4-AMINO-3-HYDROXY-BENZONITRILE Chemical Properties

Melting point:

149-150 °C

Boiling point:

314.1±37.0 °C(Predicted)

Density 

1.33±0.1 g/cm3(Predicted)

storage temp. 

2-8°C(protect from light)

form 

powder

pka

8.37±0.10(Predicted)

color 

Brown

Safety Information

HS Code 

2926907090

4-AMINO-3-HYDROXY-BENZONITRILE Usage And Synthesis

用途

4-氨基-3-羟基-苯甲腈用作研究用化合物。

Synthesis

The general procedure for the synthesis of 4-amino-3-hydroxybenzonitrile from 3-hydroxy-4-nitrobenzonitrile was as follows: 3-hydroxy-4-nitrobenzonitrile (1.6 g, 9.6 mmol) was dissolved in a solvent mixture of ethanol (40 mL) and N,N-dimethylformamide (20 mL). Palladium hydroxide (30 mg) was added to this solution to form a reaction mixture. The reaction mixture was stirred overnight at room temperature in a hydrogen atmosphere. Upon completion of the reaction, the reaction mixture was filtered to remove the catalyst and the solvent was subsequently removed by distillation under reduced pressure. The residue was dried to afford crystals of 4-amino-3-hydroxybenzonitrile (771 mg, 60% yield). The product was characterized by 1H-NMR (DMSO-d6) with the following chemical shifts: δ 5.57 (2H, broad peak), 6.62 (1H, double peak, J = 8.4 Hz), 6.86 (1H, double peak, J = 2.2 Hz), and 6.99 (1H, double-double peak, J = 1.9 Hz, 8.1 Hz).

References

[1] Journal of Medicinal Chemistry, 2004, vol. 47, # 6, p. 1319 - 1321
[2] Journal of the American Chemical Society, 2012, vol. 134, # 44, p. 18193 - 18196
[3] Patent: US2017/298081, 2017, A1. Location in patent: Paragraph 0307; 0310; 0311
[4] Fortsch. Ch. Phys., 1924, vol. 18, p. Heft 2, S. 37
[5] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 12, p. 1545 - 1548

4-AMINO-3-HYDROXY-BENZONITRILE(55586-26-0)Related Product Information

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