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258822

Sigma-Aldrich

4-Methylmorpholine N-oxide solution

50 wt. % in H2O

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Synonym(s):
NMMO solution, NMO solution, NSC 73198, NSC 82153
Empirical Formula (Hill Notation):
C5H11NO2
CAS Number:
Molecular Weight:
117.15
MDL number:
PubChem Substance ID:
NACRES:
NA.22

form

liquid

reaction suitability

reagent type: oxidant

concentration

50 wt. % in H2O

refractive index

n20/D 1.4201

pH

9.00 ( in neat)

bp

118.5 °C

mp

−20 °C

density

1.13 g/mL at 25 °C

storage temp.

2-8°C

SMILES string

C[N+]1([O-])CCOCC1

InChI

1S/C5H11NO2/c1-6(7)2-4-8-5-3-6/h2-5H2,1H3

InChI key

LFTLOKWAGJYHHR-UHFFFAOYSA-N

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1 of 4

This Item
224286M5655767870
4-Methylmorpholine ReagentPlus®, 99%

Sigma-Aldrich

M56557

4-Methylmorpholine

4-Methylmorpholine purum, ≥98.0% (GC)

Sigma-Aldrich

67870

4-Methylmorpholine

reaction suitability

reagent type: oxidant

reaction suitability

reagent type: oxidant

reaction suitability

-

reaction suitability

-

refractive index

n20/D 1.4201

refractive index

-

refractive index

n20/D 1.435 (lit.)

refractive index

n20/D 1.435 (lit.)

bp

118.5 °C

bp

-

bp

115-116 °C/750 mmHg (lit.)

bp

115-116 °C/750 mmHg (lit.)

mp

−20 °C

mp

180-184 °C (lit.)

mp

−66 °C (lit.)

mp

−66 °C (lit.)

density

1.13 g/mL at 25 °C

density

-

density

0.92 g/mL at 25 °C (lit.)

density

0.918 g/mL at 20 °C, 0.92 g/mL at 25 °C (lit.)

Application

  • 4-Methylmorpholine N-oxide (NMO) is widely used as a co-oxidant to regenerate osmium tetroxide (OsO4) catalyst during dihydroxylation of alkenes.
  • In the presence of catalytic amounts of tetra-n-propylammonium perruthenate (TPAP), NMO oxidizes secondary amines to the corresponding imines.
  • 4-Methylmorpholine N-oxide solution can be used to oxidize activated primary halides to aldehydes and secondary halides to ketones, respectively.
  • It can also be used to promote stereoselective intermolecular Pauson-Khand reaction for the synthesis of cyclopentenones.

Oxidant for synthesis of novel organic polymer - inorganic hybrid for use as a catalyst for asymmetrical epoxidation

Reagent or Reactant for:
  • Cyclocondensation and cyclization in the enantioselective synthesis of oxazolomycin A
  • Wharton rearrangement and stereoselective dihydroxylation reactions
  • Reduction of amine N-oxides by diboron reagents
  • Synthesis of polysaccharide blend fibers
  • Synthesis of cellulose / modified nano-SiO2 composite packaging films
  • Copper-catalyzed oxidative coupling for preparation of propargylamines

Used as a pretreatment for techno-economical study of ethanol and biogas production from spruce wood

Pictograms

Health hazard

Signal Word

Warning

Hazard Statements

Hazard Classifications

Repr. 2

Storage Class Code

10 - Combustible liquids

WGK

WGK 1

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Catalytic Osmium Tetroxide Oxidation of Olefins: cis?1, 2?Cyclohexanediol.
VanRheenen V, et al.
Organic Syntheses, 43-43 (1988)
Catalytic oxidation of secondary amines with tetra-n-propylammonium perruthenate.
Goti A and Romani M
Tetrahedron Letters, 35(35), 6567-6570 (1994)
Oxidation of activated halides to aldehydes and ketones by N-methylmorpholine-N-oxide.
Griffith W P, et al.
Synthetic Communications, 22(13), 1967-1971 (1992)
Asymmetric dihydroxylation via ligand-accelerated catalysis.
Jacobsen E N, et al.
Journal of the American Chemical Society, 110(6), 1968-1970 (1988)
N-oxide promoted Pauson-Khand cyclizations at room temperature.
Shambayani S, et al.
Tetrahedron Letters, 31(37), 5289-5292 (1990)

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