258822
4-Methylmorpholine N-oxide solution
50 wt. % in H2O
Synonym(s):
NMMO solution, NMO solution, NSC 73198, NSC 82153
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About This Item
Empirical Formula (Hill Notation):
C5H11NO2
CAS Number:
Molecular Weight:
117.15
MDL number:
UNSPSC Code:
12352005
PubChem Substance ID:
NACRES:
NA.22
Recommended Products
form
liquid
Quality Level
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
functional group
ether
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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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:
Used as a pretreatment for techno-economical study of ethanol and biogas production from spruce wood
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
Signal Word
Warning
Hazard Statements
Precautionary 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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Asymmetric dihydroxylation via ligand-accelerated catalysis.
Jacobsen E N, et al.
Journal of the American Chemical Society, 110(6), 1968-1970 (1988)
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)
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)
Patrik R Lennartsson et al.
Bioresource technology, 102(6), 4425-4432 (2011-01-21)
A complete process for the production of bioethanol and fungal biomass from spruce and birch was investigated. The process included milling, pretreatment with N-methylmorpholine-N-oxide (NMMO), washing of the pretreated wood, enzymatic hydrolysis, and cultivation of the zygomycetes fungi Mucor indicus.
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