._%D0%90%D0%B4%D0%B8%D1%86%D0%B8%D1%98%D0%B0_%D0%BD%D0%B0_%D1%85%D0%BB%D0%BE%D1%80_%D0%BD%D0%B0_%D0%B5%D1%82%D0%B8%D0%BD.ogg.144p.mjpeg.mov" type="video/quicktime" data-transcodekey="144p.mjpeg.mov" data-width="256" data-height="144" /><source src="//upload.wikimedia.org/wikipedia/commons/transcoded/5/51/96._%D0%90%D0%B4%D0%B8%D1%86%D0%B8%D1%98%D0%B0_%D0%BD%D0%B0_%D1%85%D0%BB%D0%BE%D1%80_%D0%BD%D0%B0_%D0%B5%D1%82%D0%B8%D0%BD.ogg/96._%D0%90%D0%B4%D0%B8%D1%86%D0%B8%D1%98%D0%B0_%D0%BD%D0%B0_%D1%85%D0%BB%D0%BE%D1%80_%D0%BD%D0%B0_%D0%B5%D1%82%D0%B8%D0%BD.ogg.240p.vp9.webm" type="video/webm; codecs="vp9, opus"" data-transcodekey="240p.vp9.webm" data-width="426" data-height="240" /><source src="//upload.wikimedia.org/wikipedia/commons/transcoded/5/51/96._%D0%90%D0%B4%D0%B8%D1%86%D0%B8%D1%98%D0%B0_%D0%BD%D0%B0_%D1%85%D0%BB%D0%BE%D1%80_%D0%BD%D0%B0_%D0%B5%D1%82%D0%B8%D0%BD.ogg/96._%D0%90%D0%B4%D0%B8%D1%86%D0%B8%D1%98%D0%B0_%D0%BD%D0%B0_%D1%85%D0%BB%D0%BE%D1%80_%D0%BD%D0%B0_%D0%B5%D1%82%D0%B8%D0%BD.ogg.360p.vp9.webm" type="video/webm; codecs="vp9, opus"" data-transcodekey="360p.vp9.webm" data-width="640" data-height="360" /><source src="//upload.wikimedia.org/wikipedia/commons/transcoded/5/51/96._%D0%90%D0%B4%D0%B8%D1%86%D0%B8%D1%98%D0%B0_%D0%BD%D0%B0_%D1%85%D0%BB%D0%BE%D1%80_%D0%BD%D0%B0_%D0%B5%D1%82%D0%B8%D0%BD.ogg/96._%D0%90%D0%B4%D0%B8%D1%86%D0%B8%D1%98%D0%B0_%D0%BD%D0%B0_%D1%85%D0%BB%D0%BE%D1%80_%D0%BD%D0%B0_%D0%B5%D1%82%D0%B8%D0%BD.ogg.360p.webm" type="video/webm; codecs="vp8, vorbis"" data-transcodekey="360p.webm" data-width="640" data-height="360" /></video></span><figcaption>Double-addition of <a href="/wiki/Chlorine_gas" class="mw-redirect" title="Chlorine gas">chlorine gas</a> to <a href="/wiki/Ethyne" class="mw-redirect" title="Ethyne">ethyne</a></figcaption></figure> <p><a href="/wiki/Unsaturated_compound" class="mw-redirect" title="Unsaturated compound">Unsaturated compounds</a>, especially <a href="/wiki/Alkenes" class="mw-redirect" title="Alkenes">alkenes</a> and <a href="/wiki/Alkynes" class="mw-redirect" title="Alkynes">alkynes</a>, <i>add</i> halogens: </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">R−CH=CH−R' + X<sub class="template-chem2-sub">2</sub> → R−CHX−CHX−R'</span></dd></dl> <p>In <a href="/wiki/Oxychlorination" title="Oxychlorination">oxychlorination</a>, the combination of <a href="/wiki/Hydrogen_chloride" title="Hydrogen chloride">hydrogen chloride</a> and <a href="/wiki/Oxygen" title="Oxygen">oxygen</a> serves as the equivalent of <a href="/wiki/Chlorine" title="Chlorine">chlorine</a>, as illustrated by this route to <a href="/wiki/1,2-dichloroethane" class="mw-redirect" title="1,2-dichloroethane">1,2-dichloroethane</a>: </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">4 HCl + 2 CH<sub class="template-chem2-sub">2</sub>=CH<sub class="template-chem2-sub">2</sub> + O<sub class="template-chem2-sub">2</sub> → 2 Cl−CH<sub class="template-chem2-sub">2</sub>−CH<sub class="template-chem2-sub">2</sub>−Cl + 2 H<sub class="template-chem2-sub">2</sub>O</span></dd></dl> <figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Biadamantylidene-bromonium-ion-from-xtal-1994-2D-skeletal.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/64/Biadamantylidene-bromonium-ion-from-xtal-1994-2D-skeletal.png/170px-Biadamantylidene-bromonium-ion-from-xtal-1994-2D-skeletal.png" decoding="async" width="170" height="110" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/64/Biadamantylidene-bromonium-ion-from-xtal-1994-2D-skeletal.png/255px-Biadamantylidene-bromonium-ion-from-xtal-1994-2D-skeletal.