N,N-dimethylmethanamine oxide dihydrate

• ChemBase ID: 104753
• Molecular Formular: C3H13NO3
• Molecular Mass: 111.14022
• Monoisotopic Mass: 111.08954328
• SMILES: O.O.C[N+](C)(C)[O-]
• Canonical SMILES: [O-][N+](C)(C)C.O.O
• InChI: InChI=1S/C3H9NO.2H2O/c1-4(2,3)5;;/h1-3H3;2*1H2
• InChIKey: PGFPZGKEDZGJQZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N,N-dimethylmethanamine oxide dihydrate
• IUPAC Traditional name: trimethylamine-n-oxide dihydrate
• Synonyms: N,N-Dimethylmethanamine oxide, Dihydrate; TRIMETHYLAMINE-N-OXIDE DIHYDRATE; TMANO; Trimethylamine N-oxide dihydrate; 三甲基N氧化二水合物; 三甲胺N-氧化物 二水合物

Database IDs

• CAS Number: 62637-93-8
• EC Number: 214-675-6
• MDL Number: MFCD00149077
• Beilstein Number: 3612927
• Merck Index: 149710
• PubChem SID: 24889631; 162091700; 24899893
• PubChem CID: 198430

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): -0.9441224
• LogD (pH = 7.4): -0.93434685
• Log P: -0.9342057
• Molar Refractivity: 22.033 cm^3
• Polarizability: 7.9283214 Å^3
• Polar Surface Area: 23.06 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 95-99 °C; 95-99 °C(lit.); 96-101°C; 97-100°C

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• RTECS: YH2850000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 2
• Risk Statements: 36/38
• Safety Statements: 26-36; 26-37
• TSCA Listed: 是
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319
• GHS Precautionary statements: P280-P305+P351+P338-P302+P352-P321-P362-P332+P313; P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥99.0% (NT); 98%; 98+%
• Grade: purum
• Linear Formula: (CH3)3NO · 2H2O

DETAILS

MP Biomedicals - 02157068

Dihydrate

Sigma Aldrich - T0514

包装
100 g in glass bottle
Application
Reactant for:
• C-H bond cleavage1
• Oxidation reactions (oxidant)2,3
• Decarbonylating agent for solvent-free reactions4

Sigma Aldrich - 176869

Application
Reactant for:
• C-H bond cleavage1
• Oxidation reactions (oxidant)2,3
• Decarbonylating agent for solvent-free reactions4

Sigma Aldrich - 92277

Other Notes
Oxidant for the catalytic OsO4 cis-hydroxylation of hindered olefins5; preparation of the unstable, crystalline anhydrous compound6
Application
Reactant for:
• C-H bond cleavage1
• Oxidation reactions (oxidant)2,3
• Decarbonylating agent for solvent-free reactions4

REFERENCES

• For use as a reoxidant in the catalytic cis-hydroxylation of alkenes with Osmium(VIII) oxide, 12103, see: Tetrahedron Lett., 21, 449 (1980).
• Deprotonation by LDA at low temperature gives the unstable azomethine ylide, which undergoes 1,3-dipolar addition, even with unactivated alkenes, to give pyrrolidines: J. Chem. Soc., Chem. Commun., 31 (1983):
  
• Reagent for the liberation of organics from their complexes with iron carbonyls. Partial oxidation of CO to CO₂ takes place: J. Chem. Soc., Chem. Commun., 336 (1974).
• Also oxidizes alkylboranes to alcohols, giving less interference with other functionality than the more usual H₂O₂: J. Org. Chem., 40, 1776 (1975).
• Has been used in the oxidation of alkyl halides to aldehydes. For a procedure, including dehydration of the N-oxide by distillation of water with DMF, see: Org. Synth. Coll., 5, 872 (1973):
  
• For an improved procedure using DMSO, see: Tetrahedron Lett., 31, 4825 (1990).
• Reviews: Trimethylamine as a useful oxidizing agent: J. Prakt. Chem./ Chem. Ztg., 338, 190 (1996); The utility of N-oxides in synthesis: Synthesis, 263 (1993).
• Compare also 4-Methylmorpholine N-oxide monohydrate, A15996.