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317594

Sigma-Aldrich

Trimethylamine N-oxide

95%

Synonym(s):

TMANO

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About This Item

Linear Formula:
(CH3)3N(O)
CAS Number:
1184-78-7
Molecular Weight:
75.11
EC Number:
214-675-6
MDL number:
MFCD00002048
UNSPSC Code:
12352116
PubChem Substance ID:
24859089
NACRES:
NA.22

Quality Level

100

assay

95%

reaction suitability

reagent type: oxidant

mp

220-222 °C (lit.)

SMILES string

C[N+](C)(C)[O-]

InChI

1S/C3H9NO/c1-4(2,3)5/h1-3H3

InChI key

UYPYRKYUKCHHIB-UHFFFAOYSA-N

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General description

Trimethylamine N-oxide is an organic compound that belongs to the class of amine oxides. It is generally found in the tissues of marine organisms, wherein it helps protect them from harsh conditions like salinity, hydrostatic pressure, temperature, and high urea.

Application

Trimethylamine N-oxide can be used:
  • As a demetallation and decarbonylation reagent for organometallic compounds.
  • To prepare azomethine ylide by reaction with lithium di-isopropylamide. This, in turn, may be reacted with simple alkenes to obtain corresponding pyrrolidines.
  • To mediate the conversion of thiols to disulfides.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Acute Tox. 4 Inhalation - Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
SHBN0643
SHBN1901
SHBL0520
SHBK5768
SHBK5534

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Journal of Organometallic Chemistry, 471, 241-241 (1994)
Trimethylamine N-oxide: the good, the bad and the unknown
Velasquez MT, et al.
Toxins, 8(11), 326-326 (2016)
Trimethylamine N-oxide as a precursor of azomethine ylides
Beugelmans R, et al.
Journal of the Chemical Society. Chemical Communications, 471(1), 31-32 (1983)
Demir Djekic et al.
Journal of the American Heart Association, 9(18), e016518-e016518 (2020-09-08)
Background A vegetarian diet (VD) may reduce future cardiovascular risk in patients with ischemic heart disease. Methods and Results A randomized crossover study was conducted in subjects with ischemic heart disease, assigned to 4-week intervention periods of isocaloric VD and
Site selectivity studies on heterobimetallic complexes: substitution reactions of (.eta.5-C5H5)MM'(CO)8 (M = Mo, W; M' = Mn, Re)
Ingham WL and Coville NJ
Inorganic Chemistry, 31(20), 4084-4090 (1992)
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