| Identification | More | [Name]
Ethyl 2,3,4,5-tetrafluorobenzoyl acetate | [CAS]
94695-50-8 | [Synonyms]
ETHYL 2,3,4,5-TETRAFLUOROBENZOYL ACETATE
2,3,4,5-Tetrafluorobenzoyl acetic acid, ethyl ester
Methyl (2,3,4,5-Tetrafluoro-Benzoyl)Acetate
3-oxo-3-(2,3,4,5-tetrafluoro-phenyl)-propionic acid ethyl ester
Ethyl(2,3,4,5-tetrafluorobenzo
Benzenepropanoicacid, 2,3,4,5-tetrafluoro--oxo-ethylester | [Molecular Formula]
C11H8F4O3 | [MDL Number]
MFCD00523020 | [Molecular Weight]
264.17 | [MOL File]
94695-50-8.mol |
| Chemical Properties | Back Directory | [Melting point ]
41-44°C | [Boiling point ]
100 °C / 0.1mmHg | [density ]
1.384 | [Fp ]
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) |
| Hazard Information | Back Directory | [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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