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<body class="skin--responsive skin-vector skin-vector-search-vue mediawiki ltr sitedir-ltr mw-hide-empty-elt ns-0 ns-subject page-Hexadecanthiol rootpage-Hexadecanthiol skin-vector-2022 action-view">
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<h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Hexadecanthiol</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
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<tr>
<td style="width:33%;">Name
</td>
<td>Hexadecanthiol
</td></tr>
<tr>
<td>Andere Namen
</td>
<td>
<ul><li>1-Hexadecanthiol</li>
<li>Hexadecylmercaptan</li>
<li>Hexadecan-1-thiol</li>
<li>Cetylmercaptan</li></ul>
</td></tr>
<tr>
<td><a href="Summenformel" title="Summenformel">Summenformel</a>
</td>
<td>C<sub>16</sub>H<sub>34</sub>S
</td></tr>
<tr>
<td>Kurzbeschreibung
</td>
<td>
<p>farblose Flüssigkeit mit unangenehmem Geruch<sup id="cite_ref-GESTIS_1-0" class="reference"><a href="#cite_note-GESTIS-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=2917-26-2">2917-26-2</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">220-846-6
</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/100.018.952">100.018.952</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/18015">18015</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/Q424840" class="extiw external" title="d:Q424840">Q424840</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>258,51 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
</p>
</td></tr>
<tr>
<td><a href="Dichte" title="Dichte">Dichte</a>
</td>
<td>
<p>0,85 g·cm<sup>−3</sup><sup id="cite_ref-GESTIS_1-1" class="reference"><a href="#cite_note-GESTIS-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>18–20 <a href="Grad_Celsius" title="Grad Celsius">°C</a><sup id="cite_ref-GESTIS_1-2" class="reference"><a href="#cite_note-GESTIS-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>334 °C<sup id="cite_ref-GESTIS_1-3" class="reference"><a href="#cite_note-GESTIS-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup>
</p>
</td></tr>
<tr>
<td><a href="Dampfdruck" title="Dampfdruck">Dampfdruck</a>
</td>
<td>
<p>0,1 <a href="Pascal_(Einheit)" title="Pascal (Einheit)">mbar</a> (20 °C)<sup id="cite_ref-GESTIS_1-4" class="reference"><a href="#cite_note-GESTIS-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>
<ul><li>praktisch unlöslich in Wasser<sup id="cite_ref-GESTIS_1-5" class="reference"><a href="#cite_note-GESTIS-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup></li>
<li>schlecht löslich in <a href="Ethanol" title="Ethanol">Ethanol</a><sup id="cite_ref-CRC_2-0" class="reference"><a href="#cite_note-CRC-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup></li>
<li>löslich in <a href="Diethylether" title="Diethylether">Diethylether</a><sup id="cite_ref-CRC_2-1" class="reference"><a href="#cite_note-CRC-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup></li></ul>
</td></tr>
<tr>
<td><a href="Brechungsindex" title="Brechungsindex">Brechungsindex</a>
</td>
<td>
<p>1,462 (20 °C, 589 nm)<sup id="cite_ref-Merck_3-0" class="reference"><a href="#cite_note-Merck-3"><span class="cite-bracket">[</span>3<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-GESTIS_1-6" class="reference"><a href="#cite_note-GESTIS-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-GESTIS_1-7" class="reference"><a href="#cite_note-GESTIS-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). 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>1-Hexadecanthiol</b> ist eine <a href="Chemische_Verbindung" title="Chemische Verbindung">chemische Verbindung</a> aus der Gruppe der <a href="Thiole" title="Thiole">Thiole</a>.
