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)<ref>[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 }}</ref> }} | 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}} }} }}

'''''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.<ref name=Ullmann>{{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}}</ref> It is the precursor to ''N''-methylmorpholine ''N''-oxide, a commercially important oxidant.

== References == {{reflist}}

{{DEFAULTSORT:Methylmorpholine, N-}} Category:4-Morpholinyl compounds Category:Reagents for organic chemistry