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<h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Chinaldinrot</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 typeof="mw:File"></span>
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<th colspan="2" style="background:#FFDEAD; color:#202122;">Allgemeines
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<td style="width:33%;">Name
</td>
<td>Chinaldinrot
</td></tr>
<tr>
<td>Andere Namen
</td>
<td>
<ul><li>2-{(<i>E</i>)-2-[4-(Dimethylamino)phenyl]vinyl}-1-ethylchinoliniumiodid (<a href="IUPAC-Nomenklatur" class="mw-redirect" title="IUPAC-Nomenklatur">IUPAC</a>)</li>
<li>4-(2-[4-(Dimethylamino)phenyl]ethenyl)-1-ethylchinoliniumiodid</li>
<li>2-[<i>p</i>-(Dimethylamino)styryl]-1-ethylchinoliniumiodid</li></ul>
</td></tr>
<tr>
<td><a href="Summenformel" title="Summenformel">Summenformel</a>
</td>
<td>C<sub>22</sub>H<sub>23</sub>IN<sub>2</sub>
</td></tr>
<tr>
<td>Kurzbeschreibung
</td>
<td>
<p>Dunkelgrünes bis grauschwarzes, feinkristallines Pulver<sup id="cite_ref-Römpp_1-0" class="reference"><a href="#cite_note-Römpp-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=117-92-0">117-92-0</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">204-221-5
</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/100.003.838">100.003.838</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/5702759">5702759</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.4643031.html">4643031</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/Q10389869" class="extiw external" title="d:Q10389869">Q10389869</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>430,33 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>fest<sup id="cite_ref-Römpp_1-1" class="reference"><a href="#cite_note-Römpp-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>174–176 °C<sup id="cite_ref-HGüsten_2-0" class="reference"><a href="#cite_note-HGüsten-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup>
</p>
</td></tr>
<tr>
<td><a href="L%C3%B6slichkeit" title="Löslichkeit">Löslichkeit</a>
</td>
<td>
<p>wenig löslich in Wasser, leicht löslich in Alkohol, <a href="Aceton" title="Aceton">Aceton</a>, <a href="Chloroform" title="Chloroform">Chloroform</a> und <a href="Eisessig" class="mw-redirect" title="Eisessig">Eisessig</a><sup id="cite_ref-Römpp_1-2" class="reference"><a href="#cite_note-Römpp-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-Sigma_3-0" class="reference"><a href="#cite_note-Sigma-3"><span class="cite-bracket">[</span>3<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>
</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>Chinaldinrot</b> ist eine <a href="Chemische_Verbindung" title="Chemische Verbindung">chemische Verbindung</a> aus der Gruppe der <a href="Cyaninfarbstoffe" class="mw-redirect" title="Cyaninfarbstoffe">Cyaninfarbstoffe</a>.
</p>
<div class="mw-heading mw-heading2"><h2 id="Herstellung">Herstellung</h2></div>
<p>Die Synthese von Chinaldinrot durch <a href="Kondensationsreaktion" title="Kondensationsreaktion">Kondensation</a> von 1-Ethyl-2-methylchinoliniumiodid<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> mit <a href="Dimethylaminobenzaldehyd" title="Dimethylaminobenzaldehyd"><i>p</i>-Dimethylaminobenzaldehyd</a> in Gegenwart von <a href="Piperidin" title="Piperidin">Piperidin</a> als <a href="Katalysator" title="Katalysator">Katalysator</a> wurde 1922 von <a href="William_Hobson_Mills" title="William Hobson Mills">William Hobson Mills</a> und <a href="James_Leonard_Brierley_Smith" title="James Leonard Brierley Smith">James Leonard Brierley Smith</a> veröffentlicht.<sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup>
</p>
<div style="margin-left: 1.6em;"><br></div>
<p>Die Synthese geht auf ein 1912 von <a href="Walter_K%C3%B6nig_(Chemiker)" title="Walter König (Chemiker)">Walter König</a> beschriebenes Verfahren zurück, bei dem <i>p</i>-Dimethylaminobenzaldehyd mit 1-Methyl-2-methylchinoliniumsalzen umgesetzt wird.<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>
<div class="mw-heading mw-heading2"><h2 id="Eigenschaften">Eigenschaften</h2></div>
