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92277

Sigma-Aldrich

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:
62637-93-8
Molecular Weight:
111.14
Beilstein:
3612927
EC Number:
214-675-6
MDL number:
MFCD00149077
UNSPSC Code:
12352116
PubChem Substance ID:
329769882
NACRES:
NA.22
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grade

purum

Quality Level

200

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.[1][2]

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.[3][4]

Other Notes

Oxidant for the catalytic OsO4 cis-hydroxylation of hindered olefins[5]; preparation of the unstable, crystalline anhydrous compound[6]

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319

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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Certificates of Analysis (COA)

Lot/Batch Number
BCCK6377
BCCG9276
BCCF6890
BCBW3830
BCBW5061

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R. Ray et al.
Tetrahedron Letters, 21, 449-449 (1980)
Complex formation in aqueous trimethylamine-N-oxide (TMAO) solutions.
Hunger J, et al.
The Journal of Physical Chemistry B, 116(16), 4783-4795 (2012)
J.A. Soderquist et al.
Tetrahedron Letters, 27, 3961-3961 (1986)
Counteraction of urea by trimethylamine N-oxide is due to direct interaction.
Meersman F, et al.
Biophysical Journal, 97(9), 2559-2566 (2009)
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)
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