4,4,4-TRIFLUORO-1-(2-FURYL)-1,3-BUTANEDIONE Chemical Properties

Melting point:

19-21 °C(lit.)

Boiling point:

203 °C(lit.)

Density 

1.391 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.528(lit.)

Flash point:

189 °F

storage temp. 

2-8°C

pka

5.56±0.23(Predicted)

form 

powder to lump to clear liquid

color 

White or Colorless to Yellow to Orange

FreezingPoint 

20.0 to 22.0 ℃

BRN 

168085

InChI

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

InChIKey

OWLPCALGCHDBCN-UHFFFAOYSA-N

SMILES

C(C1=CC=CO1)(=O)CC(=O)C(F)(F)F

CAS DataBase Reference

326-90-9(CAS DataBase Reference)

EPA Substance Registry System

1,3-Butanedione, 4,4,4-trifluoro-1-(2-furanyl)- (326-90-9)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39

WGK Germany 

3

TSCA 

Yes

HazardClass 

IRRITANT

HS Code 

29321900

4,4,4-TRIFLUORO-1-(2-FURYL)-1,3-BUTANEDIONE Usage And Synthesis

Chemical Properties

clear yellow liquid

Uses

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.

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.

Synthesis

GENERAL STEPS: To a 500 mL three-necked flask were added 20.0 g (181.6 mmol) of 2-acetylfuran, 50 mL of tetrahydrofuran (THF) and 24 mL of ethyl trifluoroacetate. The mixed solution was cooled to 0-3 °C in an ice-water bath, and 1.0 M lithium bis(trimethylsilyl)amide (LiHMDS, 200 mL) solution was slowly added dropwise. After the dropwise addition, the reaction system was allowed to warm up to room temperature naturally and stirred overnight. Upon completion of the reaction, THF was removed by concentration under reduced pressure with a rotary evaporator. the residue was transferred to a partition funnel and extracted with a solution of ethyl acetate and 1.0 M hydrochloric acid. The organic phase was separated, washed with saturated saline, dried over anhydrous sodium sulfate and concentrated again under reduced pressure. The final product was 4,4,4-trifluoro-1-(2-furyl)-1,3-butanedione as a brown semi-solid in a yield of 32.5 g (yield >100%).

References

[1] Patent: WO2008/73825, 2008, A1. Location in patent: Page/Page column 134
[2] Chinese Chemical Letters, 2016, vol. 27, # 4, p. 566 - 570
[3] Synthesis, 1997, # 11, p. 1321 - 1324
[4] Journal of the American Chemical Society, 1950, vol. 72, p. 2948,2949
[5] Journal of Fluorine Chemistry, 2002, vol. 118, # 1-2, p. 135 - 147

4,4,4-TRIFLUORO-1-(2-FURYL)-1,3-BUTANEDIONE(326-90-9)Related Product Information

• 1-(2-FURYL)-1,3-BUTANEDIONE