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Trimethylamine N-oxide dihydrate is used as an oxidizing agent in organic synthesis. It is also used to make quaternary ammonium compounds and a warning agent for flammable gas. Further, it acts as a flavoring agent or adjuvant. It serves as an oxidant for the catalytic osmium tetraoxide cis-hydroxylation of hindered olefins. In addition to this, it is used as a reactant for C-H bond cleavage and decarbonylating agent for solvent-free reactions.
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).
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):
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 .
Hunger, J.; Ottosson, N.; Mazur, K.; Bonn, M.; Bakker, H. J. Water-mediated interactions between trimethylamine-N-oxide and urea. Phys. Chem. Chem. Phys. 2015, 17 (1), 298-306.
Makarov, D. M.; Egorov, G. I.; Kolker, A. M. Density and Volumetric Properties of Aqueous Solutions of Trimethylamine N-Oxide in the Temperature Range from (278.15 to 323.15) K and at Pressures up to 100 MPa. J. Chem. Eng. Data 2015, 60 (5), 1291-1299.
Hazard Statements: H315-H319
Causes skin irritation. Causes serious eye irritation.
Precautionary Statements: P264b-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313-P362
Wash face, hands and any exposed skin thoroughly after handling Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN: Wash with plenty of soap and water. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. If skin irritation occurs: Get medical advice/attention. If eye irritation persists: Take off contaminated clothing and wash before reuse.