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class="firstHeading mw-first-heading"><span class="mw-page-title-main">Phosgene oxime</span></h1> <div id="p-lang-btn" class="vector-dropdown mw-portlet mw-portlet-lang" > <input type="checkbox" id="p-lang-btn-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-p-lang-btn" class="vector-dropdown-checkbox mw-interlanguage-selector" aria-label="Go to an article in another language. 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mw-list-item"><a href="https://azb.wikipedia.org/wiki/%D9%81%D8%B3%DA%98%D9%86_%D8%A7%D9%88%DA%A9%D8%B3%DB%8C%D9%88%D9%85" title="فسژن اوکسیوم – South Azerbaijani" lang="azb" hreflang="azb" data-title="فسژن اوکسیوم" 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/Fosgenoxim" title="Fosgenoxim – Czech" lang="cs" hreflang="cs" data-title="Fosgenoxim" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Oxima_de_fosgeno" title="Oxima de fosgeno – Spanish" lang="es" hreflang="es" data-title="Oxima de fosgeno" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D9%81%D8%B3%DA%98%D9%86_%D8%A7%DA%A9%D8%B3%DB%8C%D9%85" title="فسژن اکسیم – Persian" lang="fa" hreflang="fa" data-title="فسژن اکسیم" 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/Oxime_de_phosg%C3%A8ne" title="Oxime de phosgène – French" lang="fr" hreflang="fr" data-title="Oxime de phosgène" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Oksima_fosgena" title="Oksima fosgena – Indonesian" lang="id" hreflang="id" data-title="Oksima fosgena" data-language-autonym="Bahasa Indonesia" data-language-local-name="Indonesian" class="interlanguage-link-target"><span>Bahasa Indonesia</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%83%9B%E3%82%B9%E3%82%B2%E3%83%B3%E3%82%AA%E3%82%AD%E3%82%B7%E3%83%A0" title="ホスゲンオキシム – Japanese" lang="ja" hreflang="ja" data-title="ホスゲンオキシム" 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/Oksym_fosgenu" title="Oksym fosgenu – Polish" lang="pl" hreflang="pl" data-title="Oksym fosgenu" data-language-autonym="Polski" data-language-local-name="Polish" class="interlanguage-link-target"><span>Polski</span></a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%A4%D0%BE%D1%81%D0%B3%D0%B5%D0%BD%D0%BE%D0%BA%D1%81%D0%B8%D0%BC" title="Фосгеноксим – Russian" lang="ru" hreflang="ru" data-title="Фосгеноксим" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-simple mw-list-item"><a href="https://simple.wikipedia.org/wiki/Phosgene_oxime" title="Phosgene oxime – Simple English" lang="en-simple" hreflang="en-simple" data-title="Phosgene oxime" data-language-autonym="Simple English" data-language-local-name="Simple English" class="interlanguage-link-target"><span>Simple English</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Fozgen_oksim" title="Fozgen oksim – Serbian" lang="sr" hreflang="sr" data-title="Fozgen oksim" 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/Fozgen_oksim" 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<div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><style data-mw-deduplicate="TemplateStyles:r1084375498">.mw-parser-output .ib-chembox{border-collapse:collapse;text-align:left}.mw-parser-output .ib-chembox td,.mw-parser-output .ib-chembox th{border:1px solid #a2a9b1;width:40%}.mw-parser-output .ib-chembox td+td{width:60%}</style> <table class="infobox ib-chembox"> <caption>Phosgene oxime </caption> <tbody><tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:Phosgene-oxime-2D.png" class="mw-file-description" title="Full structural formula"><img alt="Full structural formula" src="//upload.wikimedia.org/wikipedia/commons/thumb/9/9c/Phosgene-oxime-2D.png/220px-Phosgene-oxime-2D.png" decoding="async" width="220" height="192" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/9c/Phosgene-oxime-2D.png/330px-Phosgene-oxime-2D.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/9c/Phosgene-oxime-2D.png/440px-Phosgene-oxime-2D.png 2x" data-file-width="1100" data-file-height="960" /></a></span> </td></tr> <tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:Phosgene-oxime-HF-3D-vdW.png" class="mw-file-description" title="Space-filling model"><img alt="Space-filling model" src="//upload.wikimedia.org/wikipedia/commons/thumb/f/fb/Phosgene-oxime-HF-3D-vdW.png/220px-Phosgene-oxime-HF-3D-vdW.png" decoding="async" width="220" height="230" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/fb/Phosgene-oxime-HF-3D-vdW.png/330px-Phosgene-oxime-HF-3D-vdW.