4-METHYLMORPHOLINE 4-OXIDE

4-Methylmorpholine 4-oxide acts as a non-metallic catalyst for the cyanosilylation of ketones.
4-Methylmorpholine 4-oxide is also employed as a co-oxidant for Sharpless asymmetric dihydroxylation in ionic liquids.
4-Methylmorpholine 4-oxide serves as a solvent in the Lyocell process to produce tencel fiber.

CAS Number: 7529-22-8
Chemical formula: C5H11NO2
Molar mass: 117.15 g/mol

Applications of 4-Methylmorpholine 4-oxide:
4-Methylmorpholine 4-oxide acts as a non-metallic catalyst for the cyanosilylation of ketones.
4-Methylmorpholine 4-oxide is also employed as a co-oxidant for Sharpless asymmetric dihydroxylation in ionic liquids.

4-Methylmorpholine 4-oxide serves as a solvent in the Lyocell process to produce tencel fiber.
Further, 4-Methylmorpholine 4-oxide is used in the preparation of aldehydes from primary alcohols in the presence of tetrapropylammonium perruthenate.

Dissolution of scleroproteins:
Another use of 4-Methylmorpholine 4-oxide is in the dissolution of scleroprotein (found in animal tissue).
This dissolution occurs in the crystal areas which are more homogeneous and contain glycine and alanine residues with a small number of other residues.

How 4-Methylmorpholine 4-oxide dissolves these proteins is scarcely studied.
Other studies, however, have been done in similar amide systems (i.e. hexapeptide).
The hydrogen bonds of the amides can be broken by 4-Methylmorpholine 4-oxide.

Oxidant:
4-Methylmorpholine 4-oxide, as an N-oxide, is an oxidant.
4-Methylmorpholine 4-oxide is generally used in stoichiometric amounts as a secondary oxidant (a cooxidant) to regenerate a primary (catalytic) oxidant after the latter has been reduced by the substrate.
Vicinal syn-dihydroxylation reactions for example, would, in theory, require stoichiometric amounts of toxic, volatile and expensive osmium tetroxide, but if continuously regenerated with 4-Methylmorpholine 4-oxide, the amount required can be reduced to catalytic quantities.

Identifiers of 4-Methylmorpholine 4-oxide:
CAS Number: 7529-22-8
CHEBI:52093
ChemSpider: 74032
ECHA InfoCard: 100.028.538
PubChem CID: 82029
UNII: ARC64PKJ0F
CompTox Dashboard (EPA): DTXSID3029287

Uses of 4-Methylmorpholine 4-oxide:
Solvent of cellulose:
4-Methylmorpholine 4-oxide is used as a solvent in the lyocell process to produce lyocell fiber.
4-Methylmorpholine 4-oxide dissolves cellulose to form a solution called dope, and the cellulose is reprecipitated in a water bath to produce a fiber.
4-Methylmorpholine 4-oxide is used as a solvent for cellulose in the lyocell process to produce cellulose fibers.

The process is similar but not analogous to the viscose process.
In the viscose process, cellulose is made soluble by conversion to its xanthate derivatives.
With 4-Methylmorpholine 4-oxide, cellulose is not derivatized but dissolves to give a homogeneous polymer solution.

The resulting fiber is similar to viscose; this was observed, for example, for Valonia cellulose microfibrils.
Dilution with water causes the cellulose to reprecipitate, i.e. the solvation of cellulose with 4-Methylmorpholine 4-oxide is a water sensitive process.

Cellulose remains insoluble to most solvents since it has a strong and highly structured intermolecular hydrogen bonding network, which resists common solvents.
4-Methylmorpholine 4-oxide is able to break the hydrogen bonding network that keeps cellulose insoluble to water and other solvents.
Similar solubility has been obtained in a few solvents, particularly a mix of lithium chloride in dimethyl acetamide and some hydrophilic ionic liquids.

General description of 4-Methylmorpholine 4-oxide:
4-Methylmorpholine N-oxide is an organic compound used as a co-oxidant along with OsO4 and ruthenates in organic synthesis.
In recent studies, 4-Methylmorpholine 4-oxide 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.

