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<h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Indazol</span></h1>
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<div id="mw-content-text" class="mw-body-content mw-content-ltr" lang="de" dir="ltr"><div class="mw-content-ltr mw-parser-output" lang="de" dir="ltr"><table class="wikitable infobox float-right" id="Vorlage_Infobox_Chemikalie" style="font-size:90%; margin-top:0; width:350px;" summary="Infobox Chemikalie">
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<th colspan="2" style="background:#FFDEAD; color:#202122;">Strukturformel
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<td colspan="2" class="hintergrundfarbe-basis skin-invert-image" style="text-align:center;"><span class="mw-default-size" typeof="mw:File"></span>
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<th colspan="2" style="background:#FFDEAD; color:#202122;">Allgemeines
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<tr>
<td style="width:33%;">Name
</td>
<td>Indazol
</td></tr>
<tr>
<td>Andere Namen
</td>
<td>
<ul><li>1<i>H</i>-Indazol</li>
<li>1,2-Benzopyrazol</li>
<li>1,2-Benzodiazol</li>
<li>Isoindazon</li></ul>
</td></tr>
<tr>
<td><a href="Summenformel" title="Summenformel">Summenformel</a>
</td>
<td>C<sub>7</sub>H<sub>6</sub>N<sub>2</sub>
</td></tr>
<tr>
<td>Kurzbeschreibung
</td>
<td>
<p>beiger geruchloser Feststoff<sup id="cite_ref-Thermofisher_1-0" class="reference"><a href="#cite_note-Thermofisher-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup>
</p>
</td></tr>
<tr>
<th colspan="2" style="background:#FFDEAD; color:#202122;">Externe Identifikatoren/Datenbanken
</th></tr>
<tr>
<td colspan="2" style="padding:0;">
<table class="mw-collapsible mw-collapsed wikitable" data-expandtext="+" data-collapsetext="−" style="border-top:none; margin:-1px; width:calc(100% + 2px);">
<tbody><tr>
<td style="width:33%;"><a href="CAS-Nummer" title="CAS-Nummer">CAS-Nummer</a>
</td>
<td><span title="Untervorlage eingebunden: CASRN"></span><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=271-44-3">271-44-3</a><span class="editoronly" style="display:none;"></span>
</td>
<td style="background:#FFDEAD; color:#202122; border-top:1px solid #FFDEAD; padding:0.2em 0; vertical-align:bottom; width:5%;">
</td></tr>
<tr>
<td><a href="EG-Nummer" title="EG-Nummer">EG-Nummer</a>
</td>
<td colspan="2">205-978-4
</td></tr>
<tr>
<td><a href="Europ%C3%A4ische_Chemikalienagentur" title="Europäische Chemikalienagentur">ECHA</a>-InfoCard
</td>
<td colspan="2"><a rel="nofollow" class="external text" href="https://www.echa.europa.eu/de/substance-information/-/substanceinfo/100.005.436">100.005.436</a>
</td></tr>
<tr>
<td><a href="PubChem" title="PubChem">PubChem</a>
</td>
<td colspan="2"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/9221">9221</a>
</td></tr>
<tr>
<td><a href="ChemSpider" title="ChemSpider">ChemSpider</a>
</td>
<td colspan="2"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.8866.html">8866</a>
</td></tr>
<tr>
<td style="border-right:1px solid #a2a9b1;"><a href="Wikidata" title="Wikidata">Wikidata</a>
</td>
<td colspan="2"><a href="https://www.wikidata.org/wiki/Q417106" class="extiw external" title="d:Q417106">Q417106</a>
</td></tr></tbody></table>
</td></tr>
<tr>
<th colspan="2" style="background:#FFDEAD; color:#202122;">Eigenschaften
</th></tr>
<tr>
<td><a href="Molare_Masse" title="Molare Masse">Molare Masse</a>
</td>
<td>118,14 <a href="Gramm" title="Gramm">g</a>·<a href="Mol" title="Mol">mol</a><sup>−1</sup>
</td></tr>
<tr>
<td><a href="Aggregatzustand" title="Aggregatzustand">Aggregatzustand</a>
</td>
<td>
<p>fest<sup id="cite_ref-Thermofisher_1-1" class="reference"><a href="#cite_note-Thermofisher-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup>