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/64/Biadamantylidene-bromonium-ion-from-xtal-1994-2D-skeletal.png/340px-Biadamantylidene-bromonium-ion-from-xtal-1994-2D-skeletal.png 2x" data-file-width="1100" data-file-height="712" /></a><figcaption>Structure of a <a href="/wiki/Bromonium_ion" class="mw-redirect" title="Bromonium ion">bromonium ion</a></figcaption></figure> <p>The addition of halogens to alkenes proceeds via <a href="/wiki/Reaction_intermediate" title="Reaction intermediate">intermediate</a> <a href="/wiki/Halonium_ion" title="Halonium ion">halonium ions</a>. In special cases, such intermediates have been isolated.<sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p><p>Bromination is more <a href="/wiki/Chemical_selectivity" class="mw-redirect" title="Chemical selectivity">selective</a> than chlorination because the reaction is less <a href="/wiki/Exothermic" class="mw-redirect" title="Exothermic">exothermic</a>. Illustrative of the bromination of an alkene is the route to the <a href="/wiki/Anesthetic" title="Anesthetic">anesthetic</a> <a href="/wiki/Halothane" title="Halothane">halothane</a> from <a href="/wiki/Trichloroethylene" title="Trichloroethylene">trichloroethylene</a>:<sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p> <dl><dd><span typeof="mw:File"><a href="/wiki/File:Halothane_synthesis.png" class="mw-file-description" title="Halothane synthesis"><img alt="Halothane synthesis" src="//upload.wikimedia.org/wikipedia/commons/thumb/4/43/Halothane_synthesis.png/600px-Halothane_synthesis.png" decoding="async" width="600" height="71" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/4/43/Halothane_synthesis.png 1.5x" data-file-width="761" data-file-height="90" /></a></span></dd></dl> <p>Iodination and bromination can be effected by the addition of <a href="/wiki/Iodine" title="Iodine">iodine</a> and <a href="/wiki/Bromine" title="Bromine">bromine</a> to alkenes. The reaction, which conveniently proceeds with the discharge of the color of <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">I<sub class="template-chem2-sub">2</sub> and Br<sub class="template-chem2-sub">2</sub></span>, is the basis of the <a href="/wiki/Analytical_method" class="mw-redirect" title="Analytical method">analytical method</a>. The <a href="/wiki/Iodine_number" class="mw-redirect" title="Iodine number">iodine number</a> and <a href="/wiki/Bromine_number" title="Bromine number">bromine number</a> are measures of the <a href="/wiki/Degree_of_unsaturation" title="Degree of unsaturation">degree of unsaturation</a> for <a href="/wiki/Fat" title="Fat">fats</a> and other organic compounds. </p> <div class="mw-heading mw-heading3"><h3 id="Halogenation_of_aromatic_compounds">Halogenation of aromatic compounds</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Halogenation&action=edit&section=5" title="Edit section: Halogenation of aromatic compounds"><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/Aryl_halide" title="Aryl halide">Aryl halide</a></div> <p><a href="/wiki/Aromatic_compound" title="Aromatic compound">Aromatic compounds</a> are subject to <a href="/wiki/Electrophilic_halogenation" title="Electrophilic halogenation">electrophilic halogenation</a>: </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">R−C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">5</sub> + X<sub class="template-chem2-sub">2</sub> → HX + R−C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">4</sub>−X</span></dd></dl> <p>This kind of reaction typically works well for <a href="/wiki/Chlorine" title="Chlorine">chlorine</a> and <a href="/wiki/Bromine" title="Bromine">bromine</a>. Often a <a href="/wiki/Lewis_acid" class="mw-redirect" title="Lewis acid">Lewis acidic</a> <a href="/wiki/Catalyst" class="mw-redirect" title="Catalyst">catalyst</a> is used, such as <a href="/wiki/Ferric_chloride" class="mw-redirect" title="Ferric chloride">ferric chloride</a>.<sup id="cite_ref-PhCl_7-0" class="reference"><a href="#cite_note-PhCl-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> Many detailed procedures are available.