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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.)

functional group

amine

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

Signal Word

Warning

Hazard Statements

H302 + H332

Hazard Classifications

Acute Tox. 4 Inhalation - Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

317594-BULK:
317594-1G:
317594-5G:
317594-VAR:

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Certificates of Analysis (COA)

Lot/Batch Number
SHBR6283
0000293120
0000293120
SHBP3793
SHBN0643

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Trimethylamine N-oxide: the good, the bad and the unknown
Velasquez MT, et al.
Toxins, 8(11), 326-326 (2016)
Preparation of cyclic and acyclic thioethers via hexacarbonyldicobalt alkyne complexes
Mohmand GF, et al.
Journal of Organometallic Chemistry, 471, 241-241 (1994)
Oliver D John et al.
International journal of molecular sciences, 21(1) (2020-01-08)
Metabolic syndrome is a cluster of disorders that increase the risk of cardiovascular disease and diabetes. This study has investigated the responses to rind of yellow mangosteen (Garcinia dulcis), usually discarded as waste, in a rat model of human metabolic
Hao Lin et al.
Annals of translational medicine, 8(16), 1009-1009 (2020-09-22)
Osteoporosis (OP) is a prevalent metabolic bone disease characterized by bone loss and structural deterioration, which increases the risk of fracture especially in older people. Recent research has shown that gut microbes play an important role in OP. Trimethylamine N-oxide
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)
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