NMO

N-Methylmorpholine N-oxide

Other Names:

4-Methylmorpholine N-oxide

General Information:

Structure:

CAS Number: 7529-22-8

Molecular Weight: 117.15 g/mol

Appearance: Colorless crystals

Melting Point: 180-184 C

Common Uses:

Co-oxidant in the conversion of alkenes to diols using OsO4

Procedure excerpt:

To a solution of the SM (1.94 g, 10.58 mmol) in a mixture of acetone (63 mL) and H2O (7.8 mL) at RT was added NMO (2.48 g, 21.16 mmol). After 2 min, OsO4 (4% in H2O, 3.37 mL) . . .

[full procedure]

Co-oxidant in the oxidation of primary alcohols to carboxylic acids using TPAP

Procedure excerpt:

To a solution of the SM (8.34 g, 18.15 mmol) in ACN (100 mL) was added NMO (8.51 g, 72.6 mmol) and TPAP (0.51 g, 1.45 mmol) in three portions. The resulting mixture . . .

[full procedure]

Safety:

NMO is an irritant, skin contact and inhalation should be avoided. NMO is a hygroscopic solid.

References:

1) Patent Reference: WO2016001341, page 126, (9.1 MB)

2) Patent Reference: WO2016085780, page 53, (6.8 MB)

3) Wikipedia: N-Methylmorpholine N-oxide (link)

4) Aldrich: 4-Methylmopholine N-oxide (link)

5) Burke, S. D.; Danheiser, R. L.; Handbook of Reagents for Organic Synthesis, Oxidizing and Reducing Agents