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class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Indan-1,3-dion" title="Indan-1,3-dion – Czech" lang="cs" hreflang="cs" data-title="Indan-1,3-dion" data-language-autonym="Čeština" data-language-local-name="Czech" 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/1,3-Indandion" title="1,3-Indandion – German" lang="de" hreflang="de" data-title="1,3-Indandion" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-eo mw-list-item"><a href="https://eo.wikipedia.org/wiki/1,3-Indanoduketono" title="1,3-Indanoduketono – Esperanto" lang="eo" hreflang="eo" data-title="1,3-Indanoduketono" data-language-autonym="Esperanto" data-language-local-name="Esperanto" class="interlanguage-link-target"><span>Esperanto</span></a></li><li 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dir="ltr"><style data-mw-deduplicate="TemplateStyles:r1084375498">.mw-parser-output .ib-chembox{border-collapse:collapse;text-align:left}.mw-parser-output .ib-chembox td,.mw-parser-output .ib-chembox th{border:1px solid #a2a9b1;width:40%}.mw-parser-output .ib-chembox td+td{width:60%}</style> <table class="infobox ib-chembox"> <caption>1,3-Indandione </caption> <tbody><tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:1,3-indanon.svg" class="mw-file-description"><img alt="Skeletal formula" src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c0/1%2C3-indanon.svg/130px-1%2C3-indanon.svg.png" decoding="async" width="130" height="152" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c0/1%2C3-indanon.svg/195px-1%2C3-indanon.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c0/1%2C3-indanon.svg/260px-1%2C3-indanon.svg.png 2x" data-file-width="184" data-file-height="215" /></a></span> </td></tr> <tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:Indandione-3D-balls.png" class="mw-file-description"><img alt="Ball-and-stick model" src="//upload.wikimedia.org/wikipedia/commons/thumb/b/bd/Indandione-3D-balls.png/160px-Indandione-3D-balls.png" decoding="async" width="160" height="130" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/bd/Indandione-3D-balls.png/240px-Indandione-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/bd/Indandione-3D-balls.png/320px-Indandione-3D-balls.png 2x" data-file-width="2000" data-file-height="1621" /></a></span> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Names </th></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/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;">1<i>H</i>-Indene-1,3(2<i>H</i>)-dione</div></div> </td></tr> <tr> <td colspan="2" style="text-align:left;">Other names <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;">Indandione; 1,3-Diketohydrindene; 1,3-Dioxoindane; 1,3-Hydrindendione</div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Identifiers </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></div> </td> <td><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</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=606-23-5">606-23-5</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><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=C1C%28%3DO%29C2%3DCC%3DCC%3DC2C1%3DO">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=O%3DC2c1ccccc1C%28%3DO%29C2">Interactive image</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChEBI" title="ChEBI">ChEBI</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><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=78877">CHEBI:78877</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChEMBL" title="ChEMBL">ChEMBL</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembldb/index.php/compound/inspect/ChEMBL283521">ChEMBL283521</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChemSpider" title="ChemSpider">ChemSpider</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.chemspider.com"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.11322.html">11322</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ECHA_InfoCard" class="mw-redirect" title="ECHA InfoCard"><span title="echa.europa.eu">ECHA InfoCard</span></a> </td> <td><a rel="nofollow" class="external text" href="https://echa.europa.eu/substance-information/-/substanceinfo/100.009.191">100.009.191</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q161510#P2566" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/PubChem" title="PubChem">PubChem</a> <abbr title="Compound ID">CID</abbr></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/11815">11815</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/Unique_Ingredient_Identifier" title="Unique Ingredient Identifier">UNII</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="precision.fda.gov"><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/4DJN7YG35G">4DJN7YG35G</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/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> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="comptox.epa.gov"><a