2-Cyano-3-fluoropyridine Chemical Properties

Melting point:

27-30°C

Boiling point:

120-125 °C(Press: 17 Torr)

Density 

1.24±0.1 g/cm3(Predicted)

Flash point:

104 °C

storage temp. 

Inert atmosphere,Room Temperature

solubility 

Chloroform (Sparingly), DMSO (Slightly)

form 

Solid

pka

-2.74±0.10(Predicted)

color 

White to Off-White

InChI

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

InChIKey

VZFPSCNTFBJZHB-UHFFFAOYSA-N

SMILES

C1(C#N)=NC=CC=C1F

CAS DataBase Reference

97509-75-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

T,Xi,Xn

Risk Statements 

20/21/22-36/37/38-41-37/38

Safety Statements 

26-36/37/39-23

RIDADR 

3276

WGK Germany 

3

Hazard Note 

Toxic

HazardClass 

6.1

PackingGroup 

III

HS Code 

29333990

2-Cyano-3-fluoropyridine Usage And Synthesis

Chemical Properties

Light yellow Cryst

Uses

2-Cyano-3-fluoropyridine is an organic intermediate that can be prepared from 3-fluoropyridine in three steps.

Synthesis

Using 3-fluoropyridine-N-oxide (Intermediate A, 2.85 g, 25.2 mmol) and trimethylcyanosilane (10.0 mL, 75.6 mmol) as raw materials, Intermediate A was dissolved in dichloromethane (25 ml) at room temperature, followed by addition of trimethylcyanosilane. The reaction mixture was heated to reflux for 10 hours. After completion of the reaction, it was cooled to room temperature and the reaction was quenched by the addition of saturated aqueous sodium bicarbonate solution (30 mL). The reaction mixture was extracted with dichloromethane (3 x 150 mL), the organic phases were combined and dried over anhydrous sodium sulfate. After filtration, the organic phase was concentrated under reduced pressure to give a light brown oily crude product (4.60 g). The crude product was purified by rapid column chromatography on silica gel, the eluent was hexane solution of 30% ethyl acetate to give a light brown oil, which solidified to light brown solid product B (2.48 g, 84% yield) after standing. The product was analyzed by HPLC with a retention time of 1.03 min.

References

[1] Patent: WO2003/90912, 2003, A1. Location in patent: Page/Page column 65
[2] Chemical and Pharmaceutical Bulletin, 1985, vol. 33, # 2, p. 565 - 571
[3] Patent: WO2006/12374, 2006, A1. Location in patent: Page/Page column 213
[4] Patent: US2004/77605, 2004, A1
[5] Patent: US2003/232842, 2003, A1. Location in patent: Page 7-8

2-Cyano-3-fluoropyridine(97509-75-6)Related Product Information

• 2-Cyano-3,5-difluoropyridine
• 2-Fluoropyridine
• 3-Methylpicolinonitrile
• 3-Fluoropyridine
• Methylene dithiocyanate
• 3-Aminopyridine
• Sodium cyanoborohydride
• 2-Cyanopyridine
• 5-Bromo-3-fluoro-pyridine-2-carbonitrile
• 5-Bromo-3-nitropyridine-2-carbonitrile
• 5-bromo-3-methylpicolinonitrile
• 2-Cyano-3-chloropyridine
• 3-bromo-5-chloropyridine-2-carbonitrile
• 5-bromo-3-chloropyridine-2-carbonitrile
• 2-Cyano-3-trifluoromethylpyridine
• 5-Chloro-3-nitropyridine-2-carbonitrile
• 3,5-Dichloro-2-cyanopyridine
• 3-Bromo-5-methylpyridine-2-carbonitrile