2-HYDROXY-5-METHOXYBENZONITRILE Chemical Properties

Melting point:

151 °C

Boiling point:

330.4±27.0 °C(Predicted)

Density 

1.24±0.1 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

pka

6.79±0.10(Predicted)

Appearance

Light yellow to yellow Solid

Safety Information

Risk Statements 

20/21/22-36/37/38

Safety Statements 

26-36/37/39

RIDADR 

3439

HS Code 

2926907090

2-HYDROXY-5-METHOXYBENZONITRILE Usage And Synthesis

Synthesis

The general procedure for the synthesis of 2-hydroxy-4-methoxybenzonitrile from 2-hydroxy-4-methoxybenzaldehyde is as follows: 2-hydroxy-4-methoxybenzaldehyde (20 g, 128.8 mmol), sodium acetate (35.05 g, 257.6 mmol), and nitroethane (19 mL, 257.6 mmol) were dissolved in glacial acetic acid (100 mL) and the mixture was heated under mild reflux conditions for 12 hours. Upon completion of the reaction, the reaction mixture was slowly poured into about 1000 mL of ice water (1:1 ratio of ice to water). The product was extracted with ethyl acetate (3 x 200 mL). The organic phases were combined and washed with sodium bicarbonate solution until the pH of the aqueous layer was about 8. Subsequently, the organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated in vacuum to afford 2-hydroxy-4-methoxybenzonitrile as a yellow oil (16.5 g, 86% yield).

References

[1] Synthetic Communications, 2004, vol. 34, # 11, p. 2025 - 2029
[2] Patent: US2004/259867, 2004, A1. Location in patent: Page/Page column 7
[3] Patent: US6399657, 2002, B1
[4] Journal of Medicinal Chemistry, 2003, vol. 46, # 8, p. 1470 - 1477
[5] Synlett, 2000, # 8, p. 1169 - 1171

2-HYDROXY-5-METHOXYBENZONITRILE(39835-11-5)Related Product Information

• 2,4-DIMETHOXY-6-METHYLBENZONITRILE
• AKOS 233-19
• 2-METHOXY-4-(TRIFLUOROMETHOXY)BENZONITRILE
• 2,4,6-Trimethoxybenzonitrile
• AKOS 233-36
• 2,4,5-TRIMETHOXYBENZONITRILE
• 2-HYDROXY-5-METHOXYBENZONITRILE
• 4-METHOXY-2-(TRIFLUOROMETHOXY)BENZONITRILE
• 2,3,4-TRIMETHOXYBENZONITRILE
• 2,4-Dimethoxybenzonitrile