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/fb/Phosgene-oxime-HF-3D-vdW.png/440px-Phosgene-oxime-HF-3D-vdW.png 2x" data-file-width="1054" data-file-height="1100" /></a></span><br /><div style="text-align:center;"><style data-mw-deduplicate="TemplateStyles:r981673959">.mw-parser-output .legend{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .legend-color{display:inline-block;min-width:1.25em;height:1.25em;line-height:1.25;margin:1px 0;text-align:center;border:1px solid black;background-color:transparent;color:black}.mw-parser-output .legend-text{}</style><div class="legend"><span class="legend-color mw-no-invert" style="background-color:black; color:white;"> </span> <a href="/wiki/Carbon" title="Carbon">Carbon</a>, C</div><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r981673959"><div class="legend"><span class="legend-color mw-no-invert" style="background-color:white; color:black;"> </span> <a href="/wiki/Hydrogen" title="Hydrogen">Hydrogen</a>, H</div><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r981673959"><div class="legend"><span class="legend-color mw-no-invert" style="background-color:red; color:black;"> </span> <a href="/wiki/Oxygen" title="Oxygen">Oxygen</a>, O</div><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r981673959"><div class="legend"><span class="legend-color mw-no-invert" style="background-color:blue; color:white;"> </span> <a href="/wiki/Nitrogen" title="Nitrogen">Nitrogen</a>, N</div><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r981673959"><div class="legend"><span class="legend-color mw-no-invert" style="background-color:lime; color:black;"> </span> <a href="/wiki/Chlorine" title="Chlorine">Chlorine</a>, Cl</div></div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Names </th></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Preferred_IUPAC_name" title="Preferred IUPAC name">Preferred IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0; max-width:22em;">1,1-Dichloro-<i>N</i>-hydroxymethanimine</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>CX</li><li>Dichloroformaldehyde oxime</li><li>Dichloroformaldoxime</li><li>Dichloroformoxime</li><li>Hydroxycarbonimidic dichloride</li></ul></div></div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Identifiers </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></div> </td> <td><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=1794-86-1">1794-86-1</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=Cl%2FC%28Cl%29%3DN%5CO">Interactive image</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChemSpider" title="ChemSpider">ChemSpider</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.chemspider.com"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.59024.html">59024</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/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/65582">65582</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/Unique_Ingredient_Identifier" title="Unique Ingredient Identifier">UNII</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="precision.fda.gov"><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/G45S3149SQ">G45S3149SQ</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CompTox_Chemicals_Dashboard" title="CompTox Chemicals Dashboard">CompTox Dashboard</a> <span style="font-weight:normal">(<abbr title="U.S. Environmental Protection Agency">EPA</abbr>)</span></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="comptox.epa.gov"><a rel="nofollow" class="external text" href="https://comptox.epa.gov/dashboard/chemical/details/DTXSID9075292">DTXSID9075292</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q3241634#P3117" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span></span></li></ul></div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal; background:transparent;"><div><a href="/wiki/International_Chemical_Identifier" title="International Chemical Identifier">InChI</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1S/CHCl2NO/c2-1(3)4-5/h5H<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: JIRJHEXNDQBKRZ-UHFFFAOYSA-N<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div></div></li><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1/CHCl2NO/c2-1(3)4-5/h5H</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: JIRJHEXNDQBKRZ-UHFFFAOYAP</div></div></li></ul> </div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal; background:transparent;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.6em; word-wrap:break-word; text-indent:-1.5em; text-align:left; font-size:97%; line-height:120%;">Cl/C(Cl)=N\O</div></li></ul> </div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Properties </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Chemical_formula" title="Chemical formula">Chemical formula</a></div> </td> <td><style data-mw-deduplicate="TemplateStyles:r1123817410">.mw-parser-output .template-chem2-su{display:inline-block;font-size:80%;line-height:1;vertical-align:-0.35em}.mw-parser-output .template-chem2-su>span{display:block;text-align:left}.mw-parser-output sub.template-chem2-sub{font-size:80%;vertical-align:-0.35em}.mw-parser-output sup.template-chem2-sup{font-size:80%;vertical-align:0.65em}</style><span class="chemf nowrap">Cl<sub class="template-chem2-sub">2</sub>CNOH</span>  </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td><span class="nowrap"><span data-sort-value="7002113930000000000♠"></span>113.93</span> g·mol<sup>−1</sup>   </td></tr> <tr> <td>Appearance </td> <td>colorless or white solid </td></tr> <tr> <td><a href="/wiki/Odor" title="Odor">Odor</a> </td> <td>Strong, disagreeable and irritating </td></tr> <tr> <td><a href="/wiki/Melting_point" title="Melting point">Melting point</a> </td> <td>35 to 40 °C (95 to 104 °F; 308 to 313 K)<sup id="cite_ref-ATSDR_1-1" class="reference"><a href="#cite_note-ATSDR-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Boiling_point" title="Boiling point">Boiling point</a> </td> <td>128 °C (262 °F; 401 K)<sup id="cite_ref-ATSDR_1-2" class="reference"><a href="#cite_note-ATSDR-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </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>70%<sup id="cite_ref-ATSDR_1-0" class="reference"><a href="#cite_note-ATSDR-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Hazards </th></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;"><b><a href="/wiki/Occupational_safety_and_health" title="Occupational safety and health">Occupational safety and health</a></b> (OHS/OSH): </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Main hazards</div> </td> <td>Highly toxic </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Related compounds </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Related compounds</div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a href="/wiki/Formaldoxime" title="Formaldoxime">Formaldoxime</a></li><li><a href="/wiki/Phosgene" title="Phosgene">Phosgene</a></li><li><a href="/wiki/Oxime" title="Oxime">Oxime</a></li></ul></div> </td></tr> <tr> <td colspan="2" style="text-align:left; background:#f8eaba; border:1px solid #a2a9b1;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Except where otherwise noted, data are given for materials in their <a href="/wiki/Standard_state" title="Standard state">standard state</a> (at 25 °C [77 °F], 100 kPa).</div> <div style="margin-top: 0.3em;"><div style="text-align:center;"><span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/12px-X_mark.svg.png" decoding="async" width="12" height="14" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/18px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/24px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span> <span class="reflink plainlinks nourlexpansion"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=464204793&page2=Phosgene+oxime">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>Phosgene oxime</b>, or <b>CX</b>, is an <a href="/wiki/Organic_compound" title="Organic compound">organic compound</a> with the <a href="/wiki/Chemical_formula" title="Chemical formula">formula</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap"><a href="/wiki/Chlorine" title="Chlorine">Cl</a><sub class="template-chem2-sub">2</sub><a href="/wiki/Carbon" title="Carbon">C</a>=<a href="/wiki/Nitrogen" title="Nitrogen">N</a>−<a href="/wiki/Oxygen" title="Oxygen">O</a><a href="/wiki/Hydrogen" title="Hydrogen">H</a></span>. It is a potent <a href="/wiki/Chemical_weapon" title="Chemical weapon">chemical weapon</a>, specifically a <a href="/wiki/Nettle_agent" title="Nettle agent">nettle agent</a>. The compound itself is a colorless solid, but impure samples are often yellowish liquids. It has a strong, disagreeable and irritating odor. It is used as a reagent in <a href="/wiki/Organic_chemistry" title="Organic chemistry">organic chemistry</a>.