4-(4-DIMETHYLAMINO-PHENYL)-BUT-3-EN-2-ONE Chemical Properties

Melting point:

234-235 °C

Boiling point:

340.6±25.0 °C(Predicted)

Density 

1.039±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

4.88±0.24(Predicted)

Appearance

Light yellow to yellow Solid

4-(4-DIMETHYLAMINO-PHENYL)-BUT-3-EN-2-ONE Usage And Synthesis

Synthesis

GENERAL METHOD: p-Dimethylaminobenzaldehyde (50 mmol) was dissolved in acetone (50 mL) and the solution was cooled to 0°C in an ice bath. A 10% aqueous NaOH solution was slowly added dropwise to the reaction mixture, followed by a natural warming of the reaction system to room temperature. The reaction mixture was stirred continuously at room temperature until the reaction was complete. After completion of the reaction, the acetone was removed by distillation under reduced pressure. The residue was dissolved in ethyl acetate and washed twice each with dilute hydrochloric acid and water sequentially. The organic layer was separated and dried over anhydrous Na2SO4, followed by concentration under reduced pressure to remove the solvent. The crude product was purified by column chromatography (silica gel, 100-200 mesh, eluent ratio 9:1 hexane/ethyl acetate) to afford the target compound 4-(4-dimethylaminophenyl)-but-3-en-2-one.

References

[1] Journal of Medicinal Chemistry, 1992, vol. 35, # 19, p. 3429 - 3447
[2] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2010, vol. 49, # 7, p. 944 - 947
[3] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 12, p. 3784 - 3787
[4] Journal of Organic Chemistry, 1939, vol. 3, p. 13
[5] Helvetica Chimica Acta, 1931, vol. 14, p. 1340,1348

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