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validation/VerifiedDataSandbox">edit</a></span><span class="mw-diff-timestamp" data-timestamp="2012-02-16T16:11:53Z"></span></strong></div><div id="mw-diff-otitle2"><a href="/wiki/User:Beetstra" class="mw-userlink" title="User:Beetstra" data-mw-revid="477203654"><bdi>Beetstra</bdi></a> <span class="mw-usertoollinks">(<a href="/wiki/User_talk:Beetstra" class="mw-usertoollinks-talk" title="User talk:Beetstra">talk</a> | <a href="/wiki/Special:Contributions/Beetstra" class="mw-usertoollinks-contribs" title="Special:Contributions/Beetstra">contribs</a>)</span><div class="mw-diff-usermetadata"><div class="mw-diff-userroles"><a href="/wiki/Wikipedia:Edit_filter_manager" title="Wikipedia:Edit filter manager">Edit filter managers</a>, <a href="/wiki/Wikipedia:Administrators" title="Wikipedia:Administrators">Administrators</a></div><div class="mw-diff-usereditcount"><span>171,990</span> edits</div></div></div><div id="mw-diff-otitle3"> <span class="comment comment--without-parentheses">Saving copy of the {{chembox}} taken from revid 458715441 of page <a href="/wiki/1,2-Dichloroethene" class="mw-redirect" title="1,2-Dichloroethene">1,2-Dichloroethene</a> for the <a href="/wiki/Wikipedia:WikiProject_Chemicals/Chembox_validation" title="Wikipedia:WikiProject Chemicals/Chembox validation">Chem/Drugbox validation project</a> (updated: '').</span></div><div id="mw-diff-otitle5"></div><div id="mw-diff-otitle4"> </div></td> <td colspan="2" class="diff-ntitle diff-side-added"><div id="mw-diff-ntitle1"><strong><a href="/w/index.php?title=1,2-Dichloroethylene&oldid=1229185653" title="1,2-Dichloroethylene">Latest revision as of 10:26, 15 June 2024</a> <span class="mw-diff-edit"><a href="/w/index.php?title=1,2-Dichloroethylene&action=edit" title="1,2-Dichloroethylene">edit</a></span><span class="mw-diff-timestamp" data-timestamp="2024-06-15T10:26:01Z"></span> </strong></div><div id="mw-diff-ntitle2"><a href="/wiki/User:Renamed_user_1e23409a06e0b7922c2dfc98dde51974" class="mw-userlink" title="User:Renamed user 1e23409a06e0b7922c2dfc98dde51974" data-mw-revid="1229185653"><bdi>Renamed user 1e23409a06e0b7922c2dfc98dde51974</bdi></a> <span class="mw-usertoollinks">(<a href="/wiki/User_talk:Renamed_user_1e23409a06e0b7922c2dfc98dde51974" class="mw-usertoollinks-talk" title="User talk:Renamed user 1e23409a06e0b7922c2dfc98dde51974">talk</a> | <a href="/wiki/Special:Contributions/Renamed_user_1e23409a06e0b7922c2dfc98dde51974" class="mw-usertoollinks-contribs" title="Special:Contributions/Renamed user 1e23409a06e0b7922c2dfc98dde51974">contribs</a>)</span><div class="mw-diff-usermetadata"><div class="mw-diff-userroles"><a href="/wiki/Wikipedia:Extended_confirmed_editors" class="mw-redirect" title="Wikipedia:Extended confirmed editors">Extended confirmed users</a></div><div class="mw-diff-usereditcount"><span>1,813</span> edits</div></div></div><div id="mw-diff-ntitle3"> <span class="comment comment--without-parentheses">They definitely don't have 4 hydrogens</span></div><div id="mw-diff-ntitle5"><span class="mw-tag-markers"><a href="/wiki/Special:Tags" title="Special:Tags">Tags</a>: <span class="mw-tag-marker mw-tag-marker-mobile_edit">Mobile edit</span> <span class="mw-tag-marker mw-tag-marker-mobile_web_edit">Mobile web edit</span> <span class="mw-tag-marker mw-tag-marker-advanced_mobile_edit">Advanced mobile edit</span></span></div><div id="mw-diff-ntitle4"> </div></td> </tr><tr> <td colspan="2" class="diff-lineno">Line 1:</td> <td colspan="2" class="diff-lineno">Line 1:</td> </tr> <tr> <td class="diff-marker" data-marker="−"></td> <td class="diff-deletedline diff-side-deleted"><div>{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid [{{fullurl:1,2-Dichloroethene|oldid=458715441}} 458715441] of page [[1,2-Dichloroethene]] with values updated to verified values.}}</div></td> <td colspan="2" class="diff-empty diff-side-added"></td> </tr> <tr> <td class="diff-marker"></td> <td class="diff-context diff-side-deleted"><div>{{chembox</div></td> <td class="diff-marker"></td> <td class="diff-context diff-side-added"><div>{{chembox</div></td> </tr> <tr> <td colspan="2" class="diff-empty diff-side-deleted"></td> <td class="diff-marker" data-marker="+"></td> <td class="diff-addedline diff-side-added"><div>| Verifiedfields = changed</div></td> </tr> <tr> <td class="diff-marker"><a class="mw-diff-movedpara-left" title="Paragraph was moved. Click to jump to new location." href="#movedpara_6_0_rhs">⚫</a></td> <td class="diff-deletedline diff-side-deleted"><div><a name="movedpara_3_0_lhs"></a>| verifiedrevid = <del class="diffchange diffchange-inline">443901242</del></div></td> <td colspan="2" class="diff-empty diff-side-added"></td> </tr> <tr> <td colspan="2" class="diff-empty diff-side-deleted"></td> <td class="diff-marker" data-marker="+"></td> <td class="diff-addedline diff-side-added"><div>| Watchedfields = changed</div></td> </tr> <tr> <td class="diff-marker" data-marker="−"></td> <td class="diff-deletedline diff-side-deleted"><div>| Name = ''cis''-1,2-Dichloroethene (Z) <small>(left)</small> and ''trans''-1,2-Dichloroethene (E) <small>(right)</small></div></td> <td colspan="2" class="diff-empty diff-side-added"></td> </tr> <tr> <td colspan="2" class="diff-empty diff-side-deleted"></td> <td class="diff-marker"><a class="mw-diff-movedpara-right" title="Paragraph was moved. Click to jump to old location." href="#movedpara_3_0_lhs">⚫</a></td> <td class="diff-addedline diff-side-added"><div><a name="movedpara_6_0_rhs"></a>| verifiedrevid = <ins class="diffchange diffchange-inline">477203654</ins></div></td> </tr> <tr> <td class="diff-marker"></td> <td class="diff-context diff-side-deleted"><div>| ImageFileL1 = Cis-1,2-dichloroethene.png</div></td> <td class="diff-marker"></td> <td class="diff-context diff-side-added"><div>| ImageFileL1 = Cis-1,2-dichloroethene.png</div></td> </tr> <tr> <td class="diff-marker" data-marker="−"></td> <td class="diff-deletedline diff-side-deleted"><div>| ImageSizeL1 = 110px</div></td> <td colspan="2" class="diff-empty diff-side-added"></td> </tr> <tr> <td class="diff-marker"></td> <td class="diff-context diff-side-deleted"><div>| ImageNameL1 = Skeletal formula of cis-1,2-dichloroethene</div></td> <td class="diff-marker"></td> <td class="diff-context diff-side-added"><div>| ImageNameL1 = Skeletal formula of cis-1,2-dichloroethene</div></td> </tr> <tr> <td class="diff-marker"></td> <td class="diff-context diff-side-deleted"><div>| ImageFileR1 = Trans-1,2-dichloroethene.png</div></td> <td class="diff-marker"></td> <td class="diff-context diff-side-added"><div>| ImageFileR1 = Trans-1,2-dichloroethene.png</div></td> </tr> <tr> <td class="diff-marker" data-marker="−"></td> <td class="diff-deletedline diff-side-deleted"><div>| ImageSizeR1 = 110px</div></td> <td colspan="2" class="diff-empty diff-side-added"></td> </tr> <tr> <td class="diff-marker"></td> <td class="diff-context diff-side-deleted"><div>| ImageNameR1 = Skeletal formula of trans-1,2-dichloroethene</div></td> <td class="diff-marker"></td> <td class="diff-context diff-side-added"><div>| ImageNameR1 = Skeletal formula of trans-1,2-dichloroethene</div></td> </tr> <tr> <td class="diff-marker" data-marker="−"></td> <td class="diff-deletedline diff-side-deleted"><div>| ImageFileL2 = Cis-<del class="diffchange diffchange-inline">dichloroethylene</del>-3D-balls.png</div></td> <td class="diff-marker" data-marker="+"></td> <td class="diff-addedline diff-side-added"><div>| ImageFileL2 = Cis-<ins class="diffchange diffchange-inline">1,2-dichloroethene</ins>-3D-balls.png</div></td> </tr> <tr> <td class="diff-marker" data-marker="−"></td> <td class="diff-deletedline diff-side-deleted"><div>| ImageSizeL2 = 110px</div></td> <td colspan="2" class="diff-empty diff-side-added"></td> </tr> <tr> <td class="diff-marker"></td> <td class="diff-context diff-side-deleted"><div>| ImageNameL2 = Ball-and-stick model of cis-1,2-dichloroethene</div></td> <td class="diff-marker"></td> <td class="diff-context diff-side-added"><div>| ImageNameL2 = Ball-and-stick model of cis-1,2-dichloroethene</div></td> </tr> <tr> <td class="diff-marker" data-marker="−"></td> <td class="diff-deletedline diff-side-deleted"><div>| ImageFileR2 = Trans-<del class="diffchange diffchange-inline">dichloroethylene</del>-3D-balls.png</div></td> <td class="diff-marker" data-marker="+"></td> <td class="diff-addedline diff-side-added"><div>| ImageFileR2 = Trans-<ins class="diffchange diffchange-inline">1,2-dichloroethene</ins>-3D-balls.png</div></td> </tr> <tr> <td class="diff-marker" data-marker="−"></td> <td class="diff-deletedline diff-side-deleted"><div>| ImageSizeR2 = 110px</div></td> <td colspan="2" class="diff-empty diff-side-added"></td> </tr> <tr> <td class="diff-marker"></td> <td class="diff-context diff-side-deleted"><div>| ImageNameR2 = Ball-and-stick model of trans-1,2-dichloroethene</div></td> <td class="diff-marker"></td> <td class="diff-context diff-side-added"><div>| ImageNameR2 = Ball-and-stick model of trans-1,2-dichloroethene</div></td> </tr> <tr> <td class="diff-marker" data-marker="−"></td> <td class="diff-deletedline diff-side-deleted"><div>| <del