2-Chloro-5-fluoronicotinonitrile Chemical Properties

Boiling point:

235℃

Density 

1.43

Flash point:

96℃

storage temp. 

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

pka

-4.51±0.10(Predicted)

form 

solid

color 

White to off-white

InChI

InChI=1S/C6H2ClFN2/c7-6-4(2-9)1-5(8)3-10-6/h1,3H

InChIKey

SUBZTZVHVGYOPM-UHFFFAOYSA-N

SMILES

C1(Cl)=NC=C(F)C=C1C#N

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

HS Code 

2933399990

2-Chloro-5-fluoronicotinonitrile Usage And Synthesis

Synthesis

Example 3A: Synthesis of 2-chloro-5-fluoronicotinonitrile 81.2 mL (582.25 mmol) of triethylamine was added to a 783 mL dichloromethane suspension containing 46.2 g (264.66 mmol) of 2-chloro-5-fluoronicotinonitrile, and the mixture was subsequently cooled to 0°C. Under continuous stirring, 41.12 mL (291.13 mmol) of trifluoroacetic anhydride was slowly added dropwise, and after completion of the dropwise addition, the reaction mixture was kept at 0 °C with continued stirring for 1.5 hours. After completion of the reaction, the reaction mixture was washed twice with saturated aqueous sodium bicarbonate (391 mL each time), and the organic phase was dried and concentrated under reduced pressure to give the crude product. The final product was 2-chloro-5-fluoronicotinonitrile with a yield of 42.1 g and 90% yield. The product was characterized by 1H NMR (400 MHz, DMSO-d6): δ= 8.66 (dd, 1H), 8.82 (d, 1H).

References

[1] Patent: WO2013/25958, 2013, A1. Location in patent: Page/Page column 57; 58
[2] Patent: TWI609011, 2017, B. Location in patent: Page/Page column 77; 78
[3] Patent: EP2680844, 2016, B1. Location in patent: Paragraph 0134
[4] Patent: EP2744501, 2016, B1. Location in patent: Paragraph 0164; 0166
[5] Patent: TW2018/8946, 2018, A. Location in patent: Page/Page column 67

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