Applications of 4-Methylmorpholine 4-oxide:
4-Methylmorpholine 4-oxide is a non-metallic catalyst for the cyanosilylation of ketones.
4-Methylmorpholine 4-oxide is a co-oxidant for Sharpless asymmetric dihydroxylation in ionic liquids.

4-Methylmorpholine 4-oxide (NMO) is available commercially as the monohydrate; it has a melting point of 70 °C, and is stable under normal conditions.
4-Methylmorpholine 4-oxide is soluble in polar solvents, especially water.

4-Methylmorpholine 4-oxide displays characteristic reactivity with various transition metals, which undergo oxidation with this reagent.
Because of this, 4-Methylmorpholine 4-oxide is a preferred stoichiometric oxidant for transition metal-catalyzed oxidations.

Chemical Properties:
Clear colorless to yellow solution

Uses of 4-Methylmorpholine 4-oxide:
4-Methylmorpholine N-Oxide is a metabolite of Morpholine (M723725).
4-Methylmorpholine 4-oxide is commonly used to dissolve cellulose as well as in the dissolution of of scleroproteins.

Uses of 4-Methylmorpholine 4-oxide:
4-Methylmorpholine 4-oxide (N-Methylmorpholine N-oxide, NMO or NMMO is an organic compound.
4-Methylmorpholine 4-oxide is used in organic chemistry as a co-oxidant and sacrificial catalyst in oxidation reactions for instance in osmium tetroxide oxidations and the Sharpless asymmetric dihydroxylation or oxidations with TPAP.

4-Methylmorpholine 4-oxide is commercially supplied both as a monohydrate C5H11NO2H2O and as the anhydrous compound.
Further, 4-Methylmorpholine 4-oxide is used in the preparation of aldehydes from primary alcohols in the presence of tetrapropylammonium perruthenate.

Uses of 4-Methylmorpholine 4-oxide:
Non-metallic catalyst for the cyanosilylation of ketones.
Co-oxidant for Sharpless asymmetric dihydroxylation in ionic liquids.

General Description of 4-Methylmorpholine 4-oxide:
4-Methylmorpholine 4-oxide is an organic compound used as a co-oxidant along with OsO4 and ruthenates in organic synthesis.
In recent studies, 4-Methylmorpholine 4-oxide 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.

Flammability and Explosibility:
Flammable

Purification Methods of 4-Methylmorpholine 4-oxide:
When the oxide is dried for 2-3hours at high vacuum, it dehydrates.
Add MeOH to the oxide and distil off the solvent under vacuum until the temperature is ca 95o.
Then add Me2CO at reflux and cool to 20o.

The crystals are filtered off, washed with Me2CO and dried.
The degree of hydration may vary and may be important for the desired reactions.

Properties of 4-Methylmorpholine 4-oxide:
Chemical formula: C5H11NO2
Molar mass: 117.15 g/mol
Melting point: 180 to 184 °C (356 to 363 °F; 453 to 457 K)

Chemical Name:
4-Methylmorpholine 4-oxide

4-Methylmorpholine 4-oxide (more correctly 4-methylmorpholine 4-oxide), NMO or NMMO is an organic compound.
This heterocyclic amine oxide and morpholine derivative is used in organic chemistry as a co-oxidant and sacrificial catalyst in oxidation reactions for instance in osmium tetroxide oxidations and the Sharpless asymmetric dihydroxylation or oxidations with TPAP.

4-Methylmorpholine 4-oxide is commercially supplied both as a monohydrate C5H11NO2·H2O and as the anhydrous compound.
4-Methylmorpholine 4-oxide is used as a solvent for cellulose in the lyocell process to produce cellulose fibers.

Applications of 4-Methylmorpholine 4-oxide:
Non-metallic catalyst for the cyanosilylation of ketones.
Co-oxidant for Sharpless asymmetric dihydroxylation in ionic liquids.

