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Sigma-Aldrich

1-(Trifluoroacetyl)imidazole

98%

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About This Item

Empirical Formula (Hill Notation):
C5H3F3N2O
CAS Number:
1546-79-8
Molecular Weight:
164.09
Beilstein:
608904
EC Number:
216-282-5
MDL number:
MFCD00014501
UNSPSC Code:
12352005
PubChem Substance ID:
24861374
NACRES:
NA.22

Assay

98%

form

liquid

refractive index

n20/D 1.424 (lit.)

bp

137 °C (lit.)
45-46 °C/14 mmHg (lit.)

density

1.442 g/mL at 25 °C (lit.)

functional group

fluoro

storage temp.

2-8°C

SMILES string

FC(F)(F)C(=O)n1ccnc1

InChI

1S/C5H3F3N2O/c6-5(7,8)4(11)10-2-1-9-3-10/h1-3H

InChI key

SINBGNJPYWNUQI-UHFFFAOYSA-N

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General description

1-(Trifluoroacetyl)imidazole (N-(Trifluroroacetyl)imidazole) is an effective reagent for specific trifluoroacetylation of an aminomethyl side chain of certain nucleosides.

Application

1-(Trifluoroacetyl)imidazole may be employed as derivatization reagent for the detection of mustard gas degradation products, thiodiglycol and thiodiglycol sulfoxide using gas chromatography-tandem mass spectrometry. It may be used as reagent for the trifluoroacetylation of amines. It was used for derivatization of ethanolamine phospholipid-alkenal Michael adducts for GC-MS analysis. It was used in the determination of quinolinic acid, a kynurenine metabolite, by GC/MS.

accessory

Product No.
Description
Pricing

Pictograms

FlameExclamation mark
GHS02,GHS07

Signal Word

Warning

Hazard Statements

H226,H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Flam. Liq. 3 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

111.2 °F - closed cup

Flash Point(C)

44 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Sandrine Bacot et al.
Journal of lipid research, 48(4), 816-825 (2007-01-16)
Hydroxy-alkenals, such as 4-hydroxy-2(E)-nonenal (4-HNE; from n-6 fatty acids), are degradation products of fatty acid hydroperoxides, including those generated by free radical attack of membrane polyunsaturated fatty acyl moieties. The cytotoxic effects of hydroxy-alkenals are well known and are mainly
Direct microwave promoted trifluoroacetylation of aromatic amines with trifluoroacetic acid.
Salazar J, et al.
Journal of Fluorine Chemistry, 124(1), 111-113 (2003)
Stanisław Popiel et al.
Analytical chemistry, 86(12), 5865-5872 (2014-05-17)
A method for detecting mustard gas degradation products thiodiglycol (TDG) and thiodiglycol sulfoxide (TDGO) in water and sediment samples using gas chromatography-tandem mass spectrometry (GC-MS/MS) after derivatization with 1-(trifluoroacetyl)imidazole (TFAI) was described. Selected reaction monitoring mode (SRM) of tandem mass
A Chiarugi et al.
FEBS letters, 453(1-2), 197-200 (1999-07-14)
The rabbit lens has an elevated content of 3-hydroxykynurenine (30HKYN) in spite of a very low activity of the enzymes leading to its synthesis. The iris/ciliary body, on the contrary, has very high activity of 30HKYN synthesizing enzymes but a
Trifluoroacetylation in Organic Synthesis: Reagents, Developments and Applications in the Construction of Trifluoromethylated Compounds.
Lopez SE, et al.
Current Organic Synthesis, 7(5), 414-432 (2010)

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