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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.)

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)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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)
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
Direct microwave promoted trifluoroacetylation of aromatic amines with trifluoroacetic acid.
Salazar J, et al.
Journal of Fluorine Chemistry, 124(1), 111-113 (2003)

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