<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><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> Because <a href="/wiki/Fluorine" title="Fluorine">fluorine</a> is so <a href="/wiki/Reactivity_(chemistry)" title="Reactivity (chemistry)">reactive</a>, other methods, such as the <a href="/wiki/Balz%E2%80%93Schiemann_reaction" title="Balz–Schiemann reaction">Balz–Schiemann reaction</a>, are used to prepare fluorinated aromatic compounds. </p> <div class="mw-heading mw-heading3"><h3 id="Other_halogenation_methods">Other halogenation methods</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Halogenation&action=edit&section=6" title="Edit section: Other halogenation methods"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In the <a href="/wiki/Hunsdiecker_reaction" title="Hunsdiecker reaction">Hunsdiecker reaction</a>, <a href="/wiki/Carboxylic_acids" class="mw-redirect" title="Carboxylic acids">carboxylic acids</a> are converted to <a href="/wiki/Organic_halide" class="mw-redirect" title="Organic halide">organic halide</a>, whose <a href="/wiki/Carbon_chain" class="mw-redirect" title="Carbon chain">carbon chain</a> is shortened by one <a href="/wiki/Carbon" title="Carbon">carbon</a> atom with respect to the carbon chain of the particular carboxylic acid. The carboxylic acid is first converted to its <a href="/wiki/Silver" title="Silver">silver</a> salt, which is then oxidized with <a href="/wiki/Halogen" title="Halogen">halogen</a>: </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">R−COO<sup class="template-chem2-sup">−</sup>Ag<sup class="template-chem2-sup">+</sup> + <a href="/wiki/Bromine" title="Bromine">Br<sub class="template-chem2-sub">2</sub></a> → R−Br + <a href="/wiki/Carbon_dioxide" title="Carbon dioxide">CO<sub class="template-chem2-sub">2</sub></a> + <a href="/wiki/Silver_bromide" title="Silver bromide">Ag<sup class="template-chem2-sup">+</sup>Br<sup class="template-chem2-sup">−</sup></a></span></dd> <dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap"><a href="/wiki/Silver_acetate" title="Silver acetate">CH<sub class="template-chem2-sub">3</sub>−COO<sup class="template-chem2-sup">−</sup>Ag<sup class="template-chem2-sup">+</sup></a> + Br<sub class="template-chem2-sub">2</sub> → <a href="/wiki/Bromomethane" title="Bromomethane">CH<sub class="template-chem2-sub">3</sub>−Br</a> + CO<sub class="template-chem2-sub">2</sub> + Ag<sup class="template-chem2-sup">+</sup>Br<sup class="template-chem2-sup">−</sup></span></dd></dl> <p>Many <a href="/wiki/Organometallic_compound" class="mw-redirect" title="Organometallic compound">organometallic compounds</a> react with halogens to give the organic halide: </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">RM + X<sub class="template-chem2-sub">2</sub> → RX + MX</span></dd> <dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap"><a href="/wiki/N-Butyllithium" title="N-Butyllithium">CH<sub class="template-chem2-sub">3</sub>CH<sub class="template-chem2-sub">2</sub>CH<sub class="template-chem2-sub">2</sub>CH<sub class="template-chem2-sub">2</sub>Li</a> + <a href="/wiki/Chlorine" title="Chlorine">Cl<sub class="template-chem2-sub">2</sub></a> → <a href="/wiki/1-chlorobutane" class="mw-redirect" title="1-chlorobutane">CH<sub class="template-chem2-sub">3</sub>CH<sub class="template-chem2-sub">2</sub>CH<sub class="template-chem2-sub">2</sub>CH<sub class="template-chem2-sub">2</sub>Cl</a> + <a href="/wiki/Lithium_chloride" title="Lithium chloride">LiCl</a></span></dd></dl> <div class="mw-heading mw-heading2"><h2 id="Inorganic_chemistry">Inorganic chemistry</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Halogenation&action=edit&section=7" title="Edit section: Inorganic