class="diffchange diffchange-inline">IUPACName </del>= 1,2-Dichloroethene</div></td> <td class="diff-marker" data-marker="+"></td> <td class="diff-addedline diff-side-added"><div>| <ins class="diffchange diffchange-inline">ImageCaptionL2</ins>= <ins class="diffchange diffchange-inline">''cis''-</ins>1,2-Dichloroethene<ins class="diffchange diffchange-inline"> (''Z'') </ins></div></td> </tr> <tr> <td colspan="2" class="diff-empty diff-side-deleted"></td> <td class="diff-marker" data-marker="+"></td> <td class="diff-addedline diff-side-added"><div>| ImageCaptionR2= ''trans''-1,2-Dichloroethene (''E'')</div></td> </tr> <tr> <td class="diff-marker" data-marker="−"></td> <td class="diff-deletedline diff-side-deleted"><div>| OtherNames = 1,2-Dichloroethylene<br />1,2-DCE</div></td> <td colspan="2" class="diff-empty diff-side-added"></td> </tr> <tr> <td colspan="2" class="diff-empty diff-side-deleted"></td> <td class="diff-marker" data-marker="+"></td> <td class="diff-addedline diff-side-added"><div>| PIN = 1,2-Dichloroethene</div></td> </tr> <tr> <td colspan="2" class="diff-empty diff-side-deleted"></td> <td class="diff-marker" data-marker="+"></td> <td class="diff-addedline diff-side-added"><div>| OtherNames = 1,2-Dichloroethene<br />1,2-DCE<br/>Acetylene dichloride<br />''sym''-Dichloroethylene</div></td> </tr> <tr> <td class="diff-marker"></td> <td class="diff-context diff-side-deleted"><div>| Section1 = {{Chembox Identifiers</div></td> <td class="diff-marker"></td> <td class="diff-context diff-side-added"><div>| Section1 = {{Chembox Identifiers</div></td> </tr> <tr> <td class="diff-marker"></td> <td class="diff-context diff-side-deleted"><div>| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}</div></td> <td class="diff-marker"></td> <td class="diff-context diff-side-added"><div>| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}</div></td> </tr> <tr> <td colspan="2" class="diff-lineno">Line 22:</td> <td colspan="2" class="diff-lineno">Line 20:</td> </tr> <tr> <td class="diff-marker"></td> <td class="diff-context diff-side-deleted"><div>| ChEBI = 18882</div></td> <td class="diff-marker"></td> <td class="diff-context diff-side-added"><div>| ChEBI = 18882</div></td> </tr> <tr> <td class="diff-marker"></td> <td class="diff-context diff-side-deleted"><div>| ChemSpiderID = 10438</div></td> <td class="diff-marker"></td> <td class="diff-context diff-side-added"><div>| ChemSpiderID = 10438</div></td> </tr> <tr> <td colspan="2" class="diff-empty diff-side-deleted"></td> <td class="diff-marker" data-marker="+"></td> <td class="diff-addedline diff-side-added"><div>| EINECS = 208-750-2</div></td> </tr> <tr> <td colspan="2" class="diff-empty diff-side-deleted"></td> <td class="diff-marker" data-marker="+"></td> <td class="diff-addedline diff-side-added"><div>| PubChem = 643833</div></td> </tr> <tr> <td colspan="2" class="diff-empty diff-side-deleted"></td> <td class="diff-marker" data-marker="+"></td> <td class="diff-addedline diff-side-added"><div>| PubChem_Comment = (''Z'')</div></td> </tr> <tr> <td colspan="2" class="diff-empty diff-side-deleted"></td> <td class="diff-marker" data-marker="+"></td> <td class="diff-addedline diff-side-added"><div>| PubChem1 = 638186</div></td> </tr> <tr> <td colspan="2" class="diff-empty diff-side-deleted"></td> <td class="diff-marker" data-marker="+"></td> <td class="diff-addedline diff-side-added"><div>| PubChem1_Comment = (''E'')</div></td> </tr> <tr> <td colspan="2" class="diff-empty diff-side-deleted"></td> <td class="diff-marker" data-marker="+"></td> <td class="diff-addedline diff-side-added"><div>| PubChem2 = 10900</div></td> </tr> <tr> <td colspan="2" class="diff-empty diff-side-deleted"></td> <td class="diff-marker" data-marker="+"></td> <td class="diff-addedline diff-side-added"><div>| PubChem2_Comment = (''E''/''Z'')</div></td> </tr> <tr> <td class="diff-marker"></td> <td class="diff-context diff-side-deleted"><div>| KEGG_Ref = {{keggcite|correct|kegg}}</div></td> <td class="diff-marker"></td> <td class="diff-context diff-side-added"><div>| KEGG_Ref = {{keggcite|correct|kegg}}</div></td> </tr> <tr> <td class="diff-marker"></td> <td class="diff-context diff-side-deleted"><div>| KEGG = C06792</div></td> <td class="diff-marker"></td> <td class="diff-context diff-side-added"><div>| KEGG = C06792</div></td> </tr> <tr> <td colspan="2" class="diff-lineno">Line 35:</td> <td colspan="2" class="diff-lineno">Line 40:</td> </tr> <tr> <td class="diff-marker"></td> <td class="diff-context diff-side-deleted"><div>| CASNo_Ref = {{cascite|correct|CAS}}</div></td> <td