I agree Our site saves small pieces of text information (cookies) on your device in order to deliver better content and for statistical purposes. You can disable the usage of cookies by changing the settings of your browser. By browsing our website without changing the browser settings you grant us permission to store that information on your device.
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.
해저드 설명서 (EU): H315-H319
Causes skin irritation. Causes serious eye irritation.
주의 설명서: P280a-P264-P305+P351+P338-P321-P332+P313-P337+P313
Wear protective gloves and eye/face protection. Wash thoroughly after handling. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Specific treatment (see label). If skin irritation occurs: Get medical advice/attention. If eye irritation persists: