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<title>5-Methoxy-1H-indol</title>

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<h1 id="firstHeading" class="firstHeading mw-first-heading">5-Methoxy-1<i>H</i>-indol</h1>

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<th colspan="2" style="background:#FFDEAD; color:#202122;">Strukturformel

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<th colspan="2" style="background:#FFDEAD; color:#202122;">Allgemeines

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<td style="width:33%;">Name

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<td>5-Methoxy-1<i>H</i>-indol

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<td>Andere Namen

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<p>5-Methoxyindol

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<td><a href="Summenformel" title="Summenformel">Summenformel</a>

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<td>C<sub>9</sub>H<sub>9</sub>NO

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<td>Kurzbeschreibung

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<p>beige Kristalle<sup id="cite_ref-SIGMA_1-0" class="reference"><a href="#cite_note-SIGMA-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup>

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<th colspan="2" style="background:#FFDEAD; color:#202122;">Externe Identifikatoren/Datenbanken

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<td style="width:33%;"><a href="CAS-Nummer" title="CAS-Nummer">CAS-Nummer</a>

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<td><a href="EG-Nummer" title="EG-Nummer">EG-Nummer</a>

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<td colspan="2">213-745-3

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<td><a href="Europ%C3%A4ische_Chemikalienagentur" title="Europäische Chemikalienagentur">ECHA</a>-InfoCard

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<td><a href="PubChem" title="PubChem">PubChem</a>

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<td><a href="ChemSpider" title="ChemSpider">ChemSpider</a>

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<td style="border-right:1px solid #a2a9b1;"><a href="Wikidata" title="Wikidata">Wikidata</a>

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<th colspan="2" style="background:#FFDEAD; color:#202122;">Eigenschaften

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<td><a href="Molare_Masse" title="Molare Masse">Molare Masse</a>

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<td><a href="Aggregatzustand" title="Aggregatzustand">Aggregatzustand</a>

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<td><a href="Schmelzpunkt" title="Schmelzpunkt">Schmelzpunkt</a>

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<td><a href="Siedepunkt" title="Siedepunkt">Siedepunkt</a>

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<th colspan="2" style="background:#FFDEAD; color:#202122;">Sicherheitshinweise

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<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-SIGMA_1-4" class="reference"><a href="#cite_note-SIGMA-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup>

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<p><b>Achtung</b>

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<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>

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<td style="border-top:1px #A7A7A7 dashed;">P: <span title="Untervorlage eingebunden: P-Sätze"></span><a href="H-_und_P-S%C3%A4tze#P-Sätze" title="H- und P-Sätze"><span style="display:inline-block;"><span style="color:#ff5400; border-bottom:1px dotted #ff5400;" title="Einatmen von Staub / Rauch / Gas / Nebel / Dampf / Aerosol vermeiden.">261</span></span></a>‐<a href="H-_und_P-S%C3%A4tze#P-Sätze" title="H- und P-Sätze"><span style="display:inline-block;"><span style="color:#ff5400; border-bottom:1px dotted #ff5400;" title="Bei Kontakt mit den Augen: Einige Minuten lang behutsam mit Wasser spülen. Eventuell vorhandene Kontaktlinsen nach Möglichkeit entfernen. Weiter spülen.

(Geänderter Text seit Inkraftreten der „8. Anpassung an den Technischen Fortschritt“ am 1. Februar 2018)">305+351+338</span></span></a><sup id="cite_ref-SIGMA_1-5" class="reference"><a href="#cite_note-SIGMA-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup>

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<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).

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</p><p><b>5-Methoxy-1<i>H</i>-indol</b> ist eine <a href="Chemische_Verbindung" title="Chemische Verbindung">chemische Verbindung</a> und ein <a href="Derivat_(Chemie)" title="Derivat (Chemie)">Derivat</a> des <a href="Indol" title="Indol">1<i>H</i>-Indols</a>.

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<div class="mw-heading mw-heading2"><h2 id="Darstellung">Darstellung</h2></div>

<p>Eine Synthese ist ausgehend von <a href="Anisidine" title="Anisidine"><i>para</i>-Aminoanisol</a> möglich. Dieses muss zunächst durch <a href="Diazotierung" title="Diazotierung">Diazotierung</a> und <a href="Reduktion_(Chemie)" title="Reduktion (Chemie)">Reduktion</a> der <a href="Azogruppe" title="Azogruppe">Azoverbindung</a> zum Hydrazin umgesetzt werden<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> und dann mit <a href="Acetaldehyd" title="Acetaldehyd">Acetaldehyd</a> im Sinne einer <a href="Fischersche_Indolsynthese" title="Fischersche Indolsynthese">Fischer-Indol-Synthese</a> reagieren.<sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup>

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<div class="mw-heading mw-heading2"><h2 id="Einzelnachweise">Einzelnachweise</h2></div>

<li id="cite_note-SIGMA-1"><span class="mw-cite-backlink">↑ <sup><a href="#cite_ref-SIGMA_1-0">a</a></sup> <sup><a href="#cite_ref-SIGMA_1-1">b</a></sup> <sup><a href="#cite_ref-SIGMA_1-2">c</a></sup> <sup><a href="#cite_ref-SIGMA_1-3">d</a></sup> <sup><a href="#cite_ref-SIGMA_1-4">e</a></sup> <sup><a href="#cite_ref-SIGMA_1-5">f</a></sup></span> <span class="reference-text">Datenblatt <span style="font-style:italic;"><a rel="nofollow" class="external text" href="https://www.sigmaaldrich.com/catalog/product/ALDRICH/M14900">5-Methoxy-1H-indol</a></span> bei <a href="Sigma-Aldrich" title="Sigma-Aldrich">Sigma-Aldrich</a>, abgerufen am 17. Oktober 2021 (<a rel="nofollow" class="external text" href="https://www.sigmaaldrich.com/DE/de/sds/ALDRICH/M14900?userType=anonymous">PDF</a>).<span class="editoronly" style="display:none;"></span><span style="display:none;">Vorlage:Sigma-Aldrich/Name nicht angegeben</span></span>

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<li id="cite_note-2"><span class="mw-cite-backlink"><a href="#cite_ref-2">↑</a></span> <span class="reference-text">S. Zhao, Y. Zhang, H. Zhou, S. Xi, B. Zou, G. Bao,

L. Wang, J. Wang, T. Zeng, P. Gong, X. Zhai: <cite style="font-style:italic">Synthesis and biological evaluation of 4-(2-fluorophenoxy)-3,3′-bipyridine derivatives as potential c-met inhibitors</cite>. In: <cite style="font-style:italic"><a href="European_Journal_of_Medicinal_Chemistry" title="European Journal of Medicinal Chemistry">Eur. J. Med. Chem.</a></cite> <span style="white-space:nowrap">Band<span style="display:inline-block;width:.2em"> </span>120</span>, 2016, <span style="white-space:nowrap">S.<span style="display:inline-block;width:.2em"> </span>3</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/10.1016/j.ejmech.2016.04.062">10.1016/j.ejmech.2016.04.062</a></span>.<span class="Z3988" title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rfr_id=info:sid/de.wikipedia.org:5-Methoxy-1H-indol&rft.atitle=Synthesis+and+biological+evaluation+of+4-%282-fluorophenoxy%29-3%2C3%E2%80%B2-bipyridine+derivatives+as+potential+c-met+inhibitors&rft.au=S.+Zhao%2C+Y.+Zhang%2C+H.+Zhou%2C+...&rft.btitle=Eur.+J.+Med.+Chem.&rft.date=2016&rft.doi=10.1016%2Fj.ejmech.2016.04.062&rft.genre=book&rft.pages=3&rft.volume=120" style="display:none"> </span></span>

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<li id="cite_note-3"><span class="mw-cite-backlink"><a href="#cite_ref-3">↑</a></span> <span class="reference-text">A. R. Maguire, S. J. Plunkett, S. Papot, M. Clynes, R. O’Connor, S. Touhey: <cite style="font-style:italic">Synthesis of Indomethacin Analogues for Evaluation as Modulators of MRP Activity</cite>. In: <cite style="font-style:italic"><a href="Bioorganic_%26_Medicinal_Chemistry" title="Bioorganic & Medicinal Chemistry">Bioorg. Med. Chem.</a></cite> <span style="white-space:nowrap">Band<span style="display:inline-block;width:.2em"> </span>9</span>, <span style="white-space:nowrap">Nr.<span style="display:inline-block;width:.2em"> </span>3</span>, 2000, <span style="white-space:nowrap">S.<span style="display:inline-block;width:.2em"> </span>745–762</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/10.1016/s0968-0896%2800%2900292-3">10.1016/s0968-0896(00)00292-3</a></span>, <a class="external mw-magiclink-pmid" rel="nofollow" href="https://www.ncbi.nlm.nih.gov/pubmed/11310610?dopt=Abstract">PMID 11310610</a>.<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:5-Methoxy-1H-indol&rft.atitle=Synthesis+of+Indomethacin+Analogues+for+Evaluation+as+Modulators+of+MRP+Activity&rft.au=A.+R.+Maguire%2C+S.+J.+Plunkett%2C+S.+Papot%2C+...&rft.date=2000&rft.doi=10.1016%2Fs0968-0896%2800%2900292-3&rft.genre=journal&rft.issue=3&rft.jtitle=Bioorg.+Med.+Chem.&rft.pages=745-762&rft.pmid=11310610&rft.volume=9" style="display:none"> </span></span>

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<li id="cite_note-4"><span class="mw-cite-backlink"><a href="#cite_ref-4">↑</a></span> <span class="reference-text">N. N. Suvorov, V. N. Shkil'kova, N. Y. Podkhalyuzina: <cite style="font-style:italic">CATALYTIC SYNTHESIS OF 4-, 5-, 6-, AND 7-METHOXYINDOLES</cite>. In: <cite style="font-style:italic"><a href="Chemistry_of_Heterocyclic_Compounds" title="Chemistry of Heterocyclic Compounds">Chem. Heterocycl. Compd.</a></cite> <span style="white-space:nowrap">Band<span style="display:inline-block;width:.2em"> </span>18</span>, 1983, <span style="white-space:nowrap">S.<span style="display:inline-block;width:.2em"> </span>802–803</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/10.1007/BF00506582">10.1007/BF00506582</a></span>.<span class="Z3988" title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rfr_id=info:sid/de.wikipedia.org:5-Methoxy-1H-indol&rft.atitle=CATALYTIC+SYNTHESIS+OF+4-%2C+5-%2C+6-%2C+AND+7-METHOXYINDOLES&rft.au=N.+N.+Suvorov%2C+V.+N.+Shkil%27kova%2C+N.+Y.+Podkhalyuzina&rft.btitle=Chem.+Heterocycl.+Compd.&rft.date=1983&rft.doi=10.1007%2FBF00506582&rft.genre=book&rft.pages=802-803&rft.volume=18" style="display:none"> </span></span>

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