4-Isopropoxyaniline Chemical Properties

Melting point:

244 °C (decomp)

Boiling point:

95°C 0,4mm

Density 

1.03

refractive index 

1.5430-1.5470

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

form 

clear liquid

pka

6.15±0.10(Predicted)

color 

Colorless to Red to Green

LogP

1.620 (est)

CAS DataBase Reference

7664-66-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39

HazardClass 

IRRITANT

HS Code 

29214200

4-Isopropoxyaniline Usage And Synthesis

Uses

4-Isopropoxyaniline is an aniline derivative used as a raw material or intermediate component in organic synthesis. It can be used in the preparation of pyrimidines and their derivatives. Anilines are toxic to humans and can cause strong skin and eye irritation on contact or ingestion, as well as some damage to the liver and kidneys.

Synthesis

GENERAL STEPS: The synthesis was carried out according to the one-step method reported by De Marco et al. 4-Aminophenol (92 mmol) and sodium hydride (suspension in mineral oil, 275 mmol) were added to anhydrous N,N-dimethylformamide (100 mL). Subsequently, 2-bromopropane (137 mmol) was added dropwise and the reaction mixture was stirred at room temperature for 24 hours. Upon completion of the reaction, distilled water (400 mL) was added to quench the reaction and the aqueous phase was extracted with ethyl acetate (3 x 150 mL). The organic layers were combined, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The final product was purified by distillation under reduced pressure.

References

[1] Molecules, 2015, vol. 20, # 6, p. 9767 - 9787
[2] Journal of Medicinal Chemistry, 2007, vol. 50, # 20, p. 4898 - 4908
[3] Molecules, 2018, vol. 23, # 7,

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