class="diff-marker"></td> <td class="diff-context diff-side-added"><div>| CASNo_Ref = {{cascite|correct|CAS}}</div></td> </tr> <tr> <td class="diff-marker"></td> <td class="diff-context diff-side-deleted"><div>| CASNo = 156-59-2</div></td> <td class="diff-marker"></td> <td class="diff-context diff-side-added"><div>| CASNo = 156-59-2</div></td> </tr> <tr> <td class="diff-marker" data-marker="−"></td> <td class="diff-deletedline diff-side-deleted"><div>| CASNo_Comment = (Z)</div></td> <td class="diff-marker" data-marker="+"></td> <td class="diff-addedline diff-side-added"><div>| CASNo_Comment = (<ins class="diffchange diffchange-inline">''</ins>Z<ins class="diffchange diffchange-inline">''</ins>)</div></td> </tr> <tr> <td colspan="2" class="diff-empty diff-side-deleted"></td> <td class="diff-marker" data-marker="+"></td> <td class="diff-addedline diff-side-added"><div>| CASNo1_Ref = {{cascite|correct|??}}</div></td> </tr> <tr> <td class="diff-marker"></td> <td class="diff-context diff-side-deleted"><div>| CASNo1 = 156-60-5</div></td> <td class="diff-marker"></td> <td class="diff-context diff-side-added"><div>| CASNo1 = 156-60-5</div></td> </tr> <tr> <td class="diff-marker" data-marker="−"></td> <td class="diff-deletedline diff-side-deleted"><div>| CASNo1_Comment = (E)</div></td> <td class="diff-marker" data-marker="+"></td> <td class="diff-addedline diff-side-added"><div>| CASNo1_Comment = (<ins class="diffchange diffchange-inline">''</ins>E<ins class="diffchange diffchange-inline">''</ins>)</div></td> </tr> <tr> <td colspan="2" class="diff-empty diff-side-deleted"></td> <td class="diff-marker" data-marker="+"></td> <td class="diff-addedline diff-side-added"><div>| CASNo2_Ref = {{cascite|correct|??}}</div></td> </tr> <tr> <td class="diff-marker"></td> <td class="diff-context diff-side-deleted"><div>| CASNo2 = 540-59-0</div></td> <td class="diff-marker"></td> <td class="diff-context diff-side-added"><div>| CASNo2 = 540-59-0</div></td> </tr> <tr> <td class="diff-marker" data-marker="−"></td> <td class="diff-deletedline diff-side-deleted"><div>| CASNo2_Comment = (<del class="diffchange diffchange-inline">racemate</del>)</div></td> <td class="diff-marker" data-marker="+"></td> <td class="diff-addedline diff-side-added"><div>| CASNo2_Comment = (<ins class="diffchange diffchange-inline">''E''/''Z''</ins>)</div></td> </tr> <tr> <td colspan="2" class="diff-empty diff-side-deleted"></td> <td class="diff-marker" data-marker="+"></td> <td class="diff-addedline diff-side-added"><div>| UNII_Ref = {{fdacite|correct|FDA}}</div></td> </tr> <tr> <td colspan="2" class="diff-empty diff-side-deleted"></td> <td class="diff-marker" data-marker="+"></td> <td class="diff-addedline diff-side-added"><div>| UNII = FYO9G15JYD</div></td> </tr> <tr> <td colspan="2" class="diff-empty diff-side-deleted"></td> <td class="diff-marker" data-marker="+"></td> <td class="diff-addedline diff-side-added"><div>| UNII_Comment = (''Z'')</div></td> </tr> <tr> <td colspan="2" class="diff-empty diff-side-deleted"></td> <td class="diff-marker" data-marker="+"></td> <td class="diff-addedline diff-side-added"><div>| UNII1_Ref = {{fdacite|correct|FDA}}</div></td> </tr> <tr> <td colspan="2" class="diff-empty diff-side-deleted"></td> <td class="diff-marker" data-marker="+"></td> <td class="diff-addedline diff-side-added"><div>| UNII1 = 41799BI61U</div></td> </tr> <tr> <td colspan="2" class="diff-empty diff-side-deleted"></td> <td class="diff-marker" data-marker="+"></td> <td class="diff-addedline diff-side-added"><div>| UNII1_Comment = (''E'')</div></td> </tr> <tr> <td colspan="2" class="diff-empty diff-side-deleted"></td> <td class="diff-marker" data-marker="+"></td> <td class="diff-addedline diff-side-added"><div>| UNII2_Ref = {{fdacite|correct|FDA}}</div></td> </tr> <tr> <td colspan="2" class="diff-empty diff-side-deleted"></td> <td class="diff-marker" data-marker="+"></td> <td class="diff-addedline diff-side-added"><div>| UNII2 = XU9RUA6YUT</div></td> </tr> <tr> <td colspan="2" class="diff-empty diff-side-deleted"></td> <td class="diff-marker" data-marker="+"></td> <td class="diff-addedline diff-side-added"><div>| UNII2_Comment = (''E''/''Z'')</div></td> </tr> <tr> <td class="diff-marker"></td> <td class="diff-context diff-side-deleted"><div>| SMILES = Cl[C@H]=CCl</div></td> <td class="diff-marker"></td> <td class="diff-context diff-side-added"><div>| SMILES = Cl[C@H]=CCl</div></td> </tr> <tr> <td class="diff-marker"></td> <td class="diff-context diff-side-deleted"><div>}}</div></td> <td class="diff-marker"></td> <td class="diff-context diff-side-added"><div>}}</div></td> </tr> <tr> <td