<!DOCTYPE html>
<html class="client-nojs vector-feature-language-in-header-enabled vector-feature-language-in-main-page-header-disabled vector-feature-page-tools-pinned-disabled vector-feature-toc-pinned-clientpref-0 vector-toc-not-available vector-feature-main-menu-pinned-disabled vector-feature-limited-width-clientpref-1 vector-feature-limited-width-content-enabled vector-feature-custom-font-size-clientpref-1 vector-feature-appearance-pinned-clientpref-0 skin-theme-clientpref-day vector-sticky-header-enabled" lang="de" dir="ltr"><head>
<meta charset="UTF-8">
<title>Diphenylethin</title>
<meta name="viewport" content="width=device-width, initial-scale=1.0">
<link rel="icon" type="image/png" href="./_res_/favicon.png">
<link rel="canonical" href="https://de.wikipedia.org/wiki/Diphenylethin"> <link href="./_mw_/ext.cite.styles.css" rel="stylesheet" type="text/css">
<link href="./_mw_/ext.wikimediamessages.styles.css" rel="stylesheet" type="text/css">
<link href="./_mw_/skins.vector.icons.css" rel="stylesheet" type="text/css">
<link href="./_mw_/skins.vector.search.codex.styles.css" rel="stylesheet" type="text/css">
<link href="./_mw_/skins.vector.styles.css" rel="stylesheet" type="text/css">
<meta name="ResourceLoaderDynamicStyles" content="">
<link href="./_mw_/ext.gadget.citeRef.css" rel="stylesheet" type="text/css">
<link href="./_mw_/ext.gadget.defaultPlainlinks.css" rel="stylesheet" type="text/css">
<link href="./_mw_/ext.gadget.dewikiCommonHide.css" rel="stylesheet" type="text/css">
<link href="./_mw_/ext.gadget.dewikiCommonLayout.css" rel="stylesheet" type="text/css">
<link href="./_mw_/ext.gadget.dewikiCommonStyle.css" rel="stylesheet" type="text/css">
<link href="./_mw_/ext.gadget.dewikiDarkmode.css" rel="stylesheet" type="text/css">
<link href="./_mw_/ext.gadget.dewikiResponsive.css" rel="stylesheet" type="text/css">
<link href="./_mw_/ext.gadget.specialSearch.css" rel="stylesheet" type="text/css">
<link rel="stylesheet" type="text/css" href="./_mw_/site.styles.css">
<link rel="stylesheet" type="text/css" href="./_mw_/noscript.css">
<link rel="stylesheet" type="text/css" href="./_res_/footer.css">
<link rel="stylesheet" type="text/css" href="./_res_/vector-2022.css">
</head>
<body class="skin--responsive skin-vector skin-vector-search-vue mediawiki ltr sitedir-ltr mw-hide-empty-elt ns-0 ns-subject page-Diphenylethin rootpage-Diphenylethin skin-vector-2022 action-view">
<div class="mw-page-container">
<div class="mw-page-container-inner">
<div class="mw-content-container">
<main id="content" class="mw-body">
<header class="mw-body-header vector-page-titlebar">
<h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Diphenylethin</span></h1>
</header>
<a id="top"></a>
<div id="bodyContent" class="vector-body ve-init-mw-desktopArticleTarget-targetContainer" aria-labelledby="firstHeading" data-mw-ve-target-container="">
<div id="contentSub">
<div id="mw-content-subtitle"></div>
</div>
<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 class="mw-default-size" typeof="mw:File"></span>
</td></tr>
<tr>
<th colspan="2" style="background:#FFDEAD; color:#202122;">Allgemeines
</th></tr>
<tr>
<td style="width:33%;">Name
</td>
<td>Diphenylethin
</td></tr>
<tr>
<td>Andere Namen
</td>
<td>
<ul><li>Tolan</li>
<li>Methintolan</li>
<li>Diphenylacetylen</li>
<li>2-Phenylethinylbenzen <small>(<a href="IUPAC-Nomenklatur" class="mw-redirect" title="IUPAC-Nomenklatur">IUPAC</a>)</small></li></ul>
</td></tr>
<tr>
<td><a href="Summenformel" title="Summenformel">Summenformel</a>
</td>
<td>C<sub>14</sub>H<sub>10</sub>
</td></tr>
<tr>
<td>Kurzbeschreibung
</td>
<td>
<p>weiße Nadeln<sup id="cite_ref-orgsyn_3_350_1-0" class="reference"><a href="#cite_note-orgsyn_3_350-1"><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=501-65-5">501-65-5</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">207-926-6
</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/100.007.206">100.007.206</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/10390">10390</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/Q902100" class="extiw external" title="d:Q902100">Q902100</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>178,23 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
</p>
</td></tr>
<tr>
<td><a href="Dichte" title="Dichte">Dichte</a>
</td>
<td>
<p>0,99 g·cm<sup>−3</sup> (25 °C)<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="Schmelzpunkt" title="Schmelzpunkt">Schmelzpunkt</a>
</td>
<td>
<p>59–61 <a href="Grad_Celsius" title="Grad Celsius">°C</a><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>
<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_2-2" 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><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-Sigma_2-3" 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).
