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Disponible en 23 langues." > <label id="p-lang-btn-label" for="p-lang-btn-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--action-progressive mw-portlet-lang-heading-23" aria-hidden="true" ><span class="vector-icon mw-ui-icon-language-progressive mw-ui-icon-wikimedia-language-progressive"></span> <span class="vector-dropdown-label-text">23 langues</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D8%B1%D8%A8%D8%A7%D8%B9%D9%8A_%D9%87%D9%8A%D8%AF%D8%B1%D9%88_%D8%A7%D9%84%D8%A8%D9%8A%D8%B1%D8%A7%D9%86" title="رباعي هيدرو البيران – arabe" lang="ar" hreflang="ar" data-title="رباعي هيدرو البيران" data-language-autonym="العربية" data-language-local-name="arabe" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%D8%AA%D8%AA%D8%B1%D8%A7%D9%87%DB%8C%D8%AF%D8%B1%D9%88%D9%BE%DB%8C%D8%B1%D8%A7%D9%86" title="تتراهیدروپیران – South Azerbaijani" lang="azb" hreflang="azb" data-title="تتراهیدروپیران" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Tetrahydropyran" title="Tetrahydropyran – tchèque" lang="cs" hreflang="cs" data-title="Tetrahydropyran" data-language-autonym="Čeština" data-language-local-name="tchèque" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Tetrahydropyran" title="Tetrahydropyran – allemand" lang="de" hreflang="de" data-title="Tetrahydropyran" data-language-autonym="Deutsch" data-language-local-name="allemand" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/%CE%A4%CE%B5%CF%84%CF%81%CE%B1%CF%8B%CE%B4%CF%81%CE%BF%CF%80%CF%85%CF%81%CE%AC%CE%BD%CE%B9%CE%BF" title="Τετραϋδροπυράνιο – grec" lang="el" hreflang="el" data-title="Τετραϋδροπυράνιο" data-language-autonym="Ελληνικά" data-language-local-name="grec" class="interlanguage-link-target"><span>Ελληνικά</span></a></li><li class="interlanguage-link interwiki-en mw-list-item"><a href="https://en.wikipedia.org/wiki/Tetrahydropyran" title="Tetrahydropyran – anglais" lang="en" hreflang="en" data-title="Tetrahydropyran" data-language-autonym="English" data-language-local-name="anglais" class="interlanguage-link-target"><span>English</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Oxano" title="Oxano – espagnol" lang="es" hreflang="es" data-title="Oxano" data-language-autonym="Español" data-language-local-name="espagnol" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-eu mw-list-item"><a href="https://eu.wikipedia.org/wiki/Oxano" title="Oxano – basque" lang="eu" hreflang="eu" data-title="Oxano" data-language-autonym="Euskara" data-language-local-name="basque" class="interlanguage-link-target"><span>Euskara</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%AA%D8%AA%D8%B1%D8%A7%D9%87%DB%8C%D8%AF%D8%B1%D9%88%D9%BE%DB%8C%D8%B1%D8%A7%D9%86" title="تتراهیدروپیران – persan" lang="fa" hreflang="fa" data-title="تتراهیدروپیران" data-language-autonym="فارسی" data-language-local-name="persan" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Tetrahydropyraani" title="Tetrahydropyraani – finnois" lang="fi" hreflang="fi" data-title="Tetrahydropyraani" data-language-autonym="Suomi" data-language-local-name="finnois" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Ox%C3%A1n" title="Oxán – hongrois" lang="hu" hreflang="hu" data-title="Oxán" data-language-autonym="Magyar" data-language-local-name="hongrois" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Tetrahidropiran" title="Tetrahidropiran – indonésien" lang="id" hreflang="id" data-title="Tetrahidropiran" data-language-autonym="Bahasa Indonesia" data-language-local-name="indonésien" class="interlanguage-link-target"><span>Bahasa Indonesia</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Tetraidropirano" title="Tetraidropirano – italien" lang="it" hreflang="it" data-title="Tetraidropirano" data-language-autonym="Italiano" data-language-local-name="italien" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%83%86%E3%83%88%E3%83%A9%E3%83%92%E3%83%89%E3%83%AD%E3%83%94%E3%83%A9%E3%83%B3" title="テトラヒドロピラン – japonais" lang="ja" hreflang="ja" data-title="テトラヒドロピラン" data-language-autonym="日本語" data-language-local-name="japonais" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Tetrahydropyraan" title="Tetrahydropyraan – néerlandais" lang="nl" hreflang="nl" data-title="Tetrahydropyraan" data-language-autonym="Nederlands" data-language-local-name="néerlandais" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Tetrahydropiran" title="Tetrahydropiran – polonais" lang="pl" hreflang="pl" data-title="Tetrahydropiran" data-language-autonym="Polski" data-language-local-name="polonais" class="interlanguage-link-target"><span>Polski</span></a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/Tetraidropirano" title="Tetraidropirano – portugais" lang="pt" hreflang="pt" data-title="Tetraidropirano" data-language-autonym="Português" data-language-local-name="portugais" class="interlanguage-link-target"><span>Português</span></a></li><li class="interlanguage-link interwiki-ro mw-list-item"><a href="https://ro.wikipedia.org/wiki/Oxan" title="Oxan – roumain" lang="ro" hreflang="ro" data-title="Oxan" data-language-autonym="Română" data-language-local-name="roumain" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%A2%D0%B5%D1%82%D1%80%D0%B0%D0%B3%D0%B8%D0%B4%D1%80%D0%BE%D0%BF%D0%B8%D1%80%D0%B0%D0%BD" title="Тетрагидропиран – russe" lang="ru" hreflang="ru" data-title="Тетрагидропиран" data-language-autonym="Русский" data-language-local-name="russe" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sh