rel="nofollow" class="external text" href="https://comptox.epa.gov/dashboard/chemical/details/DTXSID2060547">DTXSID2060547</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q161510#P3117" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span></span></li></ul></div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal; background:transparent;"><div><a href="/wiki/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/C9H6O2/c10-8-5-9(11)7-4-2-1-3-6(7)8/h1-4H,5H2<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></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: UHKAJLSKXBADFT-UHFFFAOYSA-N<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div></div></li><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=1/C9H6O2/c10-8-5-9(11)7-4-2-1-3-6(7)8/h1-4H,5H2</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: UHKAJLSKXBADFT-UHFFFAOYAR</div></div></li></ul> </div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal; background:transparent;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</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 1.6em; word-wrap:break-word; text-indent:-1.5em; text-align:left; font-size:97%; line-height:120%;">C1C(=O)C2=CC=CC=C2C1=O</div></li><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.6em; word-wrap:break-word; text-indent:-1.5em; text-align:left; font-size:97%; line-height:120%;">O=C2c1ccccc1C(=O)C2</div></li></ul> </div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Properties </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Chemical_formula" title="Chemical formula">Chemical formula</a></div> </td> <td><span title="Carbon">C</span><sub>9</sub><span title="Hydrogen">H</span><sub>6</sub><span title="Oxygen">O</span><sub>2</sub> </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td><span class="nowrap"><span data-sort-value="7002146145000000000♠"></span>146.145</span> g·mol<sup>−1</sup>   </td></tr> <tr> <td>Appearance </td> <td>white solid </td></tr> <tr> <td><a href="/wiki/Density" title="Density">Density</a> </td> <td>1.37 g/cm<sup>3</sup> </td></tr> <tr> <td><a href="/wiki/Melting_point" title="Melting point">Melting point</a> </td> <td>129 to 132 °C (264 to 270 °F; 402 to 405 K)<sup id="cite_ref-Sigma_1-0" class="reference"><a href="#cite_note-Sigma-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Acros_2-0" class="reference"><a href="#cite_note-Acros-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Aqueous_solution" title="Aqueous solution">Solubility in water</a></div> </td> <td>slight </td></tr> <tr> <td colspan="2" style="text-align:left; background:#f8eaba; 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="/wiki/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><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/12px-Yes_check.svg.png" decoding="async" width="12" height="12" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/18px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/24px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span> <span class="reflink plainlinks nourlexpansion"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=477205481&page2=1%2C3-Indandione">verify</a></span> (<a href="/wiki/Wikipedia:WikiProject_Chemicals/Chembox_validation" title="Wikipedia:WikiProject Chemicals/Chembox validation">what is</a> <sup><span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span><span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span></sup> ?) </div></div> <div style="margin-top: 0.3em; text-align: center;"><a href="/wiki/Wikipedia:Chemical_infobox#References" title="Wikipedia:Chemical infobox">Infobox references</a></div> </td></tr> </tbody></table><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Chemical compound</div> <p><b>1,3-Indandione</b> (sometimes simply <b>indanedione</b>) is an <a href="/wiki/Organic_compound" title="Organic compound">organic compound</a> with the molecular formula C<sub>6</sub>H<sub>4</sub>(CO)<sub>2</sub>CH<sub>2</sub>. It is a <a href="/wiki/Dicarbonyl#1,3-Diketones" title="Dicarbonyl">β-diketone</a> with <a href="/wiki/Indane" title="Indane">indane</a> as its structural nucleus. It is a colorless or white solid, but old samples can appear yellowish<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> or even green. It is a popular <a href="/w/index.php?title=Scaffold_(chemistry)&action=edit&redlink=1" class="new" title="Scaffold (chemistry) (page does not exist)">chemical scaffold</a> (building block of various useful chemical compounds).