<p>Chinaldinrot verhält sich im <a href="PH-Wert" title="PH-Wert">pH-Bereich</a> 1,4–3,2 als <a href="Indikator_(Chemie)" title="Indikator (Chemie)">Indikator</a> mit einem Farbumschlag von farblos nach rot.<sup id="cite_ref-IMKolthoff_7-0" class="reference"><a href="#cite_note-IMKolthoff-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup>
</p><p>In halogenierten <a href="L%C3%B6sungsmittel" title="Lösungsmittel">Lösungsmitteln</a> wie zum Beispiel <a href="Chloroform" title="Chloroform">Chloroform</a> oder <a href="Bromoform" title="Bromoform">Bromoform</a> erfolgt beim Belichten mit blauem Licht (400–490 <a href="Nanometer" class="mw-redirect" title="Nanometer">nm</a>) eine photochemische Reaktion, die sich durch die Abnahme der <i>trans</i>-<a href="Extinktion_(Optik)" title="Extinktion (Optik)">Extinktion</a> der entsprechenden <a href="Absorptionsbande" title="Absorptionsbande">Absorptionsbande</a> zeigt. Es handelt sich dabei vermutlich um eine <a href="Irreversibler_Prozess" title="Irreversibler Prozess">irreversible</a> <a href="Oxidation" title="Oxidation">Oxidation</a>. Beim Belichten einer Farbstofflösung in einem mit <a href="Chlorwasserstoff" title="Chlorwasserstoff">HCl</a> begasten <a href="Protisch" class="mw-redirect" title="Protisch">protischen</a> oder <a href="Aprotisch" class="mw-redirect" title="Aprotisch">aprotischen</a> Lösungsmittel erfolgt dagegen durch eine photochemische <a href="Cis-trans-Isomerie" title="Cis-trans-Isomerie"><i>trans</i>-<i>cis</i>-Isomerisierung</a> eine reversible Extinktionsänderung.<sup id="cite_ref-HGüsten_2-1" class="reference"><a href="#cite_note-HGüsten-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>Chinaldinrot findet Verwendung als <a href="S%C3%A4ure-Base-Indikator" class="mw-redirect" title="Säure-Base-Indikator">Säure-Base-Indikator</a> bei <a href="Titration" title="Titration">Titrationen</a> in nichtwässrigen Lösungsmitteln, beispielsweise bei der titrimetrischen Bestimmung <a href="Schwache_Basen" title="Schwache Basen">schwacher Basen</a> mit <a href="Perchlors%C3%A4ure" title="Perchlorsäure">Perchlorsäure</a> oder bei der Bestimmung der Wasserstoffionenkonzentration in der <a href="Magens%C3%A4ure" class="mw-redirect" title="Magensäure">Magensäure</a>.<sup id="cite_ref-Römpp_1-3" class="reference"><a href="#cite_note-Römpp-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><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><p>Mit <a href="Nukleins%C3%A4uren" title="Nukleinsäuren">Nukleinsäuren</a> bildet Chinaldinrot <a href="Fluoreszenz" title="Fluoreszenz">fluoreszierende</a> Verbindungen, die im pH-Bereich 3,2–3,6 ihre maximalen Fluoreszenz aufweisen. Der Farbstoff kann daher als <a href="Fluorometrie" class="mw-redirect" title="Fluorometrie">fluorometrische</a> Methode zur schnellen Bestimmung von Nukleinsäuren verwendet werden.<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>
</p>
<div class="mw-heading mw-heading2"><h2 id="Einzelnachweise">Einzelnachweise</h2></div>
<ol class="references">
<li id="cite_note-Römpp-1"><span class="mw-cite-backlink">↑ <sup><a href="#cite_ref-Römpp_1-0">a</a></sup> <sup><a href="#cite_ref-Römpp_1-1">b</a></sup> <sup><a href="#cite_ref-Römpp_1-2">c</a></sup> <sup><a href="#cite_ref-Römpp_1-3">d</a></sup></span> <span class="reference-text">Eintrag zu <a rel="nofollow" class="external text" href="https://roempp.thieme.de/lexicon/RD-03-01287"><i>Chinaldinrot</i></a>. In: <i><a href="R%C3%B6mpp_Online" class="mw-redirect" title="Römpp Online">Römpp Online</a>.</i> Georg Thieme Verlag, abgerufen am 25. Juni 2022.<span class="editoronly" style="display:none;"></span></span>
</li>
<li id="cite_note-HGüsten-2"><span class="mw-cite-backlink">↑ <sup><a href="#cite_ref-HGüsten_2-0">a</a></sup> <sup><a href="#cite_ref-HGüsten_2-1">b</a></sup></span> <span class="reference-text">Hans Güsten: <cite style="font-style:italic">Notiz zur Phototropie des Chinaldinrots</cite>. In: <cite style="font-style:italic"><a href="Liebigs_Annalen_der_Chemie" class="mw-redirect" title="Liebigs Annalen der Chemie">Liebigs Annalen der Chemie</a></cite>. <span style="white-space:nowrap">Band<span style="display:inline-block;width:.2em"> </span>1981</span>, <span style="white-space:nowrap">Nr.<span style="display:inline-block;width:.2em"> </span>10</span>, 1981, <span style="white-space:nowrap">S.<span style="display:inline-block;width:.2em"> </span>1896–1898</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/jlac.198119811018">10.1002/jlac.198119811018</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:Chinaldinrot&rft.atitle=Notiz+zur+Phototropie+des+Chinaldinrots&rft.au=Hans+G%C3%BCsten&rft.date=1981&rft.doi=10.1002%2Fjlac.198119811018&rft.genre=journal&rft.issue=10&rft.jtitle=Liebigs+Annalen+der+Chemie&rft.pages=1896-1898&rft.volume=1981" style="display:none"> </span></span>
