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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

Formule empirique (notation de Hill):
C8H5F3O3
Numéro CAS:
326-90-9
Poids moléculaire :
206.12
Numéro CE :
206-315-1
Numéro MDL:
MFCD00020935
Code UNSPSC :
12352100
ID de substance PubChem :
24866679
Nomenclature NACRES :
NA.22

Pureté

99%

Forme

liquid

Indice de réfraction

n20/D 1.528 (lit.)

Point d'ébullition

203 °C (lit.)

Pf

19-21 °C (lit.)

Densité

1.391 g/mL at 25 °C (lit.)

Température de stockage

2-8°C

Chaîne SMILES 

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

Clé InChI

OWLPCALGCHDBCN-UHFFFAOYSA-N

Description générale

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.

Code de la classe de stockage

10 - Combustible liquids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

188.6 °F - closed cup

Point d'éclair (°C)

87 °C - closed cup

Équipement de protection individuelle

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

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X-ray structure and temperature dependent luminescent properties of two bimetallic europium complexes.
Swavey S, et al.
Polyhedron, 27(3), 1061-1069 (2008)
An efficient entry to perfluoroalkyl substituted azoles starting from β-perfluoroalkyl-β-dicarbonyl compounds.
Bravo P, et al.
Tetrahedron, 50(29), 8827-8836 (1994)
Kensuke Nakano et al.
Anticancer research, 24(2B), 711-717 (2004-05-27)
A variety of beta-diketones were evaluated for their cytotoxic profiles against oral human normal and tumor cells. Among 22 compounds (BD1-22) tested, the cytotoxicity of 3-formylchromone (BD17) (CC50=7.8 microg/mL) against human oral squamous cell carcinoma (HSC-2) cells was higher than
Conformation, structure, intramolecular hydrogen bonding, and vibrational assignment of 4,4, 4-trifluoro-1-(2-furyl)-1,3-butanedione.
Tayyari SF, et al.
Journal of Molecular Structure, 8882(1), 153-167 (2008)
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
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