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Sigma-Aldrich

4-Methylmorpholine N-oxide

97%

Synonym(s):

NMO

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About This Item

Empirical Formula (Hill Notation):
C5H11NO2
CAS Number:
7529-22-8
Molecular Weight:
117.15
Beilstein/REAXYS Number:
507437
EC Number:
231-391-8
MDL number:
MFCD00005947
UNSPSC Code:
12352005
PubChem Substance ID:
24853425

Quality Level

200

assay

97%

reaction suitability

reagent type: oxidant

mp

180-184 °C (lit.)

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

Related Categories

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.

Application

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

pictograms

FlameHealth hazard
GHS02,GHS08

signalword

Danger

Hazard Classifications

Flam. Sol. 1 - Repr. 2

Storage Class

4.1B - Flammable solid hazardous materials

wgk_germany

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

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’.

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Synlett, 6, 1077-1079 (2004)
Marzieh Shafiei et al.
Bioresource technology, 102(17), 7879-7886 (2011-06-21)
Given that N-methylmorpholine-N-oxide (NMMO) is a promising alternative for the pretreatment of lignocelluloses, a novel process for ethanol and biogas production from wood was developed. The solvent, NMMO, is concentrated by multistage evaporation, and the wood is pretreated with the
Nicolas Dupuy et al.
The Journal of chemical physics, 142(21), 214109-214109 (2015-06-08)
We study the ionization energy, electron affinity, and the π → π(∗) ((1)La) excitation energy of the anthracene molecule, by means of variational quantum Monte Carlo (QMC) methods based on a Jastrow correlated antisymmetrized geminal power (JAGP) wave function, developed
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The Journal of organic chemistry, 69(13), 4381-4389 (2004-06-19)
The use of room-temperature ionic liquids (RTILs) in the Sharpless catalytic asymmetric dihydroxylation (AD) as a cosolvent or replacement of the tert-butanol was studied in detail by screening 11 different RTILs. The AD reaction is faster in 1-n-butyl-3-methylimidazolium hexafluorophosphate [C(4)mim][PF(6)]
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