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Merck
CN

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
NACRES:
NA.22
UNSPSC Code:
12352116
PubChem Substance ID:
EC Number:
214-675-6
Beilstein/REAXYS Number:
3612927
MDL number:
Assay:
≥99.0% (NT)
Form:
crystals
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grade

purum

Quality Level

assay

≥99.0% (NT)

form

crystals

reaction suitability

reagent type: oxidant

mp

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

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

Trimethylamine N-oxide dihydrate can react with transition-metal carbonyl cluster compounds and activate CO displacement by converting CO ligands into carbon dioxide.
Reactant for:
  • C-H bond cleavage
  • Oxidation reactions (oxidant)

  • Decarbonylating agent for solvent-free reactions

Other Notes

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


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pictograms

Exclamation mark

signalword

Warning

hcodes

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2

Storage Class

11 - Combustible Solids

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves



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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)
Complex formation in aqueous trimethylamine-N-oxide (TMAO) solutions.
Hunger J, et al.
The Journal of Physical Chemistry B, 116(16), 4783-4795 (2012)
Counteraction of urea by trimethylamine N-oxide is due to direct interaction.
Meersman F, et al.
Biophysical Journal, 97(9), 2559-2566 (2009)



Global Trade Item Number

SKUGTIN
92277-10G04061833269305
92277-50G04061833449394