ethyl 3-(4-fluorophenyl)-3-oxopropanoate

• ChemBase ID: 100522
• Molecular Formular: C11H11FO3
• Molecular Mass: 210.2016432
• Monoisotopic Mass: 210.06922243
• SMILES: O=C(CC(=O)c1ccc(cc1)F)OCC
• Canonical SMILES: CCOC(=O)CC(=O)c1ccc(cc1)F
• InChI: InChI=1S/C11H11FO3/c1-2-15-11(14)7-10(13)8-3-5-9(12)6-4-8/h3-6H,2,7H2,1H3
• InChIKey: SJUXLKYJKQBZLM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl 3-(4-fluorophenyl)-3-oxopropanoate
• IUPAC Traditional name: ethyl 3-(4-fluorophenyl)-3-oxopropanoate
• Synonyms: Ethyl (4-fluorobenzoyl)acetate; Ethyl 3-(4-fluorophenyl)-3-oxopropanoate; (p-Fluorobenzoyl)acetic acid ethyl ester; 4-Fluoro-β-oxobenzenepropanoic acid ethyl ester; Ethyl 3-(4-fluorophenyl)-3-oxopropionate; Ethyl 4-fluorobenzoylacetate; Ethyl (4-fluorobenzoyl)acetate; 对氟苯甲酰乙酸乙酯; (4-氟苯甲酰)乙酸乙酯

Database IDs

• CAS Number: 1999-00-4
• MDL Number: MFCD03093631
• PubChem SID: 24848775; 162087400
• PubChem CID: 2758844

CALCULATED PROPERTIES

• Acid pKa: 10.536779
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 2.0685217
• LogD (pH = 7.4): 2.0682092
• Log P: 2.0685258
• Molar Refractivity: 52.539 cm^3
• Polarizability: 20.080389 Å^3
• Polar Surface Area: 43.37 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 117-120 °C(lit.)
• Density: 1.174 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.5040(lit.)
• Hydrophobicity(logP): 2.1

Safety Information

• Storage Warning: Irritant
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves

Product Information

• Purity: 95%; 95+%
• Linear Formula: FC6H4COCH2CO2C2H5

DETAILS

Sigma Aldrich - 146293

Packaging
1, 5 g in glass bottle
Application
Reactant used as a precursor in:
• Condensation reactions with diamines via C-C bond cleavage for synthesis of benzimidazoles and perimidines1 for possible use as antimalarial treatments2
• Base-promoted domino Michael addition / cyclization / elimination reactions for synthesis of hydroxybenzophenones3
• Oxidative cross-coupling with indoles via dioxygen activation4
• Cyclization of keto esters for synthesis of pyrones5
• Lewis base catalyzed hydrosilylation for synthesis of α-acetoxy β-amino acid derivatives6
• Conia-ene reactions for synthesis of methylenecyclopentane derivatives7