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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:
1999-00-4
Molecular Weight:
210.20
MDL number:
MFCD03093631
UNSPSC Code:
12352100
PubChem Substance ID:
24848775
NACRES:
NA.22

refractive index

n20/D 1.5040 (lit.)

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

146293-1G:
146293-5G:
146293-VAR:
146293-BULK:

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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