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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

Fórmula empírica (notación de Hill):
C8H5F3O3
Número de CAS:
326-90-9
Peso molecular:
206.12
Número CE:
206-315-1
Número MDL:
MFCD00020935
Código UNSPSC:
12352100
ID de la sustancia en PubChem:
24866679
NACRES:
NA.22

Nivel de calidad

100

Ensayo

99%

Formulario

liquid

índice de refracción

n20/D 1.528 (lit.)

bp

203 °C (lit.)

mp

19-21 °C (lit.)

densidad

1.391 g/mL at 25 °C (lit.)

grupo funcional

fluoro
ketone

temp. de almacenamiento

2-8°C

cadena 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

Clave InChI

OWLPCALGCHDBCN-UHFFFAOYSA-N

Descripción general

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.

Aplicación

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.

Código de clase de almacenamiento

10 - Combustible liquids

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

188.6 °F - closed cup

Punto de inflamabilidad (°C)

87 °C - closed cup

Equipo de protección personal

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

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Certificados de análisis (COA)

Lot/Batch Number
MKCP8618
MKCF6302
MKBS4248V
14721PE
02001HD

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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
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)
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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