</p>
</td></tr>
<tr>
<td><a href="Schmelzpunkt" title="Schmelzpunkt">Schmelzpunkt</a>
</td>
<td>
<p>146–149 <a href="Grad_Celsius" title="Grad Celsius">°C</a><sup id="cite_ref-Thermofisher_1-2" class="reference"><a href="#cite_note-Thermofisher-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup>
</p>
</td></tr>
<tr>
<td><a href="Siedepunkt" title="Siedepunkt">Siedepunkt</a>
</td>
<td>
<p>270 °C (994 h<a href="Pascal_(Einheit)" title="Pascal (Einheit)">Pa</a>)<sup id="cite_ref-Thermofisher_1-3" class="reference"><a href="#cite_note-Thermofisher-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup>
</p>
</td></tr>
<tr>
<td><a href="L%C3%B6slichkeit" title="Löslichkeit">Löslichkeit</a>
</td>
<td>
<p>löslich in heißem Wasser<sup id="cite_ref-Thermofisher_1-4" class="reference"><a href="#cite_note-Thermofisher-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup>
</p>
</td></tr>
<tr>
<th colspan="2" style="background:#FFDEAD; color:#202122;">Sicherheitshinweise
</th></tr>
<tr>
<td colspan="2">
<table cellspacing="0" cellpadding="2" style="width:100%;">
<tbody><tr>
<td colspan="2" style="text-align:center"><b><a href="Global_harmonisiertes_System_zur_Einstufung_und_Kennzeichnung_von_Chemikalien" title="Global harmonisiertes System zur Einstufung und Kennzeichnung von Chemikalien">GHS-Gefahrstoffkennzeichnung</a></b><sup id="cite_ref-Thermofisher_1-5" class="reference"><a href="#cite_note-Thermofisher-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup>
<table class="hintergrundfarbe-neutral" style="text-align:center; margin-left:auto; margin-right:auto; display:flex; justify-content:center;">
<tbody><tr>
<td><i>keine GHS-Piktogramme</i>
</td></tr></tbody></table>
<p>
</p>
</td></tr>
<tr>
<td rowspan="2" width="33%" style="border-top:1px #A7A7A7 dashed; border-right:1px #A7A7A7 dashed;"><a href="H-_und_P-S%C3%A4tze" title="H- und P-Sätze">H- und P-Sätze</a>
</td>
<td style="border-top:1px #A7A7A7 dashed;">H: <span title="Untervorlage eingebunden: H-Sätze"></span><i>keine H-Sätze</i>
</td></tr>
<tr>
<td style="border-top:1px #A7A7A7 dashed;">P: <span title="Untervorlage eingebunden: P-Sätze"></span><i>keine P-Sätze</i><sup id="cite_ref-Thermofisher_1-6" class="reference"><a href="#cite_note-Thermofisher-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup>
</td></tr>
</tbody></table>
</td></tr>
<tr>
<td colspan="2" style="background:#FFDEAD; color:#202122; font-size:80%; text-align:center; line-height:150%; padding:.25em;">Wenn nicht anders vermerkt, gelten die angegebenen Daten bei <a href="Standardbedingungen" title="Standardbedingungen">Standardbedingungen</a> (0 °C, 1000 hPa).
</td></tr></tbody></table><p><span class="editoronly" style="display:none;"></span>
</p><p><b>Indazol</b> ist ein <a href="Aromaten" title="Aromaten">aromatischer</a> <a href="Heterocyclen" title="Heterocyclen">Heterocyclus</a> und bildet das Grundgerüst weniger <a href="Naturstoffe" class="mw-redirect" title="Naturstoffe">Naturstoffe</a> (Nigellicin, Nigellidin und Nigeglanin aus <i>Nigella sp.</i>).
</p>
<div class="mw-heading mw-heading2"><h2 id="Vorkommen">Vorkommen</h2></div>
<p>Derivate des Indazols kommen selten in der Natur vor. <a href="Nigellicin" title="Nigellicin">Nigellicin</a>, <a href="Nigeglanin" title="Nigeglanin">Nigeglanin</a> und <a href="Nigellidin" title="Nigellidin">Nigellidin</a> sind Naturstoffe, die den Indazolring enthalten. Nigellicin ist ein <a href="Alkaloide" title="Alkaloide">Alkaloid</a> aus <i>Nigella sativa</i> L. (Schwarzkümmel) und gehört zur Substanzklasse der mesomeren <a href="Betaine" title="Betaine">Betaine</a>. Nigeglanin wurde aus <i>Nigella glandulifera</i> isoliert.
