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<title>Pinacol</title>

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<span id="openzim-page-title" class="mw-page-title-main"><span class="mw-page-title-main">Pinacol</span></span>

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</style><div role="note" class="hatnote navigation-not-searchable">Not to be confused with <a href="Pinakol" title="Pinakol">Pinakol</a>, a traditional beaded ornament created and occasionally worn by the Rungus female of Sabah, Malaysia.</div>

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<caption>Pinacol

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<th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Names

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<td colspan="2" style="text-align:left;"><a href="Preferred_IUPAC_name" title="Preferred IUPAC name">Preferred IUPAC name</a>

<div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0; max-width:22em;">2,3-Dimethylbutane-2,3-diol</div></div>

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<td colspan="2" style="text-align:left;">Other names

<div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;">2,3-Dimethyl-2,3-butanediol<br>Tetramethylethylene glycol<br>1,1,2,2-Tetramethylethylene glycol<br>Pinacone</div>

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<th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Identifiers

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<td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></div>

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</style><div class="plainlist"><ul><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=76-09-5">76-09-5</a></span><sup> <span typeof="mw:File"><span></span></span><span style="display:none">Y</span></sup></li></ul></div>

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<td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">3D model (<a href="JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</div>

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<td><div class="plainlist"><ul><li><span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=CC%28C%29%28O%29C%28C%29%28C%29O">Interactive image</a></span></li><li><span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=CC%28C%29%28O%29C%28C%29%28C%29O">Interactive image</a></span></li></ul></div>

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

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<td><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=131185">CHEBI:131185</a></span><sup> <span typeof="mw:File"><span></span></span><span style="display:none">Y</span></sup></li></ul></div>

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

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<td><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembl/explore/compound/ChEMBL3289669">ChEMBL3289669</a></span></li></ul></div>

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

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<td><a href="ECHA_InfoCard" class="mw-redirect" title="ECHA InfoCard"><span title="echa.europa.eu">ECHA InfoCard</span></a>

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<td><a href="European_Community_number" title="European Community number"><span title="European Community number (chemical identifier)">EC Number</span></a>

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<td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="PubChem" title="PubChem">PubChem</a> <abbr title="Compound ID">CID</abbr></div>

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<td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="CompTox_Chemicals_Dashboard" title="CompTox Chemicals Dashboard">CompTox Dashboard</a> <span style="font-weight:normal">(<abbr title="U.S. Environmental Protection Agency">EPA</abbr>)</span></div>

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<td><div class="plainlist"><ul><li><span title="comptox.epa.gov"><a rel="nofollow" class="external text" href="https://comptox.epa.gov/dashboard/chemical/details/DTXSID3058793">DTXSID3058793</a> </span></li></ul></div>

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<div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal;"><div><a href="International_Chemical_Identifier" title="International Chemical Identifier">InChI</a></div></div>

<ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1S/C6H14O2/c1-5(2,7)6(3,4)8/h7-8H,1-4H3<sup> <span typeof="mw:File"><span></span></span><span style="display:none">Y</span></sup></div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: IVDFJHOHABJVEH-UHFFFAOYSA-N<sup> <span typeof="mw:File"><span></span></span><span style="display:none">Y</span></sup></div></div></li></ul>

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<div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal;"><div><a href="Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div>

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<th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Properties

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<td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="Chemical_formula" title="Chemical formula">Chemical formula</a></div>

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<td><a href="Molar_mass" title="Molar mass">Molar mass</a>

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<td>118.174 g/mol

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<td>Appearance

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<td>White solid

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

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<td><a href="Melting_point" title="Melting point">Melting point</a>

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<td>40 to 43 °C (104 to 109 °F; 313 to 316 K)

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<td><a href="Boiling_point" title="Boiling point">Boiling point</a>

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<td>171 to 173 °C (340 to 343 °F; 444 to 446 K)

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<th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Hazards

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<td colspan="2" style="text-align:left; background-color:#eaeaea;color:inherit;"><a href="Globally_Harmonized_System_of_Classification_and_Labelling_of_Chemicals" title="Globally Harmonized System of Classification and Labelling of Chemicals"><b>GHS</b> labelling</a>:

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<td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="GHS_hazard_pictograms" title="GHS hazard pictograms">Pictograms</a></div>

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<td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="Globally_Harmonized_System_of_Classification_and_Labelling_of_Chemicals#Signal_word" title="Globally Harmonized System of Classification and Labelling of Chemicals">Signal word</a></div>

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<td><b>Warning</b>

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<td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="GHS_hazard_statements" title="GHS hazard statements">Hazard statements</a></div>

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<td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="GHS_precautionary_statements" title="GHS precautionary statements">Precautionary statements</a></div>

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<td><a href="Flash_point" title="Flash point">Flash point</a>

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<td>77 °C (171 °F; 350 K)

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<td><a href="Safety_data_sheet" title="Safety data sheet">Safety data sheet</a> (SDS)

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<td><a rel="nofollow" class="external text" href="http://physchem.ox.ac.uk/MSDS/PI/pinacol.html">External MSDS</a>

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<th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Related compounds

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<td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Related compounds</div>

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

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<td colspan="2" style="text-align:left; background:#f8eaba; color:inherit; border:1px solid #a2a9b1;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Except where otherwise noted, data are given for materials in their <a href="Standard_state" title="Standard state">standard state</a> (at 25 °C [77 °F], 100 kPa).</div>

<div style="margin-top: 0.3em;"><div style="text-align:center;"><span typeof="mw:File"><span></span></span><span style="display:none">N</span> <span class="reflink nourlexpansion"><a class="external text external" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=433731685&page2=Pinacol">verify</a></span> (what is <sup><span typeof="mw:File"><span></span></span><span style="display:none">Y</span><span typeof="mw:File"><span></span></span><span style="display:none">N</span></sup> ?)

