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class="vector-toc-link" href="#Protein_cleavage"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.2</span> <span>Protein cleavage</span> </div> </a> <ul id="toc-Protein_cleavage-sublist" class="vector-toc-list"> <li id="toc-Mechanism" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Mechanism"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.2.1</span> <span>Mechanism</span> </div> </a> <ul id="toc-Mechanism-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Reaction_conditions" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Reaction_conditions"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.2.2</span> <span>Reaction conditions</span> </div> </a> <ul id="toc-Reaction_conditions-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Side_reactions" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Side_reactions"> <div 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id="toc-References" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Further_reading" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Further_reading"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>Further reading</span> </div> </a> <ul id="toc-Further_reading-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">7</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" title="Table of Contents" > <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">Cyanogen bromide</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 20 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-20" 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">20 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/%D8%B3%D9%8A%D8%A7%D9%86%D9%8A%D8%AF_%D8%A7%D9%84%D8%A8%D8%B1%D9%88%D9%85" title="سيانيد البروم – Arabic" lang="ar" hreflang="ar" data-title="سيانيد البروم" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%D8%B3%DB%8C%D8%A7%D9%86%D9%88%DA%98%D9%86_%D8%A8%D8%B1%D9%88%D9%85%DB%8C%D8%AF" title="سیانوژن برومید – South Azerbaijani" lang="azb" hreflang="azb" data-title="سیانوژن برومید" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Bromkyan" title="Bromkyan – Czech" lang="cs" hreflang="cs" data-title="Bromkyan" 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/Bromcyan" title="Bromcyan – German" lang="de" hreflang="de" data-title="Bromcyan" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Bromuro_de_cian%C3%B3geno" title="Bromuro de cianógeno – Spanish" lang="es" hreflang="es" data-title="Bromuro de cianógeno" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-eo mw-list-item"><a href="https://eo.wikipedia.org/wiki/Cianogena_bromido" title="Cianogena bromido – Esperanto" lang="eo" hreflang="eo" data-title="Cianogena bromido" data-language-autonym="Esperanto" data-language-local-name="Esperanto" class="interlanguage-link-target"><span>Esperanto</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%B3%DB%8C%D8%A7%D9%86%D9%88%DA%98%D9%86_%D8%A8%D8%B1%D9%85%DB%8C%D8%AF" title="سیانوژن برمید – Persian" lang="fa" hreflang="fa" data-title="سیانوژن برمید" 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/Bromure_de_cyanog%C3%A8ne" title="Bromure de cyanogène – French" lang="fr" hreflang="fr" data-title="Bromure de cyanogène" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-he mw-list-item"><a href="https://he.wikipedia.org/wiki/%D7%A6%D7%99%D7%90%D7%A0%D7%95%D7%92%D7%9F_%D7%91%D7%A8%D7%95%D7%9E%D7%99%D7%93" title="ציאנוגן ברומיד – Hebrew" lang="he" hreflang="he" data-title="ציאנוגן ברומיד" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Cyanogeenbromide" title="Cyanogeenbromide – Dutch" lang="nl" hreflang="nl" data-title="Cyanogeenbromide" 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/%E8%87%AD%E5%8C%96%E3%82%B7%E3%82%A2%E3%83%B3" title="臭化シアン – Japanese" lang="ja" hreflang="ja" data-title="臭化シアン" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Bromocyjan" title="Bromocyjan – Polish" lang="pl" hreflang="pl" data-title="Bromocyjan" 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/Brometo_de_cianog%C3%AAnio" title="Brometo de cianogênio – Portuguese" lang="pt" hreflang="pt" data-title="Brometo de cianogênio" 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/Bromur%C4%83_de_cianogen" title="Bromură de cianogen – Romanian" lang="ro" hreflang="ro" data-title="Bromură de cianogen" 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%91%D1%80%D0%BE%D0%BC%D1%86%D0%B8%D0%B0%D0%BD" title="Бромциан – Russian" lang="ru" hreflang="ru" data-title="Бромциан" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Cijanogen_bromid" title="Cijanogen bromid – Serbian" lang="sr" hreflang="sr" data-title="Cijanogen bromid" 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/Cijanogen_bromid" title="Cijanogen bromid – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Cijanogen bromid" 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/Syanogeenibromidi" title="Syanogeenibromidi – Finnish" lang="fi" hreflang="fi" data-title="Syanogeenibromidi" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link 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Not to be confused with <a href="/wiki/CBRN" class="mw-redirect" title="CBRN">CBRN</a>.</div> <style data-mw-deduplicate="TemplateStyles:r1268415487">.mw-parser-output .ib-chembox{border-collapse:collapse;text-align:left}.mw-parser-output .ib-chembox td,.mw-parser-output .ib-chembox th{border:1px solid #a2a9b1;width:40%}.mw-parser-output .ib-chembox td+td{width:60%}@media screen{html.skin-theme-clientpref-night .mw-parser-output .ib-chembox figure:not(.skin-invert-image):not(.skin-invert):not(.bg-transparent){background:var(--background-color-inverted,#f8f9fa)}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .ib-chembox figure:not(.skin-invert-image):not(.skin-invert):not(.bg-transparent){background:var(--background-color-inverted,#f8f9fa)}}</style> <table class="infobox ib-chembox"> <caption>Cyanogen bromide </caption> <tbody><tr> <td colspan="2" style="text-align:center; padding:2px;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Cyanogen-bromide-2D.png" class="mw-file-description" title="Skeletal formula of cyanogen bromide"><img alt="Skeletal formula of cyanogen bromide" src="//upload.wikimedia.org/wikipedia/commons/thumb/9/9d/Cyanogen-bromide-2D.png/100px-Cyanogen-bromide-2D.png" decoding="async" width="100" height="25" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/9d/Cyanogen-bromide-2D.png/150px-Cyanogen-bromide-2D.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/9d/Cyanogen-bromide-2D.png/200px-Cyanogen-bromide-2D.png 2x" data-file-width="1100" data-file-height="278" /></a><figcaption>Skeletal formula of cyanogen bromide</figcaption></figure> </td></tr> <tr> <td colspan="2" style="text-align:center; padding:2px;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Cyanogen-bromide-3D-vdW.png" class="mw-file-description" title="Spacefill model of cyanogen bromide"><img alt="Spacefill model of cyanogen bromide" src="//upload.wikimedia.org/wikipedia/commons/thumb/2/26/Cyanogen-bromide-3D-vdW.png/100px-Cyanogen-bromide-3D-vdW.png" decoding="async" width="100" height="66" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/26/Cyanogen-bromide-3D-vdW.png/150px-Cyanogen-bromide-3D-vdW.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/26/Cyanogen-bromide-3D-vdW.png/200px-Cyanogen-bromide-3D-vdW.png 2x" data-file-width="1100" data-file-height="731" /></a><figcaption>Spacefill model of cyanogen bromide</figcaption></figure> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Names </th></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Preferred_IUPAC_name" title="Preferred IUPAC name">Preferred IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0; max-width:22em;">Carbononitridic bromide<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></div></div> </td></tr> <tr> <td colspan="2" style="text-align:left;">Other names <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;"><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style><div class="plainlist"><ul><li>Bromine cyanide<sup id="cite_ref-Merck_1-0" class="reference"><a href="#cite_note-Merck-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup></li><li>Campilit<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></li></ul></div></div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Identifiers </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=506-68-3">506-68-3</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=BrC%23N">Interactive image</a></span></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Beilstein_database" title="Beilstein database">Beilstein Reference</a></div> </td> <td>1697296 </td></tr> <tr> <td><a href="/wiki/ChemSpider" title="ChemSpider">ChemSpider</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.chemspider.com"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.10044.html">10044</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ECHA_InfoCard" class="mw-redirect" title="ECHA InfoCard"><span title="echa.europa.eu">ECHA InfoCard</span></a> </td> <td><a rel="nofollow" class="external text" href="https://echa.europa.eu/substance-information/-/substanceinfo/100.007.320">100.007.320</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q420258#P2566" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span> </td></tr> <tr> <td><a href="/wiki/European_Community_number" title="European Community number"><span title="European Community number (chemical identifier)">EC Number</span></a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li>208-051-2</li></ul></div> </td></tr> <tr> <td><a href="/wiki/Medical_Subject_Headings" title="Medical Subject Headings">MeSH</a> </td> <td><span title="www.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://www.nlm.nih.gov/cgi/mesh/2014/MB_cgi?mode=&term=Cyanogen+Bromide">Cyanogen+Bromide</a></span> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/PubChem" title="PubChem">PubChem</a> <abbr title="Compound ID">CID</abbr></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/10476">10476</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/RTECS" class="mw-redirect" title="RTECS">RTECS number</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li>GT2100000</li></ul></div> </td></tr> <tr> <td><a href="/wiki/Unique_Ingredient_Identifier" title="Unique Ingredient Identifier">UNII</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="precision.fda.gov"><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/OS382OHJ8P">OS382OHJ8P</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/UN_number" title="UN number">UN number</a> </td> <td>1889 </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CompTox_Chemicals_Dashboard" title="CompTox Chemicals Dashboard">CompTox Dashboard</a> <span style="font-weight:normal">(<abbr title="U.S. Environmental Protection Agency">EPA</abbr>)</span></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="comptox.epa.gov"><a rel="nofollow" class="external text" href="https://comptox.epa.gov/dashboard/chemical/details/DTXSID9021550">DTXSID9021550</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q420258#P3117" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span></span></li></ul></div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal;"><div><a href="/wiki/International_Chemical_Identifier" title="International Chemical Identifier">InChI</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1S/CBrN/c2-1-3<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: ATDGTVJJHBUTRL-UHFFFAOYSA-N<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div></div></li></ul> </div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.6em; word-wrap:break-word; text-indent:-1.5em; text-align:left; font-size:97%; line-height:120%;">BrC#N</div></li></ul> </div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Properties </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Chemical_formula" title="Chemical formula">Chemical formula</a></div> </td> <td>BrCN  </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td>105.921 g mol<sup>−1</sup>    </td></tr> <tr> <td>Appearance </td> <td>Colorless solid </td></tr> <tr> <td><a href="/wiki/Density" title="Density">Density</a> </td> <td>2.015 g mL<sup>−1</sup> </td></tr> <tr> <td><a href="/wiki/Melting_point" title="Melting point">Melting point</a> </td> <td>50 to 53 °C (122 to 127 °F; 323 to 326 K) </td></tr> <tr> <td><a href="/wiki/Boiling_point" title="Boiling point">Boiling point</a> </td> <td>61 to 62 °C (142 to 144 °F; 334 to 335 K) </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Aqueous_solution" title="Aqueous solution">Solubility in water</a></div> </td> <td>Reacts </td></tr> <tr> <td><a href="/wiki/Vapor_pressure" title="Vapor pressure">Vapor pressure</a> </td> <td>16.2 kPa </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Thermochemistry </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Standard_enthalpy_change_of_formation" class="mw-redirect" title="Standard enthalpy change of formation">Std enthalpy of<br />formation</a> <span style="font-size:112%;">(Δ<sub>f</sub><i>H</i><sup>⦵</sup><sub>298</sub>)</span></div> </td> <td>136.1–144.7 kJ mol<sup>−1</sup> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Hazards </th></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;color:inherit;"><a href="/wiki/Globally_Harmonized_System_of_Classification_and_Labelling_of_Chemicals" title="Globally Harmonized System of Classification and Labelling of Chemicals"><b>GHS</b> labelling</a>: </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/GHS_hazard_pictograms" title="GHS hazard pictograms">Pictograms</a></div> </td> <td><span typeof="mw:File"><a href="/wiki/File:GHS-pictogram-acid.svg" class="mw-file-description" title="GHS05: Corrosive"><img alt="GHS05: Corrosive" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a1/GHS-pictogram-acid.svg/50px-GHS-pictogram-acid.