chemistry"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>All <a href="/wiki/Chemical_element" title="Chemical element">elements</a> aside from <a href="/wiki/Argon" title="Argon">argon</a>, <a href="/wiki/Neon" title="Neon">neon</a>, and <a href="/wiki/Helium" title="Helium">helium</a> form <a href="/wiki/Fluorides" class="mw-redirect" title="Fluorides">fluorides</a> by direct reaction with <a href="/wiki/Fluorine" title="Fluorine">fluorine</a>. <a href="/wiki/Chlorine" title="Chlorine">Chlorine</a> is slightly more selective, but still reacts with most <a href="/wiki/Metals" class="mw-redirect" title="Metals">metals</a> and heavier <a href="/wiki/Nonmetals" class="mw-redirect" title="Nonmetals">nonmetals</a>. Following the usual trend, <a href="/wiki/Bromine" title="Bromine">bromine</a> is less <a href="/wiki/Reactivity_(chemistry)" title="Reactivity (chemistry)">reactive</a> and <a href="/wiki/Iodine" title="Iodine">iodine</a> least of all. Of the many reactions possible, illustrative is the formation of <a href="/wiki/Gold(III)_chloride" title="Gold(III) chloride">gold(III) chloride</a> by the chlorination of <a href="/wiki/Gold" title="Gold">gold</a>. The chlorination of metals is usually not very important industrially since the <a href="/wiki/Chlorides" class="mw-redirect" title="Chlorides">chlorides</a> are more easily made from the <a href="/wiki/Oxides" class="mw-redirect" title="Oxides">oxides</a> and <a href="/wiki/Hydrogen_chloride" title="Hydrogen chloride">hydrogen chloride</a>. Where chlorination of <a href="/wiki/Inorganic_compounds" class="mw-redirect" title="Inorganic compounds">inorganic compounds</a> is practiced on a relatively large scale is for the production of <a href="/wiki/Phosphorus_trichloride" title="Phosphorus trichloride">phosphorus trichloride</a> and <a href="/wiki/Disulfur_dichloride" title="Disulfur dichloride">disulfur dichloride</a>.<sup id="cite_ref-10" class="reference"><a href="#cite_note-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Halogenation&action=edit&section=8" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1235681985">.mw-parser-output .side-box{margin:4px 0;box-sizing:border-box;border:1px solid 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screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .sistersitebox img[src*="Wiktionary-logo-en-v2.svg"]{background-color:white}}</style><div class="side-box side-box-right plainlinks sistersitebox"><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style> <div class="side-box-flex"> <div class="side-box-image"><span class="noviewer" typeof="mw:File"><span><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/f/fa/Wikiquote-logo.svg/34px-Wikiquote-logo.svg.png" decoding="async" width="34" height="40" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/fa/Wikiquote-logo.svg/51px-Wikiquote-logo.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/fa/Wikiquote-logo.svg/68px-Wikiquote-logo.svg.png 2x" data-file-width="300" data-file-height="355" /></span></span></div> <div class="side-box-text plainlist">Wikiquote has quotations related to <i><b><a href="https://en.wikiquote.org/wiki/Special:Search/Halogenation" class="extiw" title="q:Special:Search/Halogenation">Halogenation</a></b></i>.