2-isopropoxyaniline Chemical Properties

Melting point:

139-141℃

Boiling point:

273.23°C (rough estimate)

Density 

1.0406 (rough estimate)

refractive index 

1.5380 (estimate)

storage temp. 

2-8°C(protect from light)

form 

solid

pka

5.17±0.10(Predicted)

Appearance

Brown to black Liquid

Safety Information

HazardClass 

IRRITANT

HS Code 

2922290090

2-isopropoxyaniline Usage And Synthesis

Synthesis

General procedure for the synthesis of 2-(1-methylethoxy)aniline from 1-isopropoxy-2-nitrobenzene: The product of Example 242A (5.00 g, 27.5 mmol) was dissolved in methanol, 10% Pd/C catalyst was added, and the catalytic hydrogenation reaction was carried out under hydrogen pressure (60 psi). Upon completion of the reaction, the catalyst was removed by filtration and the filtrate was concentrated under reduced pressure to afford 3.75 g (90% yield) of the target product 2-(1-methylethoxy)aniline in the form of a brown oil. The structure of the product was confirmed by 1H NMR (400 MHz, CDCl3): δ 1.35 (d, 6H, J = 6.1 Hz), 3.77 (br s, 2H), 4.52 (m, 1H), 6.75 (m, 4H); the mass spectrum (DCI/NH3) showed m/e 152 (M + H)+.

References

[1] Organic Letters, 2011, vol. 13, # 16, p. 4320 - 4323
[2] Patent: US2003/229094, 2003, A1. Location in patent: Page 107
[3] Patent: WO2005/113498, 2005, A1. Location in patent: Page/Page column 16
[4] Patent: WO2014/11973, 2014, A2. Location in patent: Paragraph 0157; 0161
[5] Bioorganic and medicinal chemistry, 2004, vol. 12, # 16, p. 4511 - 4532

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