2-Amino-3-fluoropyridine Chemical Properties

Melting point:

41-45 °C

Boiling point:

110°C/65mmHg(lit.)

Density 

1.257±0.06 g/cm3(Predicted)

Flash point:

90℃

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

pka

3.95±0.36(Predicted)

form 

powder to crystal

color 

White to Gray to Brown

InChI

InChI=1S/C5H5FN2/c6-4-2-1-3-8-5(4)7/h1-3H,(H2,7,8)

InChIKey

WWEINXQNCAWBPD-UHFFFAOYSA-N

SMILES

C1(N)=NC=CC=C1F

CAS DataBase Reference

21717-95-3

Safety Information

Hazard Codes 

T,Xi,Xn

Risk Statements 

36/37/38-36-22

Safety Statements 

26-36/37/39

RIDADR 

UN2811

WGK Germany 

3

HazardClass 

IRRITANT

HazardClass 

6.1

HS Code 

29333990

2-Amino-3-fluoropyridine Usage And Synthesis

Chemical Properties

Light yellow Cryst

Uses

2-Amino-3-fluoropyridine is a reagent used in the synthesis of potent sigma-1 receptor antagonists and mu opioid receptor agonists for the treatment of neuropathic pain.

Synthesis

General procedure for the synthesis of 2-amino-3-fluoro-5-chloropyridine from 2-amino-3-fluoro-5-chloropyridine: 2-amino-3-fluoro-5-chloropyridine (50 g, 0.341 mol) and methanol (600 mL) were added to a 1000 mL single-necked round-bottomed flask, and stirred until completely dissolved. Ammonia (50 mL) and Pd/C catalyst (2.5 g, 23.5 mmol) were then added. The catalytic hydrogenation reaction was carried out under hydrogen atmosphere until the reaction was complete. After completion of the reaction, the Pd/C catalyst was removed by filtration and the filter cake was washed with methanol. The filtrate and washings were combined and concentrated under reduced pressure to give a white solid crude. The crude was dissolved in water (200 mL x 4) and extracted with ethyl acetate. The organic layer was collected, dried with anhydrous sodium sulfate and concentrated under reduced pressure. Finally, the concentrate was pulped with a small amount of petroleum ether and filtered to give 34.50 g of white crystal product in 90.20% yield.

References

[1] Patent: CN105669539, 2016, A. Location in patent: Paragraph 0061; 0062; 0063

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