<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><sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Structural_properties">Structural properties</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=1,3-Indandione&action=edit&section=1" title="Edit section: Structural properties"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Solid 1,3-indandione is a diketone, As a solution in water, it is partially (~2%) enolized. The enolate anion exhibits significant delocalization, and the highest electron density is on the second carbon. This acid-base behavior explains many properties of the compound.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (October 2023)">citation needed</span></a></i>]</sup> </p> <div class="mw-heading mw-heading2"><h2 id="Preparation">Preparation</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=1,3-Indandione&action=edit&section=2" title="Edit section: Preparation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>1,3-Indandione can be prepared by <a href="/wiki/Decarboxylation" title="Decarboxylation">decarboxylation</a> of the sodium salt of 2-ethoxycarbonyl-1,3-indandione, which itself is obtained by <a href="/wiki/Claisen_condensation" title="Claisen condensation">Claisen condensation</a> of <a href="/wiki/Ethyl_acetate" title="Ethyl acetate">ethyl acetate</a> and <a href="/wiki/Dimethyl_phthalate" title="Dimethyl phthalate">dimethyl phthalate</a>.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (October 2023)">citation needed</span></a></i>]</sup> </p> <dl><dd><span typeof="mw:File"><a href="/wiki/File:Indandione-decarboxilation.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b9/Indandione-decarboxilation.svg/400px-Indandione-decarboxilation.svg.png" decoding="async" width="400" height="78" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b9/Indandione-decarboxilation.svg/600px-Indandione-decarboxilation.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b9/Indandione-decarboxilation.svg/800px-Indandione-decarboxilation.svg.png 2x" data-file-width="994" data-file-height="195" /></a></span></dd></dl> <dl><dd><span typeof="mw:File"><a href="/wiki/File:NaECI_preparation.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/0c/NaECI_preparation.svg/400px-NaECI_preparation.svg.png" decoding="async" width="400" height="83" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/0c/NaECI_preparation.svg/600px-NaECI_preparation.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/0c/NaECI_preparation.svg/800px-NaECI_preparation.svg.png 2x" data-file-width="1036" data-file-height="216" /></a></span></dd></dl> <div class="mw-heading mw-heading2"><h2 id="Chemical_properties">Chemical properties</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=1,3-Indandione&action=edit&section=3" title="Edit section: Chemical properties"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The carbon at the C-2 position is <a href="/wiki/Alpha_carbon" class="mw-redirect" title="Alpha carbon">alpha</a> to both <a href="/wiki/Carbonyl" class="mw-redirect" title="Carbonyl">carbonyls</a>, and thus can act as a <a href="/wiki/Nucleophile" title="Nucleophile">nucleophile</a>. It undergoes self-<a href="/wiki/Aldol_condensation" title="Aldol condensation">aldol condensation</a> quite easily, resulting in <a href="/wiki/Bindone" title="Bindone">bindone</a>. </p> <dl><dd><span typeof="mw:File"><a href="/wiki/File:Bindone-formation.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/9f/Bindone-formation.svg/400px-Bindone-formation.svg.png" decoding="async" width="400" height="140" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/9f/Bindone-formation.svg/600px-Bindone-formation.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/9f/Bindone-formation.svg/800px-Bindone-formation.svg.png 2x" data-file-width="559" data-file-height="196" /></a></span></dd></dl> <p><a href="/wiki/Bromination" class="mw-redirect" title="Bromination">Bromination</a> occurs at the 2-position: </p> <dl><dd><span typeof="mw:File"><a href="/wiki/File:Bromination_1,3-Indanediol.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/2/23/Bromination_1%2C3-Indanediol.svg/400px-Bromination_1%2C3-Indanediol.svg.png" decoding="async" width="400" height="66" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/23/Bromination_1%2C3-Indanediol.svg/600px-Bromination_1%2C3-Indanediol.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/23/Bromination_1%2C3-Indanediol.svg/800px-Bromination_1%2C3-Indanediol.svg.png 2x" data-file-width="569" data-file-height="94" /></a></span></dd></dl> <p>One or both carbonyl groups can be <a href="/wiki/Organic_reduction_reaction" class="mw-redirect" title="Organic reduction reaction">reduced</a> to <a href="/wiki/Alcohol_(chemistry)" title="Alcohol (chemistry)">alcohol</a> groups or <a href="/wiki/Methylene_group" title="Methylene group">methylene groups</a>, depending on the method used. </p> <dl><dd><span typeof="mw:File"><a href="/wiki/File:Partial_Reduction_1,3-Indanedione.