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a1/GHS-pictogram-acid.svg/75px-GHS-pictogram-acid.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a1/GHS-pictogram-acid.svg/100px-GHS-pictogram-acid.svg.png 2x" data-file-width="724" data-file-height="724" /></a></span> <span typeof="mw:File"><a href="/wiki/File:GHS-pictogram-skull.svg" class="mw-file-description" title="GHS06: Toxic"><img alt="GHS06: Toxic" src="//upload.wikimedia.org/wikipedia/commons/thumb/5/58/GHS-pictogram-skull.svg/50px-GHS-pictogram-skull.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/58/GHS-pictogram-skull.svg/75px-GHS-pictogram-skull.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/58/GHS-pictogram-skull.svg/100px-GHS-pictogram-skull.svg.png 2x" data-file-width="724" data-file-height="724" /></a></span> <span typeof="mw:File"><a href="/wiki/File:GHS-pictogram-pollu.svg" class="mw-file-description" title="GHS09: Environmental hazard"><img alt="GHS09: Environmental hazard" src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b9/GHS-pictogram-pollu.svg/50px-GHS-pictogram-pollu.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b9/GHS-pictogram-pollu.svg/75px-GHS-pictogram-pollu.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b9/GHS-pictogram-pollu.svg/100px-GHS-pictogram-pollu.svg.png 2x" data-file-width="724" data-file-height="724" /></a></span> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Globally_Harmonized_System_of_Classification_and_Labelling_of_Chemicals#Signal_word" title="Globally Harmonized System of Classification and Labelling of Chemicals">Signal word</a></div> </td> <td><b>Danger</b> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/GHS_hazard_statements" title="GHS hazard statements">Hazard statements</a></div> </td> <td><abbr class="abbr" title="H300: Fatal if swallowed">H300</abbr>, <abbr class="abbr" title="H310: Fatal in contact with skin">H310</abbr>, <abbr class="abbr" title="H314: Causes severe skin burns and eye damage">H314</abbr>, <abbr class="abbr" title="H330: Fatal if inhaled">H330</abbr>, <abbr class="abbr" title="H410: Very toxic to aquatic life with long lasting effects">H410</abbr> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/GHS_precautionary_statements" title="GHS precautionary statements">Precautionary statements</a></div> </td> <td><abbr class="abbr" title="P260: Do not breathe dust/fume/gas/mist/vapours/spray.">P260</abbr>, <abbr class="abbr" title="P273: Avoid release to the environment.">P273</abbr>, <abbr class="abbr" title="P280: Wear protective gloves/protective clothing/eye protection/face protection.">P280</abbr>, <abbr class="abbr" title="P284: Wear respiratory protection.">P284</abbr>, <abbr class="abbr" title="P302+P350: IF ON SKIN: Gently wash with soap and water.">P302+P350</abbr> </td></tr> <tr> <td><a href="/wiki/NFPA_704" title="NFPA 704"><b>NFPA 704</b></a> (fire diamond) </td> <td><style data-mw-deduplicate="TemplateStyles:r1170367383">.mw-parser-output .nfpa-704-diamond-ref{float:right;padding:1px;text-align:right}.mw-parser-output .nfpa-704-diamond-container{width:82px;font-family:sans-serif;margin:0 auto}.mw-parser-output .nfpa-704-diamond-container-ref{float:left;margin-left:1em}.mw-parser-output .nfpa-704-diamond-images{float:left;font-size:20px;text-align:center;position:relative;height:80px;width:80px;padding:1px}.mw-parser-output .nfpa-704-diamond-map{position:absolute;height:80px;width:80px}.mw-parser-output .nfpa-704-diamond .noresize{margin:0 auto}.mw-parser-output .nfpa-704-diamond-code{line-height:1em;text-align:center;position:absolute}.mw-parser-output .nfpa-704-diamond-code>a{color:black}.mw-parser-output .nfpa-704-diamond-blue{width:13px;top:31px;left:15px}.mw-parser-output .nfpa-704-diamond-red{width:12px;top:12px;left:35px}.mw-parser-output .nfpa-704-diamond-yellow{width:13px;top:31px;left:54px}.mw-parser-output .nfpa-704-diamond-white-image{position:relative;top:51px;left:0}.mw-parser-output .nfpa-704-diamond-white-text{vertical-align:middle;text-align:center;line-height:80%;position:absolute;top:52px}.mw-parser-output .nfpa-704-diamond-white-text a>span{position:absolute;color:black}.mw-parser-output .nfpa-704-diamond-white-wors{font-size:15px;width:23px;left:29px}.mw-parser-output .nfpa-704-diamond-white-wox{font-size:15px;font-stretch:condensed;width:21px;line-height:80%;top:-4px;left:29px}.mw-parser-output .nfpa-704-diamond-white-abcp{font-size:13.5px;font-stretch:condensed;width:28px;left:26px}.mw-parser-output .nfpa-704-diamond-white-ac{font-size:10px;width:30px;left:25px}.mw-parser-output .nfpa-704-diamond-white-strike{text-decoration:line-through}</style><div class="nfpa-704-diamond notheme"><div class="nfpa-704-diamond-container"><div class="nfpa-704-diamond-images nounderlines"> <div class="nfpa-704-diamond-map"><figure class="noresize" typeof="mw:File"><span><img alt="NFPA 704 four-colored diamond" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/80px-NFPA_704.svg.png" decoding="async" width="80" height="80" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/120px-NFPA_704.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/160px-NFPA_704.svg.png 2x" data-file-width="512" data-file-height="512" usemap="#ImageMap_99a93146dd5e87c9" /></span><map name="ImageMap_99a93146dd5e87c9"><area href="/wiki/NFPA_704#Blue" shape="poly" coords="23,23,47,47,23,70,0,47" alt="Health 4: Very short exposure could cause death or major residual injury. E.g. VX gas" title="Health 4: Very short exposure could cause death or major residual injury. E.g. VX gas" /><area href="/wiki/NFPA_704#Red" shape="poly" coords="47,0,70,23,47,47,23,23" alt="Flammability 0: Will not burn. E.g. water" title="Flammability 0: Will not burn. E.g. water" /><area href="/wiki/NFPA_704#Yellow" shape="poly" coords="70,23,94,47,70,70,47,47" alt="Instability 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calcium" title="Instability 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calcium" /><area href="/wiki/NFPA_704#White" shape="poly" coords="47,47,70,70,47,94,23,70" alt="Special hazards (white): no code" title="Special hazards (white): no code" /></map><figcaption></figcaption></figure></div><div class="nfpa-704-diamond-code nfpa-704-diamond-blue"> <a href="/wiki/NFPA_704#Blue" title="NFPA 704"><span title="Health 4: Very short exposure could cause death or major residual injury. E.g. VX gas" class="notheme mw-no-invert">4</span></a></div><div class="nfpa-704-diamond-code nfpa-704-diamond-red"> <a href="/wiki/NFPA_704#Red" title="NFPA 704"><span title="Flammability 0: Will not burn. E.g. water" class="notheme mw-no-invert">0</span></a></div><div class="nfpa-704-diamond-code nfpa-704-diamond-yellow"> <a href="/wiki/NFPA_704#Yellow" title="NFPA 704"><span title="Instability 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calcium" class="notheme mw-no-invert">1</span></a></div></div></div></div> </td></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;color:inherit;"><a href="/wiki/National_Institute_for_Occupational_Safety_and_Health" title="National Institute for Occupational Safety and Health"><b>NIOSH</b></a> (US health exposure limits): </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Permissible_exposure_limit" title="Permissible exposure limit">PEL</a> (Permissible)</div> </td> <td>5 mg m<sup>−3</sup> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Related compounds </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Related alkanenitriles</div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a href="/wiki/Hydrogen_cyanide" title="Hydrogen cyanide">Hydrogen cyanide</a></li><li><a href="/wiki/Thiocyanic_acid" title="Thiocyanic acid">Thiocyanic acid</a></li><li><a href="/wiki/Cyanogen_iodide" title="Cyanogen iodide">Cyanogen iodide</a></li><li><a href="/wiki/Cyanogen_chloride" title="Cyanogen chloride">Cyanogen chloride</a></li><li><a href="/wiki/Cyanogen_fluoride" title="Cyanogen fluoride">Cyanogen fluoride</a></li><li><a href="/wiki/Acetonitrile" title="Acetonitrile">Acetonitrile</a></li><li><a href="/wiki/Aminoacetonitrile" title="Aminoacetonitrile">Aminoacetonitrile</a></li><li><a href="/wiki/Glycolonitrile" title="Glycolonitrile">Glycolonitrile</a></li><li><a href="/wiki/Cyanogen" title="Cyanogen">Cyanogen</a></li></ul></div> </td></tr> <tr> <td colspan="2" style="text-align:left; background:#f8eaba; color:inherit; border:1px solid #a2a9b1;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Except where otherwise noted, data are given for materials in their <a href="/wiki/Standard_state" title="Standard state">standard state</a> (at 25 °C [77 °F], 100 kPa).</div> <div style="margin-top: 0.3em;"><div style="text-align:center;"><span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/12px-Yes_check.svg.png" decoding="async" width="12" height="12" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/18px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/24px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span> <span class="reflink plainlinks nourlexpansion"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=442343462&page2=Cyanogen+bromide">verify</a></span> (<a href="/wiki/Wikipedia:WikiProject_Chemicals/Chembox_validation" title="Wikipedia:WikiProject Chemicals/Chembox validation">what is</a> <sup><span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span><span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span></sup> ?) </div></div> <div style="margin-top: 0.3em; text-align: center;"><a href="/wiki/Wikipedia:Chemical_infobox#References" title="Wikipedia:Chemical infobox">Infobox references</a></div> </td></tr> </tbody></table><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Chemical compound</div> <p><b>Cyanogen bromide</b> is the <a href="/wiki/Inorganic_compound" title="Inorganic compound">inorganic compound</a> with the <a href="/wiki/Chemical_formula" title="Chemical formula">formula</a> (CN)Br or BrCN. It is a colorless solid that is widely used to modify <a href="/wiki/Biopolymer" title="Biopolymer">biopolymers</a>, fragment <a href="/wiki/Protein" title="Protein">proteins</a> and <a href="/wiki/Peptide" title="Peptide">peptides</a> (cuts the C-terminus of methionine), and synthesize other compounds. The compound is classified as a <a href="/wiki/Pseudohalogen" title="Pseudohalogen">pseudohalogen</a>. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Synthesis,_basic_properties,_and_structure"><span id="Synthesis.2C_basic_properties.2C_and_structure"></span>Synthesis, basic properties, and structure</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cyanogen_bromide&action=edit&section=1" title="Edit section: Synthesis, basic properties, and structure"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The <a href="/wiki/Carbon" title="Carbon">carbon</a> atom in cyanogen bromide is bonded to <a href="/wiki/Bromine" title="Bromine">bromine</a> by a single bond and to <a href="/wiki/Nitrogen" title="Nitrogen">nitrogen</a> by a <a href="/wiki/Triple_bond" title="Triple bond">triple bond</a> (i.e. <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">Br−C≡N</span>). The compound is linear and polar, but it does not spontaneously ionize in water. It dissolves in both water and polar <a href="/wiki/Organic_solvent" class="mw-redirect" title="Organic solvent">organic solvents</a>. </p><p>Cyanogen bromide can be prepared by <a href="/wiki/Oxidation" class="mw-redirect" title="Oxidation">oxidation</a> of <a href="/wiki/Sodium_cyanide" title="Sodium cyanide">sodium cyanide</a> with <a href="/wiki/Bromine" title="Bromine">bromine</a>, which proceeds in two steps via the intermediate <a href="/wiki/Cyanogen" title="Cyanogen">cyanogen</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">(CN)<sub class="template-chem2-sub">2</sub></span>): </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">2 NaCN + Br<sub class="template-chem2-sub">2</sub> → (CN)<sub class="template-chem2-sub">2</sub> + 2 NaBr</span></dd> <dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">(CN)<sub class="template-chem2-sub">2</sub> + Br<sub class="template-chem2-sub">2</sub> → 2 (CN)Br</span></dd></dl> <p>When refrigerated the material has an extended shelflife. Like some other cyanogen compounds, cyanogen bromide undergoes an exothermic trimerisation to <a href="/wiki/Cyanuric_bromide" title="Cyanuric bromide">cyanuric bromide</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">(BrCN)<sub class="template-chem2-sub">3</sub></span>). This reaction is catalyzed by traces of bromine, metal salts, acids and bases. For this reason, experimentalists avoid brownish samples.