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Sigma-Aldrich

4-Methylmorpholine N-oxide

97%

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Synonym(s):
NMO
Empirical Formula (Hill Notation):
C5H11NO2
CAS Number:
Molecular Weight:
117.15
Beilstein:
507437
EC Number:
MDL number:
PubChem Substance ID:

Quality Level

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

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This Item
258822407704317594
4-Methylmorpholine purified by redistillation, ≥99.5%

Sigma-Aldrich

407704

4-Methylmorpholine

reaction suitability

reagent type: oxidant

reaction suitability

reagent type: oxidant

reaction suitability

-

reaction suitability

reagent type: oxidant

mp

180-184 °C (lit.)

mp

−20 °C

mp

−66 °C (lit.)

mp

220-222 °C (lit.)

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

-

storage temp.

-

Quality Level

200

Quality Level

-

Quality Level

-

Quality Level

-

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

Signal Word

Danger

Hazard Statements

Hazard Classifications

Flam. Sol. 1 - Repr. 2

Storage Class Code

4.1B - Flammable solid hazardous materials

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


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Synlett, 6, 1077-1079 (2004)
Luís C Branco et al.
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)]
N?Methylmorpholine N?Oxide
Encyclopedia of Reagents for Organic Synthesis, Second Edition (2008)
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
The N-Methylmorpholine-N-Oxide (NMMO) Process of Producing Regenerated Fibers
Innovative Biofibers from Renewable Resources (2014)

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