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/4/4b/Partial_Reduction_1%2C3-Indanedione.svg/400px-Partial_Reduction_1%2C3-Indanedione.svg.png" decoding="async" width="400" height="70" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/4b/Partial_Reduction_1%2C3-Indanedione.svg/600px-Partial_Reduction_1%2C3-Indanedione.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/4b/Partial_Reduction_1%2C3-Indanedione.svg/800px-Partial_Reduction_1%2C3-Indanedione.svg.png 2x" data-file-width="543" data-file-height="95" /></a></span></dd></dl> <dl><dd><span typeof="mw:File"><a href="/wiki/File:Reduction_1,3-Indanedione.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/8e/Reduction_1%2C3-Indanedione.svg/400px-Reduction_1%2C3-Indanedione.svg.png" decoding="async" width="400" height="131" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/8e/Reduction_1%2C3-Indanedione.svg/600px-Reduction_1%2C3-Indanedione.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/8e/Reduction_1%2C3-Indanedione.svg/800px-Reduction_1%2C3-Indanedione.svg.png 2x" data-file-width="287" data-file-height="94" /></a></span></dd></dl> <p><br /> </p> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=1,3-Indandione&action=edit&section=4" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Vitamin_K_antagonist" title="Vitamin K antagonist">Vitamin K antagonist</a></li></ul> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=1,3-Indandione&action=edit&section=5" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap"><ol class="references"> <li id="cite_note-Sigma-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-Sigma_1-0">^</a></b></span> <span class="reference-text"><a rel="nofollow" class="external text" href="http://www.sigmaaldrich.com/catalog/product/riedel/45790?lang=en&region=US">1,3-Indandione</a> at <a href="/wiki/Sigma-Aldrich" title="Sigma-Aldrich">Sigma-Aldrich</a></span> </li> <li id="cite_note-Acros-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-Acros_2-0">^</a></b></span> <span class="reference-text"><a rel="nofollow" class="external text" href="http://www.acros.com/Ecommerce/msds.aspx?PrdNr=12209&Country=UK&Language=en">MSDS</a> at <i>Acros Organics</i>, retrieved on June 16, 2011</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"><span class="languageicon">(in Russian)</span> Нейланд О. Я. Органическая химия: Учеб. для хим. спец. вузов. Москва: Высшая школа, 1990.— с. 481—490.</span> </li> <li id="cite_note-4"><span class="mw-cite-backlink"><b><a href="#cite_ref-4">^</a></b></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite id="CITEREFDumur2021" class="citation journal cs1">Dumur, Frédéric (2021). <a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.eurpolymj.2020.110178">"Recent advances on visible light photoinitiators of polymerization based on Indane-1,3-dione and related derivatives"</a>. <i>European Polymer Journal</i>. <b>143</b>: 110178. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.eurpolymj.2020.110178">10.1016/j.eurpolymj.2020.110178</a></span>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:229445473">229445473</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=European+Polymer+Journal&rft.atitle=Recent+advances+on+visible+light+photoinitiators+of+polymerization+based+on+Indane-1%2C3-dione+and+related+derivatives&rft.volume=143&rft.pages=110178&rft.date=2021&rft_id=info%3Adoi%2F10.1016%2Fj.eurpolymj.2020.110178&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A229445473%23id-name%3DS2CID&rft.aulast=Dumur&rft.aufirst=Fr%C3%A9d%C3%A9ric&rft_id=https%3A%2F%2Fdoi.org%2F10.1016%252Fj.eurpolymj.2020.110178&rfr_id=info%3Asid%2Fen.wikipedia.org%3A1%2C3-Indandione" class="Z3988"></span></span> </li> <li id="cite_note-5"><span class="mw-cite-backlink"><b><a href="#cite_ref-5">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFPluskotaKoba2018" class="citation journal cs1">Pluskota, Robert; Koba, Marcin (2018). "Indandione and Its Derivatives - Chemical Compounds with High Biological Potential". <i>Mini-Reviews in Medicinal Chemistry</i>. <b>18</b> (15): 1321–1330. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.2174%2F1389557518666180330101809">10.2174/1389557518666180330101809</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/29600759">29600759</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:4516564">4516564</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Mini-Reviews+in+Medicinal+Chemistry&rft.atitle=Indandione+and+Its+Derivatives+-+Chemical+Compounds+with+High+Biological+Potential&rft.volume=18&rft.issue=15&rft.pages=1321-1330&rft.date=2018&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A4516564%23id-name%3DS2CID&rft_id=info%3Apmid%2F29600759&rft_id=info%3Adoi%2F10.2174%2F1389557518666180330101809&rft.aulast=Pluskota&rft.aufirst=Robert&rft.au=Koba%2C+Marcin&rfr_id=info%3Asid%2Fen.wikipedia.org%3A1%2C3-Indandione" class="Z3988"></span></span> </li> </ol></div></div> <div class="mw-heading mw-heading2"><h2 id="External_links">External