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Please update your browser bookmarks and please use the default browser print function instead.</div></div><div class="mw-content-ltr mw-parser-output" lang="en" 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>1,2-Dichloroethylene </caption> <tbody><tr> <td colspan="2" class="borderless" style="text-align:center"> <table border="0" style="width:100%;display:inline-table;"> <tbody><tr> <td style="border-right:1px solid #aaa; width:50%;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Cis-1,2-dichloroethene.png" class="mw-file-description" title="Skeletal formula of cis-1,2-dichloroethene"><img alt="Skeletal formula of cis-1,2-dichloroethene" src="//upload.wikimedia.org/wikipedia/commons/thumb/2/2d/Cis-1%2C2-dichloroethene.png/110px-Cis-1%2C2-dichloroethene.png" decoding="async" width="110" height="84" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/2d/Cis-1%2C2-dichloroethene.png/165px-Cis-1%2C2-dichloroethene.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/2d/Cis-1%2C2-dichloroethene.png/220px-Cis-1%2C2-dichloroethene.png 2x" data-file-width="708" data-file-height="541" /></a><figcaption>Skeletal formula of cis-1,2-dichloroethene</figcaption></figure> </td> <td style="width:50%;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Trans-1,2-dichloroethene.png" class="mw-file-description" title="Skeletal formula of trans-1,2-dichloroethene"><img alt="Skeletal formula of trans-1,2-dichloroethene" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/ad/Trans-1%2C2-dichloroethene.png/110px-Trans-1%2C2-dichloroethene.png" decoding="async" width="110" height="84" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/ad/Trans-1%2C2-dichloroethene.png/165px-Trans-1%2C2-dichloroethene.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/ad/Trans-1%2C2-dichloroethene.png/220px-Trans-1%2C2-dichloroethene.png 2x" data-file-width="708" data-file-height="543" /></a><figcaption>Skeletal formula of trans-1,2-dichloroethene</figcaption></figure> </td></tr></tbody></table> </td></tr> <tr> <td colspan="2" class="borderless" style="text-align:center"> <table border="0" style="width:100%;display:inline-table;"> <tbody><tr> <td style="border-right:1px solid #aaa; width:50%;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Cis-1,2-dichloroethene-3D-balls.png" class="mw-file-description" title="Ball-and-stick model of cis-1,2-dichloroethene"><img alt="Ball-and-stick model of cis-1,2-dichloroethene" src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d1/Cis-1%2C2-dichloroethene-3D-balls.png/110px-Cis-1%2C2-dichloroethene-3D-balls.png" decoding="async" width="110" height="92" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/d1/Cis-1%2C2-dichloroethene-3D-balls.png/165px-Cis-1%2C2-dichloroethene-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/d1/Cis-1%2C2-dichloroethene-3D-balls.png/220px-Cis-1%2C2-dichloroethene-3D-balls.png 2x" data-file-width="1100" data-file-height="916" /></a><figcaption>Ball-and-stick model of cis-1,2-dichloroethene</figcaption></figure><div style="text-align:center"><i>cis</i>-1,2-Dichloroethene (<i>Z</i>)</div> </td> <td style="width:50%;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Trans-1,2-dichloroethene-3D-balls.png" class="mw-file-description" title="Ball-and-stick model of trans-1,2-dichloroethene"><img alt="Ball-and-stick model of trans-1,2-dichloroethene" src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b0/Trans-1%2C2-dichloroethene-3D-balls.png/110px-Trans-1%2C2-dichloroethene-3D-balls.png" decoding="async" width="110" height="108" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b0/Trans-1%2C2-dichloroethene-3D-balls.png/165px-Trans-1%2C2-dichloroethene-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b0/Trans-1%2C2-dichloroethene-3D-balls.png/220px-Trans-1%2C2-dichloroethene-3D-balls.png 2x" data-file-width="1100" data-file-height="1078" /></a><figcaption>Ball-and-stick model of trans-1,2-dichloroethene</figcaption></figure><div style="text-align:center"><i>trans</i>-1,2-Dichloroethene (<i>E</i>)</div> </td></tr></tbody></table> </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;">1,2-Dichloroethene</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;">1,2-Dichloroethene<br />1,2-DCE<br />Acetylene dichloride<br /><i>sym</i>-Dichloroethylene</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=156-59-2">156-59-2</a></span> (<i>Z</i>)<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><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=156-60-5">156-60-5</a></span> (<i>E</i>)<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><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=540-59-0">540-59-0</a></span> (<i>E</i>/<i>Z</i>)<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=Cl%5BC%40H%5D%3DCCl">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=ClC%3DCCl">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=18882">CHEBI:18882</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.10438.html">10438</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/100.007.956">100.007.956</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q161475#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><a href="/wiki/European_Community_number" title="European Community number"><span title="European Community number (chemical identifier)">EC Number</span></a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li>208-750-2</li></ul></div> </td></tr> <tr> <td><a href="/wiki/KEGG" title="KEGG">KEGG</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.kegg.jp"><a rel="nofollow" class="external text" href="https://www.kegg.jp/entry/C06792">C06792</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/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/643833">643833</a></span> (<i>Z</i>)</li><li><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/638186">638186</a></span> (<i>E</i>)</li><li><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/10900">10900</a></span> (<i>E</i>/<i>Z</i>)</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/FYO9G15JYD">FYO9G15JYD</a></span> (<i>Z</i>)<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><li><span title="precision.fda.gov"><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/41799BI61U">41799BI61U</a></span> (<i>E</i>)<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><li><span title="precision.fda.gov"><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/XU9RUA6YUT">XU9RUA6YUT</a></span> (<i>E</i>/<i>Z</i>)<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/DTXSID8024991">DTXSID8024991</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q161475#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/C2H2Cl2/c3-1-2-4/h1-2H<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: KFUSEUYYWQURPO-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/C2H2Cl2/c3-1-2-4/h1-2H/b2-1-</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: KFUSEUYYWQURPO-UPHRSURJBI</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/C2H2Cl2/c3-1-2-4/h1-2H</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: KFUSEUYYWQURPO-UHFFFAOYAW</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%;">Cl[C@H]=CCl</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%;">ClC=CCl</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>C<sub>2</sub>H<sub>2</sub>Cl<sub>2</sub>  </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td>96.95 g/mol    </td></tr> <tr> <td>Appearance </td> <td>colorless liquid </td></tr> <tr> <td><a href="/wiki/Odor" title="Odor">Odor</a> </td> <td>sweet<sup id="cite_ref-Ullmann_1-0" class="reference"><a href="#cite_note-Ullmann-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Density" title="Density">Density</a> </td> <td><i>Z</i>: 1.28 g/cm<sup>3</sup><br /><i>E</i>: 1.26 g/cm<sup>3</sup> </td></tr> <tr> <td><a href="/wiki/Melting_point" title="Melting point">Melting point</a> </td> <td><i>Z</i>: −81.47 °C<br /><i>E</i>: −49.44 °C </td></tr> <tr> <td><a href="/wiki/Boiling_point" title="Boiling point">Boiling point</a> </td> <td><i>Z</i>: 60.2 °C<br /><i>E</i>: 48.5 °C </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Magnetic_susceptibility" title="Magnetic susceptibility">Magnetic susceptibility</a> (χ)</div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"> <ul><li>−51.0·10<sup>−6</sup> cm<sup>3</sup>/mol (cis)</li> <li>−48.9·10<sup>−6</sup> cm<sup>3</sup>/mol (trans)</li></ul> </div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Dipole#Molecular_dipoles" title="Dipole">Dipole moment</a></div> </td> <td><i>Z</i>: 1.9 <a href="/wiki/Debye" title="Debye">D</a><br /><i>E</i>: 0 <a href="/wiki/Debye" title="Debye">D</a> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Hazards </th></tr> <tr> <td><a href="/wiki/Flash_point" title="Flash point">Flash point</a> </td> <td>2–4 °C; 36–39 °F; 275–277 K </td></tr> <tr> <td><a href="/wiki/Explosive_limit" class="mw-redirect" title="Explosive limit">Explosive limits</a> </td> <td>5.6–12.8%<sup