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426016

Sigma-Aldrich

4,4,4-Trifluoro-1-(2-furyl)-1,3-butanedione

99%

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About This Item

Empirical Formula (Hill Notation):
C8H5F3O3
CAS Number:
Molecular Weight:
206.12
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

99%

form

liquid

refractive index

n20/D 1.528 (lit.)

bp

203 °C (lit.)

mp

19-21 °C (lit.)

density

1.391 g/mL at 25 °C (lit.)

functional group

fluoro
ketone

storage temp.

2-8°C

SMILES string

FC(F)(F)C(=O)CC(=O)c1ccco1

InChI

1S/C8H5F3O3/c9-8(10,11)7(13)4-5(12)6-2-1-3-14-6/h1-3H,4H2

InChI key

OWLPCALGCHDBCN-UHFFFAOYSA-N

General description

4,4,4-Trifluoro-1-(2-furyl)-1,3-butanedione (furoyltrifluoroacetone, FTFA) is a β-diketone. Its cytotoxic activity against human cultured tumor and normal cells has been evaluated. Reports suggest that 4,4,4-trifluoro-1-(2-furyl)-1,3-butanedione partially inhibits the oxidation of ferrocyanide in ETP (electron transport particles) isolated from beef heart mitochondria. Its reaction with N,N,N′,N′-tetramethylalkyl diamines to form ionic adducts has been investigated. The conformational analysis of the enol and keto form of FTFA has been reported.

Application

4,4,4-Trifluoro-1-(2-furyl)-1,3-butanedione (tfa) may be used in the following studies:
  • As capping ligand in the synthesis of [Eu(tfa)3]2bpm complexes (bpm=2,2′-bipyrimidine).
  • As reagent in the multistep synthesis of [13CD2]benzylamine.
  • As reagent in the synthesis of 3-trifluoromethyl-2-arylcarbonylquinoxaline 1,4-di-N-oxide derivatives by reacting with corresponding benzofurazan oxides.
  • In the efficient syntheses of perfluoroalkyl substituted azoles.
  • Synthesis of 2-arylcarbonyl-3-trifluoromethylquinoxaline 1,4-di-N-oxide derivatives.

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

188.6 °F - closed cup

Flash Point(C)

87 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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A Mutlib et al.
Drug metabolism and disposition: the biological fate of chemicals, 29(10), 1296-1306 (2001-09-19)
The role of gamma-glutamyltranspeptidase (GGT) in transferring glutamate from endogenous glutathione (GSH) to the benzylamine moiety of a compound, such as 1-[3-(aminomethyl)phenyl]-N-[3-fluoro-2'-(methylsulfonyl)-[1,1'-biphenyl]-4-yl]-3-(trifluoromethyl)-1H-pyrazole-5-carboxamide (DPC 423), is described. Studies were performed with structurally related analogs of DPC 423 to demonstrate that this
Topography of the cristae membrane as elucidated by a new inhibitor, trifluorofurylbutanedione.
H J Harmon et al.
Biochemical and biophysical research communications, 55(1), 169-173 (1973-11-01)
Acyclic tertiary diamines and 1, 4, 7,10-tetraazacyclododecane with fluorine-containing β-diketones: Leading to low melting ionic adducts.
Gupta OD, et al.
Journal of Fluorine Chemistry, 126(8), 1222-1229 (2005)
Adoración Marin et al.
Experimental parasitology, 118(1), 25-31 (2007-07-07)
Derivatives of 3-trifluoromethyl-2-arylcarbonylquinoxaline 1,4-di-N-oxide (4b-g, 5b-g, 6a-g) were synthesized and evaluated for their capacity to inhibit the growth of chloroquine-resistant Plasmodium falciparum FCB1 strain in culture. Compound 7-chloro-2-(2-furylcarbonyl)-3-trifluoromethyl-1,4-quinoxaline di-N-oxide (5g) was the most active being almost 5 times more active
Synthesis and biological evaluation of new 2-arylcarbonyl-3-trifluoromethylquinoxaline 1,4-di-N-oxide derivatives and their reduced analogues.
Solano B, et al.
Journal of Medicinal Chemistry, 50(22), 5485-5492 (2007)

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