Skip to Content
Merck
All Photos(3)

Documents

258822

Sigma-Aldrich

4-Methylmorpholine N-oxide solution

50 wt. % in H2O

Synonym(s):

NMMO solution, NMO solution, NSC 73198, NSC 82153

Sign Into View Organizational & Contract Pricing
All Photos(3)

About This Item

Empirical Formula (Hill Notation):
C5H11NO2
CAS Number:
7529-22-8
Molecular Weight:
117.15
MDL number:
MFCD00005947
UNSPSC Code:
12352005
PubChem Substance ID:
24855662
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

Looking for similar products? Visit Product Comparison Guide

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
GHS08

Signal Word

Warning

Hazard Statements

H361f

Hazard Classifications

Repr. 2

Storage Class Code

10 - Combustible liquids

WGK

WGK 1

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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)
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service