</li>
<li id="cite_note-Sigma-3"><span class="mw-cite-backlink"><a href="#cite_ref-Sigma_3-0">↑</a></span> <span class="reference-text">Datenblatt <span style="font-style:italic;"><a rel="nofollow" class="external text" href="https://www.sigmaaldrich.com/catalog/product/SIAL/201316">Quinaldine Red</a></span> bei <a href="Sigma-Aldrich" title="Sigma-Aldrich">Sigma-Aldrich</a>, abgerufen am 25. Juni 2022 (<a rel="nofollow" class="external text" href="https://www.sigmaaldrich.com/DE/de/sds/SIAL/201316?userType=anonymous">PDF</a>).<span class="editoronly" style="display:none;"></span></span>
</li>
<li id="cite_note-4"><span class="mw-cite-backlink"><a href="#cite_ref-4">↑</a></span> <span class="reference-text">Externe Identifikatoren von bzw. Datenbank-Links zu <span style="font-style:italic">1-Ethyl-2-methylchinoliniumiodid</span>: <a href="CAS-Nummer" title="CAS-Nummer">CAS-Nr.</a>: <span title="Untervorlage eingebunden: CASRN"></span><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=606-55-3">606-55-3</a><span class="editoronly" style="display:none;"></span>, <a href="EG-Nummer" title="EG-Nummer">EG-Nr.</a>: 210-120-7, <a href="Europ%C3%A4ische_Chemikalienagentur" title="Europäische Chemikalienagentur">ECHA</a>-InfoCard: <a rel="nofollow" class="external text" href="https://www.echa.europa.eu/de/substance-information/-/substanceinfo/100.009.201">100.009.201</a>, <a href="PubChem" title="PubChem">PubChem</a>: <a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/69076">69076</a>, <a href="ChemSpider" title="ChemSpider">ChemSpider</a>: <a rel="nofollow" class="external text" href="http://www.chemspider.com/Chemical-Structure.62296.html">62296</a>, <a href="Wikidata" title="Wikidata">Wikidata</a>: <a href="https://www.wikidata.org/wiki/Q72476227" class="extiw external" title="d:Q72476227">Q72476227</a>.<span class="editoronly" style="display:none;"></span></span>
</li>
<li id="cite_note-5"><span class="mw-cite-backlink"><a href="#cite_ref-5">↑</a></span> <span class="reference-text">William Hobson Mills, James Leonard Brierley Smith: <cite style="font-style:italic">CCCXXVIII.—The reactivity of methyl groups in heterocyclic bases</cite>. In: <cite style="font-style:italic"><a href="Journal_of_the_Chemical_Society" title="Journal of the Chemical Society">Journal of the Chemical Society</a>, Transactions</cite>. <span style="white-space:nowrap">Band<span style="display:inline-block;width:.2em"> </span>121</span>, 1922, <span style="white-space:nowrap">S.<span style="display:inline-block;width:.2em"> </span>2724–2737</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/10.1039/CT9222102724">10.1039/CT9222102724</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:Chinaldinrot&rft.atitle=CCCXXVIII.%E2%80%94The+reactivity+of+methyl+groups+in+heterocyclic+bases&rft.au=William+Hobson+Mills%2C+James+Leonard+Brierley+Smith&rft.btitle=Journal+of+the+Chemical+Society%2C+Transactions&rft.date=1922&rft.doi=10.1039%2FCT9222102724&rft.genre=book&rft.pages=2724-2737&rft.volume=121" style="display:none"> </span></span>
</li>
