4-methylmorpholin-4-ium-4-olate

• ChemBase ID: 128514
• Molecular Formular: C5H11NO2
• Molecular Mass: 117.14634
• Monoisotopic Mass: 117.0789786
• SMILES: C[N+]1(CCOCC1)[O-]
• Canonical SMILES: [O-][N+]1(C)CCOCC1
• InChI: InChI=1S/C5H11NO2/c1-6(7)2-4-8-5-3-6/h2-5H2,1H3
• InChIKey: LFTLOKWAGJYHHR-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-methylmorpholin-4-ium-4-olate
• IUPAC Traditional name: N-methylmorpholine N-oxide
• Synonyms: 4-Methylmorpholine 4-Oxide; 4-Methylmorpholine Oxide; 4-Methylmorpholine N-Oxide; N-Methylmorpholine Oxide; N-methylmorpholine N-Oxide; NMMO; NMMO solution; NSC 73198; NSC 82153; NMO solution; 4-Methylmorpholine N-oxide solution; NMO; 4-Methylmorpholine N-oxide; N-Methylmorpholine N-oxide; N-甲基吗啉 N-氧化物; NMO 溶液; 4-甲基吗啡-N-氧化物 溶液; 4-甲基吗啡-N-氧化物

Database IDs

• CAS Number: 7529-22-8
• EC Number: 231-391-8
• MDL Number: MFCD00005947
• Beilstein Number: 507437
• PubChem SID: 24853425; 24855662; 162222821; 24885452
• PubChem CID: 82029
• CHEBI ID: 52093
• Chemspider ID: 74032
• Wikipedia Title: N-Methylmorpholine_N-oxide

CALCULATED PROPERTIES

• Acid pKa: 18.449717
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): -1.1536877
• LogD (pH = 7.4): -1.1527187
• Log P: -1.1527061
• Molar Refractivity: 31.1075 cm^3
• Polarizability: 11.611056 Å^3
• Polar Surface Area: 32.29 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Brown Solid
• Melting Point: 178-180°C; 180 - 184 °C; 180-184 °C(lit.); -20 °C; -20°C
• Boiling Point: 118.5 °C; 118-119°C
• Density: 1.13 g/mL at 25 °C; 1.140
• Refractive Index: 1.4220; n20/D 1.4201; n20/D 1.43
• pH: 9.00 ( in neat)

Safety Information

• Storage Condition: Refrigerator
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 1
• Risk Statements: 36/37/38
• Safety Statements: 23-26-37-60; 26; 26-36/37
• TSCA Listed: 是
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: Eyeshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: 50% w/w aq. soln.; 97%
• Concentration: ~50% in H2O; 50 wt. % in H2O
• Grade: technical
• Empirical Formula (Hill Notation): C5H11NO2

DETAILS

Sigma Aldrich - 258822

Packaging
1 kg in glass bottle
5, 100 g in glass bottle
Application
Oxidant for synthesis of novel organic polymer - inorganic hybrid for use as a catalyst for asymmetrical epoxidation1Reagent or Reactant for:
• Cyclocondensation and cyclization in the enantioselective synthesis of oxazolomycin A2
• Wharton rearrangement and stereoselective dihydroxylation reactions3
• Reduction of amine N-oxides by diboron reagents4
• Synthesis of polysaccharide blend fibers5
• Synthesis of cellulose / modified nano-SiO2 composite packaging films6
• Copper-catalyzed oxidative coupling for preparation of propargylamines7Used as a pretreatment for techno-economical study of ethanol and biogas production from spruce wood8

Sigma Aldrich - 224286

Application
Non-metallic catalyst for the cyanosilylation of ketones.1 Co-oxidant for Sharpless asymmetric dihydroxylation in ionic liquids.2
Packaging
25, 100 g in poly bottle
5 g in glass bottle

Sigma Aldrich - 67874

Application
Oxidant for synthesis of novel organic polymer - inorganic hybrid for use as a catalyst for asymmetrical epoxidation1Reagent or Reactant for:
• Cyclocondensation and cyclization in the enantioselective synthesis of oxazolomycin A2
• Wharton rearrangement and stereoselective dihydroxylation reactions3
• Reduction of amine N-oxides by diboron reagents4
• Synthesis of polysaccharide blend fibers5
• Synthesis of cellulose / modified nano-SiO2 composite packaging films6
• Copper-catalyzed oxidative coupling for preparation of propargylamines7Used as a pretreatment for techno-economical study of ethanol and biogas production from spruce wood8

Toronto Research Chemicals - M321055

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

REFERENCES

• Sohn, O.S. et al.: Toxicol. Appl. Pharmacol., 64, 486 (1982)
• Abe, Y. et al.: J. Appl. Polym. Sci., 89, 333 (1982)
• Sashina, E.S. et al.: Rus. J. Gen. Chem., 78, 139 (1982)