Ethyl 2,4,5-trifluorobenzoylacetate Chemical Properties

Melting point:

66-68°C

Boiling point:

92 °C(Press: 0.08 Torr)

Density 

1.319±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

solubility 

soluble in Toluene

form 

powder to crystal

pka

10.26±0.50(Predicted)

color 

White to Almost white

InChI

InChI=1S/C11H9F3O3/c1-2-17-11(16)5-10(15)6-3-8(13)9(14)4-7(6)12/h3-4H,2,5H2,1H3

InChIKey

OTCJYVJORKMTHX-UHFFFAOYSA-N

SMILES

C1(C(=O)CC(=O)OCC)C=C(C(F)=CC=1F)F

CAS DataBase Reference

98349-24-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

C,Xi,T

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39

RIDADR 

UN2811 6.1

HazardClass 

IRRITANT

HS Code 

2918300090

Ethyl 2,4,5-trifluorobenzoylacetate Usage And Synthesis

Chemical Properties

off-white crystall powder

Uses

Ethyl 2,4,5-Trifluoro-β-oxobenzenepropanoate can be used to prepare aminopyrrolidinyl)quinolinecarboxylates with antitumor activities.

Synthesis

Step 2. Synthesis of ethyl 3-oxo-3-(2,4,5-trifluorophenyl)propionate (B). Referring to the literature method [Wierenga, W.; Skulnick, H. I. J. Org. Chem. 1979, 44, 310-311], a mixture of monoethyl malonate (0.18 mL, 1.50 mmol) with bipyridine (1 crystal) was dissolved in tetrahydrofuran (THF, 10 mL) and cooled to -75 °C under argon protection . At -75 °C, n-butyllithium (n-BuLi, 2.8 mL, 4.48 mmol, 5.9 eq.) was slowly added. The reaction mixture was warmed to -50 °C and held for about 2 minutes until the pink color no longer faded (to ensure that the amount of n-butyllithium was sufficient to form a divalent anion), and then cooled to -75 °C again. Subsequently, a THF solution (2-3 mL) of 2,4,5-trifluorobenzoyl chloride (0.75 mmol) was slowly added. The reaction mixture was gradually warmed to room temperature, diluted with ethyl acetate (50 mL) and acidified with 1N hydrochloric acid under stirring. The organic phase was washed sequentially with 5% sodium bicarbonate solution (30 mL x 2) and saturated saline (50 mL x 2), dried with anhydrous sodium sulfate and concentrated. The oil obtained was purified by silica gel column chromatography (40 g silica gel column, 20% ethyl acetate in hexane solution, 40 min gradient) to give 185 mg (89% yield) of target product B as a white solid.

References

[1] Journal of Medicinal Chemistry, 1999, vol. 42, # 19, p. 3899 - 3909
[2] Patent: WO2008/36420, 2008, A2. Location in patent: Page/Page column 45-46
[3] Journal of Medicinal Chemistry, 1991, vol. 34, # 1, p. 168 - 174

Ethyl 2,4,5-trifluorobenzoylacetate(98349-24-7)Related Product Information

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• PHENOXYACETIC ACID
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• Ethyl butyrylacetate
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• ETHYL 3-(3-CHLORO-2,4,5-TRIFLUOROPHENYL)-3-OXOPROPANOATE