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class="vector-toc-numb">2</span> <span>Substituted pyrazoles</span> </div> </a> <ul id="toc-Substituted_pyrazoles-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Preparation_and_reactions" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Preparation_and_reactions"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Preparation and reactions</span> </div> </a> <button aria-controls="toc-Preparation_and_reactions-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Preparation and reactions subsection</span> </button> <ul id="toc-Preparation_and_reactions-sublist" class="vector-toc-list"> <li id="toc-History" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#History"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.1</span> <span>History</span> </div> </a> <ul id="toc-History-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Conversion_to_scorpionates" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Conversion_to_scorpionates"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.2</span> <span>Conversion to scorpionates</span> </div> </a> <ul id="toc-Conversion_to_scorpionates-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-3,5-Diphenyl-1H-pyrazole" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#3,5-Diphenyl-1H-pyrazole"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.3</span> <span>3,5-Diphenyl-1<i>H</i>-pyrazole</span> </div> </a> <ul id="toc-3,5-Diphenyl-1H-pyrazole-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Occurrence_and_uses" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Occurrence_and_uses"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Occurrence and uses</span> </div> </a> <ul id="toc-Occurrence_and_uses-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-See_also" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#See_also"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>See also</span> </div> </a> <ul id="toc-See_also-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</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">7</span> <span>Further reading</span> </div> </a> <ul id="toc-Further_reading-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav aria-label="Contents" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" > <input type="checkbox" id="vector-page-titlebar-toc-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-titlebar-toc" class="vector-dropdown-checkbox " aria-label="Toggle the table of contents" > <label id="vector-page-titlebar-toc-label" for="vector-page-titlebar-toc-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" ><span 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Available in 28 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-28" 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">28 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%A8%D9%8A%D8%B1%D8%A7%D8%B2%D9%88%D9%84" title="بيرازول – Arabic" lang="ar" hreflang="ar" data-title="بيرازول" 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/%D9%BE%DB%8C%D8%B1%D8%A7%D8%B2%D9%88%D9%84" title="پیرازول – South Azerbaijani" lang="azb" hreflang="azb" data-title="پیرازول" 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/Pyrazol" title="Pyrazol – Czech" lang="cs" hreflang="cs" data-title="Pyrazol" 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/Pyrazol" title="Pyrazol – German" lang="de" hreflang="de" data-title="Pyrazol" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/%CE%A0%CF%85%CF%81%CE%B1%CE%B6%CF%8C%CE%BB%CE%B9%CE%BF" title="Πυραζόλιο – Greek" lang="el" hreflang="el" data-title="Πυραζόλιο" data-language-autonym="Ελληνικά" data-language-local-name="Greek" class="interlanguage-link-target"><span>Ελληνικά</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Pirazol" title="Pirazol – Spanish" lang="es" hreflang="es" data-title="Pirazol" 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/Pirazolo" title="Pirazolo – Esperanto" lang="eo" hreflang="eo" data-title="Pirazolo" data-language-autonym="Esperanto" data-language-local-name="Esperanto" class="interlanguage-link-target"><span>Esperanto</span></a></li><li class="interlanguage-link interwiki-eu mw-list-item"><a href="https://eu.wikipedia.org/wiki/Pirazol" title="Pirazol – Basque" lang="eu" hreflang="eu" data-title="Pirazol" data-language-autonym="Euskara" data-language-local-name="Basque" class="interlanguage-link-target"><span>Euskara</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D9%BE%DB%8C%D8%B1%D8%A7%D8%B2%D9%88%D9%84" title="پیرازول – Persian" lang="fa" hreflang="fa" data-title="پیرازول" 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/Pyrazole" title="Pyrazole – French" lang="fr" hreflang="fr" data-title="Pyrazole" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%ED%94%BC%EB%9D%BC%EC%A1%B8" title="피라졸 – Korean" lang="ko" hreflang="ko" data-title="피라졸" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-hi mw-list-item"><a href="https://hi.wikipedia.org/wiki/%E0%A4%AA%E0%A4%BE%E0%A4%87%E0%A4%B0%E0%A4%BE%E0%A4%9C%E0%A5%8B%E0%A4%B2" title="पाइराजोल – Hindi" lang="hi" hreflang="hi" data-title="पाइराजोल" data-language-autonym="हिन्दी" data-language-local-name="Hindi" class="interlanguage-link-target"><span>हिन्दी</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Pirazolo" title="Pirazolo – Italian" lang="it" hreflang="it" data-title="Pirazolo" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-lv mw-list-item"><a href="https://lv.wikipedia.org/wiki/Pirazols" title="Pirazols – Latvian" lang="lv" hreflang="lv" data-title="Pirazols" data-language-autonym="Latviešu" data-language-local-name="Latvian" class="interlanguage-link-target"><span>Latviešu</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Pirazol" title="Pirazol – Hungarian" lang="hu" hreflang="hu" data-title="Pirazol" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Pyrazool" title="Pyrazool – Dutch" lang="nl" hreflang="nl" data-title="Pyrazool" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%83%94%E3%83%A9%E3%82%BE%E3%83%BC%E3%83%AB" title="ピラゾール – Japanese" lang="ja" hreflang="ja" data-title="ピラゾール" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Pirazol" title="Pirazol – Polish" lang="pl" hreflang="pl" data-title="Pirazol" 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/Pirazol" title="Pirazol – Portuguese" lang="pt" hreflang="pt" data-title="Pirazol" 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/Pirazol" title="Pirazol – Romanian" lang="ro" hreflang="ro" data-title="Pirazol" 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%9F%D0%B8%D1%80%D0%B0%D0%B7%D0%BE%D0%BB" title="Пиразол – Russian" lang="ru" hreflang="ru" data-title="Пиразол" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sk mw-list-item"><a href="https://sk.wikipedia.org/wiki/Pyrazol" title="Pyrazol – Slovak" lang="sk" hreflang="sk" data-title="Pyrazol" data-language-autonym="Slovenčina" data-language-local-name="Slovak" class="interlanguage-link-target"><span>Slovenčina</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Pirazol" title="Pirazol – Serbian" lang="sr" hreflang="sr" data-title="Pirazol" 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/Pirazol" title="Pirazol – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Pirazol" 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/Pyratsoli" title="Pyratsoli – Finnish" lang="fi" hreflang="fi" data-title="Pyratsoli" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-sv mw-list-item"><a href="https://sv.wikipedia.org/wiki/Pyrazol" title="Pyrazol – Swedish" lang="sv" hreflang="sv" data-title="Pyrazol" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%9F%D1%96%D1%80%D0%B0%D0%B7%D0%BE%D0%BB" title="Піразол – Ukrainian" lang="uk" hreflang="uk" data-title="Піразол" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E5%90%A1%E5%94%91" title="吡唑 – Chinese" lang="zh" hreflang="zh" data-title="吡唑" data-language-autonym="中文" data-language-local-name="Chinese" class="interlanguage-link-target"><span>中文</span></a></li> </ul> <div class="after-portlet after-portlet-lang"><span class="wb-langlinks-edit wb-langlinks-link"><a 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data-unpinned-container-id="vector-appearance-unpinned-container" > <div class="vector-pinnable-header-label">Appearance</div> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-pin-button" data-event-name="pinnable-header.vector-appearance.pin">move to sidebar</button> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-unpin-button" data-event-name="pinnable-header.vector-appearance.unpin">hide</button> </div> </div> </div> </nav> </div> </div> <div id="bodyContent" class="vector-body" aria-labelledby="firstHeading" data-mw-ve-target-container> <div class="vector-body-before-content"> <div class="mw-indicators"> </div> <div id="siteSub" class="noprint">From Wikipedia, the free encyclopedia</div> </div> <div id="contentSub"><div id="mw-content-subtitle"></div></div> <div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><p> <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> </p> <table class="infobox ib-chembox"> <caption>Pyrazole </caption> <tbody><tr> <td colspan="2" class="borderless" style="text-align:center"> <table border="0" style="width:100%;display:inline-table;"> <tbody><tr> <td style="border-right:1px solid #aaa; width:50%;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Pyrazole_2D_full_aromatic.svg" class="mw-file-description"><img alt="Full structural formula" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6f/Pyrazole_2D_full_aromatic.svg/110px-Pyrazole_2D_full_aromatic.svg.png" decoding="async" width="110" height="128" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6f/Pyrazole_2D_full_aromatic.svg/165px-Pyrazole_2D_full_aromatic.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6f/Pyrazole_2D_full_aromatic.svg/220px-Pyrazole_2D_full_aromatic.svg.png 2x" data-file-width="512" data-file-height="598" /></a><figcaption></figcaption></figure> </td> <td style="width:50%;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Pyrazole_2D_numbered.svg" class="mw-file-description"><img alt="Skeletal formula with numbers" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a5/Pyrazole_2D_numbered.svg/110px-Pyrazole_2D_numbered.svg.png" decoding="async" width="110" height="130" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a5/Pyrazole_2D_numbered.svg/165px-Pyrazole_2D_numbered.