mw-list-item"><a href="https://sh.wikipedia.org/wiki/Tetrahidropiran" title="Tetrahidropiran – serbo-croate" lang="sh" hreflang="sh" data-title="Tetrahidropiran" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="serbo-croate" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</span></a></li><li class="interlanguage-link interwiki-sk mw-list-item"><a href="https://sk.wikipedia.org/wiki/Tetrahydropyr%C3%A1n" title="Tetrahydropyrán – slovaque" lang="sk" hreflang="sk" data-title="Tetrahydropyrán" data-language-autonym="Slovenčina" 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le dépôt de données connecté [g]" accesskey="g"><span>Élément Wikidata</span></a></li> </ul> </div> </div> </div> </div> </div> </div> </nav> </div> </div> </div> <div class="vector-column-end"> <div class="vector-sticky-pinned-container"> <nav class="vector-page-tools-landmark" aria-label="Outils de la page"> <div id="vector-page-tools-pinned-container" class="vector-pinned-container"> </div> </nav> <nav class="vector-appearance-landmark" aria-label="Apparence"> <div id="vector-appearance-pinned-container" class="vector-pinned-container"> <div id="vector-appearance" class="vector-appearance vector-pinnable-element"> <div class="vector-pinnable-header vector-appearance-pinnable-header vector-pinnable-header-pinned" data-feature-name="appearance-pinned" data-pinnable-element-id="vector-appearance" data-pinned-container-id="vector-appearance-pinned-container" data-unpinned-container-id="vector-appearance-unpinned-container" > <div class="vector-pinnable-header-label">Apparence</div> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-pin-button" data-event-name="pinnable-header.vector-appearance.pin">déplacer vers la barre latérale</button> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-unpin-button" data-event-name="pinnable-header.vector-appearance.unpin">masquer</button> </div> </div> </div> </nav> </div> </div> <div id="bodyContent" class="vector-body" aria-labelledby="firstHeading" data-mw-ve-target-container> <div class="vector-body-before-content"> <div class="mw-indicators"> </div> <div id="siteSub" class="noprint">Un article de Wikipédia, l'encyclopédie libre.</div> </div> <div id="contentSub"><div id="mw-content-subtitle"></div></div> <div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="fr" dir="ltr"><p class="mw-empty-elt"> </p> <table class="infobox_v2 infobox infobox--frwiki noarchive"> <tbody><tr> <td colspan="2" class="entete defaut" style="background-color:#FFDEAD;color:black;">Tétrahydropyrane </td></tr> <tr><td colspan="2" style="text-align:center; line-height: 1.5em;"><span typeof="mw:File/Frameless"><a href="/w/index.php?title=Fichier:Tetrahydropyran_2D_stereo.svg&lang=fr" class="mw-file-description"><img alt="Image illustrative de l’article Tétrahydropyrane" src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b5/Tetrahydropyran_2D_stereo.svg/langfr-250px-Tetrahydropyran_2D_stereo.svg.png" decoding="async" width="250" height="117" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b5/Tetrahydropyran_2D_stereo.svg/langfr-375px-Tetrahydropyran_2D_stereo.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b5/Tetrahydropyran_2D_stereo.svg/langfr-500px-Tetrahydropyran_2D_stereo.svg.png 2x" data-file-width="773" data-file-height="362" /></a></span> </td></tr> <tr> <td colspan="2" style="text-align:center;">Structure du tétrahydropyrane</td> </tr><tr> <th colspan="2" style="padding:4px; text-align:center; background-color:#FFDEAD; color:#000000">Identification</th></tr> <tr> <th scope="row"><a href="/wiki/Nomenclature_de_l%27UICPA" title="Nomenclature de l'UICPA">Nom UICPA</a> </th> <td><small>oxane</small> </td> </tr> <tr> <th scope="row"><a href="/wiki/Synonymie" title="Synonymie">Synonymes</a> </th> <td> <p>THP, 2<i>H</i>-tétrahydropyrane, oxacyclohexane, oxyde de pentaméthylène </p> </td> </tr> <tr> <th scope="row"><a href="/wiki/Num%C3%A9ro_CAS" title="Numéro CAS">N<sup>o</sup> CAS</a> </th> <td><span class="reflink plainlinksneverexpand"><span class="noarchive"><a class="external text" href="//tools.wmflabs.org/magnustools/cas.php?cas=142-68-7&language=fr&title=Tétrahydropyrane">142-68-7</a></span></span> </td> </tr> <tr> <th scope="row"> N<sup>o</sup> <a href="/wiki/Agence_europ%C3%A9enne_des_produits_chimiques" title="Agence européenne des produits chimiques">ECHA</a> </th> <td><span class="plainlinks"><span class="noarchive"><a rel="nofollow" class="external text" href="https://echa.europa.eu/substance-information/-/substanceinfo/100.005.048">100.005.048</a></span></span></td> </tr> <tr> <th scope="row"><a href="/wiki/Num%C3%A9ro_CE" title="Numéro CE">N<sup>o</sup> CE</a> </th> <td>205-552-8 </td> </tr> <tr> <th scope="row">DrugBank </th> <td><span class="plainlinks"><span class="noarchive"><a rel="nofollow" class="external text" href="http://www.drugbank.ca/drugs/DB02412">DB02412</a></span></span> </td> </tr> <tr> <th scope="row"><a href="/wiki/PubChem" title="PubChem">PubChem</a> </th> <td><span class="plainlinks"><span class="noarchive"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/8894">8894</a></span></span> </td> </tr> <tr> <th scope="row">ChEBI </th> <td><span class="plainlinks"><span class="noarchive"><a rel="nofollow" class="external text" href="http://www.ebi.ac.uk/chebi/searchId.do?chebiId=46941">46941</a></span></span> </td> </tr> <tr> <th