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62637-93-8 - Trimethylamine N-oxide dihydrate, 98+% - A14916 - Alfa Aesar

A14916 Trimethylamine N-oxide dihydrate, 98+%

CAS Number
62637-93-8
Synonyms

Size Price ($) Quantity Availability
5g 29.97
25g 45.22
100g 110.21
500g 438.78
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Trimethylamine N-oxide dihydrate, 98+%

MDL
MFCD00149077

Chemical Properties

Formula
(CH3)3NO•2H2O
Formula Weight
111.14 (75.11anhy)
Melting point
96-101°
Solubility
Soluble in water, ethanol, dimethyl sulfoxide and methanol. Sparingly soluble in hot chloroform. Insoluble in diethyl ether, benzene and hydrocarbon solvents.

Applications

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.

Notes

Hygroscopic. Incompatible with acids, acid chlorides, acid anhydrides and oxidizing agents.

Literature References

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.

GHS Hazard and Precautionary Statements

Hazard Statements: H315-H319

Causes skin irritation. Causes serious eye irritation.

Precautionary Statements: P280-P264-P305+P351+P338-P362-P321-P332+P313-P337+P313-P302+P352

Wear protective gloves/protective clothing/eye protection/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. Take off contaminated clothing and wash before reuse. Specific treatment (see label). If skin irritation occurs: Get medical advice/attention. If eye irritation persists: IF ON SKIN: Wash with plenty of soap and water.

Other References

Merck
14,9710
Beilstein
3612927
Harmonized Tariff Code
2922.50
TSCA
Yes
RTECS
YH2850000

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