links</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=1,3-Indandione&action=edit&section=6" title="Edit section: External links"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><span 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hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%;line-height:1.2em;font-weight:normal;"><a href="/wiki/Coumarin" title="Coumarin">Coumarins</a> /<br /><a href="/wiki/4-Hydroxycoumarins" title="4-Hydroxycoumarins">4-Hydroxycoumarins</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%;line-height:1.2em;font-weight:normal;font-size:smaller;">1st generation</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Warfarin" title="Warfarin">Warfarin</a></li> <li><a href="/wiki/Coumatetralyl" title="Coumatetralyl">Coumatetralyl</a></li> <li><a href="/wiki/Fumarin" title="Fumarin">Fumarin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;line-height:1.2em;font-weight:normal;font-size:smaller;">2nd generation (<a href="/wiki/Superwarfarin" title="Superwarfarin">Superwarfarins</a>)</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Brodifacoum" title="Brodifacoum">Brodifacoum</a></li> <li><a href="/wiki/Bromadiolone" title="Bromadiolone">Bromadiolone</a></li> <li><a href="/wiki/Difenacoum" title="Difenacoum">Difenacoum</a></li> <li><a href="/wiki/Difethialone" title="Difethialone">Difethialone</a></li> <li><a href="/wiki/Flocoumafen" title="Flocoumafen">Flocoumafen</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;line-height:1.2em;font-weight:normal;"><a class="mw-selflink selflink">1,3-Indandiones</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Chlorophacinone" title="Chlorophacinone">Chlorophacinone</a></li> <li><a href="/wiki/Pindone" title="Pindone">Pindone</a></li> <li><a href="/wiki/Diphacinone" class="mw-redirect" title="Diphacinone">Diphacinone</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background:powderblue;"><a href="/wiki/Convulsant" title="Convulsant">Convulsants</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Crimidine" title="Crimidine">Crimidine</a></li> <li><a href="/wiki/Phenylsilatrane" title="Phenylsilatrane">Phenylsilatrane</a></li> <li><a href="/wiki/Strychnine" title="Strychnine">Strychnine</a></li> <li><a href="/wiki/Tetramethylenedisulfotetramine" title="Tetramethylenedisulfotetramine">Tetramethylenedisulfotetramine</a></li> <li><a href="/wiki/Chlorophenylsilatrane" title="Chlorophenylsilatrane">Chlorophenylsilatrane</a></li> <li><a href="/wiki/RDX" title="RDX">RDX</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background:powderblue;"><a href="/wiki/Vitamin_D" title="Vitamin D">Calciferols</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cholecalciferol" title="Cholecalciferol">Cholecalciferol</a></li> <li><a href="/wiki/Ergocalciferol" title="Ergocalciferol">Ergocalciferol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background:powderblue;"><a href="/wiki/Inorganic_compound" title="Inorganic compound">Inorganic compounds</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Aluminium_phosphide" title="Aluminium phosphide">Aluminium phosphide</a></li> <li><a href="/wiki/Arsenic" title="Arsenic">Arsenic</a></li> <li><a href="/wiki/Barium_carbonate" title="Barium carbonate">Barium carbonate</a></li> <li><a href="/wiki/Calcium_phosphide" title="Calcium phosphide">Calcium phosphide</a></li> <li><a href="/wiki/Cyanide" title="Cyanide">Cyanide</a></li> <li><a href="/wiki/Thallium(I)_sulfate" title="Thallium(I) sulfate">Thallium sulfate</a></li> <li><a href="/wiki/Zinc_phosphide" title="Zinc phosphide">Zinc phosphide</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background:powderblue;"><a href="/wiki/Organochlorine" class="mw-redirect" title="Organochlorine">Organochlorine</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Chloralose" title="Chloralose">Chloralose</a></li> <li><a href="/wiki/Endrin" title="Endrin">Endrin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background:powderblue;"><a href="/wiki/Organophosphorus" class="mw-redirect" title="Organophosphorus">Organophosphorus</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Phosacetim" title="Phosacetim">Phosacetim</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background:powderblue;"><a href="/wiki/Carbamate" title="Carbamate">Carbamates</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Aldicarb" title="Aldicarb">Aldicarb</a></li> <li><a href="/wiki/T-1152" title="T-1152">T-1152</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background:powderblue;">Others</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Alpha-Naphthylthiourea" class="mw-redirect" title="Alpha-Naphthylthiourea">α-Naphthylthiourea</a></li> <li><a href="/wiki/Bromethalin" title="Bromethalin">Bromethalin</a></li> <li><a href="/wiki/Fluoroacetamide" title="Fluoroacetamide">Fluoroacetamide</a></li> <li><a