<sup id="cite_ref-EROS_4-0" class="reference"><a href="#cite_note-EROS-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p> <dl><dd><span typeof="mw:File"><a href="/wiki/File:Cyanuric_bromide_synthesis.PNG" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e5/Cyanuric_bromide_synthesis.PNG/300px-Cyanuric_bromide_synthesis.PNG" decoding="async" width="300" height="100" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e5/Cyanuric_bromide_synthesis.PNG/450px-Cyanuric_bromide_synthesis.PNG 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e5/Cyanuric_bromide_synthesis.PNG/600px-Cyanuric_bromide_synthesis.PNG 2x" data-file-width="959" data-file-height="319" /></a></span></dd></dl> <p>Cyanogen bromide is <a href="/wiki/Hydrolyzed" class="mw-redirect" title="Hydrolyzed">hydrolyzed</a> to form <a href="/wiki/Hydrogen_cyanate" class="mw-redirect" title="Hydrogen cyanate">hydrogen cyanate</a> and <a href="/wiki/Hydrobromic_acid" title="Hydrobromic acid">hydrobromic acid</a>: </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">(CN)Br + H<sub class="template-chem2-sub">2</sub>O → HOCN + HBr</span></dd></dl> <div class="mw-heading mw-heading2"><h2 id="Biochemical_applications">Biochemical applications</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cyanogen_bromide&action=edit&section=2" title="Edit section: Biochemical applications"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The main uses of cyanogen bromide are to immobilize proteins, fragment proteins by cleaving <a href="/wiki/Peptide_bond" title="Peptide bond">peptide bonds</a>, and synthesize <a href="/wiki/Cyanamide" title="Cyanamide">cyanamides</a> and other molecules. </p> <figure class="mw-halign-left" typeof="mw:File/Thumb"><a href="/wiki/File:CNBr_activated_matrices_reaction.PNG" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/9d/CNBr_activated_matrices_reaction.PNG/150px-CNBr_activated_matrices_reaction.PNG" decoding="async" width="150" height="171" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/9d/CNBr_activated_matrices_reaction.PNG/225px-CNBr_activated_matrices_reaction.PNG 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/9d/CNBr_activated_matrices_reaction.PNG/300px-CNBr_activated_matrices_reaction.PNG 2x" data-file-width="744" data-file-height="848" /></a><figcaption>Cyanogen bromide activation method</figcaption></figure> <div class="mw-heading mw-heading3"><h3 id="Protein_immobilization">Protein immobilization</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cyanogen_bromide&action=edit&section=3" title="Edit section: Protein immobilization"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Cyanogen bromide is often used to immobilize proteins by coupling them to <a href="/wiki/Reagent" title="Reagent">reagents</a> such as <a href="/wiki/Agarose" title="Agarose">agarose</a> for <a href="/wiki/Affinity_chromatography" title="Affinity chromatography">affinity chromatography</a>.<sup id="cite_ref-immobilized_5-0" class="reference"><a href="#cite_note-immobilized-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> Because of its simplicity and mild <a href="/wiki/PH" title="PH">pH</a> conditions, cyanogen bromide activation is the most common method for preparing affinity gels. Cyanogen bromide is also often used because it reacts with the <a href="/wiki/Hydroxyl" class="mw-redirect" title="Hydroxyl">hydroxyl</a> groups on agarose to form <a href="/wiki/Cyanate" title="Cyanate">cyanate</a> <a href="/wiki/Ester" title="Ester">esters</a> and <a href="/w/index.php?title=Imidocarbonate&action=edit&redlink=1" class="new" title="Imidocarbonate (page does not exist)">imidocarbonates</a>. These groups are reacted with <a href="/wiki/Primary_amine" class="mw-redirect" title="Primary amine">primary amines</a> in order to couple the protein onto the agarose matrix, as shown in the figure. Because cyanate esters are more reactive than are cyclic imidocarbonates, the amine will react mostly with the ester, yielding <a href="/w/index.php?title=Isourea&action=edit&redlink=1" class="new" title="Isourea (page does not exist)">isourea</a> derivatives, and partially with the less reactive imidocarbonate, yielding substituted imidocarbonates.<sup id="cite_ref-sigma_6-0" class="reference"><a href="#cite_note-sigma-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p><p>The disadvantages of this approach include the toxicity of cyanogen bromide and its sensitivity to oxidation. Also, cyanogen bromide activation involves the attachment of a <a href="/wiki/Ligand" title="Ligand">ligand</a> to agarose by an isourea bond, which is positively charged at neutral pH and thus unstable. Consequently, isourea derivatives may act as weak <a href="/wiki/Anion_exchanger" class="mw-redirect" title="Anion exchanger">anion exchangers</a>.<sup id="cite_ref-sigma_6-1" class="reference"><a href="#cite_note-sigma-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup><sup class="noprint Inline-Template"><span style="white-space: nowrap;">[<i><a href="/wiki/Wikipedia:Link_rot" title="Wikipedia:Link rot"><span title=" Dead link tagged June 2020">dead link</span></a></i><span style="visibility:hidden; color:transparent; padding-left:2px">‍</span>]</span></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Protein_cleavage">Protein cleavage</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cyanogen_bromide&action=edit&section=4" title="Edit section: Protein cleavage"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Cyanogen bromide hydrolyzes <a href="/wiki/Peptide_bond" title="Peptide bond">peptide bonds</a> at the C-terminus of <a href="/wiki/Methionine" title="Methionine">methionine</a> residues. This reaction is used to reduce the size of <a href="/wiki/Polypeptide" class="mw-redirect" title="Polypeptide">polypeptide</a> segments for identification and <a href="/wiki/Protein_sequencing" title="Protein sequencing">sequencing</a>. </p> <div class="mw-heading mw-heading4"><h4 id="Mechanism">Mechanism</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cyanogen_bromide&action=edit&section=5" title="Edit section: Mechanism"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-halign-left" typeof="mw:File/Thumb"><a href="/wiki/File:CNBr5.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/1/1a/CNBr5.png/150px-CNBr5.png" decoding="async" width="150" height="198" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/1a/CNBr5.png/225px-CNBr5.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/1a/CNBr5.png/300px-CNBr5.png 2x" data-file-width="704" data-file-height="931" /></a><figcaption>Cyanogen bromide peptide bond cleavage</figcaption></figure> <p>The <a href="/wiki/Electron_density" title="Electron density">electron density</a> in cyanogen bromide is shifted away from the carbon atom, making it unusually <a href="/wiki/Electrophilic" class="mw-redirect" title="Electrophilic">electrophilic</a>, and towards the more <a href="/wiki/Electronegative" class="mw-redirect" title="Electronegative">electronegative</a> bromine and nitrogen. This leaves the carbon particularly vulnerable to attack by a <a href="/wiki/Nucleophile" title="Nucleophile">nucleophile</a>, and the cleavage reaction begins with a substitution reaction in which bromine is ultimately replaced by the sulfur in methionine. This attack is followed by the formation of a five-membered ring as opposed to a six-membered ring, which would entail the formation of a <a href="/wiki/Double_bond" title="Double bond">double bond</a> in the ring between nitrogen and carbon. This double bond would result in a rigid ring conformation, thereby destabilizing the molecule. Thus, the five-membered ring is formed so that the double bond is outside the ring, as shown in the figure. </p><p>Although the nucleophilic sulfur in methionine is responsible for attacking BrCN, the sulfur in <a href="/wiki/Cysteine" title="Cysteine">cysteine</a> does not behave similarly. If the sulfur in cysteine attacked cyanogen bromide, the bromide ion would deprotonate the cyanide <a href="/wiki/Adduct" title="Adduct">adduct</a>, leaving the sulfur uncharged and the beta carbon of the cysteine not electrophilic. The strongest electrophile would then be the cyanide carbon, which, if attacked by water, would yield <a href="/wiki/Cyanic_acid" class="mw-redirect" title="Cyanic acid">cyanic acid</a> and the original cysteine. </p> <div class="mw-heading mw-heading4"><h4 id="Reaction_conditions">Reaction conditions</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cyanogen_bromide&action=edit&section=6" title="Edit section: Reaction conditions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Cleaving proteins with BrCN requires using a <a href="/wiki/Buffer_solution" title="Buffer solution">buffer</a> such as 0.1M HCl (<a href="/wiki/Hydrochloric_acid" title="Hydrochloric acid">hydrochloric acid</a>) or 70% (<a href="/wiki/Formic_acid" title="Formic acid">formic acid</a>).<sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> These are the most common buffers for cleavage. An advantage to HCl is that formic acid causes the formation of formyl esters, which complicates protein characterization. However, formic is still often used because it dissolves most proteins. Also, the oxidation of methionine to <a href="/wiki/Methionine_sulfoxide" title="Methionine sulfoxide">methionine sulfoxide</a>, which is inert to BrCN attack, occurs more readily in HCl than in formic acid, possibly because formic acid is a reducing acid. Alternative buffers for cleavage include <a href="/wiki/Guanidine" title="Guanidine">guanidine</a> or <a href="/wiki/Urea" title="Urea">urea</a> in HCl because of their ability to <a href="/wiki/Protein_folding" title="Protein folding">unfold proteins</a>, thereby making methionine more accessible to BrCN.<sup id="cite_ref-kaiser_8-0" class="reference"><a href="#cite_note-kaiser-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p><p>Water is required for normal peptide bond cleavage of the <a href="/w/index.php?title=Iminolactone&action=edit&redlink=1" class="new" title="Iminolactone (page does not exist)">iminolactone</a> intermediate. In formic acid, cleavage of Met-<a href="/wiki/Serine" title="Serine">Ser</a> and Met-<a href="/wiki/Threonine" title="Threonine">Thr</a> bonds is enhanced with increased water concentration because these conditions favor the addition of water across the <a href="/wiki/Imine" title="Imine">imine</a> rather than reaction of the side chain hydroxyl with the imine. Lowered pH tends to increase cleavage rates by inhibiting methionine side chain oxidation.<sup id="cite_ref-kaiser_8-1" class="reference"><a href="#cite_note-kaiser-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Side_reactions">Side reactions</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cyanogen_bromide&action=edit&section=7" title="Edit section: Side reactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>When methionine is followed by <a href="/wiki/Serine" title="Serine">serine</a> or <a href="/wiki/Threonine" title="Threonine">threonine</a>, side reactions can occur that destroy the methionine without peptide <a href="/wiki/Bond_cleavage" title="Bond cleavage">bond cleavage</a>. Normally, once the iminolactone is formed (refer to figure), water and acid can react with the imine to cleave the peptide bond, forming a <a href="/wiki/Homoserine_lactone" class="mw-redirect" title="Homoserine lactone">homoserine lactone</a> and new C-terminal peptide. However, if the adjacent amino acid to methionine has a <a href="/wiki/Hydroxyl" class="mw-redirect" title="Hydroxyl">hydroxyl</a> or <a href="/wiki/Sulfhydryl" class="mw-redirect" title="Sulfhydryl">sulfhydryl</a> group, this group can react with the imine to form a homoserine without peptide bond cleavage.<sup id="cite_ref-kaiser_8-2" class="reference"><a href="#cite_note-kaiser-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> These two cases are shown in the figure. </p> <div class="mw-heading mw-heading2"><h2 id="Organic_synthesis">Organic synthesis</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cyanogen_bromide&action=edit&section=8" title="Edit section: Organic synthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Cyanogen bromide is a common reagent in <a href="/wiki/Organic_synthesis" title="Organic synthesis">organic synthesis</a>. In most reactions, it acts as a source of electrophilic <a href="/wiki/Cyanide" title="Cyanide">cyanogen</a> and nucleophilic <a href="/wiki/Bromide" title="Bromide">bromide</a>; carbocations preferentially attack the nitrogen atom.<sup id="cite_ref-EROS_4-1" class="reference"><a href="#cite_note-EROS-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> In the presence of a Lewis acid, it cyanidates <a href="/wiki/Arene" class="mw-redirect" title="Arene">arenes</a>.<sup id="cite_ref-SynLett_9-0" class="reference"><a href="#cite_note-SynLett-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p><p>BrCN converts <a href="/wiki/Alcohols" class="mw-redirect" title="Alcohols">alcohols</a> to <a href="/wiki/Cyanates" class="mw-redirect" title="Cyanates">cyanates</a>; <a href="/wiki/Amine" title="Amine">amines</a> to <a href="/wiki/Cyanamide" title="Cyanamide">cyanamides</a> or <a href="/wiki/Dicyanamide" title="Dicyanamide">dicyanamides</a>.<sup id="cite_ref-EROS_4-2" class="reference"><a href="#cite_note-EROS-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> Excess BrCN continues the reaction to <a href="/wiki/Guanidine" title="Guanidine">guanidines</a>; <a href="/wiki/Hydroxylamine" title="Hydroxylamine">hydroxylamines</a> yield <a href="/w/index.php?title=Hydroxyguanidine&action=edit&redlink=1" class="new" title="Hydroxyguanidine (page does not exist)">hydroxyguanidines</a> similarly.<sup id="cite_ref-SynLett_9-1" class="reference"><a href="#cite_note-SynLett-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p><p>The cyanamides so formed <a href="/wiki/Umpolung" title="Umpolung">umpole</a> the original amine, and tends to eliminate alkyl substituents. In the <a href="/wiki/Von_Braun_reaction" title="Von Braun reaction">von Braun reaction</a>, tertiary amines react with cyanogen bromide to yield disubstituted cyanamides and an alkyl bromide.<sup id="cite_ref-SynLett_9-2" class="reference"><a href="#cite_note-SynLett-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> That net reaction is similar to the <a href="/wiki/Polonovski_reaction" class="mw-redirect" title="Polonovski reaction">Polonovski elimination</a>, but does not require N-oxidation.<sup id="cite_ref-EROS_4-3" class="reference"><a href="#cite_note-EROS-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p><p>In bromocyanation, BrCN adds across multiple bonds to give a vicinal cyanobromide. Bromocyanated <a href="/wiki/Enol" title="Enol">enols</a> spontaneously undergo a <a href="/wiki/Darzens_reaction" title="Darzens reaction">Darzens-like elimination</a> to an epoxynitrile.<sup id="cite_ref-EROS_4-4" class="reference"><a href="#cite_note-EROS-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p><p>Cyanogen bromide is also a dehydrating agent, hydrolyzing to <a href="/wiki/Hydrogen_bromide" title="Hydrogen bromide">hydrogen bromide</a> and <a href="/wiki/Cyanic_acid" class="mw-redirect" title="Cyanic acid">cyanic acid</a>.<sup id="cite_ref-SynLett_9-3" class="reference"><a href="#cite_note-SynLett-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p><p>The compound is used in the synthesis of <a href="/wiki/4-Methylaminorex" title="4-Methylaminorex">4-methylaminorex</a> ("ice") and <a href="/w/index.php?title=Viroxime&action=edit&redlink=1" class="new" title="Viroxime (page does not exist)">viroxime</a>. </p> <div class="mw-heading mw-heading2"><h2 id="Toxicity,_storage,_and_deactivation"><span id="Toxicity.2C_storage.2C_and_deactivation"></span>Toxicity, storage, and deactivation</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cyanogen_bromide&action=edit&section=9" title="Edit section: Toxicity, storage, and deactivation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Cyanogen bromide can be stored under dry conditions at 2 to 8 °C for extended periods.<sup id="cite_ref-sigma_6-2" class="reference"><a href="#cite_note-sigma-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p><p>Cyanogen bromide is volatile, and readily absorbed through the <a href="/wiki/Skin" title="Skin">skin</a> or <a href="/wiki/Gastrointestinal_tract" title="Gastrointestinal tract">gastrointestinal tract</a>. Therefore, toxic exposure may occur by inhalation, physical contact, or ingestion. It is acutely toxic, causing a variety of <a href="/wiki/Nonspecific_symptoms" class="mw-redirect" title="Nonspecific symptoms">nonspecific symptoms</a>. Exposure to even small amounts may cause convulsions or death. LD<sub>50</sub> orally in rats is reported as 25–50 mg/kg.<sup id="cite_ref-NIH_10-0" class="reference"><a href="#cite_note-NIH-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </p><p>The recommended method to deactivate cyanogen bromide is with <a href="/wiki/Sodium_hydroxide" title="Sodium hydroxide">sodium hydroxide</a> and <a href="/wiki/Bleach" title="Bleach">bleach</a>.<sup id="cite_ref-11" class="reference"><a href="#cite_note-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> The aqueous alkali hydroxide instantly hydrolyzes (CN)Br to alkali cyanide and bromide. The cyanide can then be oxidized by <a href="/wiki/Sodium_hypochlorite" title="Sodium hypochlorite">sodium</a> or <a href="/wiki/Calcium_hypochlorite" title="Calcium hypochlorite">calcium hypochlorite</a> to the less toxic cyanate ion. Deactivation is extremely <a href="/wiki/Exothermic" class="mw-redirect" title="Exothermic">exothermic</a> and may be explosive.<sup id="cite_ref-NIH_10-1" class="reference"><a href="#cite_note-NIH-10"><span class="cite-bracket">[</span>10<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=Cyanogen_bromide&action=edit&section=10" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-Merck-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-Merck_1-0">^</a></b></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite class="citation book cs1"><i>The Merck Index</i> (10th ed.). Rahway, NJ: Merck & Co. 1983. p. 385.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=The+Merck+Index&rft.place=Rahway%2C+NJ&rft.pages=385&rft.edition=10th&rft.pub=Merck+%26+Co.&rft.date=1983&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACyanogen+bromide" 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 class="citation web cs1"><a rel="nofollow" class="external text" href="https://web.archive.org/web/20230320080339/https://www.chemindustry.com/chemicals/0308894.html">"Campilit, CAS Number: 506-68-3"</a>. Archived from <a rel="nofollow" class="external text" href="http://www.chemindustry.com/chemicals/0308894.html">the original</a> on 2023-03-20<span class="reference-accessdate">. Retrieved <span class="nowrap">2013-03-14</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Campilit%2C+CAS+Number%3A+506-68-3&rft_id=http%3A%2F%2Fwww.chemindustry.com%2Fchemicals%2F0308894.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACyanogen+bromide" 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 class="citation web cs1"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=10476#x291">"Cyanogen Bromide – Compound Summary"</a>. <i>PubChem Compound</i>. USA: National Center for Biotechnology Information. 26 March 2005. Identification<span class="reference-accessdate">. Retrieved <span class="nowrap">4 June</span> 2012</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=PubChem+Compound&rft.atitle=Cyanogen+Bromide+%E2%80%93+Compound+Summary&rft.pages=Identification&rft.date=2005-03-26&rft_id=https%3A%2F%2Fpubchem.ncbi.nlm.nih.gov%2Fsummary%2Fsummary.cgi%3Fcid%3D10476%23x291&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACyanogen+bromide" class="Z3988"></span></span> </li> <li id="cite_note-EROS-4"><span class="mw-cite-backlink">^ <a href="#cite_ref-EROS_4-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-EROS_4-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-EROS_4-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-EROS_4-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-EROS_4-4"><sup><i><b>e</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFJoel_MorrisLajos_KovácsKouichi_Ohe2015" class="citation encyclopaedia cs1">Joel Morris; Lajos Kovács; Kouichi Ohe (2015). 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(1999). "Enhancement of Cyanogen Bromide Cleavage Yields for Methionyl-Serine and Methionyl-Threonine Peptide Bonds". <i>Analytical Biochemistry</i>. <b>266</b> (1): <span class="nowrap">1–</span>8. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1006%2Fabio.1998.2945">10.1006/abio.1998.2945</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/9887207">9887207</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Analytical+Biochemistry&rft.atitle=Enhancement+of+Cyanogen+Bromide+Cleavage+Yields+for+Methionyl-Serine+and+Methionyl-Threonine+Peptide+Bonds&rft.volume=266&rft.issue=1&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1-%3C%2Fspan%3E8&rft.date=1999&rft_id=info%3Adoi%2F10.1006%2Fabio.1998.2945&rft_id=info%3Apmid%2F9887207&rft.au=Kaiser%2C+R.&rft.au=Metzka%2C+L.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACyanogen+bromide" class="Z3988"></span></span> </li> <li id="cite_note-SynLett-9"><span class="mw-cite-backlink">^ <a href="#cite_ref-SynLett_9-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-SynLett_9-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-SynLett_9-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-SynLett_9-3"><sup><i><b>d</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFKumar,_V.2005" class="citation journal cs1">Kumar, V. (2005). <a rel="nofollow" class="external text" href="http://www.thieme-connect.com/ejournals/pdf/synlett/doi/10.1055/s-2005-869872.pdf">"Cyanogen Bromide (CNBr)"</a> <span class="cs1-format">(PDF)</span>. <i>Synlett</i>. <b>2005</b> (10): <span class="nowrap">1638–</span>1639. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1055%2Fs-2005-869872">10.1055/s-2005-869872</a></span>. Art ID: V12705ST.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Synlett&rft.atitle=Cyanogen+Bromide+%28CNBr%29&rft.volume=2005&rft.issue=10&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1638-%3C%2Fspan%3E1639&rft.date=2005&rft_id=info%3Adoi%2F10.1055%2Fs-2005-869872&rft.au=Kumar%2C+V.&rft_id=http%3A%2F%2Fwww.thieme-connect.com%2Fejournals%2Fpdf%2Fsynlett%2Fdoi%2F10.1055%2Fs-2005-869872.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACyanogen+bromide" class="Z3988"></span></span> </li> <li id="cite_note-NIH-10"><span class="mw-cite-backlink">^ <a href="#cite_ref-NIH_10-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-NIH_10-1"><sup><i><b>b</b></i></sup></a></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="http://toxnet.nlm.nih.gov/cgi-bin/sis/search/a?dbs+hsdb:@term+@DOCNO+708">"Cyanogen Bromide HSDB 708"</a>. <i>HSDB</i>. NIH / NLM. 2009-04-07.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=HSDB&rft.atitle=Cyanogen+Bromide+HSDB+708&rft.date=2009-04-07&rft_id=http%3A%2F%2Ftoxnet.nlm.nih.gov%2Fcgi-bin%2Fsis%2Fsearch%2Fa%3Fdbs%2Bhsdb%3A%40term%2B%40DOCNO%2B708&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACyanogen+bromide" class="Z3988"></span></span> </li> <li id="cite_note-11"><span class="mw-cite-backlink"><b><a href="#cite_ref-11">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLunn,_G.Sansone,_E._B.1985" class="citation journal cs1">Lunn, G.; Sansone, E. B. (1985). <a rel="nofollow" class="external text" href="https://zenodo.org/record/1253784">"Destruction of Cyanogen Bromide and Inorganic Cyanides"</a>. <i><a href="/wiki/Analytical_Biochemistry_(journal)" class="mw-redirect" title="Analytical Biochemistry (journal)">Analytical Biochemistry</a></i>. <b>147</b> (1): <span class="nowrap">245–</span>250. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2F0003-2697%2885%2990034-X">10.1016/0003-2697(85)90034-X</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/4025821">4025821</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Analytical+Biochemistry&rft.atitle=Destruction+of+Cyanogen+Bromide+and+Inorganic+Cyanides&rft.volume=147&rft.issue=1&rft.pages=%3Cspan+class%3D%22nowrap%22%3E245-%3C%2Fspan%3E250&rft.date=1985&rft_id=info%3Adoi%2F10.1016%2F0003-2697%2885%2990034-X&rft_id=info%3Apmid%2F4025821&rft.au=Lunn%2C+G.&rft.au=Sansone%2C+E.+B.&rft_id=https%3A%2F%2Fzenodo.org%2Frecord%2F1253784&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACyanogen+bromide" class="Z3988"></span></span> </li> </ol></div></div> <div class="mw-heading mw-heading2"><h2 id="Further_reading">Further reading</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cyanogen_bromide&action=edit&section=11" title="Edit section: Further reading"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFGross,_E.Witkop,_B.1962" class="citation journal cs1">Gross, E.; Witkop, B. (1962). <a rel="nofollow" class="external text" href="http://www.jbc.org/content/237/6/1856.full.pdf">"Nonenzymatic Cleavage of Peptide Bonds: The Methionine Residues in Bovine Pancreatic Ribonuclease"</a> <span class="cs1-format">(PDF)</span>. <i><a href="/wiki/Journal_of_Biological_Chemistry" title="Journal of Biological Chemistry">Journal of Biological Chemistry</a></i>. <b>237</b> (6): <span class="nowrap">1856–</span>1860. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1016%2FS0021-9258%2819%2973948-9">10.1016/S0021-9258(19)73948-9</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/13902203">13902203</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Biological+Chemistry&rft.atitle=Nonenzymatic+Cleavage+of+Peptide+Bonds%3A+The+Methionine+Residues+in+Bovine+Pancreatic+Ribonuclease&rft.volume=237&rft.issue=6&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1856-%3C%2Fspan%3E1860&rft.date=1962&rft_id=info%3Adoi%2F10.1016%2FS0021-9258%2819%2973948-9&rft_id=info%3Apmid%2F13902203&rft.au=Gross%2C+E.&rft.au=Witkop%2C+B.&rft_id=http%3A%2F%2Fwww.jbc.org%2Fcontent%2F237%2F6%2F1856.full.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACyanogen+bromide" class="Z3988"></span></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFInglis,_A._S.Edman,_P.1970" class="citation journal cs1">Inglis, A. S.; <a href="/wiki/Pehr_Edman" class="mw-redirect" title="Pehr Edman">Edman, P.</a> (1970). "Mechanism of Cyanogen Bromide Reaction with Methionine in Peptides and Proteins". <i><a href="/wiki/Analytical_Biochemistry_(journal)" class="mw-redirect" title="Analytical Biochemistry (journal)">Analytical Biochemistry</a></i>. <b>37</b> (1): <span class="nowrap">73–</span>80. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2F0003-2697%2870%2990259-9">10.1016/0003-2697(70)90259-9</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/5506566">5506566</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Analytical+Biochemistry&rft.atitle=Mechanism+of+Cyanogen+Bromide+Reaction+with+Methionine+in+Peptides+and+Proteins&rft.volume=37&rft.issue=1&rft.pages=%3Cspan+class%3D%22nowrap%22%3E73-%3C%2Fspan%3E80&rft.date=1970&rft_id=info%3Adoi%2F10.1016%2F0003-2697%2870%2990259-9&rft_id=info%3Apmid%2F5506566&rft.au=Inglis%2C+A.+S.&rft.au=Edman%2C+P.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACyanogen+bromide" class="Z3988"></span></li></ul> <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=Cyanogen_bromide&action=edit&section=12" title="Edit section: External links"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="http://hazard.com/msds/mf/baker/baker/files/c6600.htm">"Cyanogen Bromide MSDS Number: C6600"</a>. J. T. Baker. 1996-08-12.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Cyanogen+Bromide+MSDS+Number%3A+C6600&rft.pub=J.+T.+Baker&rft.date=1996-08-12&rft_id=http%3A%2F%2Fhazard.com%2Fmsds%2Fmf%2Fbaker%2Fbaker%2Ffiles%2Fc6600.htm&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACyanogen+bromide" class="Z3988"></span></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFTeeri,_A._E.1948" class="citation journal cs1">Teeri, A. E. (1948). <a rel="nofollow" class="external text" href="https://doi.org/10.1016%2FS0021-9258%2818%2957422-6">"Thiamine and the Cyanogen Bromide Reaction"</a>. <i>Journal of Biological Chemistry</i>. <b>173</b> (2): <span class="nowrap">503–</span>505. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1016%2FS0021-9258%2818%2957422-6">10.1016/S0021-9258(18)57422-6</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/18910706">18910706</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Biological+Chemistry&rft.atitle=Thiamine+and+the+Cyanogen+Bromide+Reaction&rft.volume=173&rft.issue=2&rft.pages=%3Cspan+class%3D%22nowrap%22%3E503-%3C%2Fspan%3E505&rft.date=1948&rft_id=info%3Adoi%2F10.1016%2FS0021-9258%2818%2957422-6&rft_id=info%3Apmid%2F18910706&rft.au=Teeri%2C+A.+E.&rft_id=https%3A%2F%2Fdoi.org%2F10.1016%252FS0021-9258%252818%252957422-6&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACyanogen+bromide" class="Z3988"></span></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 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.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><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"></div><div role="navigation" class="navbox" aria-labelledby="Agents_used_in_chemical_warfareincapacitationriot_control542" style="padding:3px"><table class="nowraplinks hlist mw-collapsible autocollapse 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:Chemical_agents" title="Template:Chemical agents"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Chemical_agents" title="Template talk:Chemical agents"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Chemical_agents" title="Special:EditPage/Template:Chemical agents"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Agents_used_in_chemical_warfareincapacitationriot_control542" style="font-size:114%;margin:0 4em"><div class="hlist"><ul><li>Agents used in <a href="/wiki/Chemical_warfare" title="Chemical warfare">chemical warfare</a></li><li><a href="/wiki/Incapacitating_agent" title="Incapacitating agent">incapacitation</a></li><li><a href="/wiki/Riot_control" title="Riot control">riot control</a></li></ul></div></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Blood_agent" title="Blood agent">Blood agents</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/Cyanogen" title="Cyanogen">Cyanogen</a></li> <li><a class="mw-selflink selflink">Cyanogen bromide</a></li> <li><a href="/wiki/Cyanogen_chloride" title="Cyanogen chloride">Cyanogen chloride</a> (CK)</li> <li><a href="/wiki/Hydrogen_cyanide" title="Hydrogen cyanide">Hydrogen cyanide</a> (AC)</li> <li><a href="/wiki/Arsine" title="Arsine">Arsine</a></li> <li><a href="/wiki/Cacodyl_cyanide" title="Cacodyl cyanide">Cacodyl cyanide</a></li> <li><a href="/wiki/Cacodyl_oxide" title="Cacodyl oxide">Cacodyl oxide</a></li> <li><a href="/wiki/Hydrogen_sulfide" title="Hydrogen sulfide">Hydrogen sulfide</a></li> <li><a href="/wiki/Phosphine" title="Phosphine">Phosphine</a></li> <li><a href="/wiki/Carbon_monoxide" title="Carbon monoxide">Carbon monoxide</a></li> <li><a href="/wiki/Phosphorus_trifluoride" title="Phosphorus trifluoride">Phosphorus trifluoride</a></li> <li><a href="/wiki/Methyl_cyanoformate" title="Methyl cyanoformate">Methyl cyanoformate</a></li> <li><a href="/wiki/Iron_pentacarbonyl" title="Iron pentacarbonyl">Iron pentacarbonyl</a></li> <li><a href="/wiki/Nickel_tetracarbonyl" title="Nickel tetracarbonyl">Nickel tetracarbonyl</a></li> <li><a href="/wiki/2,3,7,8-Tetrachlorodibenzodioxin" title="2,3,7,8-Tetrachlorodibenzodioxin">2,3,7,8-Tetrachlorodibenzodioxin</a></li> <li><a href="/wiki/Glycolonitrile" title="Glycolonitrile">Glycolonitrile</a></li> <li><a href="/wiki/Lactonitrile" title="Lactonitrile">Lactonitrile</a></li> <li><a href="/wiki/Acetone_cyanohydrin" title="Acetone cyanohydrin">Acetone cyanohydrin</a></li> <li><a href="/wiki/Stibine" title="Stibine">Stibine</a></li> <li><a href="/wiki/Chloral_cyanohydrin" title="Chloral cyanohydrin">Chloral cyanohydrin</a></li></ul></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Blister_agent" title="Blister agent">Blister agents</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Arsenical" title="Arsenical">Arsenicals</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <li><a href="/wiki/Ethyldichloroarsine" title="Ethyldichloroarsine">Ethyldichloroarsine</a> (ED)</li> <li><a href="/wiki/Methyldichloroarsine" title="Methyldichloroarsine">Methyldichloroarsine</a> (MD)</li> <li><a href="/wiki/Phenyldichloroarsine" title="Phenyldichloroarsine">Phenyldichloroarsine</a> (PD)</li> <li><a href="/wiki/Lewisite" title="Lewisite">Lewisite</a> (L)</li> <li><a href="/wiki/Lewisite_2" title="Lewisite 2">Lewisite 2</a> (L2)</li> <li><a href="/wiki/Lewisite_3" title="Lewisite 3">Lewisite 3</a> (L3)</li> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Sulfur_mustard" class="mw-redirect" title="Sulfur mustard">Sulfur mustards</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/Mustard_gas" title="Mustard gas">Levinstein mustard</a> (EA-229)</li> <li><a href="/wiki/O-Mustard" class="mw-redirect" title="O-Mustard">T</a></li> <li><a href="/wiki/Sesquimustard" title="Sesquimustard">Q</a></li> <li><a href="/wiki/2-Chloroethyl_ethyl_sulfide" title="2-Chloroethyl ethyl sulfide">CEES</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Nitrogen_mustard" title="Nitrogen mustard">Nitrogen mustards</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/HN1_(nitrogen_mustard)" title="HN1 (nitrogen mustard)">HN1</a></li> <li><a href="/wiki/Chlormethine" title="Chlormethine">HN2</a></li> <li><a href="/wiki/HN3_(nitrogen_mustard)" title="HN3 (nitrogen mustard)">HN3</a></li> <li><a href="/wiki/TL-301" title="TL-301">TL-301</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Nettle_agent" title="Nettle agent">Nettle agents</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/Phosgene_oxime" title="Phosgene oxime">Phosgene oxime</a> (CX)</li></ul> </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/KB-16" title="KB-16">KB-16</a></li> <li><a href="/wiki/Dibutylchloromethyltin_chloride" title="Dibutylchloromethyltin chloride">Dibutylchloromethyltin chloride</a></li> <li><a href="/wiki/Selenium_oxychloride" class="mw-redirect" title="Selenium oxychloride">Selenium oxychloride</a></li> <li><a href="/wiki/Phenacyl_bromide" title="Phenacyl bromide">Phenacyl bromide</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Nerve_agent" title="Nerve agent">Nerve agents</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Nerve_agent#G-Series" title="Nerve agent">G-agents</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/Tabun_(nerve_agent)" title="Tabun (nerve agent)">Tabun</a> (GA)</li> <li><a href="/wiki/Sarin" title="Sarin">Sarin (GB)</a></li> <li><a href="/wiki/Chlorosarin" title="Chlorosarin">Chlorosarin</a> (ClGB)</li> <li><a href="/wiki/Thiosarin" title="Thiosarin">Thiosarin</a> (SGB)</li> <li><a href="/wiki/Soman" title="Soman">Soman</a> (GD)</li> <li><a href="/wiki/Chlorosoman" title="Chlorosoman">Chlorosoman</a> (ClGD)</li> <li><a href="/wiki/Ethylsarin" title="Ethylsarin">Ethylsarin</a> (GE)</li> <li><a href="/wiki/GH_(nerve_agent)" title="GH (nerve agent)">GH</a></li> <li><a href="/wiki/Cyclosarin" title="Cyclosarin">Cyclosarin</a> (GF)</li> <li><a href="/wiki/GP_(nerve_agent)" title="GP (nerve agent)">GP</a></li> <li><a href="/wiki/Fluorotabun" title="Fluorotabun">Fluorotabun</a></li> <li><a href="/wiki/EA-1356" title="EA-1356">EA-1356</a></li> <li><a href="/wiki/EA-4352" title="EA-4352">EA-4352</a></li> <li><a href="/wiki/Crotylsarin" title="Crotylsarin">Crotylsarin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Nerve_agent#V-Series" title="Nerve agent">V-agents</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/EA-2192" title="EA-2192">EA-2192</a></li> <li><a href="/wiki/EA-3148" title="EA-3148">EA-3148</a></li> <li><a href="/wiki/VE_(nerve_agent)" title="VE (nerve agent)">VE</a></li> <li><a href="/wiki/VG_(nerve_agent)" title="VG (nerve agent)">VG</a></li> <li><a href="/wiki/VM_(nerve_agent)" title="VM (nerve agent)">VM</a></li> <li><a href="/wiki/3,3,5-Trimethylcyclohexyl_3-pyridyl_methylphosphonate" title="3,3,5-Trimethylcyclohexyl 3-pyridyl methylphosphonate">VP</a></li> <li><a href="/wiki/VR_(nerve_agent)" title="VR (nerve agent)">VR</a></li> <li><a href="/wiki/VS_(nerve_agent)" title="VS (nerve agent)">VS</a></li> <li><a href="/wiki/VX_(nerve_agent)" title="VX (nerve agent)">VX</a></li> <li><a href="/wiki/EA-1763" title="EA-1763">EA-1763</a></li> <li><a href="/wiki/Chinese_VX" title="Chinese VX">Chinese VX</a></li> <li><a href="/wiki/V-sub_x" title="V-sub x">V-sub x (GD-7)</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">GV agents</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/GV_(nerve_agent)" title="GV (nerve agent)">GV (EA-5365)</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Novichok_agent" class="mw-redirect" title="Novichok agent">Novichok agents</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/VR_(nerve_agent)" title="VR (nerve agent)">A-208</a></li> <li><a href="/wiki/A-232" title="A-232">A-232</a></li> <li><a href="/wiki/A-234_(nerve_agent)" title="A-234 (nerve agent)">A-234</a></li> <li><a href="/wiki/A-242" title="A-242">A-242</a></li> <li><a href="/wiki/A-262" title="A-262">A-262</a></li> <li><a href="/wiki/C01-A035" title="C01-A035">C01-A035</a></li> <li><a href="/wiki/C01-A039" title="C01-A039">C01-A039</a></li> <li><a href="/wiki/C01-A042" title="C01-A042">C01-A042</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Carbamate" title="Carbamate">Carbamates</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/Dimethylcarbamoyl_fluoride" title="Dimethylcarbamoyl fluoride">Dimethylcarbamoyl fluoride</a></li> <li><a href="/wiki/EA-3887" title="EA-3887">EA-3887</a></li> <li><a href="/wiki/EA-3887A" class="mw-redirect" title="EA-3887A">EA-3887A</a></li> <li><a href="/wiki/EA-3966" title="EA-3966">EA-3966</a></li> <li><a href="/wiki/EA-3990" title="EA-3990">EA-3990</a></li> <li><a href="/wiki/EA-4056" title="EA-4056">EA-4056</a></li> <li><a href="/wiki/T-1123" title="T-1123">T-1123</a></li> <li><a href="/wiki/T-1152" title="T-1152">T-1152</a></li> <li><a href="/wiki/T-1194" title="T-1194">T-1194</a></li> <li><a href="/wiki/Octamethylene-bis(5-dimethylcarbamoxyisoquinolinium_bromide)" title="Octamethylene-bis(5-dimethylcarbamoxyisoquinolinium bromide)">Octamethylene-bis(5-dimethylcarbamoxyisoquinolinium bromide)</a></li> <li><a href="/wiki/TL-599" title="TL-599">TL-599</a></li> <li><a href="/wiki/TL-1238" title="TL-1238">TL-1238</a></li> <li><a href="/wiki/TL-1299" class="mw-redirect" title="TL-1299">TL-1299</a></li> <li><a href="/wiki/TL-1317" class="mw-redirect" title="TL-1317">TL-1317</a></li> <li><a href="/wiki/Miotine" title="Miotine">Miotine (AR-28/T-1843)</a></li> <li><a href="/wiki/3152_CT" title="3152 CT">3152 CT</a></li> <li><a href="/wiki/4-686-293-01" title="4-686-293-01">4-686-293-01 (Agent 1-10)</a></li></ul> </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/Diisopropyl_fluorophosphate" title="Diisopropyl fluorophosphate">Diisopropyl fluorophosphate</a></li> <li><a href="/wiki/Dicyclohexyl_phosphorofluoridate" title="Dicyclohexyl phosphorofluoridate">Dicyclohexyl phosphorofluoridate</a></li> <li><a href="/wiki/EA-2012" title="EA-2012">EA-2012</a></li> <li><a href="/wiki/EA-2054" title="EA-2054">EA-2054</a></li> <li><a href="/wiki/EA-2098" title="EA-2098">EA-2098</a></li> <li><a href="/wiki/EA-2613" title="EA-2613">EA-2613</a></li> <li><a href="/wiki/2-Ethoxycarbonyl-1-methylvinyl_cyclohexyl_methylphosphonate" title="2-Ethoxycarbonyl-1-methylvinyl cyclohexyl methylphosphonate">2-Ethoxycarbonyl-1-methylvinyl cyclohexyl methylphosphonate</a></li> <li><a href="/wiki/Neopentylene_fluorophosphate" title="Neopentylene fluorophosphate">Neopentylene fluorophosphate</a></li> <li><a href="/wiki/Selenophos" title="Selenophos">Selenophos</a></li> <li><a href="/wiki/Phospholine" class="mw-redirect" title="Phospholine">Phospholine</a></li> <li><a