2-Bromo-5-fluoropyrimidine Chemical Properties

Boiling point:

255.0±32.0 °C(Predicted)

Density 

1.838±0.06 g/cm3(Predicted)

storage temp. 

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

form 

crystals

pka

-2.67±0.22(Predicted)

color 

Light brown/brown

InChI

InChI=1S/C4H2BrFN2/c5-4-7-1-3(6)2-8-4/h1-2H

InChIKey

ANSMRNCOBLTNBO-UHFFFAOYSA-N

SMILES

C1(Br)=NC=C(F)C=N1

CAS DataBase Reference

947533-45-1

Safety Information

HS Code 

2933599590

2-Bromo-5-fluoropyrimidine Usage And Synthesis

Synthesis

Step A: 2-chloro-5-fluoropyrimidine (2 mL, 22.18 mmol) was dissolved in propionitrile (20 mL) and bromotrimethylsilane (6 mL) was added. The reaction mixture was transferred to a sealed vial and heated at 150 °C for 1 hour. Upon completion of the reaction, the mixture was allowed to cool to room temperature and subsequently concentrated under reduced pressure. The concentrated residue was partitioned between ethyl acetate (EtOAc) and saturated aqueous sodium bicarbonate (NaHCO3). The organic phase was separated, dried over anhydrous sodium sulfate and concentrated again under reduced pressure. The resulting residue was dissolved in hexane and cooled overnight at -30 °C to precipitate a solid. The solid was collected by filtration to afford the target product 2-bromo-5-fluoropyrimidine (2.03 g, 51% yield). The structure of the product was confirmed by 1H NMR (300 MHz, CDCl3): δ 8.49 (s, 2H).

References

[1] Patent: US2012/53174, 2012, A1. Location in patent: Page/Page column 44

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