</div></div> </div> <style data-mw-deduplicate="TemplateStyles:r1184024115">.mw-parser-output .div-col{margin-top:0.3em;column-width:30em}.mw-parser-output .div-col-small{font-size:90%}.mw-parser-output .div-col-rules{column-rule:1px solid #aaa}.mw-parser-output .div-col dl,.mw-parser-output .div-col ol,.mw-parser-output .div-col ul{margin-top:0}.mw-parser-output .div-col li,.mw-parser-output .div-col dd{page-break-inside:avoid;break-inside:avoid-column}</style><div class="div-col" style="column-width: 30em;"> <ul><li><a href="/wiki/Dehalogenation" title="Dehalogenation">Dehalogenation</a></li> <li><a href="/wiki/Haloalkane" title="Haloalkane">Haloalkane</a> (Alkyl halide)</li> <li><a href="/wiki/Halogenoarene" class="mw-redirect" title="Halogenoarene">Halogenoarene</a> (Aryl halide)</li> <li><a href="/wiki/Free_radical_halogenation" class="mw-redirect" title="Free radical halogenation">Free radical halogenation</a></li> <li><a href="/wiki/Haloketone" class="mw-redirect" title="Haloketone">Haloketone</a></li> <li><a href="/wiki/Electrophilic_substitution" title="Electrophilic substitution">Electrophilic substitution</a></li></ul> </div> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Halogenation&action=edit&section=9" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist reflist-columns references-column-width reflist-columns-2"> <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="CITEREFHudlickyHudlicky1983" class="citation book cs1">Hudlicky, Milos; Hudlicky, Tomas (1983). "Formation of Carbon-Halogen Bonds". In S. Patai; Z. Rappoport (eds.). <i>Halides, Pseudo-Halides and Azides: Part 2 (1983)</i>. PATAI's Chemistry of Functional Groups. pp. 1021–1172. <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%2F9780470771723.ch3">10.1002/9780470771723.ch3</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9780470771723" title="Special:BookSources/9780470771723"><bdi>9780470771723</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Formation+of+Carbon-Halogen+Bonds&rft.btitle=Halides%2C+Pseudo-Halides+and+Azides%3A+Part+2+%281983%29&rft.series=PATAI%27s+Chemistry+of+Functional+Groups&rft.pages=1021-1172&rft.date=1983&rft_id=info%3Adoi%2F10.1002%2F9780470771723.ch3&rft.isbn=9780470771723&rft.aulast=Hudlicky&rft.aufirst=Milos&rft.au=Hudlicky%2C+Tomas&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHalogenation" class="Z3988"></span></span> </li> <li id="cite_note-Ullmann-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-Ullmann_2-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation encyclopaedia cs1"><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/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=book&rft.btitle=Ullmann%27s+Encyclopedia+of+Industrial+Chemistry&rft.place=Weinheim&rft.pub=Wiley-VCH&rft_id=info%3Adoi%2F10.1002%2F14356007.a06_233.pub2&rft.isbn=978-3527306732&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHalogenation" class="Z3988"></span></span> </li> <li id="cite_note-3"><span class="mw-cite-backlink"><b><a href="#cite_ref-3">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFGribble1999" class="citation journal cs1">Gribble, Gordon W. 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"Fluorine Compounds, Inorganic". <i>Ullmann's Encyclopedia of Industrial Chemistry</i>. <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.a11_307">10.1002/14356007.a11_307</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/3-527-30673-0" title="Special:BookSources/3-527-30673-0"><bdi>3-527-30673-0</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Fluorine+Compounds%2C+Inorganic&rft.btitle=Ullmann%27s+Encyclopedia+of+Industrial+Chemistry&rft.date=2000&rft_id=info%3Adoi%2F10.1002%2F14356007.a11_307&rft.isbn=3-527-30673-0&rft.aulast=Aigueperse&rft.aufirst=Jean&rft.au=Mollard%2C+Paul&rft.au=Devilliers%2C+Didier&rft.au=Chemla%2C+Marius&rft.au=Faron%2C+Robert&rft.au=Romano%2C+Ren%C3%A9&rft.au=Cuer%2C+Jean+Pierre&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHalogenation" 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 id="CITEREFT._MoriR._Rathore1998" class="citation journal cs1">T. Mori; R. Rathore (1998). "X-Ray structure of bridged 2,2′-bi(adamant-2-ylidene) chloronium cation and comparison of its reactivity with a singly bonded chloroarenium cation". <i><a href="/wiki/Chem._Commun." class="mw-redirect" title="Chem. Commun.">Chem. Commun.