href="/wiki/Flupropadine" title="Flupropadine">Flupropadine</a></li> <li><a href="/wiki/1,3-Difluoro-2-propanol" title="1,3-Difluoro-2-propanol">1,3-Difluoro-2-propanol (Gliftor)</a></li> <li><a href="/wiki/Norbormide" title="Norbormide">Norbormide</a></li> <li><a href="/wiki/Pyrinuron" title="Pyrinuron">Pyrinuron</a></li> <li><a href="/wiki/Scilliroside" title="Scilliroside">Scilliroside</a></li> <li><a href="/wiki/Sodium_fluoroacetate" title="Sodium fluoroacetate">Sodium fluoroacetate</a></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"></div><div role="navigation" class="navbox" aria-labelledby="Antithrombotics_(thrombolytics,_anticoagulants_and_antiplatelet_drugs)_(B01)" style="padding:3px"><table class="nowraplinks hlist mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Antithrombotics" title="Template:Antithrombotics"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Antithrombotics" title="Template talk:Antithrombotics"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Antithrombotics" title="Special:EditPage/Template:Antithrombotics"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Antithrombotics_(thrombolytics,_anticoagulants_and_antiplatelet_drugs)_(B01)" style="font-size:114%;margin:0 4em"><a href="/wiki/Antithrombotic" title="Antithrombotic">Antithrombotics</a> (<a href="/wiki/Thrombolytic_drug" class="mw-redirect" title="Thrombolytic drug">thrombolytics</a>, <a href="/wiki/Anticoagulant" title="Anticoagulant">anticoagulants</a> and <a href="/wiki/Antiplatelet_drug" title="Antiplatelet drug">antiplatelet drugs</a>) (<a href="/wiki/ATC_code_B01" title="ATC code B01">B01</a>)</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Antiplatelet_drug" title="Antiplatelet drug">Antiplatelet drugs</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Glycoprotein_IIb/IIIa_inhibitors" title="Glycoprotein IIb/IIIa inhibitors">Glycoprotein IIb/IIIa inhibitors</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Abciximab" title="Abciximab">Abciximab</a></li> <li><a href="/wiki/Eptifibatide" title="Eptifibatide">Eptifibatide</a></li> <li><a href="/w/index.php?title=Orbofiban&action=edit&redlink=1" class="new" title="Orbofiban (page does not exist)">Orbofiban</a></li> <li><a href="/w/index.php?title=Roxifiban&action=edit&redlink=1" class="new" title="Roxifiban (page does not exist)">Roxifiban</a></li> <li><a href="/wiki/Sibrafiban" title="Sibrafiban">Sibrafiban</a><sup>§</sup></li> <li><a href="/wiki/Tirofiban" title="Tirofiban">Tirofiban</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/P2Y12" title="P2Y12">ADP receptor/P2Y<sub>12</sub></a> <a href="/wiki/Adenosine_diphosphate_receptor_inhibitor" title="Adenosine diphosphate receptor inhibitor">inhibitors</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Thienopyridine" title="Thienopyridine">Thienopyridines</a> <ul><li><a href="/wiki/Clopidogrel" title="Clopidogrel">Clopidogrel</a></li> <li><a href="/wiki/Prasugrel" title="Prasugrel">Prasugrel</a></li> <li><a href="/wiki/Ticlopidine" title="Ticlopidine">Ticlopidine</a></li></ul></li> <li><a href="/wiki/Nucleotide" title="Nucleotide">Nucleotide</a>/<a href="/wiki/Nucleoside" title="Nucleoside">nucleoside</a> analogs <ul><li><a href="/wiki/Cangrelor" title="Cangrelor">Cangrelor</a></li> <li><a href="/wiki/Elinogrel" title="Elinogrel">Elinogrel</a></li> <li><a href="/wiki/Ticagrelor" title="Ticagrelor">Ticagrelor</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Prostaglandin_analogue" title="Prostaglandin analogue">Prostaglandin analogue</a> (<a href="/wiki/Prostacyclin" title="Prostacyclin">PGI2</a>)</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Beraprost" title="Beraprost">Beraprost</a></li> <li><a href="/wiki/Iloprost" title="Iloprost">Iloprost</a></li> <li><a href="/wiki/Prostacyclin" title="Prostacyclin">Prostacyclin</a></li> <li><a href="/wiki/Treprostinil" title="Treprostinil">Treprostinil</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Mechanism_of_action_of_aspirin" title="Mechanism of action of aspirin">COX inhibitors</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Aspirin" title="Aspirin">Acetylsalicylic acid/Aspirin</a><sup>#</sup></li> <li><a href="/wiki/Aloxiprin" title="Aloxiprin">Aloxiprin</a></li> <li><a href="/wiki/Carbasalate_calcium" title="Carbasalate calcium">Carbasalate calcium</a></li> <li><a href="/wiki/Indobufen" title="Indobufen">Indobufen</a></li> <li><a href="/wiki/Triflusal" title="Triflusal">Triflusal</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Thromboxane_inhibitors" class="mw-redirect" title="Thromboxane inhibitors">Thromboxane inhibitors</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Thromboxane_synthase_inhibitors" class="mw-redirect" title="Thromboxane synthase inhibitors">Thromboxane synthase inhibitors</a> <ul><li><a href="/wiki/Dipyridamole" title="Dipyridamole">Dipyridamole</a> (<a