scope="row"><a href="/wiki/Simplified_Molecular_Input_Line_Entry_System" title="Simplified Molecular Input Line Entry System">SMILES</a> </th> <td><div class="NavFrame" title="[afficher]/[masquer]" style="border: none; padding: 0;"><div class="NavContent" style="display: none; text-align: left;">C1CCOCC1 <br /><span class="reflink plainlinksneverexpand"><a rel="nofollow" class="external text" href="http://pubchem.ncbi.nlm.nih.gov/search/?smarts=C1CCOCC1">PubChem</a></span>, <span class="reflink plainlinksneverexpand"><a rel="nofollow" class="external text" href="http://chemapps.stolaf.edu/jmol/jmol.php?title=T%C3%A9trahydropyrane&model=C1CCOCC1">vue 3D</a></span></div></div> </td> </tr> <tr> <th scope="row"><a href="/wiki/International_Chemical_Identifier" title="International Chemical Identifier">InChI</a> </th> <td><div class="NavFrame" title="[afficher]/[masquer]" style="border: none; padding: 0;"><div class="NavContent" style="display: none; text-align: left;"><b>Std. InChI :</b> <span class="reflink plainlinksneverexpand"><a rel="nofollow" class="external text" href="http://chemapps.stolaf.edu/jmol/jmol.php?title=T%C3%A9trahydropyrane&model=InChI%3D1S%2FC5H10O%2Fc1-2-4-6-5-3-1%2Fh1-5H2">vue 3D</a></span> <br />InChI=1S/C5H10O/c1-2-4-6-5-3-1/h1-5H2 <br /><b>Std. InChIKey :</b> <br />DHXVGJBLRPWPCS-UHFFFAOYSA-N</div></div> </td> </tr> <tr> <th colspan="2" style="padding:4px; text-align:center; background-color:#FFDEAD; color:#000000">Propriétés chimiques</th></tr> <tr> <th scope="row"><a href="/wiki/Formule_chimique" title="Formule chimique">Formule</a> </th> <td><a href="/wiki/Carbone" title="Carbone">C</a><sub>5</sub><a href="/wiki/Hydrog%C3%A8ne" title="Hydrogène">H</a><sub>10</sub><a href="/wiki/Oxyg%C3%A8ne" title="Oxygène">O</a>  <span class="page_h"><a href="/wiki/C5H10O" class="mw-disambig" title="C5H10O"><small>[Isomères]</small></a></span><br /> </td> </tr> <tr> <th scope="row"><a href="/wiki/Masse_molaire" title="Masse molaire">Masse molaire</a><sup id="cite_ref-1" class="reference"><a href="#cite_note-1"><span class="cite_crochet">[</span>1<span class="cite_crochet">]</span></a></sup> </th> <td>86,132 3 ± 0,005 <a href="/wiki/Gramme" title="Gramme">g</a>/<a href="/wiki/Mole_(unit%C3%A9)" title="Mole (unité)">mol</a> <br /><small>C 69,72 %,  H 11,7 %,  O 18,58 %,  </small> </td> </tr> <tr> <th colspan="2" style="padding:4px; text-align:center; background-color:#f7efa8; color:#000000">Propriétés physiques</th></tr> <tr> <th scope="row"><a href="/wiki/Point_de_fusion" title="Point de fusion"><abbr class="abbr" title="Température">T°</abbr> fusion</a> </th> <td><span title="−56,6 °F ou 224 K">−49,2 </span><abbr class="abbr" title="degré Celsius">°C</abbr><sup id="cite_ref-GESTIS_2-0" class="reference"><a href="#cite_note-GESTIS-2"><span class="cite_crochet">[</span>2<span class="cite_crochet">]</span></a></sup> </td> </tr> <tr> <th scope="row"><a href="/wiki/Point_d%27%C3%A9bullition" title="Point d'ébullition"><abbr class="abbr" title="Température">T°</abbr> ébullition</a> </th> <td><span title="190,4 °F ou 361,2 K">88 </span><abbr class="abbr" title="degré Celsius">°C</abbr><sup id="cite_ref-GESTIS_2-1" class="reference"><a href="#cite_note-GESTIS-2"><span class="cite_crochet">[</span>2<span class="cite_crochet">]</span></a></sup> </td> </tr> <tr> <th scope="row"><a href="/wiki/Solubilit%C3%A9" title="Solubilité">Solubilité</a> </th> <td><span class="nowrap"><span title="">80</span> <span title="Gramme">g</span>·<span title="Litre">L</span><sup>-1</sup></span><sup id="cite_ref-GESTIS_2-2" class="reference"><a href="#cite_note-GESTIS-2"><span class="cite_crochet">[</span>2<span class="cite_crochet">]</span></a></sup> à <span title="68 °F ou 293,2 K">20 </span><abbr class="abbr" title="degré Celsius">°C</abbr> </td> </tr> <tr> <th scope="row"><a href="/wiki/Masse_volumique" title="Masse volumique">Masse volumique</a> </th> <td><span class="nowrap"><span title="880 kg⋅m⁻³ ou −19,77 °Baumé">0,88</span> <span title="Gramme">g</span>·<span title="centimètre">cm</span><sup>-3</sup></span><sup id="cite_ref-GESTIS_2-3" class="reference"><a href="#cite_note-GESTIS-2"><span class="cite_crochet">[</span>2<span class="cite_crochet">]</span></a></sup> à <span title="68 °F ou 293,2 K">20 </span><abbr class="abbr" title="degré Celsius">°C</abbr> </td> </tr> <tr> <th scope="row"><a href="/wiki/Point_d%27%C3%A9clair" title="Point d'éclair">Point d’éclair</a> </th> <td><span title="−4 °F ou 253,2 K">−20 </span><abbr class="abbr" title="degré Celsius">°C</abbr><sup id="cite_ref-GESTIS_2-4" class="reference"><a href="#cite_note-GESTIS-2"><span class="cite_crochet">[</span>2<span class="cite_crochet">]</span></a></sup> ; <span title="3,2 °F ou 257,2 K">−16 </span><abbr class="abbr" title="degré Celsius">°C</abbr><sup id="cite_ref-sa_3-0" class="reference"><a href="#cite_note-sa-3"><span class="cite_crochet">[</span>3<span class="cite_crochet">]</span></a></sup> </td> </tr> <tr> <th scope="row"><a href="/wiki/Pression_de_vapeur_saturante" title="Pression de vapeur saturante">Pression de vapeur saturante</a> </th> <td><span class="nowrap"><span title="0,095 3 bar ou 0,094 053 787 318 036 atm">9,53</span> <span title="kilopascal">kPa</span></span><sup id="cite_ref-GESTIS_2-5" class="reference"><a href="#cite_note-GESTIS-2"><span class="cite_crochet">[</span>2<span