3-Bromo-5-fluoropyridine Chemical Properties

Melting point:

24-28 °C

Boiling point:

78 °C / 11mmHg

Density 

1.707±0.06 g/cm3(Predicted)

Flash point:

148 °F

storage temp. 

Inert atmosphere,Room Temperature

pka

0.45±0.20(Predicted)

form 

Low Melting Solid or Liquid

color 

Colorless to white

InChI

InChI=1S/C5H3BrFN/c6-4-1-5(7)3-8-2-4/h1-3H

InChIKey

HNNNBQRRIHKFLI-UHFFFAOYSA-N

SMILES

C1=NC=C(F)C=C1Br

CAS DataBase Reference

407-20-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,Xi,F

Risk Statements 

22-37/38-41-36/37/38-20/21/22-10

Safety Statements 

26-39-36-16

RIDADR 

UN2811

WGK Germany 

3

Hazard Note 

Irritant

HazardClass 

6.1

HS Code 

29333990

MSDS

• Language:English Provider:SigmaAldrich

3-Bromo-5-fluoropyridine Usage And Synthesis

Chemical Properties

Colorless liquid

Synthesis

Step 2: Synthesis of 3-bromo-5-fluoropyridine To a cooled solution of 10.0 g (0.058 mol) of 3-amino-5-bromopyridine dissolved in 59 mL of 50% tetrafluoroboric acid was added dropwise at -10 °C a solution prepared from 4.19 g (0.06 mol) of sodium nitrite dissolved in 13 mL of water. The reaction mixture was stirred at -8°C for 1 hr and then 150 mL of ether was added. The crude diazonium salt was collected by filtration and washed with ether. Subsequently, the crude diazonium salt was added in batches to 200 mL of toluene preheated to 80°C. The reaction mixture was stirred at 90°C for 1 hour and then the organic phase was concentrated. The light yellow residue was suspended in 150 mL of water and the pH was adjusted with 32% sodium hydroxide solution to 11. The aqueous phase was extracted three times with 200 mL of dichloromethane. The organic phases were combined, washed with water, dried over magnesium sulfate, and concentrated. The crude product was purified by vacuum distillation (10 mbar, 35 °C) to give 15.4 g of brown oil, which was further purified to give 5.6 g (0.032 mol, 55% yield) of the target compound 3-bromo-5-fluoropyridine as a colorless oil (ISP): m/e = 176.1, 178.1 (M + H+).

References

[1] Patent: US2006/199960, 2006, A1. Location in patent: Page/Page column 21
[2] Recueil des Travaux Chimiques des Pays-Bas, 1955, vol. 74, p. 1062,1068

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