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4-Methylmorpholine N-oxide

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CAS:7529-22-8
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4-Methylmorpholine N-oxide Basic information
Product Name:4-Methylmorpholine N-oxide
Synonyms:4-Methyl-4-oxylatomorpholinium;4-Oxylato-4-methylmorpholine-4-ium;N-Methylmorpholine N-Oxide (50% in Water, ca. 4.8mol/L);4-Methylmorpholine N-oxide,NMO;4-Methylmorpholine N-oxide solution,NMO solution;N-Methylmorpholine N-oxide - 50% w/w aqeous solution;4-MethylMorpholin-4-iuM-4-olate;(50% in Water, ca. 4.8Mol/L)
CAS:7529-22-8
MF:C5H11NO2
MW:117.15
EINECS:231-391-8
Product Categories:Heterocycles, Metabolites & Impurities, Pharmaceuticals, Intermediates & Fine Chemicals;Heterocycles;Aromatic Morpholines;Oxidation;Synthetic Organic Chemistry;bc0001;7529-22-8
Mol File:7529-22-8.mol
4-Methylmorpholine N-oxide Structure
4-Methylmorpholine N-oxide Chemical Properties
Melting point 180-184 °C(lit.)
Boiling point 118-119°C
density 1,14 g/cm3
vapor pressure 1.41hPa at 20℃
refractive index n20/D 1.43
Fp 118-119°C
storage temp. 2-8°C
solubility DMSO (Soluble), Methanol (Slightly)
pka4.93±0.20(Predicted)
form Liquid
color Clear colorless to yellow
PH9.00 ( in neat)
Water Solubility Soluble in water, methanol, ethanol, acetone, ethers and dimethylsulfoxide.
BRN 507437
Stability:Hygroscopic
LogP-1.2 at 25℃
CAS DataBase Reference7529-22-8(CAS DataBase Reference)
NIST Chemistry ReferenceN-Methylmorpholine-N-oxide(7529-22-8)
EPA Substance Registry SystemMorpholine, 4-methyl-, 4-oxide (7529-22-8)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 26-36/37
WGK Germany 1
TSCA Yes
HS Code 29349990
MSDS Information
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4-Methylmorpholine N-oxide Usage And Synthesis
Chemical PropertiesClear colorless to yellow solution
Uses4-Methylmorpholine N-oxide acts as a non-metallic catalyst for the cyanosilylation of ketones. It is also employed as a co-oxidant for Sharpless asymmetric dihydroxylation in ionic liquids. It serves as a solvent in the Lyocell process to produce tencel fiber. Further, it is used in the preparation of aldehydes from primary alcohols in the presence of tetrapropylammonium perruthenate.
UsesNon-metallic catalyst for the cyanosilylation of ketones. Co-oxidant for Sharpless asymmetric dihydroxylation in ionic liquids.
Uses4-Methylmorpholine N-Oxide is a metabolite of Morpholine (M723725). N-Methylmorpholine N-Oxide is commonly used to dissolve cellulose as well as in the dissolution of of scleroproteins.
DefinitionChEBI: N-methylmorpholine N-oxide is a morpholine N-oxide resulting from the oxidation of the amino group of N-methylmorpholine.
General Description4-Methylmorpholine?N-oxide is an organic compound used as a co-oxidant along with OsO4 and ruthenates in organic synthesis. In recent studies, it has been used as a catalyst in silylcyanation of aldehydes and ketones. Lyocell, a regenerated cellulose fiber, can be prepared using 4-methylmorpholine?N-oxide in an eco-friendly manner.
Flammability and ExplosibilityFlammable
SynthesisA preparation method of N-methylmorpholine-N-oxide comprises the following steps: (1) adding the nano metal oxide into N-methyl morpholine (NMM) and mixing and stirring to uniformly mix the nano metal oxide with the NMM; (2) dropwise adding a hydrogen peroxide solution into a mixed solution of NMM and a catalyst; (3) raising the temperature to accelerate the reaction process; (4) and (4) filtering and distilling the solution prepared in the step (3) under reduced pressure to obtain the required NMMO solution. The method for preparing NMMO provided by the present disclosure has the advantages of a fast reaction rate, low reaction temperature, few byproducts, etc.
Purification MethodsWhen the oxide is dried for 2-3hours at high vacuum, it dehydrates. Add MeOH to the oxide and distil off the solvent under vacuum until the temperature is ca 95o. Then add Me2CO at reflux and cool to 20o. The crystals are filtered off, washed with Me2CO and dried. The degree of hydration may vary and may be important for the desired reactions. [van Rheenan et al. Tetrahedron Lett 1973 1076, Schneider & Hanze US Pat 2 769 823; see also Sharpless et al. Tetrahedron Lett 2503 1976.]
Tag:4-Methylmorpholine N-oxide(7529-22-8) Related Product Information
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