class="diff-marker"></td> <td class="diff-context diff-side-deleted"><div>| Section2 = {{Chembox Properties</div></td> <td class="diff-marker"></td> <td class="diff-context diff-side-added"><div>| Section2 = {{Chembox Properties</div></td> </tr> <tr> <td class="diff-marker" data-marker="−"></td> <td class="diff-deletedline diff-side-deleted"><div>| Formula = C<del class="diffchange diffchange-inline"><</del>sub<del class="diffchange diffchange-inline">></del>2<del class="diffchange diffchange-inline"></sub></del>H<del class="diffchange diffchange-inline"><</del>sub<del class="diffchange diffchange-inline">></del>2<del class="diffchange diffchange-inline"></sub></del>Cl<del class="diffchange diffchange-inline"><</del>sub<del class="diffchange diffchange-inline">></del>2<del class="diffchange diffchange-inline"></sub></del></div></td> <td class="diff-marker" data-marker="+"></td> <td class="diff-addedline diff-side-added"><div>| Formula = C<ins class="diffchange diffchange-inline">{{</ins>sub<ins class="diffchange diffchange-inline">|</ins>2<ins class="diffchange diffchange-inline">}}</ins>H<ins class="diffchange diffchange-inline">{{</ins>sub<ins class="diffchange diffchange-inline">|</ins>2<ins class="diffchange diffchange-inline">}}</ins>Cl<ins class="diffchange diffchange-inline">{{</ins>sub<ins class="diffchange diffchange-inline">|</ins>2<ins class="diffchange diffchange-inline">}}</ins></div></td> </tr> <tr> <td class="diff-marker"></td> <td class="diff-context diff-side-deleted"><div>| MolarMass = 96.95 g/mol</div></td> <td class="diff-marker"></td> <td class="diff-context diff-side-added"><div>| MolarMass = 96.95 g/mol</div></td> </tr> <tr> <td class="diff-marker" data-marker="−"></td> <td class="diff-deletedline diff-side-deleted"><div>| Density = Z: 1.28 g/cm<del class="diffchange diffchange-inline">³</del><br />E: 1.26 g/cm<del class="diffchange diffchange-inline">³</del></div></td> <td class="diff-marker" data-marker="+"></td> <td class="diff-addedline diff-side-added"><div>| Density = <ins class="diffchange diffchange-inline">''</ins>Z<ins class="diffchange diffchange-inline">''</ins>: 1.28 g/cm<ins class="diffchange diffchange-inline">{{sup|3}}</ins><br /><ins class="diffchange diffchange-inline">''</ins>E<ins class="diffchange diffchange-inline">''</ins>: 1.26 g/cm<ins class="diffchange diffchange-inline">{{sup|3}}</ins></div></td> </tr> <tr> <td class="diff-marker" data-marker="−"></td> <td class="diff-deletedline diff-side-deleted"><div>| MeltingPt = Z: <del class="diffchange diffchange-inline">-81</del> °C<br />E: <del class="diffchange diffchange-inline">-81</del> °C</div></td> <td class="diff-marker" data-marker="+"></td> <td class="diff-addedline diff-side-added"><div>| MeltingPt = <ins class="diffchange diffchange-inline">''</ins>Z<ins class="diffchange diffchange-inline">''</ins>: <ins class="diffchange diffchange-inline">−81.47</ins> °C<br /><ins class="diffchange diffchange-inline">''</ins>E<ins class="diffchange diffchange-inline">''</ins>: <ins class="diffchange diffchange-inline">−49.44</ins> °C</div></td> </tr> <tr> <td class="diff-marker" data-marker="−"></td> <td class="diff-deletedline diff-side-deleted"><div>| BoilingPt = Z: 60.<del class="diffchange diffchange-inline">3</del> °C<br />E: <del class="diffchange diffchange-inline">47</del>.5 °C</div></td> <td class="diff-marker" data-marker="+"></td> <td class="diff-addedline diff-side-added"><div>| BoilingPt = <ins class="diffchange diffchange-inline">''</ins>Z<ins class="diffchange diffchange-inline">''</ins>: 60.<ins class="diffchange diffchange-inline">2</ins> °C<br /><ins class="diffchange diffchange-inline">''</ins>E<ins class="diffchange diffchange-inline">''</ins>: <ins class="diffchange diffchange-inline">48</ins>.5 °C</div></td> </tr> <tr> <td class="diff-marker" data-marker="−"></td> <td class="diff-deletedline diff-side-deleted"><div>| Dipole = Z<del class="diffchange diffchange-inline"> (cis)</del>: 1.9 [[Debye|D]]<br />E<del class="diffchange diffchange-inline"> (trans)</del>: 0 [[Debye|D]]</div></td> <td class="diff-marker" data-marker="+"></td> <td class="diff-addedline diff-side-added"><div>| Dipole = <ins class="diffchange diffchange-inline">''</ins>Z<ins class="diffchange diffchange-inline">''</ins>: 1.9 [[Debye|D]]<br /><ins class="diffchange diffchange-inline">''</ins>E<ins class="diffchange diffchange-inline">''</ins>: 0 [[Debye|D]]</div></td> </tr> <tr> <td colspan="2" class="diff-empty diff-side-deleted"></td> <td class="diff-marker" data-marker="+"></td> <td class="diff-addedline