<li id="cite_note-6"><span class="mw-cite-backlink"><a href="#cite_ref-6">↑</a></span> <span class="reference-text">W. König: <cite style="font-style:italic">Zur Frage der Konstitution der Cyaninfarbstoffe</cite>. In: <cite style="font-style:italic"><a href="Journal_f%C3%BCr_Praktische_Chemie" class="mw-redirect" title="Journal für Praktische Chemie">Journal für Praktische Chemie</a></cite>. <span style="white-space:nowrap">Band<span style="display:inline-block;width:.2em"> </span>86</span>, <span style="white-space:nowrap">Nr.<span style="display:inline-block;width:.2em"> </span>1</span>, 1912, <span style="white-space:nowrap">S.<span style="display:inline-block;width:.2em"> </span>166–174</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/prac.19120860110">10.1002/prac.19120860110</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:Chinaldinrot&rft.atitle=Zur+Frage+der+Konstitution+der+Cyaninfarbstoffe&rft.au=W.+K%C3%B6nig&rft.date=1912&rft.doi=10.1002%2Fprac.19120860110&rft.genre=journal&rft.issue=1&rft.jtitle=Journal+f%C3%BCr+Praktische+Chemie&rft.pages=166-174&rft.volume=86" style="display:none"> </span></span>
</li>
<li id="cite_note-IMKolthoff-7"><span class="mw-cite-backlink"><a href="#cite_ref-IMKolthoff_7-0">↑</a></span> <span class="reference-text"><a href="Izaak_Maurits_Kolthoff" class="mw-redirect" title="Izaak Maurits Kolthoff">Izaak Maurits Kolthoff</a>, <a href="Harry_Fischgold" title="Harry Fischgold">Harry Fischgold</a>: <cite style="font-style:italic">Säure-Basen-Indicatoren</cite>. Ihre Anwendung bei der colorimetrischen Bestimmung der Wasserstoffionenkonzentration. 4. Auflage. Springer-Verlag, Berlin, Heidelberg 1932, ISBN 978-3-642-52567-4, <span style="white-space:nowrap">S.<span style="display:inline-block;width:.2em"> </span>161</span> (<a rel="nofollow" class="external text" href="https://books.google.de/books?id=sVGdBgAAQBAJ&pg=PA161#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:Chinaldinrot&rft.au=Izaak+Maurits+Kolthoff%2C+Harry+Fischgold&rft.btitle=S%C3%A4ure-Basen-Indicatoren&rft.date=1932&rft.edition=4&rft.genre=book&rft.isbn=9783642525674&rft.pages=161&rft.place=Berlin%2C+Heidelberg&rft.pub=Springer-Verlag" style="display:none"> </span></span>
</li>
<li id="cite_note-8"><span class="mw-cite-backlink"><a href="#cite_ref-8">↑</a></span> <span class="reference-text">J.F. McClendon: <cite style="font-style:italic">the Determination of Hydrogen Ions in the Gastric Contents</cite>. In: <cite style="font-style:italic"><a href="Journal_of_Biological_Chemistry" title="Journal of Biological Chemistry">Journal of Biological Chemistry</a></cite>. <span style="white-space:nowrap">Band<span style="display:inline-block;width:.2em"> </span>59</span>, <span style="white-space:nowrap">Nr.<span style="display:inline-block;width:.2em"> </span>2</span>, 1924, <span style="white-space:nowrap">S.<span style="display:inline-block;width:.2em"> </span>437–442</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/s0021-9258%2818%2985280-2">10.1016/s0021-9258(18)85280-2</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:Chinaldinrot&rft.atitle=the+Determination+of+Hydrogen+Ions+in+the+Gastric+Contents&rft.au=J.F.+McClendon&rft.date=1924&rft.doi=10.1016%2Fs0021-9258%2818%2985280-2&rft.genre=journal&rft.issue=2&rft.jtitle=Journal+of+Biological+Chemistry&rft.pages=437-442&rft.volume=59" style="display:none"> </span></span>
</li>
<li id="cite_note-9"><span class="mw-cite-backlink"><a href="#cite_ref-9">↑</a></span> <span class="reference-text">Wen-You Li, Kun Miao, Hui-Ling Wu, Xi-Wen He, Hong Liang: <cite style="font-style:italic">The Fluorescent Reaction Between Quinaldine Red and Nucleic Acids and its Application to Fluorescent Assay of DNA and RNA</cite>. In: <cite style="font-style:italic"><a href="Microchimica_Acta" title="Microchimica Acta">Microchimica Acta</a></cite>. <span style="white-space:nowrap">Band<span style="display:inline-block;width:.2em"> </span>143</span>, <span style="white-space:nowrap">Nr.<span style="display:inline-block;width:.2em"> </span>1</span>, 2003, <span style="white-space:nowrap">S.<span style="display:inline-block;width:.2em"> </span>33–37</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/s00604-003-0032-2">10.1007/s00604-003-0032-2</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:Chinaldinrot&rft.atitle=The+Fluorescent+Reaction+Between+Quinaldine+Red+and+Nucleic+Acids+and+its+Application+to+Fluorescent+Assay+of+DNA+and+RNA&rft.au=Wen-You+Li%2C+Kun+Miao%2C+Hui-Ling+Wu%2C+...&rft.date=2003&rft.doi=10.1007%2Fs00604-003-0032-2&rft.genre=journal&rft.issue=1&rft.jtitle=Microchimica+Acta&rft.pages=33-37&rft.volume=143" style="display:none"> </span></span>
</li>
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