General description of 4-Methylmorpholine 4-oxide:
4-Methylmorpholine 4-oxide is an organic compound used as a co-oxidant along with OsO4 and ruthenates in organic synthesis.
In recent studies, 4-Methylmorpholine 4-oxide has been used as a catalyst in silylcyanation of aldehydes and ketones.
Lyocell, a regenerated cellulose fiber, can be prepared using 4-Methylmorpholine 4-oxide in an eco-friendly manner.

Synonyms:
4-Methylmorpholine 4-Oxide
4-Methylmorpholine Oxide
4-Methylmorpholine N-Oxide
N-Methylmorpholine Oxide
4-Methylmorpholine 4-oxide
NMMO
NMO
NSC 73198
NSC 82153

4-Methylmorpholine 4-oxide is an organic compound used as a co-oxidant along with OsO4 and ruthenates in organic synthesis.

KEYWORDS:
7529-22-8, 4-Methylmorpholine 4-Oxide, NMMO, NSC 73198, DSSTox_RID_78750, NCIOpen2_000398, CHEMBL3184330, DTXSID3029287, 4-Methylmorpholine N-oxide 97%, METHYL MORPHOLINE OXIDE

Description of 4-Methylmorpholine 4-oxide:
4-Methylmorpholine N-oxide acts as a non-metallic catalyst for the cyanosilylation of ketones.
4-Methylmorpholine 4-oxide is also employed as a co-oxidant for Sharpless asymmetric dihydroxylation in ionic liquids.

Solubility of 4-Methylmorpholine 4-oxide:
Soluble in water, methanol, ethanol, acetone, ethers and dimethylsulfoxide.

Notes about 4-Methylmorpholine 4-oxide:
Hygroscopic.
Store 4-Methylmorpholine 4-oxide in a cool place.
4-Methylmorpholine 4-oxide is incompatible with strong oxidizing agents, acid chlorides, acid anhydrides and chloroformates.

CAS Number: 7529-22-8
Molecular Formula: C₅H₁₁NO₂
Appearance: Pale Yellow to Brown Solid
Melting Point: 90-93°C
Molecular Weight: 117.15
Storage: 4°C, Hygroscopic
Solubility: DMSO (Soluble), Methanol (Slightly)
Stability: Hygroscopic
Category: Building Blocks; Pharmaceutical/API Drug Impurities/Metabolites;

Applications of 4-Methylmorpholine 4-oxide:
4-Methylmorpholine 4-oxide is a metabolite of Morpholine (M723725).
4-Methylmorpholine 4-oxide is commonly used to dissolve cellulose as well as in the dissolution of scleroproteins.

N-Methylmorpholine N-(17O-oxide) and N-methylmorpholine 15N-(17O-oxide) were prepared from N-methylmorpholine and 15N-methylmorpholine by oxidation with H2 17O2.
The facile one-pot procedure provided yields of 82 and 76%, respectively.
The labeled hydrogen peroxide was obtained by electrolysis of H2 17O followed by autoxidation of 2-ethylanthraquinol with the molecular oxygen 17O2 generated.
The compounds serve for mechanistic studies into gold nanoparticle generation in NMMO solution.

Synonym(s): NMO
Empirical Formula (Hill Notation): C5H11NO2
CAS Number: 7529-22-8
Molecular Weight: 117.15
Beilstein: 507437
EC Number: 231-391-8
MDL number: MFCD00005947
PubChem Substance ID: 24853425

PROPERTIES of 4-Methylmorpholine 4-oxide:
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

Native crystalline cellulose is notoriously difficult to dissolve due to its dense hydrogen bond network between chains and weaker hydrophobic forces between cellulose sheets.
4-Methylmorpholine 4-oxide (NMMO), the solvent behind the Lyocell process, is one of the most successful commercial solvents for the nonderivatized dissolution of cellulose.
In this process, water plays a very important role.

