2-Cyano-5-fluoropyridine Chemical Properties

Melting point:

35-41 °C

Boiling point:

214.9±20.0 °C(Predicted)

Density 

1.24±0.1 g/cm3(Predicted)

Flash point:

99 °C

storage temp. 

Inert atmosphere,Room Temperature

solubility 

soluble in Methanol

form 

powder to crystal

pka

-2.74±0.10(Predicted)

color 

White to Almost white

InChI

InChI=1S/C6H3FN2/c7-5-1-2-6(3-8)9-4-5/h1-2,4H

InChIKey

BHXHRMVSUUPOLX-UHFFFAOYSA-N

SMILES

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

Safety Information

Hazard Codes 

Xn,N

Risk Statements 

22-41-50/53

Safety Statements 

26-39-60-61

RIDADR 

UN3439

WGK Germany 

3

HazardClass 

6.1

PackingGroup 

III

HS Code 

2933399990

2-Cyano-5-fluoropyridine Usage And Synthesis

Uses

5-Fluoro-2-pyridinecarbonitrile is a biochemical reagent that can be used as a biological material or organic compound for life science related research.

Definition

ChEBI: 2-Cyano-5-fluoropyridine is a member of pyridines.

Synthesis

General procedure for the synthesis of 2-cyano-5-fluoropyridine from 3-amino-6-cyanopyridine: Sodium nitrite (8.7 g, 126 mmol) was added in batches to ice-salt-bath-cooled 5-amino-pyridine-2-carbonitrile (10.03 g, 84.2 mmol) dissolved in a solution of 70% hydrogen fluoride-pyridine (Aldrich, 100 g, 3.5 mol HF) ( Note: the reaction was carried out in a special reaction flask). The reaction solution was dark red in color, and after stirring in an ice-salt bath for 45 min, the ice bath was removed and the mixture continued to be stirred at room temperature for 30 min, followed by heating at 80 °C for 1.5 h. The reaction was carried out in a special reaction flask. Upon completion of the reaction, the reaction mixture was quenched by slowly pouring it into an ice/water mixture (about 400 g), extracted with dichloromethane (6 x 150 mL), the organic phase was dried over anhydrous magnesium sulfate, filtered and the solvent was concentrated under reduced pressure. The resulting crude product (10.08 g, 98% yield, orange solid) was pure enough for subsequent use and did not require further purification. The product was characterized by 1H NMR (CDCl3, 300 MHz): δ= 8.61 (d, 1H), 7.78 (m, 1H), 7.58 (m, 1H).GC-MS showed the molecular ion peak M+ 122.

References

[1] Patent: WO2005/66155, 2005, A1. Location in patent: Page/Page column 23
[2] Patent: EP1621537, 2006, A1. Location in patent: Page/Page column 57-58
[3] Patent: EP1640366, 2006, A1. Location in patent: Page/Page column 137-138
[4] Patent: EP1803719, 2007, A1. Location in patent: Page/Page column 27
[5] Patent: US2010/41717, 2010, A1. Location in patent: Page/Page column 41-42

2-Cyano-5-fluoropyridine(327056-62-2)Related Product Information

• 2-Pyrimidinecarbonitrile, 5-chloro- (9CI)
• 4-CHLORO-PYRIDINE-2-CARBONITRILE
• 5-Bromo-6-methyl-2-pyridinecarbonitrile
• 2-Cyano-5-methylpyridine
• 4-Bromomethyl-2-cyanobiphenyl
• 5-Bromo-2-pyridinecarbonitrile
• 2-BROMO-5-NITRO-6-PICOLINE
• 3-Amino-5-fluoropyridine
• 2-METHOXY-5-NITRO-6-PICOLINE
• 2-Pyridinecarboxylic acid, 3-fluoro-4-iodo-
• 3-FLUOROPYRIDINE-2-CARBOXYLIC ACID
• 4-Methoxy-3-nitropyridine
• 2-HYDROXY-5-NITRO-3-(TRIFLUOROMETHYL)PYRIDINE
• 2-Cyano-4-fluoropyridine
• 3-Bromo-2-cyanopyridine
• 6-Methylpyridine-2-carbonitrile
• (5-TRIFLUOROMETHYL-PYRIDIN-2-YL)-ACETONITRILE
• 2-Cyano-5-nitropyridine