href="/wiki/R-16661" title="R-16661">R-16661</a></li> <li><a href="/wiki/Ro_3-0422" title="Ro 3-0422">Ro 3-0422</a></li> <li><a href="/wiki/Methanesulfonyl_fluoride" title="Methanesulfonyl fluoride">Methanesulfonyl fluoride</a></li> <li><a href="/wiki/Dimefox" title="Dimefox">Dimefox (TL-792)</a></li> <li><a href="/wiki/MSPI_(nerve_agent)" title="MSPI (nerve agent)">MSPI</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Precursors</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acetonitrile" title="Acetonitrile">Acetonitrile</a></li> <li><a href="/wiki/Arsenic_trichloride" title="Arsenic trichloride">AT</a></li> <li><a href="/wiki/Arsenic_trioxide" title="Arsenic trioxide">ATO</a></li> <li><a href="/wiki/Aluminium_phosphide" title="Aluminium phosphide">AlP</a></li> <li><a href="/wiki/Kinnear%E2%80%93Perren_reaction" title="Kinnear–Perren reaction">A.P.C. complex</a></li> <li><a href="/wiki/Chlorosarin" title="Chlorosarin">Chlorosarin</a></li> <li><a href="/wiki/Chlorosoman" title="Chlorosoman">Chlorosoman</a></li> <li><a href="/wiki/Cyclohexanol" title="Cyclohexanol">Cyclohexanol</a></li> <li><a href="/wiki/1,8-Dibromooctane" title="1,8-Dibromooctane">1,8-Dibromooctane</a></li> <li><a href="/wiki/N,N-Diisopropylaminoethanol" title="N,N-Diisopropylaminoethanol">N,N-Diisopropylaminoethanol</a> (KB)</li> <li><a href="/wiki/Diisopropyl_methylphosphonate" title="Diisopropyl methylphosphonate">EA-1250</a></li> <li><a href="/wiki/Diisopropylphosphite" title="Diisopropylphosphite">DIHP</a></li> <li><a href="/wiki/Ethanol" title="Ethanol">ZS</a></li> <li><a href="/wiki/Diethylphosphite" title="Diethylphosphite">DEHP</a></li> <li><a href="/wiki/Dimethyl_methylphosphonate" title="Dimethyl methylphosphonate">EA-1224</a></li> <li><a href="/wiki/Dimethylamidophosphoric_dichloride" title="Dimethylamidophosphoric dichloride">Dimethylamidophosphoric dichloride</a></li> <li><a href="/wiki/Dimethylamidophosphoric_dicyanide" title="Dimethylamidophosphoric dicyanide">Dimethylamidophosphoric dicyanide</a></li> <li><a href="/wiki/Dimethylphosphite" title="Dimethylphosphite">DMHP</a></li> <li><a href="/wiki/Ethylphosphonoselenoic_dichloride" title="Ethylphosphonoselenoic dichloride">Ethylphosphonoselenoic dichloride</a></li> <li><a href="/wiki/Formaldoxime" title="Formaldoxime">Formaldoxime</a></li> <li><a href="/wiki/Fulminic_acid" title="Fulminic acid">Nital</a></li> <li><a href="/wiki/4-Hydroxycoumarin" title="4-Hydroxycoumarin">4-Hydroxycoumarin</a></li> <li><a href="/wiki/Isopropyl_alcohol" title="Isopropyl alcohol">Isopropyl alcohol</a> (TB)</li> <li><a href="/wiki/Methyldichlorophosphine" title="Methyldichlorophosphine">Methyldichlorophosphine</a> (SW)</li> <li><a href="/wiki/Methylphosphonyl_difluoride" title="Methylphosphonyl difluoride">Methylphosphonyl difluoride (difluoro)</a> (DF)</li> <li><a href="/wiki/Methylphosphonyl_dichloride" title="Methylphosphonyl dichloride">Methylphosphonyl dichloride (dichloro)</a></li> <li><a href="/wiki/Nitromethane" title="Nitromethane">Nitromethane</a></li> <li><a href="/wiki/OPA_mixture" title="OPA mixture">OPA mixture</a></li> <li><a href="/wiki/Phosphoryl_chloride" title="Phosphoryl chloride">Phosphoryl chloride</a></li> <li><a href="/wiki/Phosphorus_pentachloride" title="Phosphorus pentachloride">Phosphorus pentachloride</a></li> <li><a href="/wiki/Phosphorus_trichloride" title="Phosphorus trichloride">Phosphorus trichloride</a> (TH)</li> <li><a href="/wiki/Pinacolone" title="Pinacolone">Pinacolone</a></li> <li><a href="/wiki/Pinacolyl_alcohol" title="Pinacolyl alcohol">Pinacolyl alcohol</a></li> <li><a href="/wiki/Phenacyl_chloride" title="Phenacyl chloride">Phenacyl chloride</a></li> <li><a href="/wiki/QL_(chemical)" title="QL (chemical)">QL</a></li> <li><a href="/wiki/2,4,5-Trichlorophenol" title="2,4,5-Trichlorophenol">2,4,5-Trichlorophenol</a></li> <li><a href="/wiki/3,3,5-Trimethylcyclohexanol" title="3,3,5-Trimethylcyclohexanol">3,3,5-Trimethylcyclohexanol</a></li> <li><a href="/wiki/Triethyl_phosphite" title="Triethyl phosphite">Triethyl phosphite</a></li> <li><a href="/wiki/Trimethyl_phosphite" title="Trimethyl phosphite">Trimethyl phosphite</a></li> <li><a href="/wiki/Thionyl_chloride" title="Thionyl chloride">TC</a></li> <li><a href="/wiki/Thiodiglycol" title="Thiodiglycol">TG</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Neurotoxin" title="Neurotoxin">Neurotoxins</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/Anatoxin-a" title="Anatoxin-a">Anatoxin-a</a></li> <li><a href="/wiki/Saxitoxin" title="Saxitoxin">Saxitoxin</a> (TZ)</li> <li><a href="/wiki/Coniine" title="Coniine">Coniine</a></li> <li><a href="/wiki/Bungarotoxin" title="Bungarotoxin">Bungarotoxin</a></li> <li><a href="/wiki/Botulinum_toxin" title="Botulinum toxin">Botulinum toxin</a> (BTX)</li> <li><a href="/wiki/Tetanospasmin" class="mw-redirect" title="Tetanospasmin">Tetanospasmin</a> (TeNT)</li> <li><a href="/wiki/Ryanodine" title="Ryanodine">Ryanodine</a></li> <li><a href="/wiki/Ciguatoxin" title="Ciguatoxin">Ciguatoxin</a> (CTX)</li> <li><a href="/wiki/Guanitoxin" title="Guanitoxin">Guanitoxin</a> (GTX)</li> <li><a href="/wiki/Chlorophenylsilatrane" title="Chlorophenylsilatrane">Chlorophenylsilatrane</a></li> <li><a href="/wiki/Palytoxin" title="Palytoxin">Palytoxin</a> (PTX)</li> <li><a href="/wiki/Maitotoxin" title="Maitotoxin">Maitotoxin</a> (MTX)</li> <li><a href="/wiki/Tetrodotoxin" title="Tetrodotoxin">Tetrodotoxin</a></li> <li><a href="/wiki/Veratridine" title="Veratridine">Veratridine</a></li> <li><a href="/wiki/Aconitine" title="Aconitine">Aconitine</a></li> <li><a href="/wiki/Brevetoxin" title="Brevetoxin">Brevetoxin</a> (PbTX)</li> <li><a href="/wiki/Strychnine" title="Strychnine">Strychnine</a></li> <li><a href="/wiki/Antillatoxin" title="Antillatoxin">Antillatoxin</a> (ATX)</li> <li><a href="/wiki/Tetraethyllead" title="Tetraethyllead">Tetraethyllead</a></li> <li><a href="/wiki/Dimethylmercury" title="Dimethylmercury">Dimethylmercury</a></li> <li><a href="/wiki/HN1_(nitrogen_mustard)" title="HN1 (nitrogen mustard)">HN1 hydrochloride</a></li> <li><a href="/wiki/HN2" class="mw-redirect" title="HN2">HN2 hydrochloride</a></li> <li><a href="/wiki/Tris(2-chloroethyl)amine" class="mw-redirect" title="Tris(2-chloroethyl)amine">HN3 hydrochloride</a></li> <li><a href="/wiki/IDPN_(chemical)" title="IDPN (chemical)">A-8564</a></li> <li><a href="/wiki/Picrotoxin" title="Picrotoxin">Picrotoxin</a></li> <li><a href="/wiki/Gelsemine" title="Gelsemine">Gelsemine</a></li> <li><a href="/wiki/Sulfuryl_fluoride" title="Sulfuryl fluoride">Sulfuryl fluoride</a></li> <li><a href="/wiki/Tremorine" title="Tremorine">Tremorine</a></li> <li><a href="/wiki/Oxotremorine" title="Oxotremorine">Oxotremorine</a></li> <li><a href="/wiki/Batrachotoxin" title="Batrachotoxin">Batrachotoxin</a></li> <li><a href="/wiki/Tetramethylenedisulfotetramine" title="Tetramethylenedisulfotetramine">Tetramethylenedisulfotetramine (TETS)</a></li> <li><a href="/wiki/Bicyclic_phosphate" title="Bicyclic phosphate">Bicyclic phosphates</a> <ul><li><a href="/wiki/IPTBO" title="IPTBO">IPTBO</a></li> <li><a href="/wiki/TBPO" title="TBPO">TBPO</a></li> <li><a href="/wiki/TBPS" title="TBPS">TBPS</a></li></ul></li> <li><a href="/wiki/Cloflubicyne" title="Cloflubicyne">Cloflubicyne</a></li> <li><a href="/wiki/Trimethylolpropane_phosphite" title="Trimethylolpropane phosphite">Trimethylolpropane phosphite</a></li> <li><a href="/wiki/Domoic_acid" title="Domoic acid">Domoic acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Pulmonary_agent" title="Pulmonary agent">Pulmonary/<br />choking agents</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/Chlorine" title="Chlorine">Chlorine</a></li> <li><a href="/wiki/Bromine" title="Bromine">Bromine</a></li> <li><a href="/wiki/Phosgene" title="Phosgene">Phosgene</a> (CG)</li> <li><a href="/wiki/Fluorine" title="Fluorine">Fluorine</a></li> <li><a href="/wiki/Perfluoroisobutene" title="Perfluoroisobutene">Perfluoroisobutene</a></li> <li><a href="/wiki/Chloropicrin" title="Chloropicrin">Chloropicrin</a> (PS)</li> <li><a href="/wiki/Dimethyl(trifluoromethylthio)arsine" title="Dimethyl(trifluoromethylthio)arsine">Dimethyl(trifluoromethylthio)arsine</a></li> <li><a href="/wiki/Diphosgene" title="Diphosgene">Diphosgene</a> (DP)</li> <li><a href="/wiki/Disulfur_decafluoride" title="Disulfur decafluoride">Disulfur decafluoride</a> (Z)</li> <li><a href="/wiki/Acrolein" title="Acrolein">Acrolein</a></li> <li><a href="/wiki/Ethyl_bromoacetate" title="Ethyl bromoacetate">Ethyl bromoacetate</a></li> <li><a href="/wiki/Perchloromethyl_mercaptan" title="Perchloromethyl mercaptan">Perchloromethyl mercaptan</a></li> <li><a href="/wiki/Phenylcarbylamine_chloride" title="Phenylcarbylamine chloride">Phenylcarbylamine chloride</a></li> <li><a href="/wiki/Tetranitromethane" title="Tetranitromethane">Tetranitromethane</a></li> <li><a href="/wiki/Tetrachlorodinitroethane" title="Tetrachlorodinitroethane">Tetrachlorodinitroethane</a></li> <li><a href="/wiki/Chlorine_trifluoride" title="Chlorine trifluoride">Chlorine trifluoride</a></li> <li><a href="/wiki/Perchloryl_fluoride" title="Perchloryl fluoride">Perchloryl fluoride</a></li> <li><a href="/wiki/Cadmium_oxide" title="Cadmium oxide">Cadmium oxide</a></li> <li><a href="/wiki/Cadmium_chloride" title="Cadmium chloride">Cadmium chloride</a></li> <li><a href="/wiki/Mercury(II)_chloride" title="Mercury(II) chloride">Mercuric chloride</a></li> <li><a href="/wiki/Selenium_dioxide" title="Selenium dioxide">Selenium dioxide</a></li> <li><a href="/wiki/Selenoyl_fluoride" title="Selenoyl fluoride">Selenoyl fluoride</a></li> <li><a href="/wiki/Trifluoronitrosomethane" title="Trifluoronitrosomethane">Trifluoronitrosomethane</a></li> <li><a href="/wiki/Trichloronitrosomethane" title="Trichloronitrosomethane">Trichloronitrosomethane</a></li> <li><a href="/wiki/Nitric_oxide" title="Nitric oxide">Nitric oxide</a></li> <li><a href="/wiki/Nitrogen_dioxide" title="Nitrogen dioxide">Nitrogen dioxide</a></li> <li><a href="/wiki/Dinitrogen_tetroxide" title="Dinitrogen tetroxide">Dinitrogen tetroxide</a></li> <li><a href="/wiki/Sulfur_dioxide" title="Sulfur dioxide">Sulfur dioxide</a></li> <li><a href="/wiki/Phosphorus_trichloride" title="Phosphorus trichloride">Phosphorus trichloride</a></li> <li><a href="/wiki/Methyl_isocyanate" title="Methyl isocyanate">Methyl isocyanate</a></li> <li><a href="/wiki/Ethenone" title="Ethenone">Ethenone</a></li> <li><a href="/wiki/Methyl_vinyl_ketone" title="Methyl vinyl ketone">Methyl vinyl ketone</a></li> <li><a href="/wiki/Trifluoroacetyl_chloride" title="Trifluoroacetyl chloride">Trifluoroacetyl chloride</a></li> <li><a href="/wiki/Salcomine" title="Salcomine">Salcomine</a></li> <li><a href="/wiki/Fluomine" title="Fluomine">Fluomine</a></li> <li><a href="/wiki/Uranium_hexafluoride" title="Uranium hexafluoride">Uranium hexafluoride</a></li> <li><a href="/wiki/Diborane" title="Diborane">Diborane</a></li> <li><a href="/wiki/Green_Cross_(chemical_warfare)" title="Green Cross (chemical warfare)">Green Cross</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Vomiting_agent" title="Vomiting agent">Vomiting agents</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/Adamsite" title="Adamsite">Adamsite</a> (DM)</li> <li><a href="/wiki/Chloropicrin" title="Chloropicrin">Chloropicrin</a></li> <li><a href="/wiki/Litharge" title="Litharge">Litharge</a>-<a href="/wiki/Glycerine" class="mw-redirect" title="Glycerine">glycerine</a></li> <li><a href="/wiki/Diphenylchlorarsine" title="Diphenylchlorarsine">Diphenylchlorarsine</a></li> <li><a href="/wiki/Diphenylcyanoarsine" title="Diphenylcyanoarsine">Diphenylcyanoarsine</a></li> <li><a href="/wiki/Cacodyl_cyanide" title="Cacodyl cyanide">Cacodyl cyanide</a></li> <li><a href="/wiki/O-Dianisidine" title="O-Dianisidine">o-Dianisidine</a></li> <li><a href="/wiki/Antimony_potassium_tartrate" title="Antimony potassium tartrate">Antimony potassium tartrate</a></li> <li><a href="/wiki/Lobeline" title="Lobeline">Lobeline</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Incapacitating_agent" title="Incapacitating agent">Incapacitating<br />agents</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/3-Quinuclidinyl_benzilate" title="3-Quinuclidinyl benzilate">BZ</a> (CS-4030)</li> <li><a href="/wiki/Apomorphine" title="Apomorphine">Apomorphine</a></li> <li><a href="/wiki/Butyrophenone" title="Butyrophenone">Butyrophenone</a></li> <li><a href="/wiki/Etonitazene" title="Etonitazene">EA-4941</a> (CS-4640)</li> <li><a href="/wiki/Etorphine" title="Etorphine">Etorphine</a></li> <li><a href="/wiki/Benactyzine" title="Benactyzine">EA-2092</a></li> <li><a href="/wiki/Ditran" title="Ditran">CS-4297</a></li> <li><a href="/wiki/Etoxadrol" title="Etoxadrol">Etoxadrol</a></li> <li><a href="/wiki/Dimethylheptylpyran" title="Dimethylheptylpyran">Dimethylheptylpyran</a> (DMHP)</li> <li><a href="/wiki/Canbisol" title="Canbisol">Canbisol</a></li> <li><a href="/wiki/Phencyclidine" title="Phencyclidine">EA-2148</a></li> <li><a href="/wiki/EA-3167" title="EA-3167">EA-3167</a></li> <li><a href="/wiki/Nicotine" title="Nicotine">Nicotine</a></li> <li><a href="/wiki/EA-3443" title="EA-3443">EA-3443</a></li> <li><a href="/wiki/Methaqualone" title="Methaqualone">Methaqualone</a></li> <li><a