<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> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Preparation_and_reactions">Preparation and reactions</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phosgene_oxime&action=edit&section=1" title="Edit section: Preparation and reactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Phosgene oxime can be prepared by <a href="/wiki/Reduction_(chemistry)" class="mw-redirect" title="Reduction (chemistry)">reduction</a> of <a href="/wiki/Chloropicrin" title="Chloropicrin">chloropicrin</a> using a combination of <a href="/wiki/Tin" title="Tin">tin</a> metal and <a href="/wiki/Hydrochloric_acid" title="Hydrochloric acid">hydrochloric acid</a> as the source of the <a href="/wiki/Active_hydrogen" class="mw-redirect" title="Active hydrogen">active hydrogen</a> <a href="/wiki/Reducing_agent" title="Reducing agent">reducing agent</a>: </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Cl<sub class="template-chem2-sub">3</sub>CNO<sub class="template-chem2-sub">2</sub> + 4 [H] → Cl<sub class="template-chem2-sub">2</sub>C=N−OH + <a href="/wiki/Hydrogen_chloride" title="Hydrogen chloride">HCl</a> + H<sub class="template-chem2-sub">2</sub>O</span></dd></dl> <p>The observation of a transient violet color in the reaction suggests intermediate formation of <a href="/wiki/Trichloronitrosomethane" title="Trichloronitrosomethane">trichloronitrosomethane</a> (Cl<sub>3</sub>CNO). Early preparations, using stannous chloride as the reductant, also started with chloropicrin.<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> </p><p>The compound is <a href="/wiki/Electrophilic" class="mw-redirect" title="Electrophilic">electrophilic</a> and thus sensitive to <a href="/wiki/Nucleophiles" class="mw-redirect" title="Nucleophiles">nucleophiles</a>, including <a href="/wiki/Base_(chemistry)" title="Base (chemistry)">bases</a>, which destroy it: </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Cl<sub class="template-chem2-sub">2</sub>CNOH + 2 <a href="/wiki/Sodium_hydroxide" title="Sodium hydroxide">NaOH</a> → <a href="/wiki/Carbon_dioxide" title="Carbon dioxide">CO<sub class="template-chem2-sub">2</sub></a> + <a href="/wiki/Hydroxylamine" title="Hydroxylamine">NH<sub class="template-chem2-sub">2</sub>OH</a> + 2 <a href="/wiki/Sodium_chloride" title="Sodium chloride">NaCl</a> + H<sub class="template-chem2-sub">2</sub>O</span></dd></dl> <p>Phosgene oxime has been used to prepare <a href="/wiki/Heterocyclic_compound" title="Heterocyclic compound">heterocycles</a> that contain N-O bonds, such as <a href="/wiki/Isoxazole" title="Isoxazole">isoxazoles</a>.<sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p><p><a href="/wiki/Dehydrohalogenation" title="Dehydrohalogenation">Dehydrohalogenation</a> upon contact with <a href="/wiki/Mercuric_oxide" class="mw-redirect" title="Mercuric oxide">mercuric oxide</a> generates <a href="/w/index.php?title=Chlorine_fulminate&action=edit&redlink=1" class="new" title="Chlorine fulminate (page does not exist)">chlorine fulminate</a>, a reactive <a href="/wiki/Nitrile_oxide" class="mw-redirect" title="Nitrile oxide">nitrile oxide</a>:<sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Cl<sub class="template-chem2-sub">2</sub>CNOH → Cl−C≡N<sup class="template-chem2-sup">+</sup>−O<sup class="template-chem2-sup">−</sup> + HCl</span></dd></dl> <div class="mw-heading mw-heading2"><h2 id="Toxicity">Toxicity</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phosgene_oxime&action=edit&section=2" title="Edit section: Toxicity"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Phosgene oxime is classified as a <a href="/wiki/Blister_agent" title="Blister agent">vesicant</a> even though it does not produce blisters.<sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> It is <a href="/wiki/Toxic" class="mw-redirect" title="Toxic">toxic</a> by inhalation, ingestion, or skin contact. The effects of the poisoning occur almost immediately. No antidote for phosgene oxime poisoning is known. Generally, any treatment is supportive. Typical physical symptoms of CX exposure are as follows: </p> <ul><li>Skin: Blanching surrounded by an <a href="/wiki/Erythema" title="Erythema">erythematous</a> ring can be observed within 30 seconds of exposure. A <a href="/wiki/Wheal_response" class="mw-redirect" title="Wheal response">wheal</a> develops on exposed skin within 30 minutes. The original blanched area acquires a brown pigmentation by 24 hours. An <a href="/wiki/Eschar" title="Eschar">eschar</a> forms in the pigmented area by 1 week and sloughs after approximately 3 weeks. Initially, the effects of CX can easily be misidentified as <a href="/wiki/Mustard_gas" title="Mustard gas">mustard gas</a> exposure. However, the onset of skin irritation resulting from CX exposure is a great deal faster than mustard gas, which typically takes several hours or more to cause skin irritation.</li> <li>Eyes: Eye examination typically demonstrates <a href="/wiki/Conjunctivitis" title="Conjunctivitis">conjunctivitis</a>, <a href="/wiki/Lacrimation" class="mw-redirect" title="Lacrimation">lacrimation</a>, lid edema, and <a href="/wiki/Blepharospasm" title="Blepharospasm">blepharospasm</a> after even minute exposures. More severe exposures can result in <a href="/wiki/Keratitis" title="Keratitis">keratitis</a>, <a href="/wiki/Iritis" class="mw-redirect" title="Iritis">iritis</a>, <a href="/wiki/Corneal" class="mw-redirect" title="Corneal">corneal</a> perforation, and <a href="/wiki/Blindness" class="mw-redirect" title="Blindness">blindness</a>.</li> <li>Respiratory: Irritation of the <a href="/wiki/Mucous_membranes" class="mw-redirect" title="Mucous membranes">mucous membranes</a> may be observed on examination of the oropharynx and nose. Evidence of pulmonary edema, including rales and wheezes, may be noted on <a href="/wiki/Auscultation" title="Auscultation">auscultation</a>. <a href="/wiki/Pulmonary_embolism" title="Pulmonary embolism">Pulmonary thromboses</a> are prominent features of severe CX exposure.</li> <li>Gastrointestinal: Some animal data suggest that CX may cause hemorrhagic inflammatory changes in the GI tract.</li></ul> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phosgene_oxime&action=edit&section=3" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap"><ol class="references"> <li id="cite_note-ATSDR-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-ATSDR_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-ATSDR_1-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-ATSDR_1-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"><a rel="nofollow" class="external text" href="https://web.archive.org/web/20030802032513/http://www.atsdr.cdc.gov/MHMI/mmg167.html">ATSDR Medical Management Guidelines for Phosgene Oxime</a></span> </li> <li id="cite_note-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-2">^</a></b></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite id="CITEREFWangChen2017" class="citation book cs1">Wang, Xinyan; Chen, Wenwen (2017). "Dichloroformaldehyde Oxime". <i>Encyclopedia of Reagents for Organic Synthesis</i>. pp. 1–2. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2F047084289X.rn02011">10.1002/047084289X.rn02011</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9780470842898" title="Special:BookSources/9780470842898"><bdi>9780470842898</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Dichloroformaldehyde+Oxime&rft.btitle=Encyclopedia+of+Reagents+for+Organic+Synthesis&rft.pages=1-2&rft.date=2017&rft_id=info%3Adoi%2F10.1002%2F047084289X.rn02011&rft.isbn=9780470842898&rft.aulast=Wang&rft.aufirst=Xinyan&rft.au=Chen%2C+Wenwen&rfr_id=info%3Asid%2Fen.wikipedia.org%3APhosgene+oxime" class="Z3988"></span></span> </li> <li id="cite_note-3"><span class="mw-cite-backlink"><b><a href="#cite_ref-3">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFPrandtl,_W.Dollfus,_W.1932" class="citation journal cs1">Prandtl, W.; Dollfus, W. 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"Unstable Chloronitrile Oxide, ClCNO, and Its Stable Ring Dimer: Generation, Spectroscopy, and Structure". <i>The Journal of Physical Chemistry A</i>. <b>102</b> (25): 4939–4947. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/1998JPCA..102.4939P">1998JPCA..102.4939P</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2FJP981262E">10.1021/JP981262E</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+Journal+of+Physical+Chemistry+A&rft.atitle=Unstable+Chloronitrile+Oxide%2C+ClCNO%2C+and+Its+Stable+Ring+Dimer%3A+Generation%2C+Spectroscopy%2C+and+Structure&rft.volume=102&rft.issue=25&rft.pages=4939-4947&rft.date=1998&rft_id=info%3Adoi%2F10.1021%2FJP981262E&rft_id=info%3Abibcode%2F1998JPCA..102.4939P&rft.aulast=Pasinszki&rft.aufirst=Tibor&rft.au=Westwood%2C+Nicholas+P.