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a5/Pyrazole_2D_numbered.svg/220px-Pyrazole_2D_numbered.svg.png 2x" data-file-width="512" data-file-height="604" /></a><figcaption></figcaption></figure> </td></tr></tbody></table> </td></tr> <tr> <td colspan="2" class="borderless" style="text-align:center"> <table border="0" style="width:100%;display:inline-table;"> <tbody><tr> <td style="border-right:1px solid #aaa; width:50%;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Pyrazole-3D-balls.png" class="mw-file-description"><img alt="Ball-and-stick model" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/68/Pyrazole-3D-balls.png/110px-Pyrazole-3D-balls.png" decoding="async" width="110" height="121" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/68/Pyrazole-3D-balls.png/165px-Pyrazole-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/68/Pyrazole-3D-balls.png/220px-Pyrazole-3D-balls.png 2x" data-file-width="1814" data-file-height="2000" /></a><figcaption></figcaption></figure> </td> <td style="width:50%;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Pyrazole-3D-spacefills.png" class="mw-file-description"><img alt="Space-filling model" src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b5/Pyrazole-3D-spacefills.png/110px-Pyrazole-3D-spacefills.png" decoding="async" width="110" height="116" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b5/Pyrazole-3D-spacefills.png/165px-Pyrazole-3D-spacefills.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b5/Pyrazole-3D-spacefills.png/220px-Pyrazole-3D-spacefills.png 2x" data-file-width="1895" data-file-height="2000" /></a><figcaption></figcaption></figure> </td></tr></tbody></table> </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<i>H</i>-Pyrazole<sup id="cite_ref-iupac2013_1-0" class="reference"><a href="#cite_note-iupac2013-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup></div></div> </td></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Chemical_nomenclature#Systematic_name" title="Chemical nomenclature">Systematic 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;">1,2-Diazacyclopenta-2,4-diene</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;">1,2-Diazole</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><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style><div class="plainlist"><ul><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=288-13-1">288-13-1</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=c1cn%5BnH%5Dc1">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>103775 </td></tr> <tr> <td><a href="/wiki/ChEBI" title="ChEBI">ChEBI</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=17241">CHEBI:17241</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/ChEMBL" title="ChEMBL">ChEMBL</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembl/explore/compound/ChEMBL15967">ChEMBL15967</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChemSpider" title="ChemSpider">ChemSpider</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.chemspider.com"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.1019.html">1019</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/DrugBank" title="DrugBank">DrugBank</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.drugbank.ca"><a rel="nofollow" class="external text" href="https://www.drugbank.ca/drugs/DB02757">DB02757</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ECHA_InfoCard" class="mw-redirect" title="ECHA InfoCard"><span title="echa.europa.eu">ECHA InfoCard</span></a> </td> <td><a rel="nofollow" class="external text" href="https://echa.europa.eu/substance-information/-/substanceinfo/100.005.471">100.005.471</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q408908#P2566" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span> </td></tr> <tr> <td><a href="/wiki/European_Community_number" title="European Community number"><span title="European Community number (chemical identifier)">EC Number</span></a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li>206-017-1</li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Gmelin_database" title="Gmelin database">Gmelin Reference</a></div> </td> <td>1360 </td></tr> <tr> <td><a href="/wiki/KEGG" title="KEGG">KEGG</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.kegg.jp"><a rel="nofollow" class="external text" href="https://www.kegg.jp/entry/C00481">C00481</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/1048">1048</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/3QD5KJZ7ZJ">3QD5KJZ7ZJ</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/DTXSID2059774">DTXSID2059774</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q408908#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/C3H4N2/c1-2-4-5-3-1/h1-3H,(H,4,5)<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: WTKZEGDFNFYCGP-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/C3H4N2/c1-2-4-5-3-1/h1-3H,(H,4,5)</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: WTKZEGDFNFYCGP-UHFFFAOYAW</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%;">c1cn[nH]c1</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><span title="Carbon">C</span><sub>3</sub><span title="Hydrogen">H</span><sub>4</sub><span title="Nitrogen">N</span><sub>2</sub> </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td><span class="nowrap"><span data-sort-value="7001680789999999999♠"></span>68.079</span> g·mol<sup>−1</sup>   </td></tr> <tr> <td><a href="/wiki/Melting_point" title="Melting