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317594

Sigma-Aldrich

Trimethylamine N-oxide

95%

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Synonym(s):
TMANO
Linear Formula:
(CH3)3N(O)
CAS Number:
Molecular Weight:
75.11
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

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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1 of 4

This Item
T051490340224286
vibrant-m

317594

Trimethylamine N-oxide

vibrant-m

T0514

Trimethylamine N-oxide dihydrate

vibrant-m

90340

Triethylamine

vibrant-m

224286

4-Methylmorpholine N-oxide

assay

95%

assay

98%

assay

≥99.5% (GC)

assay

97%

reaction suitability

reagent type: oxidant

reaction suitability

reagent type: oxidant

reaction suitability

-

reaction suitability

reagent type: oxidant

mp

220-222 °C (lit.)

mp

95-99 °C (lit.)

mp

−115 °C (lit.)

mp

180-184 °C (lit.)

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

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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Hydride ion transfer from carbon-hydrogen bonds to carbon disulfide, carbonyl sulfide, and carbon dioxide. Synthesis, reactivity, and structure of manganese complexes (η 5-C6MenH7-n) Mn (CO) LL'
Snyder DB, et al.
Journal of the American Chemical Society, 115(15), 6718-6729 (1993)
Vanessa Siegmund et al.
Scientific reports, 6, 39291-39291 (2016-12-17)
Spontaneous isopeptide bond formation, a stabilizing posttranslational modification that can be found in gram-positive bacterial cell surface proteins, has previously been used to develop a peptide-peptide ligation technology that enables the polymerization of tagged-proteins catalyzed by SpyLigase. Here we adapted
Marina Spörrer et al.
EBioMedicine, 44, 502-515 (2019-05-13)
Missense mutations in keratin 5 and 14 genes cause the severe skin fragility disorder epidermolysis bullosa simplex (EBS) by collapsing of the keratin cytoskeleton into cytoplasmic protein aggregates. Despite intense efforts, no molecular therapies are available, mostly due to the
J Klysik et al.
FEBS letters, 333(3), 261-267 (1993-11-01)
The ability of the Escherichia coli single-stranded DNA-binding protein (SSB) to recognize structural features associated with intramolecular triplex formation in oligopurine.oligopyrimidine (pur.pyr) inserts in recombinant plasmids was evaluated. The SSB protein binds to supercoiled plasmids and causes a site-preferential increase
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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