</td></tr></tbody></table><p><span class="editoronly" style="display:none;"></span>
</p><p><b>Diphenylethin</b> ist die chemische Verbindung C<sub>6</sub>H<sub>5</sub>–C≡C–C<sub>6</sub>H<sub>5</sub>. Das Molekül besteht aus zwei <a href="Phenylrest" class="mw-redirect" title="Phenylrest">Phenylresten</a>, die an beide Enden einer <a href="Alkin" class="mw-redirect" title="Alkin">alkinischen</a> Dreifachbindung gebunden sind. Die Verbindung kann deshalb sowohl als <a href="Ethin" title="Ethin">Ethinderivat</a> als auch als <a href="Benzol" title="Benzol">Benzolderivat</a> angesehen werden.
</p><p>Diphenylethin ist ein farbloser kristalliner Feststoff, der sowohl als Grundbaustein in der <a href="Organische_Chemie" title="Organische Chemie">organischen Synthese</a> als auch als Ligand in der <a href="Organometallchemie" class="mw-redirect" title="Organometallchemie">Organometallchemie</a> häufig verwendet wird.
</p>
<div class="mw-heading mw-heading2"><h2 id="Herstellung">Herstellung</h2></div>
<p>Diphenylethin kann auf verschiedene Weisen hergestellt werden:
</p>
<ul><li>Kondensation von <a href="Benzil" title="Benzil">Benzil</a> mit <a href="Hydrazin" title="Hydrazin">Hydrazin</a> liefert das Dihydrazon, welches dann mit <a href="Quecksilber(II)-oxid" title="Quecksilber(II)-oxid">Quecksilber(II)-oxid</a> oxidiert wird.<sup id="cite_ref-cv4p0377_3-0" class="reference"><a href="#cite_note-cv4p0377-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup></li>
<li>Bromierung von <a href="Stilben" title="Stilben">Stilben</a> (Diphenylethen) und anschließende Dehydrohalogenierung.<sup id="cite_ref-orgsyn_3_350_1-1" class="reference"><a href="#cite_note-orgsyn_3_350-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> Das Produkt kann jedoch mit schwer abtrennbarem Stilben verunreinigt sein.<sup id="cite_ref-cv4p0377_3-1" class="reference"><a href="#cite_note-cv4p0377-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup></li>
<li><a href="Stephens-Castro-Kupplung" class="mw-redirect" title="Stephens-Castro-Kupplung">Stephens-Castro-Kupplung</a> von <a href="Iodbenzol" title="Iodbenzol">Iodbenzol</a> mit dem Kupfersalz des Phenylethins.</li></ul>
<div class="mw-heading mw-heading2"><h2 id="Bedeutende_Derivate">Bedeutende Derivate</h2></div>
<ul><li>Die Reaktion mit <a href="Tetraphenylcyclopentadienon" title="Tetraphenylcyclopentadienon">Tetraphenylcyclopentadienon</a> liefert <a href="Hexaphenylbenzol" title="Hexaphenylbenzol">Hexaphenylbenzol</a>.<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></li>
<li>Die Reaktion mit <a href="Benzalchlorid" title="Benzalchlorid">Benzalchlorid</a> in Gegenwart von <a href="Kalium-tert-butanolat" title="Kalium-tert-butanolat">Kalium-<i>tert</i>-butanolat</a> liefert das 3-Alkoxy<a href="Cyclopropen" title="Cyclopropen">cyclopropen</a>, welches sich in Bromwasserstoff zu Triphenylcyclopropeniumbromid umwandelt.<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></li></ul>
<div class="mw-heading mw-heading2"><h2 id="Einzelnachweise">Einzelnachweise</h2></div>
<ol class="references">
