M-AMINOBENZYL CYANIDE

M-AMINOBENZYL CYANIDE Property

Melting point:

137-138 °C

Boiling point:

183-187 °C(Press: 13 Torr)

Density 

1.120±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

pka

4.12±0.10(Predicted)

Appearance

Yellow to brown Liquid

Safety

HS Code 

2926907090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

M-AMINOBENZYL CYANIDE Chemical Properties,Usage,Production

Uses

2-(3-Aminophenyl)acetonitrile is a useful reagent in the synthesis of aminophenylalkylaminopyrrolopyrimidines with antiinfluenza activity.

Synthesis

GENERAL METHOD: To a solution of m-nitrobenzeneacetonitrile (150.1 mg, 0.66 mmol) and ammonium chloride (NH4Cl, 183.6 mg, 3.43 mmol) in a solvent mixture of ethanol/water (EtOH/H2O, 5:1, 6 mL) was added powdered iron (Fe, 184.4 mg, 3.30 mmol) and vigorously stirred for 1 hour at 85 °C. . After completion of the reaction, the mixture was cooled to room temperature and filtered through a diatomaceous earth pad to remove solid impurities. The filtrate was concentrated and the residue was purified by column chromatography (eluent: ethyl acetate/hexane, 20:70) to afford 2-(3-aminophenyl)acetonitrile (10a, 99.2 mg, 76% yield) as a brown oil.

References

[1] Bioorganic and Medicinal Chemistry Letters, 2018, vol. 28, # 4, p. 577 - 583
[2] Patent: US2015/175557, 2015, A1. Location in patent: Paragraph 0347
[3] Patent: CN107098786, 2017, A. Location in patent: Paragraph 0049-0050
[4] Patent: WO2011/47156, 2011, A1. Location in patent: Page/Page column 82
[5] Patent: WO2009/122180, 2009, A1. Location in patent: Page/Page column 95