class="cite_crochet">]</span></a></sup> à <span title="77 °F ou 298,2 K">25 </span><abbr class="abbr" title="degré Celsius">°C</abbr> </td> </tr> <tr> <th colspan="2" style="padding:4px; text-align:center; background-color:#ffb4b4; color:#000000">Précautions</th></tr> <tr> <th colspan="2" style="padding:4px; text-align:center; background-color:#eeeeee; color:#000000"><a href="/wiki/Syst%C3%A8me_g%C3%A9n%C3%A9ral_harmonis%C3%A9_de_classification_et_d%27%C3%A9tiquetage_des_produits_chimiques" title="Système général harmonisé de classification et d'étiquetage des produits chimiques">SGH</a><sup id="cite_ref-GESTIS_2-6" class="reference"><a href="#cite_note-GESTIS-2"><span class="cite_crochet">[</span>2<span class="cite_crochet">]</span></a></sup><sup class="reference cite_virgule">,</sup><sup id="cite_ref-sa_3-1" class="reference"><a href="#cite_note-sa-3"><span class="cite_crochet">[</span>3<span class="cite_crochet">]</span></a></sup></th></tr> <tr> <td colspan="2" style="text-align:center;"><div style="text-align: center;"><span typeof="mw:File"><a href="/wiki/Fichier:GHS-pictogram-flamme.svg" class="mw-file-description" title="SGH02 : Inflammable"><img alt="SGH02 : Inflammable" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6d/GHS-pictogram-flamme.svg/60px-GHS-pictogram-flamme.svg.png" decoding="async" width="60" height="60" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6d/GHS-pictogram-flamme.svg/90px-GHS-pictogram-flamme.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6d/GHS-pictogram-flamme.svg/120px-GHS-pictogram-flamme.svg.png 2x" data-file-width="512" data-file-height="512" /></a></span><span typeof="mw:File"><a href="/wiki/Fichier:GHS-pictogram-exclam.svg" class="mw-file-description" title="SGH07 : Toxique, irritant, sensibilisant, narcotique"><img alt="SGH07 : Toxique, irritant, sensibilisant, narcotique" src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c3/GHS-pictogram-exclam.svg/60px-GHS-pictogram-exclam.svg.png" decoding="async" width="60" height="60" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c3/GHS-pictogram-exclam.svg/90px-GHS-pictogram-exclam.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c3/GHS-pictogram-exclam.svg/120px-GHS-pictogram-exclam.svg.png 2x" data-file-width="512" data-file-height="512" /></a></span><br />Danger</div><span title="Liquide et vapeurs très inflammables">H225</span>, <span title="Provoque une irritation cutanée">H315</span>, <span title="Provoque une sévère irritation des yeux">H319</span>, <span title="Peut irriter les voies respiratoires">H335</span>, <span title="Peut former des peroxydes explosifs">EUH019</span>, <span title="Tenir à l’écart de la chaleur/des étincelles/des flammes nues/des surfaces chaudes. — Ne pas fumer.">P210</span>, <span title="Éviter de respirer les poussières/fumées/gaz/brouillards/vapeurs/aérosols.">P261</span> et <span title="En cas de contact avec les yeux : rincer avec précaution à l’eau pendant plusieurs minutes. Enlever les lentilles de contact si la victime en porte et si elles peuvent être facilement enlevées. Continuer à rincer.">P305+P351+P338</span><div class="NavFrame" title="[+]/[–]" style="border:none; padding : 0;"><div class="NavContent" style="display:none; text-align:left;"><b>H225</b> : Liquide et vapeurs très inflammables<br /><b>H315</b> : Provoque une irritation cutanée<br /><b>H319</b> : Provoque une sévère irritation des yeux<br /><b>H335</b> : Peut irriter les voies respiratoires<br /><b>EUH019</b> : Peut former des peroxydes explosifs<br /><b>P210</b> : Tenir à l’écart de la chaleur/des étincelles/des flammes nues/des surfaces chaudes. — Ne pas fumer.<br /><b>P261</b> : Éviter de respirer les poussières/fumées/gaz/brouillards/vapeurs/aérosols.<br /><b>P305+P351+P338</b> : En cas de contact avec les yeux : rincer avec précaution à l’eau pendant plusieurs minutes. Enlever les lentilles de contact si la victime en porte et si elles peuvent être facilement enlevées. Continuer à rincer.<br /></div></div></td> </tr><tr> <th colspan="2" style="padding:4px; text-align:center; background-color:#eeeeee; color:#000000"><a href="/wiki/Accord_relatif_au_transport_international_des_marchandises_dangereuses_par_route" title="Accord relatif au transport international des marchandises dangereuses par route">Transport</a><sup id="cite_ref-GESTIS_2-7" class="reference"><a href="#cite_note-GESTIS-2"><span class="cite_crochet">[</span>2<span class="cite_crochet">]</span></a></sup><sup class="reference cite_virgule">,</sup><sup id="cite_ref-sa_3-2" class="reference"><a href="#cite_note-sa-3"><span class="cite_crochet">[</span>3<span class="cite_crochet">]</span></a></sup></th></tr> <tr> <td colspan="2" style="text-align:center;"><div class="center"><style data-mw-deduplicate="TemplateStyles:r222907466">.mw-parser-output .tableau-adr td{background-color:#ff950e;border:1px solid var(--color-emphasized,#101418)!important;text-align:center;padding-left:14px;padding-right:14px}.mw-parser-output .tableau-adr a>span{color:var(--color-emphasized,#101418)}@media screen{html.skin-theme-clientpref-night .mw-parser-output .tableau-adr td{background-color:#663a01!important}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .tableau-adr td{background-color:#663a01!important}}.mw-parser-output div.NavFrame.adr-NavFrame{border:none;padding:0}.mw-parser-output div.NavFrame.adr-NavFrame div.NavContent{text-align:left}</style><table