point">Melting point</a> </td> <td>66 to 70 °C (151 to 158 °F; 339 to 343 K) </td></tr> <tr> <td><a href="/wiki/Boiling_point" title="Boiling point">Boiling point</a> </td> <td>186 to 188 °C (367 to 370 °F; 459 to 461 K) </td></tr> <tr> <td><a href="/wiki/Acid_dissociation_constant" title="Acid dissociation constant">Basicity</a> (p<i>K</i><sub>b</sub>) </td> <td>11.5 </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;"><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>:<sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td 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-exclam.svg" class="mw-file-description" title="GHS07: Exclamation mark"><img alt="GHS07: Exclamation mark" src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c3/GHS-pictogram-exclam.svg/50px-GHS-pictogram-exclam.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c3/GHS-pictogram-exclam.svg/75px-GHS-pictogram-exclam.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c3/GHS-pictogram-exclam.svg/100px-GHS-pictogram-exclam.svg.png 2x" data-file-width="512" data-file-height="512" /></a></span><span typeof="mw:File"><a href="/wiki/File:GHS-pictogram-silhouette.svg" class="mw-file-description" title="GHS08: Health hazard"><img alt="GHS08: Health hazard" src="//upload.wikimedia.org/wikipedia/commons/thumb/2/21/GHS-pictogram-silhouette.svg/50px-GHS-pictogram-silhouette.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/21/GHS-pictogram-silhouette.svg/75px-GHS-pictogram-silhouette.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/21/GHS-pictogram-silhouette.svg/100px-GHS-pictogram-silhouette.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="H302: Harmful if swallowed">H302</abbr>, <abbr class="abbr" title="H311: Toxic in contact with skin">H311</abbr>, <abbr class="abbr" title="H315: Causes skin irritation">H315</abbr>, <abbr class="abbr" title="H318: Causes serious eye damage">H318</abbr>, <abbr class="abbr" title="H319: Causes serious eye irritation">H319</abbr>, <abbr class="abbr" title="H335: May cause respiratory irritation">H335</abbr>, <abbr class="abbr" title="H372: Causes damage to organs through prolonged or repeated exposure">H372</abbr>, <abbr class="abbr" title="H412: Harmful to aquatic life with long lasting effects">H412</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="P261: Avoid breathing dust/fume/gas/mist/vapours/spray.">P261</abbr>, <abbr class="abbr" title="P262: Do not get in eyes, on skin, or on clothing.">P262</abbr>, <abbr class="abbr" title="P264: Wash ... thoroughly after handling.">P264</abbr>, <abbr class="abbr" title="P264+P265: Wash ... thoroughly after handling. Do not touch eyes.">P264+P265</abbr>, <abbr class="abbr" title="P270: Do not eat, drink or smoke when using this product.">P270</abbr>, <abbr class="abbr" title="P271: Use only outdoors or in a well-ventilated area.">P271</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="P301+P317: IF SWALLOWED: IF SWALLOWED: Get medical help.">P301+P317</abbr>, <abbr class="abbr" title="P302+P352: IF ON SKIN: Wash with soap and water.">P302+P352</abbr>, <abbr class="abbr" title="P304+P340: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing.">P304+P340</abbr>, <abbr class="abbr" title="P305+P351+P338: IF IN EYES: Rinse continuously with water for several minutes. Remove contact lenses if present and easy to do. Continue rinsing.">P305+P351+P338</abbr>, <abbr class="abbr" title="P305+P354+P338: IF IN EYES: Immediately rinse with water for several minutes. Remove contact lenses if present and easy to do. Continue rinsing.">P305+P354+P338</abbr>, <abbr class="abbr" title="P316: Get immediate emergency medical help.">P316</abbr>, <abbr class="abbr" title="P317: Get emergency medical help.">P317</abbr>, <abbr class="abbr" title="P319: Get medical help if you feel unwell.">P319</abbr>, <abbr class="abbr" title="P321: Specific treatment (see ... on this label).">P321</abbr>, <abbr class="abbr" title="P330: Rinse mouth.">P330</abbr>, <abbr class="abbr" title="P332+P317: If skin irritation occurs: Get medical help.">P332+P317</abbr>, <abbr class="abbr" title="P337+P317: If eye irritation persists: Get medical help.">P337+P317</abbr>, <abbr class="abbr" title="P361+P364: Take off immediately all contaminated clothing and wash it before reuse.">P361+P364</abbr>, <abbr class="abbr" title="P362+P364: Take off contaminated clothing and wash it before reuse.">P362+P364</abbr>, <abbr class="abbr" title="P403+P233: Store in a well ventilated place. Keep container tightly closed.">P403+P233</abbr>, <abbr class="abbr" title="P405: Store locked up.">P405</abbr>, <abbr class="abbr" title="P501: Dispose of contents/container to ...">P501</abbr> </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="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=464376682&page2=Pyrazole">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>Pyrazole</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> <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">(CH)<sub class="template-chem2-sub">3</sub>N<sub class="template-chem2-sub">2</sub>H</span>. It is a <a href="/wiki/Heterocycle" class="mw-redirect" title="Heterocycle">heterocycle</a> characterized as an <a href="/wiki/Azole" title="Azole">azole</a> with a 5-membered ring of three <a href="/wiki/Carbon" title="Carbon">carbon</a> atoms and two adjacent nitrogen atoms, which are in <a href="/wiki/Arene_substitution_pattern" title="Arene substitution pattern">ortho-substitution</a>. Pyrazole itself has few applications but many substituted pyrazoles are of commercial interest. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Properties">Properties</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Pyrazole&action=edit&section=1" title="Edit section: Properties"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Pyrazole is a weak base, with p<i>K</i><sub>b</sub> 11.5 (p<i>K</i><sub>a</sub> of the conjugate acid 2.49 at 25 °C).<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> According to <a href="/wiki/X-ray_crystallography" title="X-ray crystallography">X-ray crystallography</a>, the compound is planar. The two C-N distances are similar, both near 1.33 Å<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> <div class="mw-heading mw-heading2"><h2 id="Substituted_pyrazoles">Substituted pyrazoles</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Pyrazole&action=edit&section=2" title="Edit section: Substituted pyrazoles"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Pyrazoles are also a class of compounds that have the ring C<sub>3</sub>N<sub>2</sub> with adjacent nitrogen atoms.<sup id="cite_ref-Eicher_5-0" class="reference"><a href="#cite_note-Eicher-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> Notable drugs containing a pyrazole ring are <a href="/wiki/Celecoxib" title="Celecoxib">celecoxib</a> (celebrex) and the anabolic steroid <a href="/wiki/Stanozolol" title="Stanozolol">stanozolol</a>. </p> <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=Pyrazole&action=edit&section=3" title="Edit section: Preparation and reactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Pyrazoles are synthesized by the reaction of α,β-unsaturated <a href="/wiki/Aldehyde" title="Aldehyde">aldehydes</a> with <a href="/wiki/Hydrazine" title="Hydrazine">hydrazine</a> and subsequent <a href="/wiki/Dehydrogenation" title="Dehydrogenation">dehydrogenation</a>:<sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p> <dl><dd><span typeof="mw:File"><a href="/wiki/File:Pyrazoles_synthesis.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/7a/Pyrazoles_synthesis.png/300px-Pyrazoles_synthesis.png" decoding="async" width="300" height="94" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/7a/Pyrazoles_synthesis.png/450px-Pyrazoles_synthesis.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/7a/Pyrazoles_synthesis.png/600px-Pyrazoles_synthesis.png 2x" data-file-width="636" data-file-height="199" /></a></span></dd></dl> <p>Substituted pyrazoles are prepared by condensation of 1,3-<a href="/wiki/Diketone" class="mw-redirect" title="Diketone">diketones</a> with hydrazine (<a href="/wiki/Knorr_pyrrole_synthesis" title="Knorr pyrrole synthesis">Knorr</a>-type reactions).<sup id="cite_ref-KnorrEx_7-0" class="reference"><a href="#cite_note-KnorrEx-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> For example, <a href="/wiki/Acetylacetone" title="Acetylacetone">acetylacetone</a> and <a href="/wiki/Hydrazine" title="Hydrazine">hydrazine</a> gives 3,5-dimethylpyrazole:<sup id="cite_ref-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p> <dl><dd>CH<sub>3</sub>C(O)CH<sub>2</sub>C(O)CH<sub>3</sub>   +   N<sub>2</sub>H<sub>4</sub>   →   (CH<sub>3</sub>)<sub>2</sub>C<sub>3</sub>HN<sub>2</sub>H   +   2 H<sub>2</sub>O</dd></dl> <p>A wide variety of pyrazoles can be made so:<sup id="cite_ref-KnorrEx_7-1" class="reference"><a href="#cite_note-KnorrEx-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </p> <dl><dd><span class="mw-default-size" typeof="mw:File/Frameless"><a href="/wiki/File:Aryl_camphor-fused_pyrazole_synth.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e6/Aryl_camphor-fused_pyrazole_synth.png/550px-Aryl_camphor-fused_pyrazole_synth.png" decoding="async" width="550" height="137" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e6/Aryl_camphor-fused_pyrazole_synth.png/825px-Aryl_camphor-fused_pyrazole_synth.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e6/Aryl_camphor-fused_pyrazole_synth.png/1100px-Aryl_camphor-fused_pyrazole_synth.png 2x" data-file-width="1190" data-file-height="297" /></a></span><span class="mw-default-size" typeof="mw:File/Frameless"><a href="/wiki/File:Aryl-alicyclic_quinol-pyrazole_synth.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/a/ab/Aryl-alicyclic_quinol-pyrazole_synth.png/550px-Aryl-alicyclic_quinol-pyrazole_synth.png" decoding="async" width="550" height="110" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/ab/Aryl-alicyclic_quinol-pyrazole_synth.png/825px-Aryl-alicyclic_quinol-pyrazole_synth.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/ab/Aryl-alicyclic_quinol-pyrazole_synth.png/1100px-Aryl-alicyclic_quinol-pyrazole_synth.png 2x" data-file-width="1190" data-file-height="239" /></a></span><span class="mw-default-size" typeof="mw:File/Frameless"><a href="/wiki/File:Aryl-fused_quinol-pyrazole_synth.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/4/40/Aryl-fused_quinol-pyrazole_synth.png/550px-Aryl-fused_quinol-pyrazole_synth.png" decoding="async" width="550" height="107" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/40/Aryl-fused_quinol-pyrazole_synth.png/825px-Aryl-fused_quinol-pyrazole_synth.