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HomeProduct name listEthyl 3-oxo-4-phenylbutanoate

Ethyl 3-oxo-4-phenylbutanoate

  • CAS NO.:718-08-1
  • Empirical Formula: C12H14O3
  • Molecular Weight: 206.24
  • MDL number: MFCD03844818
  • EINECS: 226-500-0
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-10-09 17:25:53
Ethyl 3-oxo-4-phenylbutanoate Structural

What is Ethyl 3-oxo-4-phenylbutanoate?

Chemical properties

Light-yellow Liquid.

The Uses of Ethyl 3-oxo-4-phenylbutanoate

Ethyl 3-oxo-4-phenylbutanoate is a useful synthetic intermediate. It is used to prepare pyrazolone derivatives as antiprion compounds. It is also used to prepare pyrrolinylaminopyrimidine analogs as inhibitors of AP-1 and NF-κB mediated gene expression.

Synthesis Reference(s)

Journal of Medicinal Chemistry, 44, p. 78, 2001 DOI: 10.1021/jm001034k
Chemical and Pharmaceutical Bulletin, 30, p. 2440, 1982 DOI: 10.1248/cpb.30.2440

Synthesis

The synthesis of Ethyl 3-oxo-4-phenylbutanoate is as follows:Monoethyl monopotassium malonate (12.9 g, 2.3 equivalents) was mixed with tetrahydrofuran (200 ml), and the mixture was cooled to 5°C. Triethylamine (8.2 g, 2.5 equivalents) and magnesium chloride (8.62 g, 2.8 equivalents) were added, and the mixture was stirred at 5 to 20°C for 3 hours. The reaction mixture was cooled to 5°C. Phenacyl chloride (5 g, 32 mmol, 1 equivalent) was gradually added, and the mixture was stirred at 5 to 20°C for 63 hours. The mixture was cooled to 5°C, and 1 N hydrochloric acid (30 ml) was added. Tetrahydrofuran was evaporated away under reduced pressure, and extraction was carried out with ethyl acetate (50 ml). The organic layer was washed with 1 N hydrochloric acid (30 ml), water (10 ml), saturated aqueous solution of sodium hydrogencarbonate (30 ml) and water (10 ml) in order. The solvent was evaporated away under reduced pressure to obtain the Ethyl 3-oxo-4-phenylbutanoate as a pale yellow oil (5.82 g, yield: 86 %).
718-08-1.png

Properties of Ethyl 3-oxo-4-phenylbutanoate

Boiling point: 290℃
Density  1.091
refractive index  1.054-1.059
Flash point: 124℃
storage temp.  Inert atmosphere,Room Temperature
solubility  Chloroform (Slightly), DMSO (Slightly), Methanol (Sparingly)
form  Oil
pka 10.49±0.46(Predicted)
color  Colourless to Light Yellow
InChI InChI=1S/C12H14O3/c1-2-15-12(14)9-11(13)8-10-6-4-3-5-7-10/h3-7H,2,8-9H2,1H3

Safety information for Ethyl 3-oxo-4-phenylbutanoate

Computed Descriptors for Ethyl 3-oxo-4-phenylbutanoate

InChIKey BOZNWXQZCYZCSH-UHFFFAOYSA-N
SMILES C1(C=CC=CC=1)CC(=O)CC(=O)OCC

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