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<h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Isoindolin</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">
<tbody><tr>
<th colspan="2" style="background:#FFDEAD; color:#202122;">Strukturformel
</th></tr>
<tr>
<td colspan="2" class="hintergrundfarbe-basis skin-invert-image" style="text-align:center;"><span typeof="mw:File"></span>
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<tr>
<th colspan="2" style="background:#FFDEAD; color:#202122;">Allgemeines
</th></tr>
<tr>
<td style="width:33%;">Name
</td>
<td>Isoindolin
</td></tr>
<tr>
<td>Andere Namen
</td>
<td>
<ul><li>2,3-Dihydro-1<i>H</i>-isoindol</li>
<li>2<i>H</i>-Isoindol</li></ul>
</td></tr>
<tr>
<td><a href="Summenformel" title="Summenformel">Summenformel</a>
</td>
<td>C<sub>8</sub>H<sub>9</sub>N
</td></tr>
<tr>
<td>Kurzbeschreibung
</td>
<td>
<p>farblose Flüssigkeit<sup id="cite_ref-DOI10.1002/jps.2600530840_1-0" class="reference"><a href="#cite_note-DOI10.1002/jps.2600530840-1"><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=496-12-8">496-12-8</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> (<a href="EG-Nummer#Listennummern" title="EG-Nummer">Listennummer</a>)
</td>
<td colspan="2">628-708-0
</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/100.156.955">100.156.955</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/422478">422478</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.373951.html">373951</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/Q2598923" class="extiw external" title="d:Q2598923">Q2598923</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>119,16 g·<a href="Mol" title="Mol">mol</a><sup>−1</sup>
</td></tr>
<tr>
<td><a href="Aggregatzustand" title="Aggregatzustand">Aggregatzustand</a>
</td>
<td>
<p>flüssig<sup id="cite_ref-Sigma_2-0" class="reference"><a href="#cite_note-Sigma-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup>
</p>
</td></tr>
<tr>
<td><a href="Dichte" title="Dichte">Dichte</a>
</td>
<td>
<p>1,05 g·cm<sup>−3</sup> (25 °C)<sup id="cite_ref-Sigma_2-1" class="reference"><a href="#cite_note-Sigma-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup>
</p>
</td></tr>
<tr>
<td><a href="Schmelzpunkt" title="Schmelzpunkt">Schmelzpunkt</a>
</td>
<td>
<p>17 <a href="Grad_Celsius" title="Grad Celsius">°C</a><sup id="cite_ref-Sigma_2-2" class="reference"><a href="#cite_note-Sigma-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup>
</p>
</td></tr>
<tr>
<td><a href="Siedepunkt" title="Siedepunkt">Siedepunkt</a>
</td>
<td>
<p>221 °C<sup id="cite_ref-Sigma_2-3" class="reference"><a href="#cite_note-Sigma-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup>
</p>
</td></tr>
<tr>
<td><a href="Brechungsindex" title="Brechungsindex">Brechungsindex</a>
</td>
<td>
<p>1,57 (20 °C)<sup id="cite_ref-Sigma_2-4" class="reference"><a href="#cite_note-Sigma-2"><span class="cite-bracket">[</span>2<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-Sigma_2-5" class="reference"><a href="#cite_note-Sigma-2"><span class="cite-bracket">[</span>2<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><span typeof="mw:File"><a href="Global_harmonisiertes_System_zur_Einstufung_und_Kennzeichnung_von_Chemikalien#Übersicht:_EU-Gefahrensymbole,_UN/GHS-Gefahrenpiktogramme,_UN/ADR-Gefahrensymbole" title="07 – Achtung"></a></span>
</td></tr></tbody></table>
<p><b>Achtung</b>
</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><a href="H-_und_P-S%C3%A4tze#H-Sätze" title="H- und P-Sätze"><span style="display:inline-block;"><span style="color:#ff5400; border-bottom:1px dotted #ff5400;" title="Verursacht Hautreizungen.">315</span></span></a>‐<a href="H-_und_P-S%C3%A4tze#H-Sätze" title="H- und P-Sätze"><span style="display:inline-block;"><span style="color:#ff5400; border-bottom:1px dotted #ff5400;" title="Verursacht schwere Augenreizung.">319</span></span></a>‐<a href="H-_und_P-S%C3%A4tze#H-Sätze" title="H- und P-Sätze"><span style="display:inline-block;"><span style="color:#ff5400; border-bottom:1px dotted #ff5400;" title="Kann die Atemwege reizen.">335</span></span></a>
</td></tr>
<tr>
<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_2-6" class="reference"><a href="#cite_note-Sigma-2"><span class="cite-bracket">[</span>2<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). Brechungsindex: <a href="Natrium-D-Linie" title="Natrium-D-Linie">Na-D-Linie</a>, 20 °C
</td></tr></tbody></table><p><span class="editoronly" style="display:none;"></span>
</p><p><b>Isoindolin</b> ist eine <a href="Chemische_Verbindung" title="Chemische Verbindung">chemische Verbindung</a> aus der Gruppe der Heterocyclen.