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/40/Aryl-fused_quinol-pyrazole_synth.png/1100px-Aryl-fused_quinol-pyrazole_synth.png 2x" data-file-width="1190" data-file-height="232" /></a></span></dd></dl> <div class="mw-heading mw-heading3"><h3 id="History">History</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Pyrazole&action=edit&section=4" title="Edit section: History"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The term pyrazole was given to this class of compounds by German Chemist <a href="/wiki/Ludwig_Knorr" title="Ludwig Knorr">Ludwig Knorr</a> in 1883.<sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> In a classical method developed by German chemist <a href="/wiki/Hans_von_Pechmann" title="Hans von Pechmann">Hans von Pechmann</a> in 1898, pyrazole was synthesized from <a href="/wiki/Acetylene" title="Acetylene">acetylene</a> and <a href="/wiki/Diazomethane" title="Diazomethane">diazomethane</a>.<sup id="cite_ref-10" class="reference"><a href="#cite_note-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Conversion_to_scorpionates">Conversion to scorpionates</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Pyrazole&action=edit&section=5" title="Edit section: Conversion to scorpionates"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Pyrazoles react with <a href="/wiki/Potassium_borohydride" class="mw-redirect" title="Potassium borohydride">potassium borohydride</a> to form a class of ligands known as <a href="/wiki/Scorpionate_ligand" title="Scorpionate ligand">scorpionate</a>. Pyrazole itself reacts with <a href="/wiki/Potassium_borohydride" class="mw-redirect" title="Potassium borohydride">potassium borohydride</a> at high temperatures (~200 °C) to form a <a href="/wiki/Tridentate_ligand" title="Tridentate ligand">tridentate ligand</a> known as <a href="/wiki/Trispyrazolylborate" title="Trispyrazolylborate">Tp ligand</a>: </p> <dl><dd><span typeof="mw:File"><a href="/wiki/File:Potassium_scorpionate.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/4/47/Potassium_scorpionate.svg/400px-Potassium_scorpionate.svg.png" decoding="async" width="400" height="111" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/47/Potassium_scorpionate.svg/600px-Potassium_scorpionate.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/47/Potassium_scorpionate.svg/800px-Potassium_scorpionate.svg.png 2x" data-file-width="280" data-file-height="78" /></a></span></dd></dl> <div class="mw-heading mw-heading3"><h3 id="3,5-Diphenyl-1H-pyrazole"><span id="3.2C5-Diphenyl-1H-pyrazole"></span>3,5-Diphenyl-1<i>H</i>-pyrazole</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Pyrazole&action=edit&section=6" title="Edit section: 3,5-Diphenyl-1H-pyrazole"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>3,5-Diphenyl-1<i>H</i>-pyrazole is produced when <a href="/wiki/Chalcone" title="Chalcone">(<i>E</i>)-1,3-diphenylprop-2-en-1-one</a> is reacted with <a href="/wiki/Hydrazine_hydrate" class="mw-redirect" title="Hydrazine hydrate">hydrazine hydrate</a> in the presence of elemental <a href="/wiki/Sulfur" title="Sulfur">sulfur</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> or <a href="/wiki/Sodium_persulfate" title="Sodium persulfate">sodium persulfate</a>,<sup id="cite_ref-12" class="reference"><a href="#cite_note-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> or by using a <a href="/wiki/Hydrazone" title="Hydrazone">hydrazone</a> in which case an <a href="/wiki/Azine" title="Azine">azine</a> is produced as a by-product.<sup id="cite_ref-13" class="reference"><a href="#cite_note-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> </p> <dl><dd><span typeof="mw:File"><a href="/wiki/File:Lasri_condensation_reaction.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/95/Lasri_condensation_reaction.svg/700px-Lasri_condensation_reaction.svg.png" decoding="async" width="700" height="114" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/95/Lasri_condensation_reaction.svg/1050px-Lasri_condensation_reaction.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/95/Lasri_condensation_reaction.svg/1400px-Lasri_condensation_reaction.svg.png 2x" data-file-width="1685" data-file-height="275" /></a></span></dd></dl> <div class="mw-heading mw-heading2"><h2 id="Occurrence_and_uses">Occurrence and uses</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Pyrazole&action=edit&section=7" title="Edit section: Occurrence and uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size mw-halign-left" typeof="mw:File/Thumb"><a href="/wiki/File:Celecoxib_structure.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/a/ae/Celecoxib_structure.png/220px-Celecoxib_structure.png" decoding="async" width="220" height="168" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/ae/Celecoxib_structure.png/330px-Celecoxib_structure.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/ae/Celecoxib_structure.png/440px-Celecoxib_structure.png 2x" data-file-width="1295" data-file-height="991" /></a><figcaption><a href="/wiki/Celecoxib" title="Celecoxib">Celecoxib</a>, a pyrazole-derived analgesic</figcaption></figure> <p>In 1959, the first natural pyrazole, <a href="/w/index.php?title=1-pyrazolyl-alanine&action=edit&redlink=1" class="new" title="1-pyrazolyl-alanine (page does not exist)">1-pyrazolyl-alanine</a>, was isolated from seeds of <a href="/wiki/Watermelons" class="mw-redirect" title="Watermelons">watermelons</a>.