href="/wiki/Pethidine" title="Pethidine">Pethidine</a></li> <li><a href="/wiki/EA-3580" title="EA-3580">EA-3580</a></li> <li><a href="/wiki/Ibogaine" title="Ibogaine">Ibogaine</a></li> <li><a href="/wiki/EA-3834" title="EA-3834">EA-3834</a></li> <li><a href="/wiki/Kolokol-1" title="Kolokol-1">Kolokol-1</a></li> <li><a href="/wiki/LSD" title="LSD">LSD-25</a></li> <li><a href="/wiki/PAVA_spray" title="PAVA spray">PAVA spray</a></li> <li><a href="/wiki/Psilocybin" title="Psilocybin">Psilocybin</a></li> <li><a href="/wiki/Incapacitating_agent#Sleeping_gas" title="Incapacitating agent">Sleeping gas</a></li> <li><a href="/wiki/Carfentanil" title="Carfentanil">Carfentanil</a></li> <li><a href="/wiki/N-Ethyl-3-piperidyl_benzilate" title="N-Ethyl-3-piperidyl benzilate">JB-318</a></li> <li><a href="/wiki/N-Methyl-3-piperidyl_benzilate" title="N-Methyl-3-piperidyl benzilate">JB-336</a></li> <li><a href="/wiki/CS-27349" title="CS-27349">CS-27349</a></li> <li><a href="/wiki/CAR-226,086" title="CAR-226,086">CAR-226,086</a></li> <li><a href="/wiki/CAR-301,060" title="CAR-301,060">CAR-301,060</a></li> <li><a href="/wiki/CAR-302,196" title="CAR-302,196">CAR-302,196</a></li> <li><a href="/wiki/CAR-302,282" title="CAR-302,282">CAR-302,282</a></li> <li><a href="/wiki/CAR-302,668" title="CAR-302,668">CAR-302,668</a></li> <li><a href="/wiki/Benperidol" title="Benperidol">Benperidol</a></li> <li><a href="/wiki/Desflurane" title="Desflurane">Desflurane</a></li> <li><a href="/wiki/Enflurane" title="Enflurane">Enflurane</a></li> <li><a href="/wiki/Bufotenin" title="Bufotenin">Bufotenin</a></li> <li><a href="/wiki/Isoflurane" title="Isoflurane">Isoflurane</a></li> <li><a href="/wiki/Halothane" title="Halothane">Halothane</a></li> <li><a href="/wiki/Sevoflurane" title="Sevoflurane">Sevoflurane</a></li> <li><a href="/wiki/Pentazocine" title="Pentazocine">Pentazocine</a></li> <li><a href="/wiki/Procarbazine" title="Procarbazine">Procarbazine</a></li> <li><a href="/wiki/Fluphenazine" title="Fluphenazine">Fluphenazine</a></li> <li><a href="/wiki/Chlorpromazine" title="Chlorpromazine">Chlorpromazine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Tear_gas" title="Tear gas">Lachrymatory<br />agents</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/Xylyl_bromide" title="Xylyl bromide">Xylyl bromide</a></li> <li><a href="/wiki/Pepper_spray" title="Pepper spray">Pepper spray</a> (OC)</li> <li><a href="/wiki/Mace_(spray)" title="Mace (spray)">Mace (spray)</a></li> <li><a href="/wiki/Phenacyl_chloride" title="Phenacyl chloride">CN</a></li> <li><a href="/wiki/CS_gas" title="CS gas">CS</a></li> <li><a href="/wiki/CR_gas" title="CR gas">CR</a></li> <li><a href="/wiki/CNS_(chemical_weapon)" title="CNS (chemical weapon)">CNS</a></li> <li><a href="/wiki/Benzyl_chloride" title="Benzyl chloride">Benzyl chloride</a></li> <li><a href="/wiki/Benzyl_bromide" title="Benzyl bromide">Benzyl bromide</a></li> <li><a href="/wiki/Benzyl_iodide" title="Benzyl iodide">Benzyl iodide</a></li> <li><a href="/wiki/Bromobenzyl_cyanide" title="Bromobenzyl cyanide">Bromobenzyl cyanide</a></li> <li><a href="/wiki/Thiophosgene" title="Thiophosgene">Thiophosgene</a></li> <li><a href="/wiki/Chloroacetone" title="Chloroacetone">Chloroacetone</a></li> <li><a href="/wiki/Bromoacetone" title="Bromoacetone">Bromoacetone</a></li> <li><a href="/wiki/Bromomethyl_ethyl_ketone" title="Bromomethyl ethyl ketone">Bromomethyl ethyl ketone</a></li> <li><a href="/wiki/Acrolein" title="Acrolein">Acrolein</a></li> <li><a href="/wiki/Phenacyl_bromide" title="Phenacyl bromide">Phenacyl bromide</a></li> <li><a href="/wiki/Chloroacetophenone_oxime" title="Chloroacetophenone oxime">Chloroacetophenone oxime</a></li> <li><a href="/wiki/Ethyl_bromoacetate" title="Ethyl bromoacetate">Ethyl bromoacetate</a></li> <li><a href="/wiki/Ethyl_iodoacetate" title="Ethyl iodoacetate">Ethyl iodoacetate</a></li> <li><a href="/wiki/Iodoacetone" title="Iodoacetone">Iodoacetone</a></li> <li><a href="/wiki/Allyl_isothiocyanate" title="Allyl isothiocyanate">Allyl isothiocyanate</a></li> <li><a href="/wiki/Hexamethylene_diisocyanate" title="Hexamethylene diisocyanate">Hexamethylene diisocyanate</a></li> <li><a href="/wiki/Crotonaldehyde" title="Crotonaldehyde">Crotonaldehyde</a></li> <li><a href="/wiki/DRC-5593" title="DRC-5593">DRC-5593</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Malodorant" title="Malodorant">Malodorant</a> agents</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/Thioacetone" title="Thioacetone">Thioacetone</a></li> <li><a href="/wiki/Allicin" title="Allicin">Allicin</a></li> <li><a href="/wiki/Skatole" title="Skatole">Skatole</a></li> <li><a href="/wiki/Cadaverine" title="Cadaverine">Cadaverine</a></li> <li><a href="/wiki/Putrescine" title="Putrescine">Putrescine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Cornea-clouding agents</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/Lewisite" title="Lewisite">Lewisite</a></li> <li><a href="/wiki/Phosgene_oxime" title="Phosgene oxime">CX</a></li> <li><a href="/wiki/KB-16" title="KB-16">KB-16</a></li> <li><a href="/wiki/Methyl_cyanoacrylate" title="Methyl cyanoacrylate">Methyl cyanoacrylate</a></li> <li><a href="/wiki/N-Methylmorpholine" title="N-Methylmorpholine">N-Methylmorpholine</a></li> <li><a href="/wiki/Allyl_alcohol" title="Allyl alcohol">Allyl alcohol</a></li> <li><a href="/wiki/Osmium_tetroxide" title="Osmium tetroxide">Osmium tetroxide</a></li> <li><a href="/wiki/Acrolein" title="Acrolein">Acrolein</a></li> <li><a href="/wiki/Cacodyl_cyanide" title="Cacodyl cyanide">Cacodyl cyanide</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Biological toxins</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/Abrin" title="Abrin">Abrin</a></li> <li><a href="/wiki/Aconitine" title="Aconitine">Aconitine</a></li> <li><a href="/wiki/Cyclopiazonic_acid" title="Cyclopiazonic acid">Cyclopiazonic acid</a></li> <li><a href="/wiki/Histrionicotoxins" title="Histrionicotoxins">Histrionicotoxins</a></li> <li><a href="/wiki/Aflatoxins" class="mw-redirect" title="Aflatoxins">Aflatoxins</a></li> <li><a href="/wiki/Anatoxin-a" title="Anatoxin-a">Anatoxin-a</a></li> <li><a href="/wiki/Batrachotoxin" title="Batrachotoxin">Batrachotoxin</a></li> <li><a href="/wiki/Botulinum_toxin" title="Botulinum toxin">Botulinum toxin</a></li> <li><a href="/wiki/Brevetoxin" title="Brevetoxin">Brevetoxin</a></li> <li><a href="/wiki/Ciguatoxin" title="Ciguatoxin">Ciguatoxin</a></li> <li><a href="/wiki/Domoic_acid" title="Domoic acid">Domoic acid</a></li> <li><a href="/wiki/Enterotoxin_type_B" title="Enterotoxin type B">Enterotoxin type B</a></li> <li><a href="/wiki/Grayanotoxin" title="Grayanotoxin">Grayanotoxin</a></li> <li><a href="/wiki/Guanitoxin" title="Guanitoxin">Guanitoxin</a></li> <li><a href="/wiki/Maitotoxin" title="Maitotoxin">Maitotoxin</a></li> <li><a href="/wiki/Modeccin" title="Modeccin">Modeccin</a></li> <li><a href="/wiki/Palytoxin" title="Palytoxin">Palytoxin</a></li> <li><a href="/wiki/Ricin" title="Ricin">Ricin</a></li> <li><a href="/wiki/Saxitoxin" title="Saxitoxin">Saxitoxin</a></li> <li><a href="/wiki/Shiga_toxin" title="Shiga toxin">Shiga toxin</a></li> <li><a href="/wiki/T-2_mycotoxin" title="T-2 mycotoxin">T-2 mycotoxin</a></li> <li><a href="/wiki/Tetanospasmin" class="mw-redirect" title="Tetanospasmin">Tetanospasmin</a></li> <li><a href="/wiki/Tetrodotoxin" title="Tetrodotoxin">Tetrodotoxin</a></li> <li><a href="/wiki/Volkensin" title="Volkensin">Volkensin</a></li> <li><a href="/wiki/Veratridine" title="Veratridine">Veratridine</a></li></ul> </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/Methyl_fluoroacetate" title="Methyl fluoroacetate">Methyl fluoroacetate</a></li> <li><a href="/wiki/Napalm" title="Napalm">Napalm</a> (variants and mixtures)</li> <li><a href="/wiki/Fluoroethyl_fluoroacetate" title="Fluoroethyl fluoroacetate">Fluoroethyl fluoroacetate</a></li> <li><a href="/wiki/Depleted_uranium" title="Depleted uranium">Depleted uranium</a> <ul><li>post-combustion <a href="/wiki/Uranium_oxide" title="Uranium oxide">uranium oxides</a></li></ul></li> <li><a href="/wiki/Plutonium" title="Plutonium">Plutonium</a> and <a href="/wiki/Plutonium_compounds" title="Plutonium compounds">its compounds</a></li> <li><a href="/wiki/Polonium" title="Polonium">Polonium</a></li> <li><a href="/wiki/White_phosphorus_munitions" class="mw-redirect" title="White phosphorus munitions">White phosphorus</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <ul><li><a href="/wiki/List_of_chemical_warfare_agents" title="List of chemical warfare agents">List of chemical warfare agents</a></li> <li><a href="/wiki/CB_military_symbol" title="CB military symbol">CB military symbol</a></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Salts_and_covalent_derivatives_of_the_cyanide_ion134" style="display:table;;padding:3px"><table class="nowraplinks mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit;table-layout:fixed;"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Cyanides" title="Template:Cyanides"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Cyanides" title="Template talk:Cyanides"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Cyanides" title="Special:EditPage/Template:Cyanides"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Salts_and_covalent_derivatives_of_the_cyanide_ion134" style="font-size:114%;margin:0 4em">Salts and covalent derivatives of the <a href="/wiki/Cyanide" title="Cyanide">cyanide</a> ion</div></th></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0;border-width:0;"><div style="padding:0"><div class="mw-collapsible-content" style="overflow-x:auto"> <table class="center"> <tbody><tr style="background-color:mistyrose"> <td><a href="/wiki/Hydrogen_cyanide" title="Hydrogen cyanide">HCN</a> </td> <td style="background-color:white;color:inherit;border:none"> </td> <td style="background-color:white;color:inherit;border:none" colspan="11" rowspan="3"> </td> <td style="background-color:white;color:inherit;border:none" colspan="5"> </td> <td>He </td></tr> <tr style="background-color:mistyrose;color:black;"> <td><a href="/wiki/Lithium_cyanide" title="Lithium cyanide">LiCN</a> </td> <td><a href="/w/index.php?title=Beryllium_cyanide&action=edit&redlink=1" class="new" title="Beryllium cyanide (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Be(CN)<sub class="template-chem2-sub">2</sub></span></a> </td> <td><a href="/w/index.php?title=Boron_cyanide&action=edit&redlink=1" class="new" title="Boron cyanide (page does not exist)">B(CN)<sub>3</sub></a> </td> <td><a href="/wiki/Tetracyanomethane" title="Tetracyanomethane">C(CN)<sub>4</sub></a><br /><a href="/wiki/Dicyanoacetylene" title="Dicyanoacetylene">C<sub>2</sub>(CN)<sub>2</sub></a> </td> <td><a href="/wiki/Ammonium_cyanide" title="Ammonium cyanide"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">NH<sub class="template-chem2-sub">4</sub>CN</span></a><br /><a href="/wiki/Nitrosyl_cyanide" title="Nitrosyl cyanide">ONCN</a><br /><a href="/wiki/Nitryl_cyanide" title="Nitryl cyanide"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">O<sub class="template-chem2-sub">2</sub>NCN</span></a><br /><a href="/wiki/Cyanogen_azide" title="Cyanogen azide"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">N<sub class="template-chem2-sub">3</sub>CN</span></a> </td> <td><a href="/wiki/Cyanate" title="Cyanate"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">OCN<sup class="template-chem2-sup">−</sup></span></a><br /><a href="/wiki/Isocyanate" title="Isocyanate">-NCO</a><br /><a href="/w/index.php?title=Dicyanoether&action=edit&redlink=1" class="new" title="Dicyanoether (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">O(CN)<sub class="template-chem2-sub">2</sub></span></a> </td> <td><a href="/wiki/Cyanogen_fluoride" title="Cyanogen fluoride">FCN</a> </td> <td>Ne </td></tr> <tr style="background-color:mistyrose;color:black;"> <td><a href="/wiki/Sodium_cyanide" title="Sodium cyanide">NaCN</a> </td> <td><a href="/wiki/Magnesium_cyanide" title="Magnesium cyanide"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Mg(CN)<sub class="template-chem2-sub">2</sub></span></a> </td> <td><a href="/wiki/Aluminium_cyanide" title="Aluminium cyanide"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Al(CN)<sub class="template-chem2-sub">3</sub></span></a> </td> <td><a href="/w/index.php?title=Silicon_tetracyanide&action=edit&redlink=1" class="new" title="Silicon tetracyanide (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Si(CN)<sub class="template-chem2-sub">4</sub></span></a><br /><a href="/wiki/Trimethylsilyl_cyanide" title="Trimethylsilyl cyanide"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">(CH<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">3</sub>SiCN</span></a> </td> <td><a href="/wiki/Phosphorus_tricyanide" title="Phosphorus tricyanide"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">P(CN)<sub class="template-chem2-sub">3</sub></span></a> </td> <td><a href="/wiki/Thiocyanate" title="Thiocyanate"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">SCN<sup class="template-chem2-sup">−</sup></span></a><br /><a href="/wiki/Isothiocyanate" title="Isothiocyanate">-NCS</a><br /><a href="/wiki/Thiocyanogen" title="Thiocyanogen"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">(SCN)<sub