92277
Trimethylamine N-oxide dihydrate
purum, ≥99.0% (NT)
Synonym(s):
TMANO
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About This Item
Linear Formula:
(CH3)3NO · 2H2O
CAS Number:
Molecular Weight:
111.14
Beilstein:
3612927
EC Number:
MDL number:
UNSPSC Code:
12352116
PubChem Substance ID:
NACRES:
NA.22
Recommended Products
grade
purum
Quality Level
Assay
≥99.0% (NT)
form
crystals
reaction suitability
reagent type: oxidant
mp
95-99 °C (lit.)
95-99 °C
functional group
amine
SMILES string
O.O.C[N+](C)(C)[O-]
InChI
1S/C3H9NO.2H2O/c1-4(2,3)5;;/h1-3H3;2*1H2
InChI key
PGFPZGKEDZGJQZ-UHFFFAOYSA-N
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General description
Trimethylamine N-oxide (TMAO) is an amphiphilic osmolyte that can counteract the denaturing effects of urea, pressure, and ice and stabilize the proteins.
Application
Reactant for:
- C-H bond cleavage
- Oxidation reactions (oxidant)
- Decarbonylating agent for solvent-free reactions
Trimethylamine N-oxide dihydrate can react with transition-metal carbonyl cluster compounds and activate CO displacement by converting CO ligands into carbon dioxide.
Other Notes
Oxidant for the catalytic OsO4 cis-hydroxylation of hindered olefins; preparation of the unstable, crystalline anhydrous compound
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2
Storage Class Code
11 - Combustible Solids
WGK
WGK 2
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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Counteraction of urea by trimethylamine N-oxide is due to direct interaction.
Meersman F, et al.
Biophysical Journal, 97(9), 2559-2566 (2009)
J.A. Soderquist et al.
Tetrahedron Letters, 27, 3961-3961 (1986)
Trimethylamine N-oxide promoted reactions of manganese, molybdenum and tungsten carbonyl complexes.
Blumer DJ, et al.
Journal of Organometallic Chemistry, 173(1), 71-76 (1979)
Cluster synthesis. 10. Reaction of Os3 (CO) 10 (. mu. 3-S) with trimethylamine N-oxide dihydrate. Syntheses and structural characterizations of Os3 (CO) 8 (NMe3)(. mu.-OH)(. mu. 3-S)(. mu.-H) and the six-atom-chain cluster Os6 (CO) 18 (. mu.-OH)(. mu. 4-S)(. mu. 3-S)(. mu.-H).
Adams RD, et al.
Inorganic Chemistry, 25(8), 1122-1127 (1986)
R. Ray et al.
Tetrahedron Letters, 21, 449-449 (1980)
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