4-methylmorpholin-4-ium-4-olate hydrate

• ChemBase ID: 80161
• Molecular Formular: C5H13NO3
• Molecular Mass: 135.16162
• Monoisotopic Mass: 135.08954328
• SMILES: [N+]1([O-])(CCOCC1)C.O
• Canonical SMILES: [O-][N+]1(C)CCOCC1.O
• InChI: InChI=1S/C5H11NO2.H2O/c1-6(7)2-4-8-5-3-6;/h2-5H2,1H3;1H2
• InChIKey: WAZPLXZGZWWXDQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-methylmorpholin-4-ium-4-olate hydrate
• IUPAC Traditional name: N-methylmorpholine N-oxide hydrate
• Synonyms: 4-Methylmorpholine 4-oxide hydrate; 4-Methylmorpholine N-oxide monohydrate; 4-methyl-1,4-oxazinan-4-ium-4-olate hydrate; N-Methylmorpholine N-oxide monohydrate; NMMO; 4-甲基吗啡-N-氧化物 一水合物; 4-甲基吗啉-N-氧化物单水合物

Database IDs

• CAS Number: 70187-32-5
• EC Number: 231-391-8
• MDL Number: MFCD00149388
• Beilstein Number: 5449441; 507437
• PubChem SID: 162067281; 24885450
• PubChem CID: 2724197

CALCULATED PROPERTIES

• 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
• Acid pKa: 18.449717

PROPERTIES

Physical Property

• Melting Point: 71-75 °C; 73-76°C

Safety Information

• Storage Warning: Hygroscopic
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 1
• Risk Statements: 36/37/38
• Safety Statements: 26-36; 26-37
• 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: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥95.0% (N); 98%; 98+%
• Empirical Formula (Hill Notation): C5H11NO2 · H2O

DETAILS

Sigma Aldrich - 67873

Other Notes
Reagent for an improved catalytic OsO4 oxidation of olefins to cis-1,2-diols1,2; Review3; For a ruthenium catalysed oxidation of alcohols to aldehydes and ketones4
Packaging
25, 100 g in poly bottle

REFERENCES

• In the presence of Ru catalysts such as RuCl₃ or Dichlorotris(triphenylphosphine)ruthenium(II), L00373, oxidizes various types of alcohol to carbonyl compounds: Tetrahedron Lett., 2503 (1976). See also Tetra-n-propylammonium perruthenate(VII), B24511.
• Boronic esters formed by treatment of aryl bromides in THF with n-BuLi, followed by trimethyl borate, can be oxidized in situ to phenols without isolation of the boronic acid: Synlett, 931 (1995).
• In the presence of 4A molecular sieves in acetonitrile, activated (e.g. benzylic) halides can be oxidized to aldehydes and ketones: Synth. Commun., 22, 1967 (1992).
• Stoichiometric oxidant permitting the use of Osmium(VIII) oxide, 12103, catalytically in the cis-hydroxylation of alkenes: Tetrahedron Lett., 1973 (1976): Org. Synth. Coll., 6, 342 (1988). For use in the asymmetric dihydroxylation (ADH) reaction, catalyzed by Osmium(VIII) oxide, 12103, see: J. Am. Chem. Soc., 110, 1968 (1988); Org. Synth. Coll., 9, 383 (1998).