class="template-chem2-sub">2</sub></span></a><br /><a href="/wiki/Sulfur_dicyanide" title="Sulfur dicyanide"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">S(CN)<sub class="template-chem2-sub">2</sub></span></a> </td> <td><a href="/wiki/Cyanogen_chloride" title="Cyanogen chloride">ClCN</a> </td> <td>Ar </td></tr> <tr style="background-color:mistyrose;color:black;"> <td><a href="/wiki/Potassium_cyanide" title="Potassium cyanide">KCN</a> </td> <td><a href="/wiki/Calcium_cyanide" title="Calcium cyanide"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Ca(CN)<sub class="template-chem2-sub">2</sub></span></a> </td> <td style="background-color:white;color:inherit;border:none"> </td> <td><a href="/w/index.php?title=Scandium_cyanide&action=edit&redlink=1" class="new" title="Scandium cyanide (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Sc(CN)<sub class="template-chem2-sub">3</sub></span></a> </td> <td>Ti </td> <td>V </td> <td><a href="/wiki/Potassium_hexacyanochromate(III)" title="Potassium hexacyanochromate(III)">Cr(CN)<sub>6</sub><sup>3−</sup></a> </td> <td>Mn </td> <td><a href="/wiki/Iron(II)_cyanide" title="Iron(II) cyanide">Fe(CN)<sub>2</sub></a><br /><a href="/wiki/Ferrocyanide" title="Ferrocyanide">Fe(CN)<sub>6</sub><sup>4−</sup></a><br /><a href="/wiki/Ferricyanide" title="Ferricyanide">Fe(CN)<sub>6</sub><sup>3−</sup></a> </td> <td><a href="/wiki/Cobalt(II)_cyanide" title="Cobalt(II) cyanide"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Co(CN)<sub class="template-chem2-sub">2</sub></span></a><br /><a href="/wiki/Pentacyanocobaltate" title="Pentacyanocobaltate">Co(CN)<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1.2em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline">3−</sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">5</sub></span></span></a> </td> <td><a href="/wiki/Nickel_dicyanide" title="Nickel dicyanide"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Ni(CN)<sub class="template-chem2-sub">2</sub></span></a><br /><a href="/wiki/Cyanonickelate" title="Cyanonickelate">Ni(CN)<sub>4</sub><sup>2−</sup></a><br /><a href="/w/index.php?title=Cyanonickelate(0)&action=edit&redlink=1" class="new" title="Cyanonickelate(0) (page does not exist)">Ni(CN)<sub>4</sub><sup>4−</sup></a> </td> <td><a href="/wiki/Copper(I)_cyanide" title="Copper(I) cyanide">CuCN</a> </td> <td><a href="/wiki/Zinc_cyanide" title="Zinc cyanide"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Zn(CN)<sub class="template-chem2-sub">2</sub></span></a> </td> <td><a href="/wiki/Gallium(III)_cyanide" title="Gallium(III) cyanide"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Ga(CN)<sub class="template-chem2-sub">3</sub></span></a> </td> <td><a href="/w/index.php?title=Germanium_dicyanide&action=edit&redlink=1" class="new" title="Germanium dicyanide (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Ge(CN)<sub class="template-chem2-sub">2</sub></span></a><br /><a href="/w/index.php?title=Germanium_tetracyanide&action=edit&redlink=1" class="new" title="Germanium tetracyanide (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Ge(CN)<sub class="template-chem2-sub">4</sub></span></a> </td> <td><a href="/w/index.php?title=Arsenic_tricyanide&action=edit&redlink=1" class="new" title="Arsenic tricyanide (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">As(CN)<sub class="template-chem2-sub">3</sub></span></a><br /><a href="/wiki/Cacodyl_cyanide" title="Cacodyl cyanide"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">(CH<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">2</sub>AsCN</span></a><br /><a href="/wiki/Diphenylcyanoarsine" title="Diphenylcyanoarsine"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">(C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">5</sub>)<sub class="template-chem2-sub">2</sub>AsCN</span></a> </td> <td><a href="/wiki/Selenocyanate" title="Selenocyanate"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">SeCN<sup class="template-chem2-sup">−</sup></span></a><br /><a href="/w/index.php?title=Selenocyanogen&action=edit&redlink=1" class="new" title="Selenocyanogen (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">(SeCN)<sub class="template-chem2-sub">2</sub></span></a><br /><a href="/w/index.php?title=Selenium_dicyanide&action=edit&redlink=1" class="new" title="Selenium dicyanide (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Se(CN)<sub class="template-chem2-sub">2</sub></span></a> </td> <td><a class="mw-selflink selflink">BrCN</a> </td> <td>Kr </td></tr> <tr style="background-color:mistyrose;color:black;"> <td><a href="/wiki/Rubidium_cyanide" title="Rubidium cyanide">RbCN</a> </td> <td><a href="/w/index.php?title=Strontium_cyanide&action=edit&redlink=1" class="new" title="Strontium cyanide (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Sr(CN)<sub class="template-chem2-sub">2</sub></span></a> </td> <td style="background-color:white;color:inherit;border:none"> </td> <td><a href="/w/index.php?title=Yttrium_cyanide&action=edit&redlink=1" class="new" title="Yttrium cyanide (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Y(CN)<sub class="template-chem2-sub">3</sub></span></a> </td> <td>Zr </td> <td>Nb </td> <td><a href="/wiki/Potassium_octacyanomolybdate(IV)" title="Potassium octacyanomolybdate(IV)">Mo(CN)<sub>8</sub><sup>4−</sup></a> </td> <td>Tc </td> <td>Ru </td> <td>Rh </td> <td><a href="/wiki/Palladium_dicyanide" title="Palladium dicyanide"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Pd(CN)<sub class="template-chem2-sub">2</sub></span></a> </td> <td><a href="/wiki/Silver_cyanide" title="Silver cyanide">AgCN</a> </td> <td><a href="/wiki/Cadmium_cyanide" title="Cadmium cyanide"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Cd(CN)<sub class="template-chem2-sub">2</sub></span></a> </td> <td><a href="/w/index.php?title=Indium_cyanide&action=edit&redlink=1" class="new" title="Indium cyanide (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">In(CN)<sub class="template-chem2-sub">3</sub></span></a> </td> <td><a href="/w/index.php?title=Tin(II)_cyanide&action=edit&redlink=1" class="new" title="Tin(II) cyanide (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Sn(CN)<sub class="template-chem2-sub">2</sub></span></a> </td> <td><a href="/w/index.php?title=Antimony_cyanide&action=edit&redlink=1" class="new" title="Antimony cyanide (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Sb(CN)<sub class="template-chem2-sub">3</sub></span></a> </td> <td><a href="/w/index.php?title=Tellurium_dicyanide&action=edit&redlink=1" class="new" title="Tellurium dicyanide (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Te(CN)<sub class="template-chem2-sub">2</sub></span></a><br /><a href="/w/index.php?title=Tellurium_tetracyanide&action=edit&redlink=1" class="new" title="Tellurium tetracyanide (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Te(CN)<sub class="template-chem2-sub">4</sub></span></a> </td> <td><a href="/wiki/Cyanogen_iodide" title="Cyanogen iodide">ICN</a> </td> <td>Xe </td></tr> <tr style="background-color:mistyrose;color:black;"> <td><a href="/wiki/Caesium_cyanide" title="Caesium cyanide">CsCN</a> </td> <td><a href="/wiki/Barium_cyanide" title="Barium cyanide"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Ba(CN)<sub class="template-chem2-sub">2</sub></span></a> </td> <td style="background-color:white;color:inherit;border:none">* </td> <td><a href="/w/index.php?title=Lutetium(III)_cyanide&action=edit&redlink=1" class="new" title="Lutetium(III) cyanide (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Lu(CN)<sub class="template-chem2-sub">3</sub></span></a> </td> <td>Hf </td> <td>Ta </td> <td><a href="/w/index.php?title=Potassium_octacyanotungstate(IV)&action=edit&redlink=1" class="new" title="Potassium octacyanotungstate(IV) (page does not exist)">W(CN)<sub>8</sub><sup>4−</sup></a> </td> <td>Re </td> <td>Os </td> <td>Ir </td> <td><a href="/wiki/Platinocyanide" title="Platinocyanide">Pt(CN)<sub>4</sub><sup>2-</sup></a><br /><a href="/w/index.php?title=Platinicyanide&action=edit&redlink=1" class="new" title="Platinicyanide (page does not exist)">Pt(CN)<sub>6</sub><sup>4-</sup></a><br /> </td> <td><a href="/wiki/Gold(I)_cyanide" title="Gold(I) cyanide">AuCN</a><br /><a href="/wiki/Potassium_dicyanoaurate" title="Potassium dicyanoaurate">Au(CN)<sub>2</sub><sup>−</sup></a> </td> <td><a href="/w/index.php?title=Mercury(I)_cyanide&action=edit&redlink=1" class="new" title="Mercury(I) cyanide (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Hg<sub class="template-chem2-sub">2</sub>(CN)<sub class="template-chem2-sub">2</sub></span></a><br /><a href="/wiki/Mercury(II)_cyanide" title="Mercury(II) cyanide"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Hg(CN)<sub class="template-chem2-sub">2</sub></span></a> </td> <td><a href="/w/index.php?title=Thallium(I)_cyanide&action=edit&redlink=1" class="new" title="Thallium(I) cyanide (page does not exist)">TlCN</a> </td> <td><a href="/w/index.php?title=Lead_cyanide&action=edit&redlink=1" class="new" title="Lead cyanide (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Pb(CN)<sub class="template-chem2-sub">2</sub></span></a> </td> <td><a href="/w/index.php?title=Bismuth(III)_cyanide&action=edit&redlink=1" class="new" title="Bismuth(III) cyanide (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Bi(CN)<sub class="template-chem2-sub">3</sub></span></a> </td> <td>Po </td> <td>At </td> <td>Rn </td></tr> <tr style="background-color:mistyrose;color:black;"> <td>Fr </td> <td>Ra </td> <td style="background-color:white;color:inherit;border:none">** </td> <td>Lr </td> <td>Rf </td> <td>Db </td> <td>Sg </td> <td>Bh </td> <td>Hs </td> <td>Mt </td> <td>Ds </td> <td>Rg </td> <td>Cn </td> <td>Nh </td> <td>Fl </td> <td>Mc </td> <td>Lv </td> <td>Ts </td> <td>Og </td></tr> <tr> <td style="background-color:white;color:inherit;border:none" colspan="2" rowspan="3"> </td> <td style="background-color:white;color:inherit;border:none" colspan="20">  </td></tr> <tr style="background-color:mistyrose;color:black;"> <td style="background-color:white;color:inherit;border:none">* </td> <td><a href="/w/index.php?title=Lanthanum_cyanide&action=edit&redlink=1" class="new" title="Lanthanum cyanide (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">La(CN)<sub class="template-chem2-sub">3</sub></span></a> </td> <td><a href="/w/index.php?title=Cerium(III)_cyanide&action=edit&redlink=1" class="new" title="Cerium(III) cyanide (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Ce(CN)<sub class="template-chem2-sub">3</sub></span></a><br /> <a href="/w/index.php?title=Cerium(IV)_cyanide&action=edit&redlink=1" class="new" title="Cerium(IV) cyanide (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Ce(CN)<sub class="template-chem2-sub">4</sub></span></a> </td> <td><a href="/w/index.php?title=Praseodymium(III)_cyanide&action=edit&redlink=1" class="new" title="Praseodymium(III) cyanide (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Pr(CN)<sub class="template-chem2-sub">3</sub></span></a> </td> <td>Nd </td> <td>Pm </td> <td><a href="/w/index.php?title=Samarium(III)_cyanide&action=edit&redlink=1" class="new" title="Samarium(III) cyanide (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Sm(CN)<sub class="template-chem2-sub">3</sub></span></a> </td> <td><a href="/w/index.php?title=Europium(III)_cyanide&action=edit&redlink=1" class="new" title="Europium(III) cyanide (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Eu(CN)<sub class="template-chem2-sub">3</sub></span></a> </td> <td><a href="/w/index.php?title=Gadolinium(III)_cyanide&action=edit&redlink=1" class="new" title="Gadolinium(III) cyanide (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Gd(CN)<sub class="template-chem2-sub">3</sub></span></a> </td> <td>Tb </td> <td><a href="/w/index.php?title=Dysprosium(III)_cyanide&action=edit&redlink=1" class="new" title="Dysprosium(III) cyanide (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Dy(CN)<sub class="template-chem2-sub">3</sub></span></a> </td> <td><a href="/w/index.php?title=Holmium(III)_cyanide&action=edit&redlink=1" class="new" title="Holmium(III) cyanide (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Ho(CN)<sub class="template-chem2-sub">3</sub></span></a> </td> <td>Er </td> <td>Tm </td> <td><a href="/wiki/Ytterbium(III)_cyanide" title="Ytterbium(III) cyanide"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Yb(CN)<sub class="template-chem2-sub">3</sub></span></a> </td></tr> <tr style="background-color:mistyrose;color:black;"> <td style="background-color:white;color:inherit;border:none">** </td> <td><a href="/w/index.php?title=Actinium(III)_cyanide&action=edit&redlink=1" class="new" title="Actinium(III) cyanide (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Ac(CN)<sub class="template-chem2-sub">3</sub></span></a> </td> <td><a href="/w/index.php?title=Thorium(IV)_cyanide&action=edit&redlink=1" class="new" title="Thorium(IV) cyanide (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Th(CN)<sub class="template-chem2-sub">4</sub></span></a> </td> <td>Pa </td> <td><a href="/w/index.php?title=Uranyl_cyanide&action=edit&redlink=1" class="new" title="Uranyl cyanide (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">UO<sub class="template-chem2-sub">2</sub>(CN)<sub 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