<li id="cite_note-orgsyn_3_350-1"><span class="mw-cite-backlink">↑ <sup><a href="#cite_ref-orgsyn_3_350_1-0">a</a></sup> <sup><a href="#cite_ref-orgsyn_3_350_1-1">b</a></sup></span> <span class="reference-text">Lee Irvin Smith, M. M. Falkof: <span style="font-style:italic;"><a rel="nofollow" class="external text" href="http://www.orgsyn.org/demo.aspx?prep=CV3P0350">Diphenylacetylene</a></span> In: <i><a href="Organic_Syntheses" title="Organic Syntheses">Organic Syntheses</a></i>. 22, 1942, S. 50, <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/10.15227/orgsyn.022.0050">10.15227/orgsyn.022.0050</a></span>; Coll. Vol. 3, 1955, S. 350 (<a rel="nofollow" class="external text" href="http://www.orgsyn.org/Content/pdfs/procedures/CV3P0350.pdf">PDF</a>).<span class="editoronly" style="display:none;"></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></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/D204803">Diphenylacetylene, 98 %</a></span> bei <a href="Sigma-Aldrich" title="Sigma-Aldrich">Sigma-Aldrich</a>, abgerufen am 10. Mai 2012 (<a rel="nofollow" class="external text" href="https://www.sigmaaldrich.com/DE/de/sds/ALDRICH/D204803?userType=anonymous">PDF</a>).<span class="editoronly" style="display:none;"></span></span>
</li>
<li id="cite_note-cv4p0377-3"><span class="mw-cite-backlink">↑ <sup><a href="#cite_ref-cv4p0377_3-0">a</a></sup> <sup><a href="#cite_ref-cv4p0377_3-1">b</a></sup></span> <span class="reference-text">Arthur C. Cope, Douglas S. Smith, Robert J. Cotter: <span style="font-style:italic;"><a rel="nofollow" class="external text" href="http://www.orgsyn.org/demo.aspx?prep=CV4P0377">Diphenylacetylene</a></span> In: <i><a href="Organic_Syntheses" title="Organic Syntheses">Organic Syntheses</a></i>. 34, 1954, S. 42, <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/10.15227/orgsyn.034.0042">10.15227/orgsyn.034.0042</a></span>; Coll. Vol. 4, 1963, S. 377 (<a rel="nofollow" class="external text" href="http://www.orgsyn.org/Content/pdfs/procedures/CV4P0377.pdf">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">Louis F. Fieser: <span style="font-style:italic;"><a rel="nofollow" class="external text" href="http://www.orgsyn.org/demo.aspx?prep=CV5P0604">Hexaphenylbenzene</a></span> In: <i><a href="Organic_Syntheses" title="Organic Syntheses">Organic Syntheses</a></i>. 46, 1966, S. 44, <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/10.15227/orgsyn.046.0044">10.15227/orgsyn.046.0044</a></span>; Coll. Vol. 5, 1973, S. 604 (<a rel="nofollow" class="external text" href="http://www.orgsyn.org/Content/pdfs/procedures/CV5P0604.pdf">PDF</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">Ruo Xu, Ronald Breslow: <span style="font-style:italic;"><a rel="nofollow" class="external text" href="http://www.orgsyn.org/demo.aspx?prep=CV9P0730">1,2,3-Triphenylcyclopropendium Bromide</a></span> In: <i><a href="Organic_Syntheses" title="Organic Syntheses">Organic Syntheses</a></i>. 74, 1997, S. 72, <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/10.15227/orgsyn.074.0072">10.15227/orgsyn.074.0072</a></span>; Coll. Vol. 9, 1998, S. 730 (<a rel="nofollow" class="external text" href="http://www.orgsyn.org/Content/pdfs/procedures/CV9P0730.pdf">PDF</a>).<span class="editoronly" style="display:none;"></span></span>
</li>
</ol></div><!--htdig_noindex--><div><div class="zim-footer">
Dieser Artikel wurde von <a class="external text" title="Zuletzt bearbeitet am 2023-03-02" href="https://de.wikipedia.org/wiki/?title=Diphenylethin&oldid=231409246">Wikipedia</a> herausgegeben. Der Text ist unter <a class="external text" href="https://creativecommons.org/licenses/by-sa/4.0/deed.de">Creative Commons Attribution-Share Alike 4.0</a> verfügbar, sofern nicht anders angegeben. Für die Mediendateien können zusätzliche Bedingungen gelten.
</div>
</div><!--/htdig_noindex--></div>
</div>
</main>
</div>
</div>
</div>
<script src="./_webp_/webpHandler.js"></script>
</body></html>