</p>
<div class="mw-heading mw-heading2"><h2 id="Gewinnung_und_Darstellung">Gewinnung und Darstellung</h2></div>
<p>1-Hexadecanthiol kann durch Reaktion von 1-Bromhexadecan mit <a href="Thioharnstoff" title="Thioharnstoff">Thioharnstoff</a> gewonnen werden.<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>
</p>
<div class="mw-heading mw-heading2"><h2 id="Eigenschaften">Eigenschaften</h2></div>
<p>1-Hexadecanthiol ist eine brennbare farblose Flüssigkeit mit unangenehmem Geruch, welche praktisch unlöslich in Wasser ist.<sup id="cite_ref-GESTIS_1-8" class="reference"><a href="#cite_note-GESTIS-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>1-Hexadecanthiol wird als Synthesechemikalie verwendet.<sup id="cite_ref-GESTIS_1-9" class="reference"><a href="#cite_note-GESTIS-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> Es wird weiterhin zur Herstellung von Nanopartikeln und <a href="Hydrophob" class="mw-redirect" title="Hydrophob">hydrophoben</a> <a href="Selbstorganisierende_Monoschicht" title="Selbstorganisierende Monoschicht">selbstorganisierenden Monoschichten</a> verwendet. Die hohe Affinität der Thiolgruppe zu Elementen der <a href="Kupfergruppe" title="Kupfergruppe">Kupfergruppe</a> führt dazu, dass sich die Thiole spontan in einer hochgeordneten Schicht ablagern wenn ein entsprechendes Metall einer 1-Hexadecanthiol-Lösung exponiert wird.<sup id="cite_ref-Sigma_5-0" class="reference"><a href="#cite_note-Sigma-5"><span class="cite-bracket">[</span>5<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-GESTIS-1"><span class="mw-cite-backlink">↑ <sup><a href="#cite_ref-GESTIS_1-0">a</a></sup> <sup><a href="#cite_ref-GESTIS_1-1">b</a></sup> <sup><a href="#cite_ref-GESTIS_1-2">c</a></sup> <sup><a href="#cite_ref-GESTIS_1-3">d</a></sup> <sup><a href="#cite_ref-GESTIS_1-4">e</a></sup> <sup><a href="#cite_ref-GESTIS_1-5">f</a></sup> <sup><a href="#cite_ref-GESTIS_1-6">g</a></sup> <sup><a href="#cite_ref-GESTIS_1-7">h</a></sup> <sup><a href="#cite_ref-GESTIS_1-8">i</a></sup> <sup><a href="#cite_ref-GESTIS_1-9">j</a></sup></span> <span class="reference-text">Eintrag zu <span style="font-style:italic;"><a rel="nofollow" class="external text" href="https://gestis.dguv.de/data?name=494327">CAS-Nr. 2917-26-2</a></span> in der <a href="GESTIS-Stoffdatenbank" title="GESTIS-Stoffdatenbank">GESTIS-Stoffdatenbank</a> des <a href="Institut_f%C3%BCr_Arbeitsschutz_der_Deutschen_Gesetzlichen_Unfallversicherung" title="Institut für Arbeitsschutz der Deutschen Gesetzlichen Unfallversicherung">IFA</a>, abgerufen am 28. November 2011.<small class="noscript"><span></span> (JavaScript erforderlich)</small></span>
</li>
<li id="cite_note-CRC-2"><span class="mw-cite-backlink">↑ <sup><a href="#cite_ref-CRC_2-0">a</a></sup> <sup><a href="#cite_ref-CRC_2-1">b</a></sup></span> <span class="reference-text">David R. Lide (Hrsg.): <cite style="font-style:italic">CRC Handbook of Chemistry and Physics</cite>. 90. Auflage. CRC Press, 2009, ISBN 978-1-4200-9084-0.<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:Hexadecanthiol&rft.btitle=CRC+Handbook+of+Chemistry+and+Physics&rft.date=2009&rft.edition=90.&rft.genre=book&rft.isbn=9781420090840&rft.pub=CRC+Press" style="display:none"> </span></span>
</li>
<li id="cite_note-Merck-3"><span class="mw-cite-backlink"><a href="#cite_ref-Merck_3-0">↑</a></span> <span class="reference-text">Datenblatt <span style="font-style:italic;"><a rel="nofollow" class="external text" href="https://www.merckmillipore.com/DE/de/product/msds/MDA_CHEM-822063?Origin=PDP">Hexadecanthiol</a></span> bei <a href="Merck_KGaA" title="Merck KGaA">Merck</a>, abgerufen am 28. November 2011.<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">
William J. Ferrell, Antonio Garces, Etienne A. Desmyter: <cite style="font-style:italic">Synthesis and properties of 35S, 14C and 3H labeled S-alkyl glycerol ethers and derivatives</cite>. In: <cite style="font-style:italic">Chemistry and Physics of Lipids</cite>. 16. Jahrgang, <span style="white-space:nowrap">Nr.<span style="display:inline-block;width:.2em"> </span>4</span>, Juli 1976, <span style="white-space:nowrap">S.<span style="display:inline-block;width:.2em"> </span>276–284</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/10.1016/0009-3084%2876%2990022-0">10.1016/0009-3084(76)90022-0</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:Hexadecanthiol&rft.atitle=Synthesis+and+properties+of+35S%2C+14C+and+3H+labeled+S-alkyl+glycerol+ethers+and+derivatives&rft.au=William+J.+Ferrell%2C+Antonio+Garces%2C+Etienne+A.+Desmyter&rft.date=1976-07&rft.doi=10.1016%2F0009-3084%2876%2990022-0&rft.genre=journal&rft.issue=4&rft.jtitle=Chemistry+and+Physics+of+Lipids&rft.pages=276-284&rft.volume=16.+Jahrgang" style="display:none"> </span></span>
</li>
<li id="cite_note-Sigma-5"><span class="mw-cite-backlink"><a href="#cite_ref-Sigma_5-0">↑</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/ALDRICH/674516">Hexadecanthiol</a></span> bei <a href="Sigma-Aldrich" title="Sigma-Aldrich">Sigma-Aldrich</a>, abgerufen am 28. November 2011 (<a rel="nofollow" class="external text" href="https://www.sigmaaldrich.com/DE/de/sds/ALDRICH/674516?userType=anonymous">PDF</a>).<span class="editoronly" style="display:none;"></span><span style="display:none;">Vorlage:Sigma-Aldrich/Name nicht angegeben</span></span>
</li>
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