N -methylmorpholine- N -oxide

Structural formula
General
Surname	N -methylmorpholine- N -oxide
other names	4-methylmorpholine- N -oxide; NMO; NMMO;
Molecular formula	C 5 H 11 NO 2
Brief description	light yellow crystalline solid
External identifiers / databases
ECHA InfoCard	100,028,538
PubChem	82029
Wikidata	Q416248
properties
Molar mass	117.15 g mol −1
Physical state	firmly
Melting point	180-184 ° C
solubility	easily in water
safety instructions
GHS labeling of hazardous substances Caution
H and P phrases	H: 315-319-335
	P: 261-305 + 351 + 338
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

N -Methylmorpholine- N -oxide (or commonlyabbreviatedas NMO ) is an organic compound from the series of amine N -oxides and is used as an oxidizing agent in chemical reactions. NMO is used in bishydroxylation with osmium tetroxide , in asymmetric Sharpless dihydroxylation , oxidation with TPAP and Jacobsen epoxidation . It iscommercially availableas a pure crystalline substance, as a monohydrate and as an aqueous solution.

Extraction and presentation

NMO is made by oxidizing N -methylmorpholine with hydrogen peroxide at 75 ° C.

use

In organic synthesis, NMO is used as an oxidizing agent. In combination with TPAP, it is used to produce aldehydes from primary alcohols , whereby the water is removed by molecular sieves . A carboxylic acid is obtained in the presence of unbound water . In the Upjohn dihydroxylation of olefins with osmium tetroxide , NMO is used as a co-oxidant. Sharpless dihydroxylation is an asymmetric variant . NMO can be used to remove O- and N -allyl protective groups under oxidative conditions.

NMO is used technically as a solubilizer in lyocell production. Cellulose is precipitated here from a solution in NMO with water.

Individual evidence

↑ ^a ^b ^c Data sheet 4-Methylmorpholine N-oxide from Sigma-Aldrich , accessed on June 14, 2011 ( PDF ).
↑ ^a ^b ^c Entry on 4-methylmorpholine-4-oxide in the GESTIS substance database of the IFA , accessed on February 14, 2017(JavaScript required) .
↑ N. Meyer, W. Wykypiel, D. Seebach: Catalytic Osmium Tetroxide Oxidation of Olefins: cis-1,2-Cyclohexanediol In: Organic Syntheses . 58, 1978, p. 43, doi : 10.15227 / orgsyn.058.0043 ; Coll. Vol. 6, 1988, pp. 342-348 ( PDF ).
↑ Steven V. Ley, Joanne Norman, William P. Griffith, Stephen P. Marsden: Tetrapropylammonium Perruthenate, Pr 4 N + RuO 4 -, TPAP: A Catalytic Oxidant for Organic Synthesis . In: Synthesis . tape 1994 , no. 7 , January 1994, pp. 639-666 , doi : 10.1055 / s-1994-25538 .
↑ BM Choudary, NS Chodari, K. Jyothi, ML Kantam: In J. Am. Chem. Soc. , 2002 , 124 , pp. 5341-5349.
↑ PI Kitov, DR Bundle: In Org. Lett. , 2004 , 3 , pp. 2835-2838.
↑ patent GB2337990 : Process for shaping cellulose. Published December 8, 1999 , Inventors: Stephen Byron Smith, Sudith Kanishke Atureliya. ‌

[Sigma-1] Data sheet 4-Methylmorpholine N-oxide from Sigma-Aldrich , accessed on June 14, 2011 ( PDF ).

[GESTIS-2] Entry on 4-methylmorpholine-4-oxide in the GESTIS substance database of the IFA , accessed on February 14, 2017(JavaScript required) .

[3] N. Meyer, W. Wykypiel, D. Seebach: Catalytic Osmium Tetroxide Oxidation of Olefins: cis-1,2-Cyclohexanediol In: Organic Syntheses . 58, 1978, p. 43, doi : 10.15227 / orgsyn.058.0043 ; Coll. Vol. 6, 1988, pp. 342-348 ( PDF ).

[4] Steven V. Ley, Joanne Norman, William P. Griffith, Stephen P. Marsden: Tetrapropylammonium Perruthenate, Pr 4 N + RuO 4 -, TPAP: A Catalytic Oxidant for Organic Synthesis . In: Synthesis . tape 1994 , no. 7 , January 1994, pp. 639-666 , doi : 10.1055 / s-1994-25538 .

[5] BM Choudary, NS Chodari, K. Jyothi, ML Kantam: In J. Am. Chem. Soc. , 2002 , 124 , pp. 5341-5349.

[6] PI Kitov, DR Bundle: In Org. Lett. , 2004 , 3 , pp. 2835-2838.

[7] tent GB2337990 : Process for shaping cellulose. Published December 8, 1999 , Inventors: Stephen Byron Smith, Sudith Kanishke Atureliya. ‌