Its presence at low concentrations allows 4-Methylmorpholine 4-oxide to dissolve substantial amounts of cellulose, while at much higher concentrations it precipitates the crystalline fibers.
Using all-atom molecular dynamics, we study the thermodynamic and structural properties of ternary solutions of cellulose, 4-Methylmorpholine 4-oxide, and water.
Using the two-phase thermodynamic method to calculate solvent entropy, we estimate the free energy of dissolution of cellulose as a function of the water concentration and find a transition of spontaneity that is in excellent agreement with experiment.

In pure water, we find that cellulose dissolution is nonspontaneous, a result that is due entirely to strong decreases in water entropy.
Although the combined effect of enthalpy on dissolution in water is negligible, we observe a net loss of hydrogen bonds, resulting in a change in hydrogen bond energy that opposes dissolution.
At lower water concentrations, cellulose dissolution is spontaneous and largely driven by decreases in enthalpy, with solvent entropy playing only a very minor role.

When searching for the root causes of this enthalpy decrease, a complex picture emerges in which not one but many different factors contribute to 4-Methylmorpholine 4-oxide’s good solvent behavior.
The reduction in enthalpy is led by the formation of strong hydrogen bonds between cellulose and 4-Methylmorpholine 4-oxide’s N-oxide, intensified through van der Waals interactions between NMMO’s nonpolar body and the nonpolar surfaces of cellulose and unhindered by water at low concentrations due to the formation of efficient hydrogen bonds between water and cellulose.

The hazards of handling N-methylmorpholine-N-oxide (NMMO) cannot be described often enough, although it is a rather common (co-)solvent for cellulose.
Inaccuracies in the literature regarding the chemistry of 4-Methylmorpholine 4-oxide, such as its role in solvent systems and in redox systems involving transition metal ions, increase the risk of dangerous failure of the intended reactions which might result in uncontrolled exothermicities, damage of laboratory equipment or even accidents and work safety issues.
Therefore, suitable cautionary and mitigation strategy statements regarding the hazards of handling 4-Methylmorpholine 4-oxide are encouraged for future publications regarding NMMO and cellulose.

Molecular Weight: 117.15
XLogP3-AA: -0.7
Hydrogen Bond Donor Count: 0
Hydrogen Bond Acceptor Count: 2
Rotatable Bond Count: 0
Exact Mass: 117.078978594
Monoisotopic Mass: 117.078978594
Topological Polar Surface Area: 27.3 Å²
Heavy Atom Count: 8
Formal Charge: 0
Complexity: 78.5
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes

Synonyms:
4-Methylmorpholine N-oxide
7529-22-8
4-Methylmorpholine 4-oxide
N-Methylmorpholine oxide
4-Methylmorpholine 4-oxide
Morpholine, 4-methyl-, 4-oxide
4-methyl-4-oxidomorpholin-4-ium
Methyl morpholine oxide
N-Methylmorpholine-N-oxide
4-Methylmorpholine-4-oxide
NMO
NMMO
4-Methylmorpholine Oxide
4-methylmorpholine-N-oxide
N-Methylmorpholine 4-oxide
MFCD00005947
ARC64PKJ0F
CHEBI:52093
4-methylmorpholin-4-ium-4-olate
NSC73198
NSC-73198
NSC-82153
Morpholine, 4-oxide
NMO solution
NSC 73198
NSC 82153
EINECS 231-391-8
UNII-ARC64PKJ0F
4-methylmorpholine 4-oxide, monohydrate
N-Methyl morpholine N-oxide
4-methyl morpholine N-oxide
4-methyl-4-oxido-morpholin-4-ium
4-methylmorpholine-4-oxide solution
n-methylmorpholineoxide
methylmorpholine N-oxide
methylmorpholine-N-oxide
4-Methylmorpholine-oxide
N-methylmorpholin-N-oxid
4methylmorpholine N-oxide
4methylmorpholine-N oxide
4methylmorpholine-N-oxide
N-methyl morpholine oxide
N-methyl morpholine-oxide
N-methyl-morpholine oxide
4-methyl morpholine oxide
N-methylmopholine N-oxide
N-methylmorphline N-oxide
N-methylmorpholin-N-oxide
N-methymorpholine N-oxide
4-methylmopholine N-oxide
4-methylmorpholin-N-oxide
4-Methylmorpholine4-oxide
4-methymorpholine N-oxide
DSSTox_CID_9287
4-methylmorpholin-4-oxide
N-methyimorpholine N-oxide
4-methylmorpholine N oxide
4-methylmorpholine-N oxide
EC 231-391-8
N-methyl morpholin-N-oxide
4-methy-morpholine-N-oxide
4-methyl morpholin N-oxide
4-methylnnorpholine N-oxide
SCHEMBL1845
N-methyl morpholine-N-oxide
N-methyl-morpholine N-oxide
N-methyl-morpholine-N-oxide
4-methyl morpholine-N-oxide
4-methyl-morpholine N-oxide
4-methyl-morpholine-N-oxide
4-methylmorpholine-N- oxide
DSSTox_RID_78750
NCIOpen2_000398
NCIOpen2_000960
4-methyl morpholine-4-oxide
4-methyl-morpholine 4-oxide
4-methyl-morpholine-4-oxide
DSSTox_GSID_29287
4-methyl-morpholine-N- oxide
CHEMBL3184330
DTXSID3029287
LFTLOKWAGJYHHR-UHFFFAOYSA-
ZINC157080
4-Methylmorpholine N-oxide, 97%
NSC82153
Tox21_200479
c1367
AKOS009159059
METHYL MORPHOLINE OXIDE [INCI]
4-methyl-4-oxidanidyl-morpholin-4-ium
4-Methylmorpholine 4-oxide [MI]
NCGC00248649-01
NCGC00258033-01
BP-30197
4-Methyl-1,4.lambda.~5~-oxazinan-4-ol
CAS-7529-22-8
CS-0016218
M0981
M2192
EN300-37514
D71257
A840005
Q416248
W-104395
4-Methylmorpholine N-oxide solution, 50 wt. % in H2O
4-Methylmorpholine N-oxide, 50 wt.% solution in water
4-methylmorpholine n-oxide (50% in water, ca. 4.8mol/l)
4-Methylmorpholine N-oxide solution, technical, ~50% in H2O
Morpholine N-oxide, polymer-bound, 50-100 mesh, extent of labeling: 2.0-3.0 mmol/g loading, 1 % cross-linked with divinylbenzene
231-391-8 [EINECS]
4-Methylmorpholin-4-oxid [German] [ACD/IUPAC Name]
4-Methylmorpholine 4-oxide [ACD/IUPAC Name]
4-Methylmorpholine N-oxide
4-Méthylmorpholine-4-oxyde [French]
4-Oxyde de 4-méthylmorpholine [French] [ACD/IUPAC Name]
507437 [Beilstein]
7529-22-8 [RN]
ARC64PKJ0F
Methyl morpholine oxide
MFCD00005947 [MDL number]
Morpholine, 4-methyl-, 4-oxide [ACD/Index Name]
N-Methylmorpholine 4-oxide
4-Methylmorpholine 4-oxide
N-Methylmorpholine oxide
N-methylmorpholine-N-oxide [Wiki]
NMO
N-óxido de N-metilmorfolina [Portuguese]
231-391-8MFCD00005947
4-hydroxy-4-methylmorpholin-4-ium [ACD/IUPAC Name]
4-Methyl-1,4λ5-oxazinan-4-ol
4-methyl-4-oxidomorpholin-4-ium
4-Methyl-4-oxido-morpholin-4-ium
4-methylmorpholin-4-ium-4-olate
4-methylmorpholin-4-ol
4-Methylmorpholine N-oxidemissing
4-METHYLMORPHOLINE OXIDE
4-Methylmorpholine-4-oxide
4-methylmorpholinen-oxide
4-Methylmorpholine-N-oxide
4-Methyl-morpholine-N-oxide
MFCD00149388 [MDL number]
morpholine, 4-methyl-, 4-oxide
N-methylmorpholine-N'-oxide
N-methyl-morpholine-N-oxide
UNII:ARC64PKJ0F
UNII-ARC64PKJ0F