href="/wiki/Acetylsalicylic_acid/dipyridamole" title="Acetylsalicylic acid/dipyridamole">+ aspirin</a>)</li> <li><a href="/wiki/Picotamide" title="Picotamide">Picotamide</a></li> <li><a href="/wiki/Terbogrel" title="Terbogrel">Terbogrel</a></li></ul></li> <li><a href="/wiki/Thromboxane_receptor_antagonist" class="mw-redirect" title="Thromboxane receptor antagonist">Receptor antagonists</a> <ul><li><a href="/wiki/Terbogrel" title="Terbogrel">Terbogrel</a></li> <li><a href="/wiki/Terutroban" title="Terutroban">Terutroban</a><sup>§</sup></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Phosphodiesterase_inhibitor" title="Phosphodiesterase inhibitor">Phosphodiesterase inhibitors</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cilostazol" title="Cilostazol">Cilostazol</a></li> <li><a href="/wiki/Dipyridamole" title="Dipyridamole">Dipyridamole</a></li> <li><a href="/wiki/Triflusal" title="Triflusal">Triflusal</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cloricromen" title="Cloricromen">Cloricromen</a></li> <li><a href="/wiki/Ditazole" title="Ditazole">Ditazole</a></li> <li><a href="/wiki/Vorapaxar" title="Vorapaxar">Vorapaxar</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Anticoagulant" title="Anticoagulant">Anticoagulants</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Vitamin_K_antagonist" title="Vitamin K antagonist">Vitamin K antagonists</a><br />(inhibit <a href="/wiki/Thrombin" title="Thrombin">II</a>, <a href="/wiki/Factor_VII" title="Factor VII">VII</a>, <a href="/wiki/Factor_IX" title="Factor IX">IX</a>, <a href="/wiki/Factor_X" title="Factor X">X</a>)</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Coumarin" title="Coumarin">Coumarins</a>: <a href="/wiki/Acenocoumarol" title="Acenocoumarol">Acenocoumarol</a></li> <li><a href="/wiki/Coumatetralyl" title="Coumatetralyl">Coumatetralyl</a></li> <li><a href="/wiki/Dicoumarol" title="Dicoumarol">Dicoumarol</a></li> <li><a href="/wiki/Ethyl_biscoumacetate" title="Ethyl biscoumacetate">Ethyl biscoumacetate</a></li> <li><a href="/wiki/Phenprocoumon" title="Phenprocoumon">Phenprocoumon</a></li> <li><a href="/wiki/Warfarin" title="Warfarin">Warfarin</a><sup>#</sup></li> <li><a class="mw-selflink selflink">1,3-Indandiones</a>: <a href="/wiki/Clorindione" title="Clorindione">Clorindione</a></li> <li><a href="/wiki/Diphenadione" title="Diphenadione">Diphenadione</a></li> <li><a href="/wiki/Phenindione" title="Phenindione">Phenindione</a></li> <li>Other: <a href="/wiki/Tioclomarol" title="Tioclomarol">Tioclomarol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Factor_Xa" class="mw-redirect" title="Factor Xa">Factor Xa</a> inhibitors<br />(with some II inhibition)</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Heparin" title="Heparin">Heparin</a> group/<br /><a href="/wiki/Glycosaminoglycan" title="Glycosaminoglycan">glycosaminoglycans</a>/<br />(bind <a href="/wiki/Antithrombin" title="Antithrombin">antithrombin</a>)</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Low-molecular-weight_heparin" title="Low-molecular-weight heparin">Low-molecular-weight heparin</a> <ul><li><a href="/wiki/Bemiparin_sodium" title="Bemiparin sodium">Bemiparin</a></li> <li><a href="/wiki/Certoparin_sodium" title="Certoparin sodium">Certoparin</a></li> <li><a href="/wiki/Dalteparin_sodium" title="Dalteparin sodium">Dalteparin</a></li> <li><a href="/wiki/Enoxaparin_sodium" title="Enoxaparin sodium">Enoxaparin</a></li> <li><a href="/wiki/Nadroparin_calcium" title="Nadroparin calcium">Nadroparin</a></li> <li><a href="/wiki/Parnaparin_sodium" title="Parnaparin sodium">Parnaparin</a></li> <li><a href="/wiki/Reviparin_sodium" title="Reviparin sodium">Reviparin</a></li> <li><a href="/wiki/Tinzaparin_sodium" title="Tinzaparin sodium">Tinzaparin</a></li></ul></li> <li><a href="/wiki/Oligosaccharide" title="Oligosaccharide">Oligosaccharides</a> <ul><li><a href="/wiki/Fondaparinux" title="Fondaparinux">Fondaparinux</a></li> <li><a href="/wiki/Idraparinux" title="Idraparinux">Idraparinux</a><sup>§</sup></li></ul></li> <li><a href="/wiki/Heparinoid" title="Heparinoid">Heparinoids</a> <ul><li><a href="/wiki/Danaparoid" title="Danaparoid">Danaparoid</a></li> <li><a href="/wiki/Dermatan_sulfate" title="Dermatan sulfate">Dermatan sulfate</a></li> <li><a href="/wiki/Sulodexide" title="Sulodexide">Sulodexide</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Direct_factor_Xa_inhibitors" title="Direct factor Xa inhibitors">Direct Xa inhibitors</a> ("xabans")</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Apixaban" title="Apixaban">Apixaban</a></li> <li><a href="/wiki/Betrixaban" title="Betrixaban">Betrixaban</a></li> <li><a href="/wiki/Darexaban" title="Darexaban">Darexaban</a><sup>§</sup></li> <li><a href="/wiki/Edoxaban" title="Edoxaban">Edoxaban</a></li> <li><a