Ethyl 2,3,4,5-tetrafluorobenzoyl acetate Chemical Properties

Melting point:

41-44°C

Boiling point:

100 °C / 0.1mmHg

Density 

1.384

Flash point:

123℃

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

DMSO, Methanol

form 

Solid

pka

10.51±0.50(Predicted)

color 

Off-White to Beige

InChI

InChI=1S/C11H8F4O3/c1-2-18-8(17)4-7(16)5-3-6(12)10(14)11(15)9(5)13/h3H,2,4H2,1H3

InChIKey

KWDVJYLIAJHEOW-UHFFFAOYSA-N

SMILES

C(OCC)(=O)CC(C1=CC(F)=C(F)C(F)=C1F)=O

CAS DataBase Reference

94695-50-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Safety Statements 

24/25

Hazard Note 

Irritant

HS Code 

29183000

Ethyl 2,3,4,5-tetrafluorobenzoyl acetate Usage And Synthesis

Chemical Properties

White or off-white crystal

Uses

2,3,4,5-Tetrafluorobenzoylacetic Acid Ethyl Ester is a fluorinated benzoylacetate used as a synthetic reagent in the preparation of antibacterial and potential antitumor agents.

Uses

Ethyl 2,3,4,5-tetrafluorobenzoyl acetate is a fluorinated benzoylacetate used as a synthetic reagent in the preparation of antibacterial and potential antitumor agents.

Synthesis Reference(s)

Journal of Heterocyclic Chemistry, 24, p. 453, 1987 DOI: 10.1002/jhet.5570240228
Synthesis, p. 290, 1993 DOI: 10.1055/s-1993-25849

Synthesis

General procedure for the synthesis of ethyl 3-oxo-3-(2,3,4,5-tetrafluorophenyl)propionate from monoethyl malonate potassium salt and tetrafluorobenzoyl chloride: monoethyl malonate potassium salt (3.66 g, 21.5 mmol), MgCl? (2.44 g, 25.7 mmol) and triethylamine (TEA, 2.05 g, 20.3 mmol) were dissolved in acetonitrile (70 mL) in acetonitrile (70 mL) and the reaction was stirred for 2.5 h at 10-15 °C. Subsequently, a solution of 2,3,4,5-tetrafluorobenzoyl chloride (2.00 g, 10.3 mmol) in acetonitrile (10 mL) was slowly added dropwise at 0 °C for a controlled time of 15 min. After dropwise addition, TEA (0.23 g, 2.3 mmol) was added again. The reaction mixture was gradually warmed to room temperature and stirring was continued for 16 hours. After completion of the reaction, the volatiles were evaporated under reduced pressure. Toluene (30 mL) was added and evaporated again under reduced pressure. Subsequently, toluene (60 mL) was added and 1.5 M HCl (40 mL) was carefully added, controlling the reaction temperature to not exceed 25°C. The reaction was carried out under reduced pressure. The organic phase was washed sequentially with 1.5 M HCl (2 x 25 mL) and water (2 x 25 mL), dried with MgSO? and finally concentrated under reduced pressure to give the target product ([M + 1]? 265, 99% yield).

References

[1] Patent: WO2008/131134, 2008, A1. Location in patent: Page/Page column 57-58
[2] Synthesis, 1993, # 3, p. 290 - 292
[3] Patent: US2006/63761, 2006, A1. Location in patent: Page/Page column 5; 10-11
[4] Chemical Communications, 2013, vol. 49, # 46, p. 5313 - 5315

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