</p>
<div class="mw-heading mw-heading2"><h2 id="Darstellung">Darstellung</h2></div>
<p>Die Herstellung der Indazole erfolgt beispielsweise über die Indazolsynthese nach Jacobson (siehe Schema unten).<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>
<div class="mw-heading mw-heading2"><h2 id="Verwendung">Verwendung</h2></div>
<p>Indazol hat Bedeutung für die Herstellung bestimmter <a href="Farbstoffe" title="Farbstoffe">Farbstoffe</a>. Derivate des Indazols sind auch in der <a href="Pharmakologie" title="Pharmakologie">Pharmakologie</a> von Interesse, so wird das 1-Benzyl-3-(3-dimethylaminopropoxy)-1<i>H</i>-indazol (<a href="Benzydamin" title="Benzydamin">Benzydamin</a>) wegen seiner <a href="Lokalan%C3%A4sthesie" title="Lokalanästhesie">lokalanästhetischen</a> und <a href="Antiphlogistikum" class="mw-redirect" title="Antiphlogistikum">entzündungshemmenden</a> Wirkung bei schmerzhaften Entzündungen der <a href="Schleimhaut" title="Schleimhaut">Schleimhäute</a> eingesetzt.<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>
<div class="mw-heading mw-heading2"><h2 id="Literatur">Literatur</h2></div>
<ul><li>Synthese (Vereinfacht, nach Jacobson): <i>Synthesis</i>, 1972, Issue 07, S. 375; <a href="Digital_Object_Identifier" title="Digital Object Identifier">doi</a>:<span class="uri-handle" style="white-space:nowrap"><a rel="nofollow" class="external text" href="https://doi.org/10.1055/s-1972-21885">10.1055/s-1972-21885</a></span>.</li>
<li>Synthesemethoden: W. Stadlbauer, in: <i>Science of Synthesis</i> 2002, 12, S. 227.</li>
<li>Synthesemethoden: W. Stadlbauer, in: <i>Houben-Weyl</i>, 1994, E8b, S. 764.</li>
<li>Übersichtsartikel (Synthese, Eigenschaften, Biol. Aktivitäten etc.): A. Schmidt, A. Beutler, B. Snovydovych: <i>Recent Advances in the Chemistry of Indazoles.</i> In: <i>Eur. J. Org. Chem</i>. 2008, S. 4073–4095.</li></ul>
<div class="mw-heading mw-heading2"><h2 id="Einzelnachweise">Einzelnachweise</h2></div>
<ol class="references">
<li id="cite_note-Thermofisher-1"><span class="mw-cite-backlink">↑ <sup><a href="#cite_ref-Thermofisher_1-0">a</a></sup> <sup><a href="#cite_ref-Thermofisher_1-1">b</a></sup> <sup><a href="#cite_ref-Thermofisher_1-2">c</a></sup> <sup><a href="#cite_ref-Thermofisher_1-3">d</a></sup> <sup><a href="#cite_ref-Thermofisher_1-4">e</a></sup> <sup><a href="#cite_ref-Thermofisher_1-5">f</a></sup> <sup><a href="#cite_ref-Thermofisher_1-6">g</a></sup></span> <span class="reference-text">Eintrag zu <span style="font-style:italic;"><a rel="nofollow" class="external text" href="https://www.thermofisher.com/order/catalog/product/A11665.14?SID=srch-srp-A11665.14">1H-Indazole</a></span> bei <i><a href="Thermo_Fisher_Scientific" title="Thermo Fisher Scientific">Thermo Fisher Scientific</a></i>, abgerufen am 13. Oktober 2023.<span class="editoronly" style="display:none;"></span></span>
</li>
<li id="cite_note-2"><span class="mw-cite-backlink"><a href="#cite_ref-2">↑</a></span> <span class="reference-text">P. Jacobson, M. Huber: <cite style="font-style:italic">Über Bildung von Indazolkörpern aus orthomethylierten Anilinbasen.</cite> In: <cite style="font-style:italic"><a href="Berichte_der_deutschen_chemischen_Gesellschaft" class="mw-redirect" title="Berichte der deutschen chemischen Gesellschaft">Chem. Ber.</a></cite> <span style="white-space:nowrap">Band<span style="display:inline-block;width:.2em"> </span>41</span>, <span style="white-space:nowrap">Nr.<span style="display:inline-block;width:.2em"> </span>01</span>, 1908, <span style="white-space:nowrap">S.<span style="display:inline-block;width:.2em"> </span>660–671</span>, <a href="Digital_Object_Identifier" title="Digital Object Identifier">doi</a>:<span class="uri-handle" style="white-space:nowrap"><a rel="nofollow" class="external text" href="https://doi.org/10.1002/cber.190804101127">10.1002/cber.190804101127</a></span>.<span class="Z3988" title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rfr_id=info:sid/de.wikipedia.org:Indazol&rft.atitle=%C3%9Cber+Bildung+von+Indazolk%C3%B6rpern+aus+orthomethylierten+Anilinbasen.&rft.au=P.+Jacobson%2C+M.+Huber&rft.date=1908&rft.doi=10.1002%2Fcber.190804101127&rft.genre=journal&rft.issue=01&rft.jtitle=Chem.+Ber.&rft.pages=660-671&rft.volume=41" style="display:none"> </span></span>
</li>
<li id="cite_note-3"><span class="mw-cite-backlink"><a href="#cite_ref-3">↑</a></span> <span class="reference-text"><a href="Harry_Auterhoff" title="Harry Auterhoff">Harry Auterhoff</a>: <i>Lehrbuch der pharmazeutischen Chemie</i>, Wissenschaftliche Verlagsgesellschaft, Stuttgart 1968.</span>
</li>
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