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146293

Sigma-Aldrich

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

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About This Item

Linear Formula:
FC6H4COCH2CO2C2H5
CAS Number:
Molecular Weight:
210.20
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

refractive index

n20/D 1.5040 (lit.)

Quality Level

bp

117-120 °C (lit.)

density

1.174 g/mL at 25 °C (lit.)

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

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

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

Certificates of Analysis (COA)

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Comparative Use of Solvent-free KF-Al2O3 and K2CO3 in Acetone in the Synthesis of Quinoxaline 1, 4-Dioxide Derivatives Designed as Antimalarial Drug Candidates.
Lima LM, et al.
Journal of Heterocyclic Chemistry, 42(7), 1381-1385 (2005)

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