</p>
<div class="mw-heading mw-heading2"><h2 id="Gewinnung_und_Darstellung">Gewinnung und Darstellung</h2></div>
<p>Isoindolin kann aus <a href="Phthals%C3%A4ureanhydrid" title="Phthalsäureanhydrid">Phthalsäureanhydrid</a> mit <a href="Harnstoff" title="Harnstoff">Harnstoff</a> über Isoindolinon gewonnen werden.<sup id="cite_ref-C.A._Heaton_3-0" class="reference"><a href="#cite_note-C.A._Heaton-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup>
</p><p>Bornstein stellte Isoindolin durch hydrolytische Spaltung von 2-(<i>p</i>-Tolylsulfonyl)-isoindolin (hergestellt aus o-Xylylendibromid und <a href="P-Toluolsulfonamid" title="P-Toluolsulfonamid">p-Toluolsulfonamid</a>) mit <a href="Phenol" title="Phenol">Phenol</a> und <a href="Bromwasserstoffs%C3%A4ure" title="Bromwasserstoffsäure">Bromwasserstoffsäure</a> in <a href="Propions%C3%A4ure" title="Propionsäure">Propionsäure</a> her.<sup id="cite_ref-DOI10.1002/jps.2600530840_1-1" class="reference"><a href="#cite_note-DOI10.1002/jps.2600530840-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup>
</p>
<div class="mw-heading mw-heading2"><h2 id="Eigenschaften">Eigenschaften</h2></div>
<p>Isoindolin ist eine farblose Flüssigkeit.<sup id="cite_ref-DOI10.1002/jps.2600530840_1-2" class="reference"><a href="#cite_note-DOI10.1002/jps.2600530840-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup>
</p>
<div class="mw-heading mw-heading2"><h2 id="Verwendung">Verwendung</h2></div>
<p>Isoindolinderivate werden als <a href="Pigment" class="mw-redirect" title="Pigment">Pigmente</a> für Kunststoffe und Lacke verwendet.<sup id="cite_ref-Willy_Herbst,_Klaus_Hunger_4-0" class="reference"><a href="#cite_note-Willy_Herbst,_Klaus_Hunger-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup>
</p>
<div class="mw-heading mw-heading2"><h2 id="Einzelnachweise">Einzelnachweise</h2></div>
<ol class="references">
<li id="cite_note-DOI10.1002/jps.2600530840-1"><span class="mw-cite-backlink">↑ <sup><a href="#cite_ref-DOI10.1002/jps.2600530840_1-0">a</a></sup> <sup><a href="#cite_ref-DOI10.1002/jps.2600530840_1-1">b</a></sup> <sup><a href="#cite_ref-DOI10.1002/jps.2600530840_1-2">c</a></sup></span> <span class="reference-text">John L. Neumeyer: <i>Facile Synthesis of Isoindoline and Substituted Isoindolines.</i> In: <i>Journal of Pharmaceutical Sciences.</i> 53, 1964, S. 981, <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/jps.2600530840">10.1002/jps.2600530840</a></span>.</span>
</li>
<li id="cite_note-Sigma-2"><span class="mw-cite-backlink">↑ <sup><a href="#cite_ref-Sigma_2-0">a</a></sup> <sup><a href="#cite_ref-Sigma_2-1">b</a></sup> <sup><a href="#cite_ref-Sigma_2-2">c</a></sup> <sup><a href="#cite_ref-Sigma_2-3">d</a></sup> <sup><a href="#cite_ref-Sigma_2-4">e</a></sup> <sup><a href="#cite_ref-Sigma_2-5">f</a></sup> <sup><a href="#cite_ref-Sigma_2-6">g</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/515574">Isoindolin, 97%</a></span> bei <a href="Sigma-Aldrich" title="Sigma-Aldrich">Sigma-Aldrich</a>, abgerufen am 11. August 2018 (<a rel="nofollow" class="external text" href="https://www.sigmaaldrich.com/DE/de/sds/ALDRICH/515574?userType=anonymous">PDF</a>).<span class="editoronly" style="display:none;"></span></span>
</li>
<li id="cite_note-C.A._Heaton-3"><span class="mw-cite-backlink"><a href="#cite_ref-C.A._Heaton_3-0">↑</a></span> <span class="reference-text">C.A. Heaton: <cite style="font-style:italic">The Chemical Industry</cite>. Springer Science & Business Media, 2012, ISBN 978-94-011-1318-2, <span style="white-space:nowrap">S.<span style="display:inline-block;width:.2em"> </span>170</span> (<a rel="nofollow" class="external text" href="https://books.google.de/books?id=Y2IOBwAAQBAJ&pg=PA170#v=onepage">eingeschränkte Vorschau</a> in der Google-Buchsuche).<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:Isoindolin&rft.au=C.A.+Heaton&rft.btitle=The+Chemical+Industry&rft.date=2012&rft.genre=book&rft.isbn=9789401113182&rft.pages=170&rft.pub=Springer+Science+%26+Business+Media" style="display:none"> </span></span>
</li>
<li id="cite_note-Willy_Herbst,_Klaus_Hunger-4"><span class="mw-cite-backlink"><a href="#cite_ref-Willy_Herbst,_Klaus_Hunger_4-0">↑</a></span> <span class="reference-text">Willy Herbst, Klaus Hunger: <cite style="font-style:italic">Industrielle Organische Pigmente</cite>. John Wiley & Sons, 2009, ISBN 3-527-62496-1, <span style="white-space:nowrap">S.<span style="display:inline-block;width:.2em"> </span>418</span> (<a rel="nofollow" class="external text" href="https://books.google.de/books?id=zP0JXdYsWP0C&pg=PA418#v=onepage">eingeschränkte Vorschau</a> in der Google-Buchsuche).<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:Isoindolin&rft.au=Willy+Herbst%2C+Klaus+Hunger&rft.btitle=Industrielle+Organische+Pigmente&rft.date=2009&rft.genre=book&rft.isbn=3527624961&rft.pages=418&rft.pub=John+Wiley+%26+Sons" style="display:none"> </span></span>
</li>
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