2-(4-AMINOPHENYL)-2-METHYLPROPANENITRILE Chemical Properties

Boiling point:

173-174 °C(Press: 10 Torr)

Density 

1.055±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

pka

3.63±0.10(Predicted)

Appearance

Light brown to off-white Solid

InChI

InChI=1S/C10H12N2/c1-10(2,7-11)8-3-5-9(12)6-4-8/h3-6H,12H2,1-2H3

InChIKey

VXDPOGVDHHJTDY-UHFFFAOYSA-N

SMILES

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

Safety Information

HS Code 

2926907090

2-(4-AMINOPHENYL)-2-METHYLPROPANENITRILE Usage And Synthesis

Uses

2-(4-Aminophenyl)-2-methylpropionitrile is used as an organic and pharmaceutical intermediate.

Chemical Properties

light yellow crystalline

Synthesis

General procedure for the synthesis of 2-(4-aminophenyl)-2-methylpropionitrile from 2-methyl-2-(4-nitrophenyl)propanenitrile: 2-methyl-2-(4-nitrophenyl)propanenitrile (1.0 mmol) was dissolved in ethyl acetate (20 mL) and stannous chloride dihydrate (3.52 g, 15.86 mmol) was added. The reaction mixture was stirred at room temperature overnight. Upon completion of the reaction, the reaction mixture was alkalized with aqueous sodium carbonate. The organic layer was separated, washed with water, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the crude product. The crude product was purified by silica gel column chromatography with the eluent of ethyl acetate/petroleum ether (1:9, v/v) to afford 2-(4-aminophenyl)-2-methylpropanenitrile (0.45 g, 89% yield) as an oil.

References

[1] Journal of Medicinal Chemistry, 2014, vol. 57, # 11, p. 4834 - 4848
[2] Patent: US2009/137595, 2009, A1
[3] Patent: WO2012/116237, 2012, A2. Location in patent: Page/Page column 119
[4] Patent: US2015/320727, 2015, A1. Location in patent: Paragraph 0555; 0556
[5] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 24, p. 7585 - 7596

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