class="wikitable centre tableau-adr"><tbody><tr><td><div><a href="/wiki/Liste_des_codes_Kemler#33" title="Liste des codes Kemler"><span title="matière liquide très inflammable (point d'éclair inférieur à 23 °C)">33</span></a></div></td></tr><tr><td><div><a href="/wiki/Liste_des_num%C3%A9ros_ONU" title="Liste des numéros ONU"><span title="numéro ONU">3271</span></a></div></td></tr></tbody></table><div class="NavFrame adr-NavFrame" title="[+]/[–]"><div class="NavContent" style="display:none;"><b>Code Kemler :</b><br /><b>33</b> : matière liquide très inflammable (point d'éclair inférieur à <span title="73,4 °F ou 296,2 K">23 </span><abbr class="abbr" title="degré Celsius">°C</abbr>)<br /><b><a href="/wiki/Num%C3%A9ro_ONU" title="Numéro ONU">Numéro ONU</a> :</b><br /><b><a href="/wiki/Liste_des_num%C3%A9ros_ONU" title="Liste des numéros ONU">3271</a></b> : ÉTHERS, N.S.A.<br /><b>Classe :</b><br />3<br /><b>Étiquette :</b><br /><span typeof="mw:File"><a href="/wiki/Fichier:ADR_3.svg" class="mw-file-description"><img alt="pictogramme ADR 3" src="//upload.wikimedia.org/wikipedia/commons/thumb/9/94/ADR_3.svg/75px-ADR_3.svg.png" decoding="async" width="75" height="74" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/94/ADR_3.svg/113px-ADR_3.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/94/ADR_3.svg/150px-ADR_3.svg.png 2x" data-file-width="104" data-file-height="103" /></a></span><br /><b>3</b> : Liquides inflammables<br /><b>Emballage :</b><br />Groupe d'emballage <abbr class="abbr" title="2"><span class="romain" style="text-transform:uppercase">II</span></abbr> : matières moyennement dangereuses ;<br /></div></div></div></td> </tr><tr> <th colspan="2" style="padding:4px; text-align:center; background-color:#FFDEAD; color:#000000">Composés apparentés</th></tr> <tr> <th scope="row">Autres composés </th> <td> <p><a href="/wiki/Pyrane" title="Pyrane">Pyrane</a> </p> </td> </tr> <tr> <td colspan="2"><hr style="height:2px; background-color:#FFDEAD;" /></td></tr> <tr> <td colspan="2" style="text-align:center;">Unités du <a href="/wiki/Syst%C3%A8me_international_d%27unit%C3%A9s" title="Système international d'unités">SI</a> et <a href="/wiki/Conditions_normales_de_temp%C3%A9rature_et_de_pression" title="Conditions normales de température et de pression"><abbr title="conditions normales de température et de pression">CNTP</abbr></a>, sauf indication contraire.</td> </tr><tr> <td class="navigation-only" colspan="2" style="border-top: 2px #FFDEAD solid; font-size: 80%; background:inherit; color: inherit; text-align: right;"><span class="plainlinks" style="float:left;"><a class="external text" href="https://fr.wikipedia.org/w/index.php?title=T%C3%A9trahydropyrane&action=edit&section=0"><span class="infodoc">modifier</span></a></span> <span typeof="mw:File"><a href="/wiki/Mod%C3%A8le:Infobox_Chimie" title="Consultez la documentation du modèle"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/3/38/Info_Simple.svg/12px-Info_Simple.svg.png" decoding="async" width="12" height="12" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/38/Info_Simple.svg/18px-Info_Simple.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/38/Info_Simple.svg/24px-Info_Simple.svg.png 2x" data-file-width="512" data-file-height="512" /></a></span></td> </tr> </tbody></table> <p>Le <b>tétrahydropyrane</b> (<b>THP</b>), est un <a href="/wiki/%C3%89ther-oxyde" title="Éther-oxyde">éther</a> <a href="/wiki/Compos%C3%A9_cyclique" title="Composé cyclique">cyclique</a> de <a href="/wiki/Formule_brute" title="Formule brute">formule brute</a> <a href="/wiki/C5H10O" class="mw-disambig" title="C5H10O">C<sub>5</sub>H<sub>10</sub>O<sub></sub><sub></sub><sub></sub><sub></sub><sub></sub><sub></sub><sub></sub><sub></sub></a>. C'est le plus simple des <a href="/wiki/Oxane" title="Oxane">oxanes</a>, constitué d'un cycle à six <a href="/wiki/Atome" title="Atome">atomes</a> dont un d'<a href="/wiki/Oxyg%C3%A8ne" title="Oxygène">oxygène</a> et cinq de <a href="/wiki/Carbone" title="Carbone">carbone</a>. Il s'agit d'un liquide incolore volatil inflammable. On rencontre plus fréquemment ses dérivés, les éthers de tétrahydropyranyle (THP-) étant des intermédiaires courants en <a href="/wiki/Synth%C3%A8se_organique" title="Synthèse organique">synthèse organique</a> par réaction d'<a href="/wiki/Alcool_(chimie)" title="Alcool (chimie)">alcools</a> sur du <a href="/wiki/Dihydropyrane" title="Dihydropyrane">dihydropyrane</a>. Le cycle du tétrahydropyrane est notamment présent dans tous les <a href="/wiki/Ose" title="Ose">oses</a> en configuration <a href="/wiki/Pyranose" title="Pyranose">pyranose</a>, par exemple dans le <a href="/wiki/Glucose" title="Glucose">glucopyranose</a>. En <a href="/wiki/Phase_gazeuse" class="mw-redirect" title="Phase gazeuse">phase gazeuse</a>, il se présente en conformation chaise de <span class="nowrap">symétrie Cs</span><sup id="cite_ref-10.1063/1.4813237_4-0" class="reference"><a href="#cite_note-10.1063/1.4813237-4"><span class="cite_crochet">[</span>4<span class="cite_crochet">]</span></a></sup>. </p> <div class="mw-heading mw-heading2"><h2 id="Préparation"><span id="Pr.C3.A9paration"></span>Préparation</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=T%C3%A9trahydropyrane&veaction=edit&section=1" title="Modifier la section : Préparation" class="mw-editsection-visualeditor"><span>modifier</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=T%C3%A9trahydropyrane&action=edit&section=1" title="Modifier le code source de la section : Préparation"><span>modifier le code</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>L'<a href="/wiki/Hydrog%C3%A9nation" title="Hydrogénation">hydrogénation</a> du <a href="/wiki/Dihydropyrane" title="Dihydropyrane">dihydropyrane</a> au <a href="/wiki/Nickel_de_Raney" title="Nickel de Raney">nickel de Raney</a> est un mode de synthèse organique classique du tétrahydropyrane<sup id="cite_ref-10.15227/orgsyn.023.0090_5-0" class="reference"><a href="#cite_note-10.15227/orgsyn.023.0090-5"><span class="cite_crochet">[</span>5<span class="cite_crochet">]</span></a></sup>. </p> <div class="mw-heading mw-heading2"><h2 id="Utilisation">Utilisation</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=T%C3%A9trahydropyrane&veaction=edit&section=2" title="Modifier la section : Utilisation" class="mw-editsection-visualeditor"><span>modifier</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=T%C3%A9trahydropyrane&action=edit&section=2" title="Modifier le code source de la section : Utilisation"><span>modifier le code</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Le groupe 2-tétrahydropyranyle est utilisé comme <a href="/wiki/Groupe_protecteur" title="Groupe protecteur">groupe protecteur</a> de <a href="/wiki/Groupe_fonctionnel" title="Groupe fonctionnel">groupes</a> <a href="/wiki/Alcool_(chimie)" title="Alcool (chimie)">alcool</a> lors de <a href="/wiki/Synth%C3%A8se_organique" title="Synthèse organique">synthèses organiques</a><sup id="cite_ref-10.15227/orgsyn.060.0081_6-0" class="reference"><a href="#cite_note-10.15227/orgsyn.060.0081-6"><span class="cite_crochet">[</span>6<span class="cite_crochet">]</span></a></sup><sup class="reference cite_virgule">,</sup><sup id="cite_ref-10.15227/orgsyn.064.0080_7-0" class="reference"><a href="#cite_note-10.15227/orgsyn.064.0080-7"><span class="cite_crochet">[</span>7<span class="cite_crochet">]</span></a></sup>. La réaction d'un alcool avec le <a href="/wiki/Dihydropyrane" title="Dihydropyrane">dihydropyrane</a> forme un <a href="/wiki/C%C3%A9tal" class="mw-redirect" title="Cétal">cétal</a>, un <a href="/wiki/Position_alpha" class="mw-redirect" title="Position alpha">α</a>-<a href="/wiki/%C3%89ther-oxyde" title="Éther-oxyde">éther</a> de tétrahydropyranyle, qui protège le groupe alcool d'un grand nombre de réactions : </p> <ul class="gallery mw-gallery-packed"> <li class="gallerybox" style="width: 147.33333333333px"> <div class="thumb" style="width: 145.33333333333px;"><span typeof="mw:File"><a href="/wiki/Fichier:THP_Ether.png" class="mw-file-description" title="Éther de THP."><img alt="Éther de THP." src="//upload.wikimedia.org/wikipedia/commons/thumb/8/8b/THP_Ether.png/218px-THP_Ether.png" decoding="async" width="146" height="110" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/8b/THP_Ether.png/328px-THP_Ether.png 1.5x, //upload.wikimedia.org/wikipedia/commons/8/8b/THP_Ether.png 2x" data-file-width="332" data-file-height="251" /></a></span></div> <div class="gallerytext"><div class="center"><a href="/wiki/%C3%89ther-oxyde" title="Éther-oxyde">Éther</a> de THP.</div></div> </li> </ul> <p>L'alcool peut être rétabli ultérieurement par <a href="/wiki/Hydrolyse" title="Hydrolyse">hydrolyse</a> acide avec formation de <a href="/w/index.php?title=5-Hydroxypentanal&action=edit&redlink=1" class="new" title="5-Hydroxypentanal (page inexistante)">5-hydroxypentanal</a>. </p> <ul class="gallery mw-gallery-packed"> <li class="gallerybox" style="width: 520px"> <div class="thumb" style="width: 518px;"><span typeof="mw:File"><a href="/wiki/Fichier:THP_ether.png" class="mw-file-description" title="Groupe protecteur au THP en synthèse organique."><img alt="Groupe protecteur au THP en synthèse organique." src="//upload.wikimedia.org/wikipedia/commons/thumb/5/5b/THP_ether.png/777px-THP_ether.png" decoding="async" width="518" height="220" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/5b/THP_ether.png/1165px-THP_ether.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/5b/THP_ether.png/1554px-THP_ether.png 2x" data-file-width="1786" data-file-height="759" /></a></span></div> <div class="gallerytext"><div class="center"><a href="/wiki/Groupe_protecteur" title="Groupe protecteur">Groupe protecteur</a> au THP en <a href="/wiki/Synth%C3%A8se_organique" title="Synthèse organique">synthèse organique</a>.</div></div> </li> </ul> <div class="mw-heading mw-heading2"><h2 id="Notes_et_références"><span id="Notes_et_r.C3.A9f.C3.A9rences"></span>Notes et références</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=T%C3%A9trahydropyrane&veaction=edit&section=3" title="Modifier la section : Notes et références" class="mw-editsection-visualeditor"><span>modifier</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=T%C3%A9trahydropyrane&action=edit&section=3" title="Modifier le code source de la section : Notes et références"><span>modifier le code</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="references-small decimal" style=""><div class="mw-references-wrap"><ol class="references"> <li id="cite_note-1"><span class="mw-cite-backlink"><a href="#cite_ref-1">↑</a> </span><span class="reference-text">Masse molaire calculée d’après <span class="ouvrage">« <a rel="nofollow" class="external text" href="http://www.chem.qmul.ac.uk/iupac/AtWt/"><cite style="font-style:normal;"><span class="lang-en" lang="en">Atomic weights of the elements 2007</span></cite></a> », sur <span class="italique">www.chem.qmul.ac.uk</span></span>.