N-Methylmorpholine
{{DISPLAYTITLE:N-Methylmorpholine}}
{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 357297423
| Name = N-Methylmorpholine
| ImageFileL1 = N-Methylmorpholine.svg
| ImageFileR1 = N-Methylmorpholine-3D.png
| IUPACName = 4-Methylmorpholine
| Section1 = {{Chembox Identifiers
| Abbreviations = NMM
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 109-02-4
| ChEMBL = 2448839
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 7684
| EC_number = 203-640-0
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 11P91ANU5X
| PubChem = 7972
| UNNumber = 2535
| SMILES = O1CCN(C)CC1
| InChI = 1/C5H11NO/c1-6-2-4-7-5-3-6/h2-5H2,1H3
| InChIKey = SJRJJKPEHAURKC-UHFFFAOYAK
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 1S/C5H11NO/c1-6-2-4-7-5-3-6/h2-5H2,1H3
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = SJRJJKPEHAURKC-UHFFFAOYSA-N
}}
| Section2 = {{Chembox Properties
| Formula = |C=5|H=11|N=1|O=1
| MolarMass =
| Appearance = Liquid
| Odor = Strongly unpleasant, fish-like
| Density = 0.92 g/cm3
| MeltingPtC = -66
| BoilingPtC = 115 to 116
| pKa = 7.38 (for the conjugate acid) (H2O)[http://www2.lsdiv.harvard.edu/labs/evans/pdf/evans_pKa_table.pdf David Evans Research Group] {{webarchive|url=https://web.archive.org/web/20120121150933/http://www2.lsdiv.harvard.edu/labs/evans/pdf/evans_pKa_table.pdf |date=2012-01-21 }}
}}
| Section7 = {{Chembox Hazards
| GHSPictograms = {{GHS02}}{{GHS05}}{{GHS07}}
| GHSSignalWord = Danger
| HPhrases = {{H-phrases|225|302|312|314|332}}
| PPhrases = {{P-phrases |210|233|240 |241|242|243|260|261|264|270 |271|280|301+312|301+330+331|302+352|303+361+353|304+312 |304+340|305+351+338 |310|312|321|322 |330|363|370+378|403+235 |405|501}}
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N-Methylmorpholine is the organic compound with the formula O(CH2CH2)2NCH3. It is a colorless liquid. It is a cyclic tertiary amine. It is used as a base catalyst for generation of polyurethanes and other reactions. It is produced by the reaction of methylamine and diethylene glycol as well as by the hydrogenolysis of N-formylmorpholine.{{cite encyclopedia|author=Karsten Eller |author2=Erhard Henkes |author3=Roland Rossbacher |author4=Hartmut Höke |title=Amines, Aliphatic|encyclopedia=Ullmann's Encyclopedia of Industrial Chemistry|year=2005|publisher=Wiley-VCH|location=Weinheim|doi=10.1002/14356007.a02_001|isbn=3-527-30673-0}} It is the precursor to N-methylmorpholine N-oxide, a commercially important oxidant.