4-Methylmorpholine N-oxide

Chemical properties

Clear colorless to yellow solution

The Uses of 4-Methylmorpholine N-oxide

4-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.

The Uses of 4-Methylmorpholine N-oxide

To a solution of the SM (1.94 g, 10.58 mmol) in a mixture of acetone (63 mL) and H2O (7.8 mL) at RT was added NMO (2.48 g, 21.16 mmol). After 2 min, OsO4 (4% in H2O, 3.37 mL) was added and the rxn mixture was stirred at RT for 23 h. The mixture was quenched with aq 0.2M Na2S2O3 (25 mL) and extracted with DCM (2 x 50 mL). The combined organics were washed with aq 0.2M Na2S2O3 (10 mL), dried (MgSO4), and concentrated in vacuo. The crude material was purified by flash chromatography (17-100% EtOAc/heptane) to provide the product as a yellow solid. [1.31 g, 57%]

The Uses of 4-Methylmorpholine N-oxide

4-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.

The Uses of 4-Methylmorpholine N-oxide

Non-metallic catalyst for the cyanosilylation of ketones. Co-oxidant for Sharpless asymmetric dihydroxylation in ionic liquids.

What are the applications of Application

4-Methylmorpholine N-oxide is a non-metallic catalyst for ketone cyanosilylations

Definition

ChEBI: N-methylmorpholine N-oxide is a morpholine N-oxide resulting from the oxidation of the amino group of N-methylmorpholine.

General Description

4-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 Explosibility

Flammable

Synthesis

A 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 Methods

When 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.]