+C.&rfr_id=info%3Asid%2Fen.wikipedia.org%3APhosgene+oxime" class="Z3988"></span></span> </li> <li id="cite_note-6"><span class="mw-cite-backlink"><b><a href="#cite_ref-6">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMcManusHuebner2005" class="citation journal cs1">McManus, J; Huebner, K (2005). <a rel="nofollow" class="external text" href="https://zenodo.org/record/1258826">"Vesicants"</a>. <i><a href="/wiki/Critical_Care_Clinics" title="Critical Care Clinics">Critical Care Clinics</a></i>. <b>21</b> (4): 707–718. <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%2Fj.ccc.2005.06.005">10.1016/j.ccc.2005.06.005</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/16168310">16168310</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Critical+Care+Clinics&rft.atitle=Vesicants&rft.volume=21&rft.issue=4&rft.pages=707-718&rft.date=2005&rft_id=info%3Adoi%2F10.1016%2Fj.ccc.2005.06.005&rft_id=info%3Apmid%2F16168310&rft.aulast=McManus&rft.aufirst=J&rft.au=Huebner%2C+K&rft_id=https%3A%2F%2Fzenodo.org%2Frecord%2F1258826&rfr_id=info%3Asid%2Fen.wikipedia.org%3APhosgene+oxime" class="Z3988"></span></span> </li> </ol></div></div> <div class="mw-heading mw-heading2"><h2 id="External_links">External links</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phosgene_oxime&action=edit&section=4" title="Edit section: External links"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a rel="nofollow" class="external text" href="http://www.emedicine.com/emerg/topic903.htm">EMedicine: Urticants, Phosgene Oxime</a></li> <li><a rel="nofollow" class="external text" href="https://web.archive.org/web/20131229033312/http://bioterrorism.slu.edu/bt/products/ahec_chem/scripts/PhosgeneOxime.pdf">Center for the Study of Bioterrorism: Phosgene Oxime</a></li> <li><a rel="nofollow" class="external text" href="https://web.archive.org/web/20060110155811/http://www.bt.cdc.gov/agent/phosgene-oxime/basics/facts.asp">Centers for Disease Control: Facts About Phosgene Oxime</a></li> <li><a rel="nofollow" class="external text" href="https://web.archive.org/web/20051122235728/http://www.vnh.org/MedAspChemBioWar/chapters/chapter_7.htm#Phosgene%20Oxime">Virtual Naval Hospital: Phosgene Oxime</a></li></ul> <style data-mw-deduplicate="TemplateStyles:r1235681985">.mw-parser-output .side-box{margin:4px 0;box-sizing:border-box;border:1px solid #aaa;font-size:88%;line-height:1.25em;background-color:var(--background-color-interactive-subtle,#f8f9fa);display:flow-root}.mw-parser-output .side-box-abovebelow,.mw-parser-output .side-box-text{padding:0.25em 0.9em}.mw-parser-output .side-box-image{padding:2px 0 2px 0.9em;text-align:center}.mw-parser-output .side-box-imageright{padding:2px 0.9em 2px 0;text-align:center}@media(min-width:500px){.mw-parser-output .side-box-flex{display:flex;align-items:center}.mw-parser-output .side-box-text{flex:1;min-width:0}}@media(min-width:720px){.mw-parser-output .side-box{width:238px}.mw-parser-output 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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_control" 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_control" 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 href="/wiki/Cyanogen_bromide" title="Cyanogen bromide">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 class="mw-selflink selflink">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></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/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/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/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></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/Phencyclidine" title="Phencyclidine">EA-2148</a></li> <li><a href="/wiki/EA-3167" title="EA-3167">EA-3167</a></li> <li><a href="/wiki/EA-3443" title="EA-3443">EA-3443</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 class="mw-selflink selflink">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></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 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