2-AMINO-3-FLUOROBENZONITRILE Chemical Properties

Boiling point:

252.4±25.0 °C(Predicted)

Density 

1.25±0.1 g/cm3(Predicted)

storage temp. 

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

pka

0.42±0.10(Predicted)

form 

Solid

Appearance

Off-white to light yellow Solid

InChI

InChI=1S/C7H5FN2/c8-6-3-1-2-5(4-9)7(6)10/h1-3H,10H2

InChIKey

UNISSOLHERSZOW-UHFFFAOYSA-N

SMILES

C(#N)C1=CC=CC(F)=C1N

Safety Information

HazardClass 

TOXIC

HazardClass 

6.1

HS Code 

2926907090

2-AMINO-3-FLUOROBENZONITRILE Usage And Synthesis

Chemical Properties

brown liquid

Uses

2-Amino-3-fluorobenzonitrile is used as an intermediate in organic synthesis and medicinal chemistry, and is mostly used in basic chemical research and modification of pharmaceutical molecules.

Synthesis

The general procedure for the synthesis of 2-amino-3-fluorobenzonitrile from 2,3-difluorobenzonitrile was as follows: a mixture of 2,3-difluorobenzonitrile (19.0 g, 137 mmol), pre-saturated with ammonia, and ethanol (200 mL) was placed in an autoclave and heated for 8 hr at 140 °C (final pressure 200 psi). Upon completion of the reaction, the mixture was cooled to room temperature and evaporated to dryness. The residue was dissolved in water (400 mL) and extracted with ether (2 x 300 mL). The organic phases were combined, washed sequentially with water (300 mL) and brine (250 mL), and then dried over anhydrous magnesium sulfate. After drying, the solvent was filtered and evaporated. The resulting solid was ground with isohexane (150 mL) to give 2-amino-3-fluorobenzonitrile (9.8 g, 50% yield) as an off-white solid. Its 1H NMR (360 MHz, CDCl3) data were as follows: δ 4.47 (2H, s), 6.65-6.71 (1H, m), 7.14-7.20 (2H, m).

References

[1] Journal of Medicinal Chemistry, 2009, vol. 52, # 2, p. 278 - 292
[2] Patent: US2003/55060, 2003, A1
[3] Patent: WO2003/99816, 2003, A1. Location in patent: Page 55
[4] Patent: WO2003/93272, 2003, A1. Location in patent: Page/Page column 36
[5] Journal of Medicinal Chemistry, 2006, vol. 49, # 4, p. 1235 - 1238

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