Trimethylamine N-oxide dihydrate

• Catalog No.: A14916
• CAS Number: 62637-93-8
• M. F.: C3H13NO3
• M. W.: 111.14022
• Purity: 98+%

SYNONYMS

• Title: 三甲基N氧化二水合物
• IUPAC name: N,N-dimethylmethanamine oxide dihydrate
• IUPAC Traditional name: trimethylamine-n-oxide dihydrate

DATABASE IDS

• Merck Index: 149710
• MDL Number: MFCD00149077
• Beilstein Number: 3612927
• CAS Number: 62637-93-8

PROPERTIES

• Purity: 98+%
• Melting Point: 96-101°C
• GHS Hazard statements: H315-H319
• European Hazard Symbols: Irritant (Xi)
• GHS Precautionary statements: P280-P305+P351+P338-P302+P352-P321-P362-P332+P313
• Risk Statements: 36/38
• RTECS: YH2850000
• Safety Statements: 26-37
• TSCA Listed: 是

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.