146293

Ethyl (4-fluorobenzoyl)acetate

• Synonym(s): (p-Fluorobenzoyl)acetic acid ethyl ester, 4-Fluoro-ß-oxobenzenepropanoic acid ethyl ester, Ethyl 3-(4-fluorophenyl)-3-oxopropionate, Ethyl 4-fluorobenzoylacetate
• Linear Formula: FC₆H₄COCH₂CO₂C₂H₅
• CAS Number: 1999-00-4
• Molecular Weight: 210.20
• MDL number: MFCD03093631
• UNSPSC Code: 12352100
• PubChem Substance ID: 24848775
• NACRES: NA.22

Properties

• refractive index: n20/D 1.5040 (lit.)
• bp: 117-120 °C (lit.)
• density: 1.174 g/mL at 25 °C (lit.)
• functional group: ester
• SMILES string: CCOC(=O)CC(=O)c1ccc(F)cc1
• InChI: 1S/C11H11FO3/c1-2-15-11(14)7-10(13)8-3-5-9(12)6-4-8/h3-6H,2,7H2,1H3
• InChI key: SJUXLKYJKQBZLM-UHFFFAOYSA-N

Description

General description

Ethyl (4-fluorobenzoyl)acetate on condensation with benzofurazan oxide yields 2-(carboethoxy)-3-(4′-fluoro)phenylquinoxaline1,4-dioxide.

Application

Reactant used as a precursor in:

• Condensation reactions with diamines via C-C bond cleavage for synthesis of benzimidazoles and perimidines for possible use as antimalarial treatments
• Base-promoted domino Michael addition / cyclization / elimination reactions for synthesis of hydroxybenzophenones
• Oxidative cross-coupling with indoles via dioxygen activation
• Cyclization of keto esters for synthesis of pyrones
• Lewis base catalyzed hydrosilylation for synthesis of α-acetoxy β-amino acid derivatives
• Conia-ene reactions for synthesis of methylenecyclopentane derivatives

Safety Information

• Storage Class Code: 10 - Combustible liquids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves