Benzonitrile, 5-amino-2-methoxy- (9CI) Chemical Properties

Melting point:

100 °C

Boiling point:

347.5±22.0 °C(Predicted)

Density 

1.17±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

form 

Solid

pka

3.39±0.10(Predicted)

Appearance

Brown to gray Solid

InChI

InChI=1S/C8H8N2O/c1-11-8-3-2-7(10)4-6(8)5-9/h2-4H,10H2,1H3

InChIKey

BZNMIDYUSWEPOM-UHFFFAOYSA-N

SMILES

C(#N)C1=CC(N)=CC=C1OC

Safety Information

HazardClass 

IRRITANT

HS Code 

2926907090

Benzonitrile, 5-amino-2-methoxy- (9CI) Usage And Synthesis

Synthesis

General procedure for the synthesis of 5-amino-2-methoxybenzonitrile from 2-methoxy-5-nitrobenzonitrile: 2-methoxy-5-nitrobenzonitrile (1 equiv., 220 mg, 1.23 mmol), methanol (20 mL), and carbon-carrying palladium (10% mass, 10 mg) were added sequentially to a 100 mL round-bottom flask. The flask was connected to a three-way system and the reaction was stirred at room temperature. Evacuation was carried out and then filled with nitrogen, and this cycle was repeated three times, each time the nitrogen was filled for not less than 5 minutes. The reaction was allowed to proceed at room temperature for 30 minutes under hydrogen protection. Upon completion of the reaction, the palladium-carbon catalyst was removed by filtration, the filtrate was concentrated and purified by column chromatography (petroleum ether:ethyl acetate = 5:1) to afford 150 mg of the target product 5-amino-2-methoxybenzonitrile (Compound 7) as a white crystalline solid in 82% yield.

References

[1] Patent: CN106892871, 2017, A. Location in patent: Paragraph 0109; 0112; 0113
[2] Patent: CN105294584, 2016, A. Location in patent: Paragraph 0018; 0019
[3] Journal of the Chemical Society, 1945, p. 861,864
[4] Chemical Biology and Drug Design, 2018, vol. 91, # 2, p. 526 - 533

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