<sup id="cite_ref-14" class="reference"><a href="#cite_note-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-15" class="reference"><a href="#cite_note-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> </p><p>In medicine, derivatives of pyrazole are widely used,<sup id="cite_ref-Kabi_16-0" class="reference"><a href="#cite_note-Kabi-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> including <a href="/wiki/Celecoxib" title="Celecoxib">celecoxib</a> and similar <a href="/wiki/COX-2_inhibitors" class="mw-redirect" title="COX-2 inhibitors">COX-2 inhibitors</a>, <a href="/wiki/Zaleplon" title="Zaleplon">zaleplon</a>, <a href="/wiki/Betazole" title="Betazole">betazole</a>, and <a href="/wiki/CDPPB" title="CDPPB">CDPPB</a>.<sup id="cite_ref-:0_17-0" class="reference"><a href="#cite_note-:0-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> The pyrazole ring is found within a variety of pesticides as fungicides, insecticides and herbicides,<sup id="cite_ref-Kabi_16-1" class="reference"><a href="#cite_note-Kabi-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> including <a href="/w/index.php?title=Fenpyroximate&action=edit&redlink=1" class="new" title="Fenpyroximate (page does not exist)">fenpyroximate</a>, <a href="/wiki/Fipronil" title="Fipronil">fipronil</a>, <a href="/wiki/Tebufenpyrad" title="Tebufenpyrad">tebufenpyrad</a> and <a href="/w/index.php?title=Tolfenpyrad&action=edit&redlink=1" class="new" title="Tolfenpyrad (page does not exist)">tolfenpyrad</a>.<sup id="cite_ref-18" class="reference"><a href="#cite_note-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> Pyrazole moieties are listed among the highly used ring systems for small molecule drugs by the US FDA<sup id="cite_ref-19" class="reference"><a href="#cite_note-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> </p> <dl><dd><span typeof="mw:File"><a href="/wiki/File:Pyrazole_SDHI_intermediate.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/f/fe/Pyrazole_SDHI_intermediate.svg/100px-Pyrazole_SDHI_intermediate.svg.png" decoding="async" width="100" height="95" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/fe/Pyrazole_SDHI_intermediate.svg/150px-Pyrazole_SDHI_intermediate.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/fe/Pyrazole_SDHI_intermediate.svg/200px-Pyrazole_SDHI_intermediate.svg.png 2x" data-file-width="512" data-file-height="488" /></a></span></dd></dl> <p><a href="/wiki/3-(Difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic_acid" title="3-(Difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid">3-(Difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid</a> is used in the manufacture of six commercial fungicides which are inhibitors of <a href="/wiki/Succinate_dehydrogenase" title="Succinate dehydrogenase">succinate dehydrogenase</a>.<sup id="cite_ref-Walter_20-0" class="reference"><a href="#cite_note-Walter-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-21" class="reference"><a href="#cite_note-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> </p><p>Pyrazole is an inhibitor of the <a href="/wiki/Alcohol_dehydrogenase" title="Alcohol dehydrogenase">alcohol dehydrogenase</a> enzyme, and, as such, is used as an adjuvant with ethanol, to induce alcohol dependency in experimental laboratory mice.<sup id="cite_ref-22" class="reference"><a href="#cite_note-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Pyrazole&action=edit&section=8" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/3,5-Dimethylpyrazole" title="3,5-Dimethylpyrazole">3,5-dimethylpyrazole</a></li> <li><a href="/wiki/Pyrazolidine" title="Pyrazolidine">Pyrazolidine</a>, fully saturated analogue</li> <li><a href="/wiki/Imidazole" title="Imidazole">imidazole</a>, structural analogue of pyrazole with two <i>non</i>-adjacent nitrogen atoms.</li> <li><a href="/wiki/Isoxazole" title="Isoxazole">isoxazole</a>, another analogue, the nitrogen atom in position 1 replaced by oxygen.</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=Pyrazole&action=edit&section=9" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-iupac2013-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-iupac2013_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 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Wiley. pp. 363–395. <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%2F9783527825158.ch11">10.1002/9783527825158.ch11</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9783527347117" title="Special:BookSources/9783527347117"><bdi>9783527347117</bdi></a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:234149806">234149806</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Current+Trends+in+the+Design+of+Fluorine-Containing+Agrochemicals&rft.btitle=Organofluorine+Chemistry&rft.pages=363-395&rft.pub=Wiley&rft.date=2021&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A234149806%23id-name%3DS2CID&rft_id=info%3Adoi%2F10.1002%2F9783527825158.ch11&rft.isbn=9783527347117&rft.aulast=Jeschke&rft.aufirst=Peter&rfr_id=info%3Asid%2Fen.wikipedia.org%3APyrazole" class="Z3988"></span></span> </li> <li id="cite_note-22"><span class="mw-cite-backlink"><b><a href="#cite_ref-22">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFXiaoChenBoisvertCole2023" class="citation journal cs1">Xiao, T.; Chen, Y.; Boisvert, A.; Cole, M.; Kimbrough, A. (2023). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11164185">"Chronic Intermittent Ethanol Vapor Exposure Paired with Two-Bottle Choice to Model Alcohol Use Disorder"</a>. <i>Journal of Visualized Experiments : Jove</i> (196). <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.3791%2F65320">10.3791/65320</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11164185">11164185</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/37427930">37427930</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+Visualized+Experiments+%3A+Jove&rft.atitle=Chronic+Intermittent+Ethanol+Vapor+Exposure+Paired+with+Two-Bottle+Choice+to+Model+Alcohol+Use+Disorder&rft.issue=196&rft.date=2023&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC11164185%23id-name%3DPMC&rft_id=info%3Apmid%2F37427930&rft_id=info%3Adoi%2F10.3791%2F65320&rft.aulast=Xiao&rft.aufirst=T.&rft.au=Chen%2C+Y.&rft.au=Boisvert%2C+A.&rft.au=Cole%2C+M.&rft.au=Kimbrough%2C+A.&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC11164185&rfr_id=info%3Asid%2Fen.wikipedia.org%3APyrazole" 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=Pyrazole&action=edit&section=10" title="Edit section: Further reading"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFA._SchmidtA._Dreger2011" class="citation journal cs1">A. Schmidt; A. Dreger (2011). "Recent Advances in the Chemistry of Pyrazoles. Part 2. Reactions and N-Heterocyclic Carbenes of Pyrazole". <i>Curr. Org. Chem</i>. <b>15</b> (16): 2897–2970. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.2174%2F138527211796378497">10.2174/138527211796378497</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Curr.+Org.+Chem.&rft.atitle=Recent+Advances+in+the+Chemistry+of+Pyrazoles.+Part+2.+Reactions+and+N-Heterocyclic+Carbenes+of+Pyrazole&rft.volume=15&rft.issue=16&rft.pages=2897-2970&rft.date=2011&rft_id=info%3Adoi%2F10.2174%2F138527211796378497&rft.au=A.+Schmidt&rft.au=A.+Dreger&rfr_id=info%3Asid%2Fen.wikipedia.org%3APyrazole" class="Z3988"></span> </p>    </div><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?type=1x1" alt="" width="1" height="1" style="border: none; position: absolute;"></noscript> <div class="printfooter" data-nosnippet="">Retrieved from "<a dir="ltr" href="https://en.wikipedia.org/w/index.php?title=Pyrazole&oldid=1259822155">https://en.wikipedia.org/w/index.php?title=Pyrazole&oldid=1259822155</a>"</div></div> <div id="catlinks" class="catlinks" data-mw="interface"><div id="mw-normal-catlinks" class="mw-normal-catlinks"><a href="/wiki/Help:Category" title="Help:Category">Categories</a>: <ul><li><a href="/wiki/Category:Pyrazoles" title="Category:Pyrazoles">Pyrazoles</a></li><li><a href="/wiki/Category:Aromatic_bases" title="Category:Aromatic bases">Aromatic bases</a></li><li><a href="/wiki/Category:Simple_aromatic_rings" title="Category:Simple aromatic rings">Simple aromatic rings</a></li><li><a href="/wiki/Category:Substances_discovered_in_the_19th_century" title="Category:Substances discovered in the 19th century">Substances discovered in the 19th century</a></li></ul></div><div id="mw-hidden-catlinks" class="mw-hidden-catlinks mw-hidden-cats-hidden">Hidden categories: <ul><li><a href="/wiki/Category:CS1_German-language_sources_(de)" title="Category:CS1 German-language sources (de)">CS1 German-language sources (de)</a></li><li><a href="/wiki/Category:CS1_errors:_missing_title" title="Category:CS1 errors: missing title">CS1 errors: missing title</a></li><li><a href="/wiki/Category:Use_dmy_dates_from_January_2024" title="Category:Use dmy dates from January 2024">Use dmy dates from January 2024</a></li><li><a href="/wiki/Category:ECHA_InfoCard_ID_from_Wikidata" title="Category:ECHA InfoCard ID from Wikidata">ECHA InfoCard ID from Wikidata</a></li><li><a href="/wiki/Category:Chembox_having_GHS_data" title="Category:Chembox having GHS data">Chembox having GHS data</a></li><li><a href="/wiki/Category:Articles_containing_unverified_chemical_infoboxes" title="Category:Articles containing unverified chemical infoboxes">Articles containing unverified chemical infoboxes</a></li><li><a href="/wiki/Category:Articles_with_short_description" title="Category:Articles with short description">Articles with short description</a></li><li><a href="/wiki/Category:Short_description_matches_Wikidata" title="Category:Short description matches Wikidata">Short description matches Wikidata</a></li></ul></div></div> </div> </main> </div> <div class="mw-footer-container"> <footer id="footer" class="mw-footer" > <ul id="footer-info"> <li id="footer-info-lastmod"> This page was last edited on 27 November 2024, at 07:11<span class="anonymous-show"> (UTC)</span>.</li> <li id="footer-info-copyright">Text is available under the <a href="/wiki/Wikipedia:Text_of_the_Creative_Commons_Attribution-ShareAlike_4.0_International_License" title="Wikipedia:Text of the Creative Commons Attribution-ShareAlike 4.0 International License">Creative Commons Attribution-ShareAlike 4.0 License</a>; additional terms may apply. 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