</span> </li> <li id="cite_note-GESTIS-2"><span class="mw-cite-backlink noprint">↑ <sup><a href="#cite_ref-GESTIS_2-0">a</a> <a href="#cite_ref-GESTIS_2-1">b</a> <a href="#cite_ref-GESTIS_2-2">c</a> <a href="#cite_ref-GESTIS_2-3">d</a> <a href="#cite_ref-GESTIS_2-4">e</a> <a href="#cite_ref-GESTIS_2-5">f</a> <a href="#cite_ref-GESTIS_2-6">g</a> et <a href="#cite_ref-GESTIS_2-7">h</a></sup> </span><span class="reference-text"><span class="noarchive">Entrée dans la base de données de produits chimiques <i>GESTIS</i> de la IFA (organisme allemand responsable de la sécurité et de la santé au travail) (<a rel="nofollow" class="external text" href="https://gestis.dguv.de/data?name=000000">allemand</a>, <a rel="nofollow" class="external text" href="https://gestis.dguv.de/data?name=000000&lang=en">anglais</a>), accès le 8 juillet 2016 <small>(JavaScript nécessaire)</small></span></span> </li> <li id="cite_note-sa-3"><span class="mw-cite-backlink noprint">↑ <sup><a href="#cite_ref-sa_3-0">a</a> <a href="#cite_ref-sa_3-1">b</a> et <a href="#cite_ref-sa_3-2">c</a></sup> </span><span class="reference-text">Fiche <a href="/wiki/Sigma-Aldrich" title="Sigma-Aldrich">Sigma-Aldrich</a> du composé <i><a rel="nofollow" class="external text" href="https://www.sigmaaldrich.com/FR/fr/product/sial/293105">Tétrahydropyrane anhydre, 99 %</a></i>, consultée le 31 mars 2022.</span> </li> <li id="cite_note-10.1063/1.4813237-4"><span class="mw-cite-backlink"><a href="#cite_ref-10.1063/1.4813237_4-0">↑</a> </span><span class="reference-text"> <span class="ouvrage" id="2013"><abbr class="abbr indicateur-langue" title="Langue : anglais">(en)</abbr> J. D. Builth-Williams, S. M. Bellm, L. Chiari, P. A. Thorn, D. B. Jones, H. Chaluvadi, D. H. Madison, C. G. Ning, B. Lohmann, G. B. da Silva et M. J. Brunger, « <cite style="font-style:normal" lang="en">A dynamical (e,2e) investigation of the structurally related cyclic ethers tetrahydrofuran, tetrahydropyran, and 1,4-dioxane</cite> », <i><span class="lang-en" lang="en">Journal of Chemical Physics</span></i>, <abbr class="abbr" title="volume">vol.</abbr> 139, <abbr class="abbr" title="numéro">n<sup>o</sup></abbr> 3,‎ <time class="nowrap" datetime="2013-07-21" data-sort-value="2013-07-21">21 juillet 2013</time>, <abbr class="abbr" title="page">p.</abbr> 034306 <small style="line-height:1em;">(<a href="/wiki/PubMed" title="PubMed">PMID</a> <span class="plainlinks noarchive nowrap"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pubmed/23883026">23883026</a></span>, <a href="/wiki/Digital_Object_Identifier" title="Digital Object Identifier">DOI</a> <span class="plainlinks noarchive nowrap"><a rel="nofollow" class="external text" href="https://dx.doi.org/10.1063/1.4813237">10.1063/1.4813237</a></span>, <a rel="nofollow" class="external text" href="http://scitation.aip.org/content/aip/journal/jcp/139/3/10.1063/1.4813237">lire en ligne</a>)</small><span class="Z3988" title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=A+dynamical+%28e%2C2e%29+investigation+of+the+structurally+related+cyclic+ethers+tetrahydrofuran%2C+tetrahydropyran%2C+and+1%2C4-dioxane&rft.jtitle=Journal+of+Chemical+Physics&rft.issue=3&rft.date=2013-07-21&rft.volume=139&rft.pages=034306&rft_id=info%3Adoi%2F10.1063%2F1.4813237&rft_id=info%3Apmid%2F23883026&rfr_id=info%3Asid%2Ffr.wikipedia.org%3AT%C3%A9trahydropyrane"></span></span></span> </li> <li id="cite_note-10.15227/orgsyn.023.0090-5"><span class="mw-cite-backlink"><a href="#cite_ref-10.15227/orgsyn.023.0090_5-0">↑</a> </span><span class="reference-text"> <span class="ouvrage" id="1943"><abbr class="abbr indicateur-langue" title="Langue : anglais">(en)</abbr> D. W. Andrus, John R. Johnson, Nathan L. Drake et Charles M. Eaker, « <cite style="font-style:normal" lang="en">Tetrahydropyran</cite> », <i><span class="lang-en" lang="en">Organic Syntheses</span></i>, <abbr class="abbr" title="volume">vol.</abbr> 23,‎ <time>1943</time>, <abbr class="abbr" title="page">p.</abbr> 90 <small style="line-height:1em;">(<a href="/wiki/Digital_Object_Identifier" title="Digital Object Identifier">DOI</a> <span class="plainlinks noarchive nowrap"><a rel="nofollow" class="external text" href="https://dx.doi.org/10.15227/orgsyn.023.0090">10.15227/orgsyn.023.0090</a></span>, <a rel="nofollow" class="external text" href="http://www.orgsyn.org/demo.aspx?prep=cv3p0794">lire en ligne</a>)</small><span class="Z3988" title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=Tetrahydropyran&rft.jtitle=Organic+Syntheses&rft.date=1943&rft.volume=23&rft.pages=90&rft_id=info%3Adoi%2F10.15227%2Forgsyn.023.0090&rfr_id=info%3Asid%2Ffr.wikipedia.org%3AT%C3%A9trahydropyrane"></span></span></span> </li> <li id="cite_note-10.15227/orgsyn.060.0081-6"><span class="mw-cite-backlink"><a href="#cite_ref-10.15227/orgsyn.060.0081_6-0">↑</a> </span><span class="reference-text"> <span class="ouvrage" id="1981"><abbr class="abbr indicateur-langue" title="Langue : anglais">(en)</abbr> R. A. Earl, L. B. Townsend, G. Saucy et G. Weber, « <cite style="font-style:normal" lang="en">Methyl 4-hydroxy-2-butynoate</cite> », <i><span class="lang-en" lang="en">Organic Syntheses</span></i>, <abbr class="abbr" title="volume">vol.