diff-side-added"><div>| Appearance = colorless liquid</div></td> </tr> <tr> <td colspan="2" class="diff-empty diff-side-deleted"></td> <td class="diff-marker" data-marker="+"></td> <td class="diff-addedline diff-side-added"><div>| Odor = sweet<ref name=Ullmann/></div></td> </tr> <tr> <td colspan="2" class="diff-empty diff-side-deleted"></td> <td class="diff-marker" data-marker="+"></td> <td class="diff-addedline diff-side-added"><div>| MagSus = {{Plainlist|</div></td> </tr> <tr> <td colspan="2" class="diff-empty diff-side-deleted"></td> <td class="diff-marker" data-marker="+"></td> <td class="diff-addedline diff-side-added"><div>* −51.0·10{{sup|−6}} cm{{sup|3}}/mol (cis)</div></td> </tr> <tr> <td colspan="2" class="diff-empty diff-side-deleted"></td> <td class="diff-marker" data-marker="+"></td> <td class="diff-addedline diff-side-added"><div>* −48.9·10{{sup|−6}} cm{{sup|3}}/mol (trans)</div></td> </tr> <tr> <td colspan="2" class="diff-empty diff-side-deleted"></td> <td class="diff-marker" data-marker="+"></td> <td class="diff-addedline diff-side-added"><div> }}</div></td> </tr> <tr> <td class="diff-marker"></td> <td class="diff-context diff-side-deleted"><div> }}</div></td> <td class="diff-marker"></td> <td class="diff-context diff-side-added"><div> }}</div></td> </tr> <tr> <td colspan="2" class="diff-empty diff-side-deleted"></td> <td class="diff-marker" data-marker="+"></td> <td class="diff-addedline diff-side-added"><div>| Section3 = {{Chembox Hazards</div></td> </tr> <tr> <td colspan="2" class="diff-empty diff-side-deleted"></td> <td class="diff-marker" data-marker="+"></td> <td class="diff-addedline diff-side-added"><div>| PEL = TWA 200 ppm (790 mg/m{{sup|3}})<ref name=NIOSH>{{PGCH|0195}}</ref></div></td> </tr> <tr> <td colspan="2" class="diff-empty diff-side-deleted"></td> <td class="diff-marker" data-marker="+"></td> <td class="diff-addedline diff-side-added"><div>| FlashPtF = 36-39<ref name=NIOSH/></div></td> </tr> <tr> <td colspan="2" class="diff-empty diff-side-deleted"></td> <td class="diff-marker" data-marker="+"></td> <td class="diff-addedline diff-side-added"><div>| ExploLimits = 5.6–12.8%<ref name=NIOSH/></div></td> </tr> <tr> <td colspan="2" class="diff-empty diff-side-deleted"></td> <td class="diff-marker" data-marker="+"></td> <td class="diff-addedline diff-side-added"><div>| IDLH = 1000 ppm<ref name=NIOSH/></div></td> </tr> <tr> <td colspan="2" class="diff-empty diff-side-deleted"></td> <td class="diff-marker" data-marker="+"></td> <td class="diff-addedline diff-side-added"><div>| REL = TWA 200 ppm (790 mg/m{{sup|3}})<ref name=NIOSH/></div></td> </tr> <tr> <td colspan="2" class="diff-empty diff-side-deleted"></td> <td class="diff-marker" data-marker="+"></td> <td class="diff-addedline diff-side-added"><div>| LC50 = 21,273 ppm (mouse, 6 hr, ''trans''-isomer)<ref name=IDLH>{{IDLH|540590|1,2-Dichloroethylene}}</ref></div></td> </tr> <tr> <td colspan="2" class="diff-empty diff-side-deleted"></td> <td class="diff-marker" data-marker="+"></td> <td class="diff-addedline diff-side-added"><div>| LD50 = 770 mg/kg (oral, rat)<br/>1275 mg/kg (oral, rat, ''trans''-isomer)<ref name=IDLH/></div></td> </tr> <tr> <td colspan="2" class="diff-empty diff-side-deleted"></td> <td class="diff-marker" data-marker="+"></td> <td class="diff-addedline diff-side-added"><div>| LCLo = 16,000 ppm (rat, 6 hr, ''cis''-isomer)<ref name=IDLH/></div></td> </tr> <tr> <td class="diff-marker"></td> <td class="diff-context diff-side-deleted"><div>}}</div></td> <td class="diff-marker"></td> <td class="diff-context diff-side-added"><div>}}</div></td> </tr> <tr> <td colspan="2" class="diff-empty diff-side-deleted"></td> <td class="diff-marker" data-marker="+"></td> <td class="diff-addedline diff-side-added"><div>}}</div></td> </tr> <tr> <td colspan="2" class="diff-empty diff-side-deleted"></td> <td class="diff-marker" data-marker="+"></td> <td class="diff-addedline diff-side-added"><br /></td> </tr> <tr> <td colspan="2" class="diff-empty diff-side-deleted"></td> <td class="diff-marker" data-marker="+"></td> <td class="diff-addedline diff-side-added"><div>'''1,2-Dichloroethylene''' or '''1,2-DCE''' is the name for a pair of [[organochloride|organochlorine compounds]] with the molecular formula {{chem2|C2H2Cl2}}. The two compounds are isomers, each being colorless liquids with a sweet odor. It can exist as either of two [[geometric isomerism|geometric isomers]], ''cis''-1,2-dichloroethene or ''trans''-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.<ref name=Ullmann>{{cite book | author = E.