2-AMINO-5-IODOBENZONITRILE Chemical Properties

Melting point:

86℃ (ethanol )

Boiling point:

333.6±37.0 °C(Predicted)

Density 

1.98±0.1 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

1.02±0.10(Predicted)

Appearance

Off-white to yellow Solid

2-AMINO-5-IODOBENZONITRILE Usage And Synthesis

Uses

2-Amino-5-iodobenzonitrile is a useful intermediate for the synthesis of lapatinib intermediate of N-[3-chloro-4-3-fluorophenzyloxyphenyl]-6-iodoquinazolin-4-amine.

Synthesis

The general procedure for the synthesis of 2-amino-5-iodobenzonitrile from 2-aminobenzonitrile is as follows: 1. A mixture of 2-aminobenzonitrile (0.02 mol) and ammonium iodide (0.02 mol) was dissolved in acetic acid (50 mL). 2. 30% aqueous hydrogen peroxide (0.13 mol) was added dropwise to the above solution slowly at 30 °C. 3. The reaction mixture was stirred at room temperature for 12 hours. 4. For 12 h. 4. After completion of the reaction, the reaction solution was treated with aqueous sodium thiosulfate (40 mL, 0.03 mol) and the pH was adjusted to about 8 by addition of 20% sodium hydroxide solution. 5. The reaction mixture was continued to be stirred at room temperature for 0.5 h. 6. The partially precipitated 2-amino-5- iodobenzonitrile (Product A) was separated by vacuum filtration to give a silvery-white flaky solid in a yield of 92.6%.

References

[1] Acta Crystallographica Section C: Crystal Structure Communications, 2007, vol. 63, # 7, p. o408-o410
[2] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 7, p. 1584 - 1587
[3] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 18, p. 4309 - 4313
[4] Bioorganic and Medicinal Chemistry, 2005, vol. 13, # 7, p. 2637 - 2649
[5] Patent: CN103896889, 2016, B. Location in patent: Paragraph 0041-0043

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