3-Fluoro-4-aminobenzonitrile Chemical Properties

Melting point:

70-74

Boiling point:

264.2±25.0 °C(Predicted)

Density 

1.25±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

soluble in Methanol

form 

powder to crystal

pka

0.33±0.10(Predicted)

color 

White to Light yellow to Light orange

InChIKey

RLMBRRQWBTWGMB-UHFFFAOYSA-N

CAS DataBase Reference

63069-50-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,T

Risk Statements 

20/21/22-36/38

Safety Statements 

26-36/37

RIDADR 

UN3439

Hazard Note 

Irritant

HazardClass 

6.1

PackingGroup 

III

HS Code 

29269090

3-Fluoro-4-aminobenzonitrile Usage And Synthesis

Chemical Properties

Off-white to brown crystalline

Uses

4-Amino-3-fluorobenzonitrile is used in preparation of substituted 1,6-Naphthyridine inhibitors of CDK5.

Synthesis

Step 1: Synthesis of 4-amino-3-fluorobenzonitrile 2-Fluoro-4-iodoaniline (2.0 g, 8.4 mmol) and cuprous cyanide (982 mg, 11.0 mmol, 1.5 eq.) were added to N,N-dimethylformamide (DMF, 30 mL). The reaction mixture was heated to 130 °C and the reaction was stirred at this temperature for 8 hours. After completion of the reaction, the mixture was cooled to room temperature and diluted with ethyl acetate. The diluted solution was washed sequentially with deionized water (2 times) and saturated saline, and then dried with anhydrous magnesium sulfate. The dried solution was concentrated by filtration and the crude product obtained was purified by column chromatography (eluent: n-hexane/ethyl acetate = 3:1, v/v) to give the white solid product 4-amino-3-fluorobenzonitrile (914 mg, 84% yield). 1H NMR (300 MHz, CDCl3): δ 7.21-7.26 (m, 2H), 6.74 (t, 1H, J = 8.3 Hz), 4.20 (bs, 2H).

References

[1] Patent: WO2007/120012, 2007, A1. Location in patent: Page/Page column 82-83; 129
[2] Patent: WO2006/63113, 2006, A2. Location in patent: Page/Page column 68-69

3-Fluoro-4-aminobenzonitrile(63069-50-1)Related Product Information

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