-L. Dreher | author2 = T. R. Torkelson | author3 = K. K. Beutel | chapter = Chlorethanes and Chloroethylenes | title = Ullmann's Encyclopedia of Industrial Chemistry | year = 2011 | publisher = Wiley-VCH | location = Weinheim | doi = 10.1002/14356007.o06_o01| isbn = 978-3527306732 }}</ref> In contrast to most [[Cis–trans isomerism|''cis-trans'' compounds]], the ''Z'' isomer (''cis'') is more stable than the ''E'' isomer (''trans'') by 0.4 kcal/mol.<ref>{{cite journal |title= ''cis''- and ''trans''-Dichloroethylenes. The Infrared Spectra from 130–400 Cm.{{sup|–1}} and the Thermodynamic Properties |first1= Kenneth S. |last1= Pitzer |first2= J. L. |last2= Hollenberg |journal= J. Am. Chem. Soc. |year= 1954 |volume= 76 |issue= 6 | pages= 1493–1496 |doi= 10.1021/ja01635a010 }}</ref></div></td> </tr> <tr> <td colspan="2" class="diff-empty diff-side-deleted"></td> <td class="diff-marker" data-marker="+"></td> <td class="diff-addedline diff-side-added"><br /></td> </tr> <tr> <td colspan="2" class="diff-empty diff-side-deleted"></td> <td class="diff-marker" data-marker="+"></td> <td class="diff-addedline diff-side-added"><div>==Production, uses and reactions==</div></td> </tr> <tr> <td colspan="2" class="diff-empty diff-side-deleted"></td> <td class="diff-marker" data-marker="+"></td> <td class="diff-addedline diff-side-added"><div>''cis''-DCE, the ''Z'' isomer, is obtainable by the controlled [[chlorination reaction|chlorination]] of [[acetylene]]:</div></td> </tr> <tr> <td colspan="2" class="diff-empty diff-side-deleted"></td> <td class="diff-marker" data-marker="+"></td> <td class="diff-addedline diff-side-added"><br /></td> </tr> <tr> <td colspan="2" class="diff-empty diff-side-deleted"></td> <td class="diff-marker" data-marker="+"></td> <td class="diff-addedline diff-side-added"><div>:C{{sub|2}}H{{sub|2}} + Cl{{sub|2}} → C{{sub|2}}H{{sub|2}}Cl{{sub|2}}</div></td> </tr> <tr> <td colspan="2" class="diff-empty diff-side-deleted"></td> <td class="diff-marker" data-marker="+"></td> <td class="diff-addedline diff-side-added"><br /></td> </tr> <tr> <td colspan="2" class="diff-empty diff-side-deleted"></td> <td class="diff-marker" data-marker="+"></td> <td class="diff-addedline diff-side-added"><div>Industrially both isomers arise as byproducts of the production of [[vinyl chloride]], which is produced on a vast scale. Unlike [[1,1-dichloroethylene]], the 1,2-dichloroethylene isomers do not polymerize.<ref name=Ullmann/></div></td> </tr> <tr> <td colspan="2" class="diff-empty diff-side-deleted"></td> <td class="diff-marker" data-marker="+"></td> <td class="diff-addedline diff-side-added"><br /></td> </tr> <tr> <td colspan="2" class="diff-empty diff-side-deleted"></td> <td class="diff-marker" data-marker="+"></td> <td class="diff-addedline diff-side-added"><div>''trans''-1,2-DCE has applications including electronics cleaning, precision cleaning, and certain metal cleaning applications.<ref>{{Cite web |url=http://www.axiall.com/Products/Chlorovinyls/Chlorinated-Solvents-and-Feedstock/ |title=Chlorinated Solvents and Feed Stock - Axiall |access-date=2016-03-23 |archive-url=https://web.archive.org/web/20160408122850/http://www.axiall.com/Products/Chlorovinyls/Chlorinated-Solvents-and-Feedstock/ |archive-date=2016-04-08 |url-status=dead }}</ref></div></td> </tr> <tr> <td colspan="2" class="diff-empty diff-side-deleted"></td> <td class="diff-marker" data-marker="+"></td> <td class="diff-addedline diff-side-added"><br /></td> </tr> <tr> <td colspan="2" class="diff-empty diff-side-deleted"></td> <td class="diff-marker" data-marker="+"></td> <td class="diff-addedline diff-side-added"><div>Both isomers participate in [[Kumada coupling]] reactions. ''trans''-1,2-Dichloroethylene participates in [[cycloaddition reaction]]s.<ref>{{cite journal |doi=10.1021/jo00078a031|title=Arene synthesis by extrusion reaction. 16. 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 |year=1993 |last1=Wang |first1=Xiao Min |last2=Hou |first2=Xuelong |last3=Zhou |first3=Zhongyuan |last4=Mak |first4=Thomas C. W. |last5=Wong |first5=Henry N. C. |journal=The Journal of Organic Chemistry |volume=58 |issue=26 |pages=7498–7506 }}</ref></div></td> </tr> <tr> <td colspan="2" class="diff-empty diff-side-deleted"></td> <td class="diff-marker" data-marker="+"></td> <td class="diff-addedline diff-side-added"><br /></td> </tr> <tr> <td colspan="2" class="diff-empty diff-side-deleted"></td> <td class="diff-marker" data-marker="+"></td> <td class="diff-addedline diff-side-added"><div>==Safety and environmental concerns==</div></td> </tr> <tr> <td colspan="2" class="diff-empty diff-side-deleted"></td> <td class="diff-marker" data-marker="+"></td> <td class="diff-addedline diff-side-added"><div>These compounds have "moderate oral toxicity to rats".