</abbr> 60,‎ <time>1981</time>, <abbr class="abbr" title="page">p.</abbr> 81 <small style="line-height:1em;">(<a href="/wiki/Digital_Object_Identifier" title="Digital Object Identifier">DOI</a> <span class="plainlinks noarchive nowrap"><a rel="nofollow" class="external text" href="https://dx.doi.org/10.15227/orgsyn.060.0081">10.15227/orgsyn.060.0081</a></span>, <a rel="nofollow" class="external text" href="http://www.orgsyn.org/demo.aspx?prep=cv7p0334">lire en ligne</a>)</small><span class="Z3988" title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=Methyl+4-hydroxy-2-butynoate&rft.jtitle=Organic+Syntheses&rft.date=1981&rft.volume=60&rft.pages=81&rft_id=info%3Adoi%2F10.15227%2Forgsyn.060.0081&rfr_id=info%3Asid%2Ffr.wikipedia.org%3AT%C3%A9trahydropyrane"></span></span></span> </li> <li id="cite_note-10.15227/orgsyn.064.0080-7"><span class="mw-cite-backlink"><a href="#cite_ref-10.15227/orgsyn.064.0080_7-0">↑</a> </span><span class="reference-text"> <span class="ouvrage" id="1986"><abbr class="abbr indicateur-langue" title="Langue : anglais">(en)</abbr> Arthur F. Kluge, A. Pilli, Kenneth S. Kirshenbaum, Clayton H. Heathcock et K. Barry Sharpless, « <cite style="font-style:normal" lang="en">Diethyl[(2-tetrahydropyranyloxy)methyl]phosphonate</cite> », <i><span class="lang-en" lang="en">Organic Syntheses</span></i>, <abbr class="abbr" title="volume">vol.</abbr> 64,‎ <time>1986</time>, <abbr class="abbr" title="page">p.</abbr> 80 <small style="line-height:1em;">(<a href="/wiki/Digital_Object_Identifier" title="Digital Object Identifier">DOI</a> <span class="plainlinks noarchive nowrap"><a rel="nofollow" class="external text" href="https://dx.doi.org/10.15227/orgsyn.064.0080">10.15227/orgsyn.064.0080</a></span>, <a rel="nofollow" class="external text" href="http://www.orgsyn.org/demo.aspx?prep=cv7p0160">lire en ligne</a>)</small><span class="Z3988" title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=Diethyl%5B%282-tetrahydropyranyloxy%29methyl%5Dphosphonate&rft.jtitle=Organic+Syntheses&rft.date=1986&rft.volume=64&rft.pages=80&rft_id=info%3Adoi%2F10.15227%2Forgsyn.064.0080&rfr_id=info%3Asid%2Ffr.wikipedia.org%3AT%C3%A9trahydropyrane"></span></span></span> </li> </ol></div> </div> <ul id="bandeau-portail" class="bandeau-portail"><li><span class="bandeau-portail-element"><span class="bandeau-portail-icone"><span class="noviewer" typeof="mw:File"><a href="/wiki/Portail:Chimie" title="Portail de la chimie"><img alt="icône décorative" src="//upload.wikimedia.org/wikipedia/commons/thumb/5/59/Nuvola_apps_edu_science.svg/24px-Nuvola_apps_edu_science.svg.png" decoding="async" width="24" height="24" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/59/Nuvola_apps_edu_science.svg/36px-Nuvola_apps_edu_science.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/59/Nuvola_apps_edu_science.svg/48px-Nuvola_apps_edu_science.svg.png 2x" data-file-width="128" data-file-height="128" /></a></span></span> <span class="bandeau-portail-texte"><a href="/wiki/Portail:Chimie" title="Portail:Chimie">Portail de la chimie</a></span> </span></li> </ul>    </div><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?useformat=desktop&type=1x1&usesul3=0" alt="" width="1" height="1" style="border: none; position: absolute;"></noscript> <div class="printfooter" data-nosnippet="">Ce document provient de « <a dir="ltr" href="https://fr.wikipedia.org/w/index.php?title=Tétrahydropyrane&oldid=192437068">https://fr.wikipedia.org/w/index.php?title=Tétrahydropyrane&oldid=192437068</a> ».</div></div> <div id="catlinks" class="catlinks" data-mw="interface"><div id="mw-normal-catlinks" class="mw-normal-catlinks"><a href="/wiki/Cat%C3%A9gorie:Accueil" title="Catégorie:Accueil">Catégories</a> : <ul><li><a href="/wiki/Cat%C3%A9gorie:Oxane" title="Catégorie:Oxane">Oxane</a></li><li><a href="/wiki/Cat%C3%A9gorie:Groupe_protecteur" title="Catégorie:Groupe protecteur">Groupe protecteur</a></li></ul></div><div id="mw-hidden-catlinks" class="mw-hidden-catlinks mw-hidden-cats-hidden">Catégories cachées : <ul><li><a href="/wiki/Cat%C3%A9gorie:Portail:Chimie/Articles_li%C3%A9s" title="Catégorie:Portail:Chimie/Articles liés">Portail:Chimie/Articles liés</a></li><li><a href="/wiki/Cat%C3%A9gorie:Article_utilisant_une_Infobox" title="Catégorie:Article utilisant une Infobox">Article utilisant une Infobox</a></li><li><a href="/wiki/Cat%C3%A9gorie:Chimiebox_%C3%A0_maintenir" title="Catégorie:Chimiebox à maintenir">Chimiebox à maintenir</a></li><li><a href="/wiki/Cat%C3%A9gorie:Portail:Sciences/Articles_li%C3%A9s" title="Catégorie:Portail:Sciences/Articles liés">Portail:Sciences/Articles liés</a></li></ul></div></div> </div> </main> </div> <div class="mw-footer-container"> <footer id="footer" class="mw-footer" > <ul id="footer-info"> <li id="footer-info-lastmod"> La dernière modification de cette page a été faite le 31 mars 2022 à 05:34.</li> <li id="footer-info-copyright"><span style="white-space: normal"><a href="/wiki/Wikip%C3%A9dia:Citation_et_r%C3%A9utilisation_du_contenu_de_Wikip%C3%A9dia" title="Wikipédia:Citation et réutilisation du contenu de Wikipédia">Droit d'auteur</a> : les textes sont disponibles sous <a rel="nofollow" class="external text" href="https://creativecommons.org/licenses/by-sa/4.0/deed.fr">licence Creative Commons attribution, partage dans les mêmes conditions</a> ; d’autres conditions peuvent s’appliquer. 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