| Revision as of 11:13, 18 April 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (changes to verified fields - added verified revid - updated 'UNII_Ref', 'ChemSpiderID_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref', 'ChEMBL_Ref', 'KEGG_Ref') per [[Misplaced Pages:WikiProject Chemicals/Chembox validation|Chem/Drugbox valid |
Latest revision as of 08:50, 2 September 2024 edit JWBE (talk | contribs)Extended confirmed users10,129 edits added Category:Methyl compounds using HotCat |
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{{DISPLAYTITLE:''N''-Methylmaleimide}} |
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{{chembox |
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{{chembox |
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| Name = ''N''-Methylmaleimide |
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| Verifiedfields = changed |
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| verifiedrevid = 401773985 |
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| verifiedrevid = 424669901 |
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| ImageFile =Dichlorobenzophenone.png |
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| ImageFile = Methylmaleimide.svg |
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| ImageSize = 120px |
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| Section1 = {{Chembox Identifiers |
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| PIN = 1-Methyl-1''H''-pyrrole-2,5-dione |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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|Section1={{Chembox Identifiers |
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| ChemSpiderID = 6767 |
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| CASNo = 930-88-1 |
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| KEGG_Ref = {{keggcite|changed|kegg}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| KEGG = C06643 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| InChI = 1/C13H8Cl2O/c14-11-5-1-9(2-6-11)13(16)10-3-7-12(15)8-4-10/h1-8H |
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| UNII = P0TFZ8R21Y |
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| SMILES = O=C(c1ccc(Cl)cc1)c2ccc(Cl)cc2 |
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| EINECS = 213-226-1 |
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| InChIKey = OKISUZLXOYGIFP-UHFFFAOYAC |
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| PubChem = 70261 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| ChemSpiderID = 63446 |
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| StdInChI = 1S/C13H8Cl2O/c14-11-5-1-9(2-6-11)13(16)10-3-7-12(15)8-4-10/h1-8H |
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| SMILES = CN1C(=O)C=CC1=O |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| InChI = 1/C5H5NO2/c1-6-4(7)2-3-5(6)8/h2-3H,1H3 |
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| StdInChIKey = OKISUZLXOYGIFP-UHFFFAOYSA-N |
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| InChIKey = SEEYREPSKCQBBF-UHFFFAOYAQ |
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| CASNo = 90-98-2 |
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| StdInChI = 1S/C5H5NO2/c1-6-4(7)2-3-5(6)8/h2-3H,1H3 |
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}} |
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| StdInChIKey = SEEYREPSKCQBBF-UHFFFAOYSA-N |
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| Section2 = {{Chembox Properties |
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}} |
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| Formula = C<sub>13</sub>H<sub>8</sub>Cl<sub>2</sub>O |
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|Section2={{Chembox Properties |
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| MolarMass = 251.11 g/mol |
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| Appearance = |
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| C=5 | H=5 | N=1 | O=2 |
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| MeltingPtC = 96 |
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| MeltingPt = 144-147 °C |
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| MeltingPt_ref = <ref>{{cite journal | doi = 10.1021/jo9621985 | title = The Elusive Antiaromaticity of Maleimides and Maleic Anhydride: Enthalpies of Formation of N-Methylmaleimide, N-Methylsuccinimide, N-Methylphthalimide, and N-Benzoyl-N-methylbenzamide | year = 1997 | last1 = Roux | first1 = María Victoria | last2 = Jiménez | first2 = Pilar | last3 = Martín-Luengo | first3 = Maria Ángeles | last4 = Dávalos | first4 = Juan Z. | last5 = Sun | first5 = Zhiyuan | last6 = Hosmane | first6 = Ramachandra S. | last7 = Liebman | first7 = Joel F. | journal = The Journal of Organic Chemistry | volume = 62 | issue = 9 | pages = 2732–2737 | pmid = 11671632 }}</ref> |
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| BoilingPt = 353 °C |
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}} |
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}} |
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| Section3 = {{Chembox Hazards |
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| RPhrases = |
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| SPhrases = |
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}} |
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'''4,4’-Dichlorobenzophenone''' is an ] with the ] of (ClC<sub>6</sub>H<sub>4</sub>)<sub>2</sub>CO. |
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'''''N''-Methylmaleimide''' (NMM) is a ]{{cn|date=February 2018}} ] with the ] of C<sub>5</sub>H<sub>5</sub>NO<sub>2</sub>. |
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==Synthesis== |
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== Spectrum == |
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The ] spectrum of ''N''-methylmaleimide contains two signals: one for the hydrogen atoms of the methyl group and one for the vinylic hydrogen atoms. |
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4,4’-Dichlorobenzophenone is prepared by the ] of ] with 4-chlorobenzoyl chloride. The conversion is typically conducted in the presence of an ] catalyst in a petroleum ether ]. |
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]{{clear-left}} |
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:ClC<sub>6</sub>H<sub>5</sub>C(O)Cl + C<sub>6</sub>H<sub>5</sub>Cl → (ClC<sub>6</sub>H<sub>4</sub>)<sub>2</sub>CO + HCl |
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==References== |
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{{DEFAULTSORT:Dichlorobenzophenone, 4,4'-}} |
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{{Reflist}} |
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] |
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] |
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{{Transient receptor potential channel modulators}} |
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{{DEFAULTSORT:Methylmaleimide, N-}} |
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] |
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] |
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{{organic-compound-stub}} |