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<div style="margin-top: 0.3em; text-align: center;">Infobox references</div>

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<p><b>Pinacol</b> is a branched <a href="Alcohol_(chemistry)" title="Alcohol (chemistry)">alcohol</a> which finds use in organic syntheses. It is a <a href="Diol" title="Diol">diol</a> that has <a href="Hydroxyl_groups" class="mw-redirect" title="Hydroxyl groups">hydroxyl groups</a> on <a href="Vicinal_(chemistry)" title="Vicinal (chemistry)">vicinal</a> carbon atoms. A white solid that melts just above room temperature, pinacol is notable for undergoing the <a href="Pinacol_rearrangement" title="Pinacol rearrangement">pinacol rearrangement</a> in the presence of <a href="Acid" title="Acid">acid</a> and for being the namesake of the <a href="Pinacol_coupling_reaction" title="Pinacol coupling reaction">pinacol coupling reaction</a>.

</p>

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

<p>It may be produced by the <a href="Pinacol_coupling_reaction" title="Pinacol coupling reaction">pinacol coupling reaction</a> from <a href="Acetone" title="Acetone">acetone</a>:<sup id="cite_ref-1" class="reference"><a href="#cite_note-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup>

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

<p>As a <a href="Vicinal_(chemistry)" title="Vicinal (chemistry)">vicinal</a> diol, it can rearrange to <a href="Pinacolone" title="Pinacolone">pinacolone</a> by the <a href="Pinacol_rearrangement" title="Pinacol rearrangement">pinacol rearrangement</a>, e.g., by heating with <a href="Sulfuric_acid" title="Sulfuric acid">sulfuric acid</a>:<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>

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</p><p>Pinacol can be used with borane and boron trichloride to produce useful synthetic intermediates such as <a href="Pinacolborane" title="Pinacolborane">pinacolborane</a>, <a href="Bis(pinacolato)diboron" title="Bis(pinacolato)diboron">bis(pinacolato)diboron</a>,<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> and pinacolchloroborane.

</p>

<ul><li><a href="Pinacol_coupling_reaction" title="Pinacol coupling reaction">Pinacol coupling reaction</a></li>

<li><a href="Pinacol_rearrangement" title="Pinacol rearrangement">Pinacol rearrangement</a></li>

<li><a href="Semipinacol_rearrangement" title="Semipinacol rearrangement">Semipinacol rearrangement</a></li></ul>

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

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</style><cite id="CITEREFRoger_Adams_and_E._W._Adams" class="citation journal cs1">Roger Adams and E. W. Adams. <a rel="nofollow" class="external text" href="http://www.orgsyn.org/demo.aspx?prep=cv1p0459">"Pinacol Hydrate"</a>. <i><a href="Organic_Syntheses" title="Organic Syntheses">Organic Syntheses</a></i></cite>; <cite class="citation cs2"><i>Collected Volumes</i>, vol. 1, p. 459</cite>.</span>

</li>

<li id="cite_note-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-2">^</a></b></span> <span class="reference-text"><cite id="CITEREFG._A._Hill_and_E._W._Flosdorf1941" class="citation journal cs1">G. A. Hill and E. W. Flosdorf (1941). <a rel="nofollow" class="external text" href="http://www.orgsyn.org/demo.aspx?prep=CV1P0462">"Pinacolone"</a>. <i><a href="Organic_Syntheses" title="Organic Syntheses">Organic Syntheses</a></i></cite>; <cite class="citation cs2"><i>Collected Volumes</i>, vol. 1, p. 462</cite>.</span>

</li>

<li id="cite_note-3"><span class="mw-cite-backlink"><b><a href="#cite_ref-3">^</a></b></span> <span class="reference-text"><cite id="CITEREFTatsuo_IshiyamaMiki_MurataTaka-aki_AhikoNorio_Miyaura2004" class="citation journal cs1">Tatsuo Ishiyama; Miki Murata; Taka-aki Ahiko; <a href="Norio_Miyaura" title="Norio Miyaura">Norio Miyaura</a> (2004). <a rel="nofollow" class="external text" href="http://www.orgsyn.org/demo.aspx?prep=v77p0176">"Bis(pinacolato)diboron"</a>. <i><a href="Organic_Syntheses" title="Organic Syntheses">Organic Syntheses</a></i></cite>; <cite class="citation cs2"><i>Collected Volumes</i>, vol. 10, p. 115</cite>.</span>

</li>

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