2-Iodo-3-methoxyaniline Chemical Properties

Boiling point:

300.9±32.0 °C(Predicted)

Density 

1.807±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Store in freezer, under -20°C

pka

2.11±0.10(Predicted)

Appearance

Off-white to gray Solid

2-Iodo-3-methoxyaniline Usage And Synthesis

Synthesis

The general procedure for the synthesis of 2-iodo-3-methoxyaniline from the compound (CAS:194869-14-2) was as follows: trifluoroacetic acid (20 mL) was slowly added dropwise to a solution of compound 11 (5 g, 14.3 mmol) in dichloromethane (60 mL) at 0 °C. The reaction mixture was gradually warmed up to room temperature and stirred for 2 h under light protection. Upon completion of the reaction, the reaction solution was concentrated by rotary evaporator and diluted with ethyl acetate (150 mL). The pH was adjusted to 7~8 by slowly adding saturated aqueous NaHCO3 solution through a dropping funnel at 0 °C. The aqueous layer was extracted with ethyl acetate (80 mL × 2). The organic phases were combined, washed with saturated aqueous NaCl (150 mL), dried over anhydrous Na2SO4, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate, 10:1) to afford 2-iodo-3-methoxyaniline (3.2 g, 90% yield) as a white solid. The product was confirmed by 1H NMR (400 MHz, CDCl3): δ 7.07 (t, J = 8.0 Hz, 1H), 6.42-6.40 (m, 1H), 6.24-6.21 (m, 1H), 4.22 (br, 2H), 3.85 (s, 3H).13C NMR (100 MHz, CDCl3) δ 158.9, 148.4, 129.5, 107.8, 100.7, 76.0, 56.3. mass spectra (ESI, m/z) measured value 250.0 ([M + H]+).

References

[1] Synlett, 2005, # 16, p. 2469 - 2472
[2] Tetrahedron Letters, 2011, vol. 52, # 19, p. 2488 - 2491

2-Iodo-3-methoxyaniline(98991-09-4)Related Product Information

• 3-Methoxy-2-methylaniline