href="/wiki/Otamixaban" title="Otamixaban">Otamixaban</a><sup>§</sup></li> <li><a href="/wiki/Rivaroxaban" title="Rivaroxaban">Rivaroxaban</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Direct_thrombin_inhibitor" title="Direct thrombin inhibitor">Direct thrombin (IIa) inhibitors</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Direct_thrombin_inhibitor#Bivalent" title="Direct thrombin inhibitor">Bivalent</a>: <a href="/wiki/Hirudin" title="Hirudin">Hirudin</a> <ul><li><a href="/wiki/Bivalirudin" title="Bivalirudin">Bivalirudin</a></li> <li><a href="/wiki/Desirudin" class="mw-redirect" title="Desirudin">Desirudin</a></li> <li><a href="/wiki/Lepirudin" title="Lepirudin">Lepirudin</a><sup>‡</sup></li></ul></li> <li><a href="/wiki/Direct_thrombin_inhibitor#Univalent" title="Direct thrombin inhibitor">Univalent</a>: <a href="/wiki/Argatroban" title="Argatroban">Argatroban</a></li> <li><a href="/wiki/Dabigatran" title="Dabigatran">Dabigatran</a></li> <li><a href="/w/index.php?title=Efegatran&action=edit&redlink=1" class="new" title="Efegatran (page does not exist)">Efegatran</a></li> <li><a href="/wiki/Inogatran" title="Inogatran">Inogatran</a><sup>§</sup></li> <li><a href="/wiki/Melagatran" class="mw-redirect" title="Melagatran">Melagatran</a><sup>‡</sup></li> <li><a href="/wiki/Ximelagatran" title="Ximelagatran">Ximelagatran</a><sup>‡</sup></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Abelacimab" title="Abelacimab">Abelacimab</a></li> <li><a href="/wiki/Antithrombin" title="Antithrombin">Antithrombin III</a></li> <li><a href="/wiki/Defibrotide" title="Defibrotide">Defibrotide</a></li> <li><a href="/wiki/Nafamostat" title="Nafamostat">Nafamostat</a></li> <li><a href="/wiki/Protein_C" title="Protein C">Protein C</a> <ul><li><a href="/wiki/Drotrecogin_alfa" title="Drotrecogin alfa">Drotrecogin alfa</a><sup>‡</sup></li></ul></li> <li><a href="/wiki/Ramatroban" title="Ramatroban">Ramatroban</a></li> <li><a href="/wiki/REG1" title="REG1">REG1</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Thrombolytic_drug" class="mw-redirect" title="Thrombolytic drug">Thrombolytic drugs</a>/<br /><a href="/wiki/Fibrinolytic" class="mw-redirect" title="Fibrinolytic">fibrinolytics</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Plasminogen_activator" title="Plasminogen activator">Plasminogen activators</a>: <a href="/wiki/Recombinant_tissue_plasminogen_activators" class="mw-redirect" title="Recombinant tissue plasminogen activators">r-tPA</a> <ul><li><a href="/wiki/Alteplase" title="Alteplase">Alteplase</a><sup>#</sup></li> <li><a href="/wiki/Reteplase" title="Reteplase">Reteplase</a></li> <li><a href="/wiki/Tenecteplase" title="Tenecteplase">Tenecteplase</a></li> <li><a href="/wiki/Desmoteplase" title="Desmoteplase">Desmoteplase</a><sup>†</sup></li></ul></li> <li>UPA <ul><li><a href="/wiki/Saruplase" title="Saruplase">Saruplase</a></li> <li><a href="/wiki/Urokinase" title="Urokinase">Urokinase</a></li></ul></li> <li><a href="/wiki/Anistreplase" title="Anistreplase">Anistreplase</a></li> <li><a href="/wiki/Monteplase" title="Monteplase">Monteplase</a></li> <li><a href="/wiki/Streptokinase" title="Streptokinase">Streptokinase</a><sup>#</sup></li> <li>Other <a href="/wiki/Serine_endopeptidase" class="mw-redirect" title="Serine endopeptidase">serine endopeptidases</a>: <a href="/wiki/Ancrod" title="Ancrod">Ancrod</a><sup>‡</sup></li> <li><a href="/wiki/Brinase" title="Brinase">Brinase</a></li> <li><a href="/wiki/Fibrinolysin" title="Fibrinolysin">Fibrinolysin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Anticoagulant" title="Anticoagulant">Non-medicinal</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Citrate" class="mw-redirect" title="Citrate">Citrate</a></li> <li><a href="/wiki/Ethylenediaminetetraacetic_acid" title="Ethylenediaminetetraacetic acid">EDTA</a></li> <li><a href="/wiki/Oxalate" title="Oxalate">Oxalate</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2" style="background: transparent; padding: 0px;"><div><div class="hlist"> <ul><li><sup>#</sup><a href="/wiki/WHO_Model_List_of_Essential_Medicines" title="WHO Model List of Essential Medicines">WHO-EM</a></li> <li><sup>‡</sup><a href="/wiki/List_of_withdrawn_drugs" title="List of withdrawn drugs">Withdrawn</a> from market</li> <li><a href="/wiki/Clinical_trial" title="Clinical trial">Clinical trials</a>: <ul><li><sup>†</sup><a href="/wiki/Phases_of_clinical_research#Phase_III" title="Phases of clinical research">Phase III</a></li> <li><sup>§</sup>Never to phase III</li></ul></li></ul> </div></div></td></tr></tbody></table></div>    </div><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?type=1x1" alt="" width="1" height="1" style="border: none; position: absolute;"></noscript> <div class="printfooter" data-nosnippet="">Retrieved from "<a dir="ltr" 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