</a></i> (8): 927–928. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1039%2Fa709063c">10.1039/a709063c</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Chem.+Commun.&rft.atitle=X-Ray+structure+of+bridged+2%2C2%E2%80%B2-bi%28adamant-2-ylidene%29+chloronium+cation+and+comparison+of+its+reactivity+with+a+singly+bonded+chloroarenium+cation&rft.issue=8&rft.pages=927-928&rft.date=1998&rft_id=info%3Adoi%2F10.1039%2Fa709063c&rft.au=T.+Mori&rft.au=R.+Rathore&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHalogenation" class="Z3988"></span></span> </li> <li id="cite_note-6"><span class="mw-cite-backlink"><b><a href="#cite_ref-6">^</a></b></span> <span class="reference-text"><i>Synthesis of Essential Drugs</i>, Ruben Vardanyan, Victor Hruby; Elsevier 2005 <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/0-444-52166-6" title="Special:BookSources/0-444-52166-6">0-444-52166-6</a></span> </li> <li id="cite_note-PhCl-7"><span class="mw-cite-backlink"><b><a href="#cite_ref-PhCl_7-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBeckLöser2011" class="citation book cs1">Beck, Uwe; Löser, Eckhard (2011). "Chlorinated Benzenes and Other Nucleus-Chlorinated Aromatic Hydrocarbons". <i>Ullmann's Encyclopedia of Industrial Chemistry</i>. <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.o06_o03">10.1002/14356007.o06_o03</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=Chlorinated+Benzenes+and+Other+Nucleus-Chlorinated+Aromatic+Hydrocarbons&rft.btitle=Ullmann%27s+Encyclopedia+of+Industrial+Chemistry&rft.date=2011&rft_id=info%3Adoi%2F10.1002%2F14356007.o06_o03&rft.isbn=978-3527306732&rft.aulast=Beck&rft.aufirst=Uwe&rft.au=L%C3%B6ser%2C+Eckhard&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHalogenation" 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">Organic chemistry by Jonathan Clayden, Nick Grieves, Stuart Warren, Oxford University Press</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="CITEREFEdward_R._Atkinson,_Donald_M._Murphy,_and_James_E._Lufkin1951" class="citation journal cs1">Edward R. 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"<i>dl</i>-4,4′,6,6′-Tetrachlorodiphenic Acid". <i><a href="/wiki/Organic_Syntheses" title="Organic Syntheses">Organic Syntheses</a></i>. <b>31</b>: 96. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.15227%2Forgsyn.031.0096">10.15227/orgsyn.031.0096</a></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Organic+Syntheses&rft.atitle=dl-4%2C4%E2%80%B2%2C6%2C6%E2%80%B2-Tetrachlorodiphenic+Acid&rft.volume=31&rft.pages=96&rft.date=1951&rft_id=info%3Adoi%2F10.15227%2Forgsyn.031.0096&rft.au=Edward+R.+Atkinson%2C+Donald+M.+Murphy%2C+and+James+E.+Lufkin&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHalogenation" class="Z3988"></span><span class="cs1-maint citation-comment"><code class="cs1-code">{{<a href="/wiki/Template:Cite_journal" title="Template:Cite journal">cite journal</a>}}</code>: CS1 maint: multiple names: authors list (<a href="/wiki/Category:CS1_maint:_multiple_names:_authors_list" title="Category:CS1 maint: multiple names: authors list">link</a>)</span>.</span> </li> <li id="cite_note-10"><span class="mw-cite-backlink"><b><a href="#cite_ref-10">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFGreenwoodEarnshaw1997" class="citation book cs1"><a href="/wiki/Norman_Greenwood" title="Norman Greenwood">Greenwood, Norman N.</a>; Earnshaw, Alan (1997). <i>Chemistry of the Elements</i> (2nd ed.). <a href="/wiki/Butterworth-Heinemann" title="Butterworth-Heinemann">Butterworth-Heinemann</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-08-037941-8" title="Special:BookSources/978-0-08-037941-8"><bdi>978-0-08-037941-8</bdi></a>.</cite><span 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