id="cite_ref-NIOSH_2-1" class="reference"><a href="#cite_note-NIOSH-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;"><b>Lethal dose</b> or concentration (LD, LC): </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">LD<sub>50</sub> (<a href="/wiki/Lethal_dose#LD50" title="Lethal dose">median dose</a>)</div> </td> <td>770 mg/kg (oral, rat)<br />1275 mg/kg (oral, rat, <i>trans</i>-isomer)<sup id="cite_ref-IDLH_3-0" class="reference"><a href="#cite_note-IDLH-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">LC<sub>50</sub> (<a href="/wiki/Lethal_dose#LC50" title="Lethal dose">median concentration</a>)</div> </td> <td>21,273 ppm (mouse, 6 hr, <i>trans</i>-isomer)<sup id="cite_ref-IDLH_3-1" class="reference"><a href="#cite_note-IDLH-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">LC<sub>Lo</sub> (<a href="/wiki/Lethal_dose#LCLo" title="Lethal dose">lowest published</a>)</div> </td> <td>16,000 ppm (rat, 6 hr, <i>cis</i>-isomer)<sup id="cite_ref-IDLH_3-2" class="reference"><a href="#cite_note-IDLH-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;"><a href="/wiki/National_Institute_for_Occupational_Safety_and_Health" title="National Institute for Occupational Safety and Health"><b>NIOSH</b></a> (US health exposure limits): </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Permissible_exposure_limit" title="Permissible exposure limit">PEL</a> (Permissible)</div> </td> <td>TWA 200 ppm (790 mg/m<sup>3</sup>)<sup id="cite_ref-NIOSH_2-2" class="reference"><a href="#cite_note-NIOSH-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Recommended_exposure_limit" title="Recommended exposure limit">REL</a> (Recommended)</div> </td> <td>TWA 200 ppm (790 mg/m<sup>3</sup>)<sup id="cite_ref-NIOSH_2-3" class="reference"><a href="#cite_note-NIOSH-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/IDLH" class="mw-redirect" title="IDLH">IDLH</a> (Immediate danger)</div> </td> <td>1000 ppm<sup id="cite_ref-NIOSH_2-4" class="reference"><a href="#cite_note-NIOSH-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </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="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/12px-X_mark.svg.png" decoding="async" width="12" height="14" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/18px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/24px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span> <span class="reflink plainlinks nourlexpansion"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=477203654&page2=1%2C2-Dichloroethylene">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>1,2-Dichloroethylene</b> or <b>1,2-DCE</b> is the name for a pair of <a href="/wiki/Organochloride" class="mw-redirect" title="Organochloride">organochlorine compounds</a> with the molecular formula <style data-mw-deduplicate="TemplateStyles:r1123817410">.mw-parser-output .template-chem2-su{display:inline-block;font-size:80%;line-height:1;vertical-align:-0.35em}.mw-parser-output .template-chem2-su>span{display:block;text-align:left}.mw-parser-output sub.template-chem2-sub{font-size:80%;vertical-align:-0.35em}.mw-parser-output sup.template-chem2-sup{font-size:80%;vertical-align:0.65em}</style><span class="chemf nowrap">C<sub class="template-chem2-sub">2</sub>H<sub class="template-chem2-sub">2</sub>Cl<sub class="template-chem2-sub">2</sub></span>. The two compounds are isomers, each being colorless liquids with a sweet odor. It can exist as either of two <a href="/wiki/Geometric_isomerism" class="mw-redirect" title="Geometric isomerism">geometric isomers</a>, <i>cis</i>-1,2-dichloroethene or <i>trans</i>-1,2-dichloroethene, but is often used as a mixture of the two. They have modest solubility in water. These compounds have some applications as a degreasing solvent.<sup id="cite_ref-Ullmann_1-1" class="reference"><a href="#cite_note-Ullmann-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> In contrast to most <a href="/wiki/Cis%E2%80%93trans_isomerism" title="Cis–trans isomerism"><i>cis-trans</i> compounds</a>, the <i>Z</i> isomer (<i>cis</i>) is more stable than the <i>E</i> isomer (<i>trans</i>) by 0.4 kcal/mol.<sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Production,_uses_and_reactions"><span id="Production.2C_uses_and_reactions"></span>Production, uses and reactions</h2></div> <p><i>cis</i>-DCE, the <i>Z</i> isomer, is obtainable by the controlled <a href="/wiki/Chlorination_reaction" class="mw-redirect" title="Chlorination reaction">chlorination</a> of <a href="/wiki/Acetylene" title="Acetylene">acetylene</a>: </p> <dl><dd>C<sub>2</sub>H<sub>2</sub> + Cl<sub>2</sub> → C<sub>2</sub>H<sub>2</sub>Cl<sub>2</sub></dd></dl> <p>Industrially both isomers arise as byproducts of the production of <a href="/wiki/Vinyl_chloride" title="Vinyl chloride">vinyl chloride</a>, which is produced on a vast scale. Unlike <a href="/wiki/1,1-dichloroethylene" class="mw-redirect" title="1,1-dichloroethylene">1,1-dichloroethylene</a>, the 1,2-dichloroethylene isomers do not polymerize.<sup id="cite_ref-Ullmann_1-2" class="reference"><a href="#cite_note-Ullmann-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </p><p><i>trans</i>-1,2-DCE has applications including electronics cleaning, precision cleaning, and certain metal cleaning applications.<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><p>Both isomers participate in <a href="/wiki/Kumada_coupling" title="Kumada coupling">Kumada coupling</a> reactions. <i>trans</i>-1,2-Dichloroethylene participates in <a href="/wiki/Cycloaddition_reaction" class="mw-redirect" title="Cycloaddition reaction">cycloaddition reactions</a>.<sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Safety_and_environmental_concerns">Safety and environmental concerns</h2></div> <p>These compounds have "moderate oral toxicity to rats".<sup id="cite_ref-Ullmann_1-3" class="reference"><a href="#cite_note-Ullmann-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </p><p>The dichloroethylene isomers occur in some polluted waters and soils, as the decomposition products of <a href="/wiki/Trichloroethylene" title="Trichloroethylene">trichloroethylene</a>. Significant attention has been paid to their further degradation, e.g. by iron particles.<sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2></div> <ul><li><a href="/wiki/1,1-Dichloroethene" class="mw-redirect" title="1,1-Dichloroethene">1,1-Dichloroethene</a></li> <li><a href="/wiki/1,2-Dichloroethane" title="1,2-Dichloroethane">1,2-Dichloroethane</a>, which is also often abbreviated as 1,2-DCE</li></ul> <div class="mw-heading mw-heading2"><h2 id="References">References</h2></div> <div class="mw-references-wrap"><ol class="references"> <li id="cite_note-Ullmann-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-Ullmann_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Ullmann_1-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Ullmann_1-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-Ullmann_1-3"><sup><i><b>d</b></i></sup></a></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="CITEREFE.-L._DreherT._R._TorkelsonK._K._Beutel2011" class="citation book cs1">E.-L. Dreher; T. R. Torkelson; K. K. Beutel (2011). "Chlorethanes and Chloroethylenes". <i>Ullmann's Encyclopedia of Industrial Chemistry</i>. Weinheim: Wiley-VCH. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2F14356007.o06_o01">10.1002/14356007.o06_o01</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3527306732" title="Special:BookSources/978-3527306732"><bdi>978-3527306732</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Chlorethanes+and+Chloroethylenes&rft.btitle=Ullmann%27s+Encyclopedia+of+Industrial+Chemistry&rft.place=Weinheim&rft.pub=Wiley-VCH&rft.date=2011&rft_id=info%3Adoi%2F10.1002%2F14356007.o06_o01&rft.isbn=978-3527306732&rft.au=E.-L.+Dreher&rft.au=T.+R.+Torkelson&rft.au=K.+K.+Beutel&rfr_id=info%3Asid%2Fen.wikipedia.org%3A1%2C2-Dichloroethylene" class="Z3988"></span></span> </li> <li id="cite_note-NIOSH-2"><span class="mw-cite-backlink">^ <a href="#cite_ref-NIOSH_2-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-NIOSH_2-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-NIOSH_2-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-NIOSH_2-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-NIOSH_2-4"><sup><i><b>e</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFNIOSH_Pocket_Guide_to_Chemical_Hazards" class="citation web cs1">NIOSH Pocket Guide to Chemical Hazards. <a rel="nofollow" class="external text" href="https://www.cdc.gov/niosh/npg/npgd0195.html">"#0195"</a>. <a href="/wiki/National_Institute_for_Occupational_Safety_and_Health" title="National Institute for Occupational Safety and Health">National Institute for Occupational Safety and Health</a> (NIOSH).</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=%230195&rft.pub=National+Institute+for+Occupational+Safety+and+Health+%28NIOSH%29&rft.au=NIOSH+Pocket+Guide+to+Chemical+Hazards&rft_id=https%3A%2F%2Fwww.cdc.gov%2Fniosh%2Fnpg%2Fnpgd0195.