DIETHYL 2-ANILINOMALONATE Chemical Properties

Melting point:

43-45 °C

Boiling point:

340.6±22.0 °C(Predicted)

Density 

1.167±0.06 g/cm3(Predicted)

storage temp. 

2-8°C(protect from light)

pka

14.73±0.59(Predicted)

Appearance

White to off-white Solid

Safety Information

HazardClass 

IRRITANT

HS Code 

2922390090

DIETHYL 2-ANILINOMALONATE Usage And Synthesis

Synthesis

(1) Synthesis of diethyl anilino malonate: Aniline (18.6 g, 0.20 mol) was dissolved in anhydrous benzene (125 mL), followed by the addition of diethyl bromomalonate (23.9 g, 0.10 mol). The reaction mixture was heated to reflux under continuous stirring and maintained for 37 hours. Upon completion of the reaction, the reaction mixture was washed with dilute hydrochloric acid to remove unreacted aniline. The organic layer was separated, washed three times with water and dried with anhydrous magnesium sulfate. Subsequently, the solvent was removed by distillation under reduced pressure. The crude product was purified by silica gel column chromatography using hexane/ethyl acetate (10:1, v/v) as eluent to afford 7.5 g (30% yield) of diethyl anilino malonate. The product was characterized by nuclear magnetic resonance (NMR) with the following data: 1H NMR (δ, TMS, CCl4): 1.20 (6H, t, J = 7 Hz), 4.20 (4H, q, J = 7 Hz), 4.66 (2H, s, br; changed to 1H after addition of D2O), 6.5-7.3 (5H, m).

References

[1] Patent: US4421914, 1983, A

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