<ref name=Ullmann/></div></td> </tr> <tr> <td colspan="2" class="diff-empty diff-side-deleted"></td> <td class="diff-marker" data-marker="+"></td> <td class="diff-addedline diff-side-added"><br /></td> </tr> <tr> <td colspan="2" class="diff-empty diff-side-deleted"></td> <td class="diff-marker" data-marker="+"></td> <td class="diff-addedline diff-side-added"><div>The dichloroethylene isomers occur in some polluted waters and soils, as the decomposition products of [[trichloroethylene]]. Significant attention has been paid to their further degradation, e.g. by iron particles.<ref>{{cite journal|doi=10.1111/j.1574-6976.2010.00210.x|title=Aerobic biodegradation of the chloroethenes: Pathways, enzymes, ecology, and evolution |year=2010 |last1=Mattes |first1=Timothy E. |last2=Alexander |first2=Anne K. |last3=Coleman |first3=Nicholas V. |journal=FEMS Microbiology Reviews |volume=34 |issue=4 |pages=445–475 |pmid=20146755 |doi-access=free }}</ref><ref>{{cite journal |doi=10.1021/cm020737i|title=Hydrodechlorination of Trichloroethylene to Hydrocarbons Using Bimetallic Nickel−Iron Nanoparticles |year=2002 |last1=Schrick |first1=Bettina |last2=Blough |first2=Jennifer L. |last3=Jones |first3=A. Daniel |last4=Mallouk |first4=Thomas E. |journal=Chemistry of Materials |volume=14 |issue=12 |pages=5140–5147 }}</ref></div></td> </tr> <tr> <td colspan="2" class="diff-empty diff-side-deleted"></td> <td class="diff-marker" data-marker="+"></td> <td class="diff-addedline diff-side-added"><br /></td> </tr> <tr> <td colspan="2" class="diff-empty diff-side-deleted"></td> <td class="diff-marker" data-marker="+"></td> <td class="diff-addedline diff-side-added"><div>==See also==</div></td> </tr> <tr> <td colspan="2" class="diff-empty diff-side-deleted"></td> <td class="diff-marker" data-marker="+"></td> <td class="diff-addedline diff-side-added"><div>* [[1,1-Dichloroethene]]</div></td> </tr> <tr> <td colspan="2" class="diff-empty diff-side-deleted"></td> <td class="diff-marker" data-marker="+"></td> <td class="diff-addedline diff-side-added"><div>* [[1,2-Dichloroethane]], which is also often abbreviated as 1,2-DCE</div></td> </tr> <tr> <td colspan="2" class="diff-empty diff-side-deleted"></td> <td class="diff-marker" data-marker="+"></td> <td class="diff-addedline diff-side-added"><br /></td> </tr> <tr> <td colspan="2" class="diff-empty diff-side-deleted"></td> <td class="diff-marker" data-marker="+"></td> <td class="diff-addedline diff-side-added"><div>==References==</div></td> </tr> <tr> <td colspan="2" class="diff-empty diff-side-deleted"></td> <td class="diff-marker" data-marker="+"></td> <td class="diff-addedline diff-side-added"><div><references/></div></td> </tr> <tr> <td colspan="2" class="diff-empty diff-side-deleted"></td> <td class="diff-marker" data-marker="+"></td> <td class="diff-addedline diff-side-added"><br /></td> </tr> <tr> <td colspan="2" class="diff-empty diff-side-deleted"></td> <td class="diff-marker" data-marker="+"></td> <td class="diff-addedline diff-side-added"><div>==External links==</div></td> </tr> <tr> <td colspan="2" class="diff-empty diff-side-deleted"></td> <td class="diff-marker" data-marker="+"></td> <td class="diff-addedline diff-side-added"><div>*{{ICSC|0436|04}}</div></td> </tr> <tr> <td colspan="2" class="diff-empty diff-side-deleted"></td> <td class="diff-marker" data-marker="+"></td> <td class="diff-addedline diff-side-added"><div>*{{PGCH|0195}}</div></td> </tr> <tr> <td colspan="2" class="diff-empty diff-side-deleted"></td> <td class="diff-marker" data-marker="+"></td> <td class="diff-addedline diff-side-added"><br /></td> </tr> <tr> <td colspan="2" class="diff-empty diff-side-deleted"></td> <td class="diff-marker" data-marker="+"></td> <td class="diff-addedline diff-side-added"><div>{{DEFAULTSORT:Dichloroethene, 1, 2-}}</div></td> </tr> <tr> <td colspan="2" class="diff-empty diff-side-deleted"></td> <td class="diff-marker" data-marker="+"></td> <td class="diff-addedline diff-side-added"><div>[[Category:Chloroalkenes]]</div></td> </tr> <tr> <td colspan="2" class="diff-empty diff-side-deleted"></td> <td class="diff-marker" data-marker="+"></td> <td class="diff-addedline diff-side-added"><div>[[Category:Halogenated solvents]]</div></td> </tr> </table><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?type=1x1&useformat=desktop" alt="" width="1" height="1" style="border: none; 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