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3A1%2C2-Dichloroethylene" class="Z3988"></span></span> </li> <li id="cite_note-IDLH-3"><span class="mw-cite-backlink">^ <a href="#cite_ref-IDLH_3-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-IDLH_3-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-IDLH_3-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://www.cdc.gov/niosh/idlh/540590.html">"1,2-Dichloroethylene"</a>. <i>Immediately Dangerous to Life or Health Concentrations (IDLH)</i>. <a href="/wiki/National_Institute_for_Occupational_Safety_and_Health" title="National Institute for Occupational Safety and Health">National Institute for Occupational Safety and Health</a> (NIOSH).</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Immediately+Dangerous+to+Life+or+Health+Concentrations+%28IDLH%29&rft.atitle=1%2C2-Dichloroethylene&rft_id=https%3A%2F%2Fwww.cdc.gov%2Fniosh%2Fidlh%2F540590.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3A1%2C2-Dichloroethylene" class="Z3988"></span></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"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFPitzerHollenberg1954" class="citation journal cs1">Pitzer, Kenneth S.; Hollenberg, J. 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Coplanar and stable derivatives of 13,14-didehydro-tribenzo[a,c,e]cyclooctene: Synthesis of 5,6-didehydro-1,1,14,14-tetramethyl-10,11-methano-1H-benzo[5,6]cycloocta[1,2,3,4-def]fluorene and 5,6-didehydro-10,11-methano-1H-benzo[5,6]cycloocta[1,2,3,4-def]fluorene-1,14-dione and x-ray crystal structures of 1,1,14,14-tetramethyl-10,11-methano-1H-benzo[5,6-cycloocta[1,2,3,4-def]fluorene and 1,12-dihydro-1,1,12,12-tetramethyldicyclopenta[def,JKL]tetraphenylene". <i>The Journal of Organic Chemistry</i>. <b>58</b> (26): 7498–7506. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fjo00078a031">10.1021/jo00078a031</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+Journal+of+Organic+Chemistry&rft.atitle=Arene+synthesis+by+extrusion+reaction.+16.+Coplanar+and+stable+derivatives+of+13%2C14-didehydro-tribenzo%5Ba%2Cc%2Ce%5Dcyclooctene%3A+Synthesis+of+5%2C6-didehydro-1%2C1%2C14%2C14-tetramethyl-10%2C11-methano-1H-benzo%5B5%2C6%5Dcycloocta%5B1%2C2%2C3%2C4-def%5Dfluorene+and+5%2C6-didehydro-10%2C11-methano-1H-benzo%5B5%2C6%5Dcycloocta%5B1%2C2%2C3%2C4-def%5Dfluorene-1%2C14-dione+and+x-ray+crystal+structures+of+1%2C1%2C14%2C14-tetramethyl-10%2C11-methano-1H-benzo%5B5%2C6-cycloocta%5B1%2C2%2C3%2C4-def%5Dfluorene+and+1%2C12-dihydro-1%2C1%2C12%2C12-tetramethyldicyclopenta%5Bdef%2CJKL%5Dtetraphenylene&rft.volume=58&rft.issue=26&rft.pages=7498-7506&rft.date=1993&rft_id=info%3Adoi%2F10.1021%2Fjo00078a031&rft.aulast=Wang&rft.aufirst=Xiao+Min&rft.au=Hou%2C+Xuelong&rft.au=Zhou%2C+Zhongyuan&rft.au=Mak%2C+Thomas+C.+W.&rft.au=Wong%2C+Henry+N.+C.&rfr_id=info%3Asid%2Fen.wikipedia.org%3A1%2C2-Dichloroethylene" class="Z3988"></span></span> </li> <li id="cite_note-7"><span class="mw-cite-backlink"><b><a href="#cite_ref-7">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMattesAlexanderColeman2010" class="citation journal cs1">Mattes, Timothy E.; Alexander, Anne K.; Coleman, Nicholas V. (2010). <a rel="nofollow" class="external text" href="https://doi.org/10.1111%2Fj.1574-6976.2010.00210.x">"Aerobic biodegradation of the chloroethenes: Pathways, enzymes, ecology, and evolution"</a>. <i>FEMS Microbiology Reviews</i>. <b>34</b> (4): 445–475. <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/10.1111%2Fj.1574-6976.2010.00210.x">10.1111/j.1574-6976.2010.00210.x</a></span>. <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/20146755">20146755</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=FEMS+Microbiology+Reviews&rft.atitle=Aerobic+biodegradation+of+the+chloroethenes%3A+Pathways%2C+enzymes%2C+ecology%2C+and+evolution&rft.volume=34&rft.issue=4&rft.pages=445-475&rft.date=2010&rft_id=info%3Adoi%2F10.1111%2Fj.1574-6976.2010.00210.x&rft_id=info%3Apmid%2F20146755&rft.aulast=Mattes&rft.aufirst=Timothy+E.&rft.au=Alexander%2C+Anne+K.&rft.au=Coleman%2C+Nicholas+V.&rft_id=https%3A%2F%2Fdoi.org%2F10.1111%252Fj.1574-6976.2010.00210.x&rfr_id=info%3Asid%2Fen.wikipedia.org%3A1%2C2-Dichloroethylene" class="Z3988"></span></span> </li> <li id="cite_note-8"><span class="mw-cite-backlink"><b><a href="#cite_ref-8">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSchrickBloughJonesMallouk2002" class="citation journal cs1">Schrick, Bettina; Blough, Jennifer L.; Jones, A. 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