4-Bromo-2-(difluoromethyl)pyridine Chemical Properties

Boiling point:

210.3±35.0 °C(Predicted)

Density 

1.640±0.06 g/cm3(Predicted)

storage temp. 

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

pka

0.27±0.10(Predicted)

form 

liquid

color 

Colourless to light yellow

InChI

InChI=1S/C6H4BrF2N/c7-4-1-2-10-5(3-4)6(8)9/h1-3,6H

InChIKey

MNMLGZMORMDPJI-UHFFFAOYSA-N

SMILES

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

Safety Information

HS Code 

2933399990

4-Bromo-2-(difluoromethyl)pyridine Usage And Synthesis

Synthesis

Step 1: Synthesis of 4-bromo-2-(difluoromethyl)pyridine: To 4-bromopyridine-2-carbaldehyde (5.0 g, 26.88 mmol) was added diethylamino sulfur trifluoride (7.03 mL, 53.7 mmol) at room temperature and the reaction mixture was stirred for 16 hours. Upon completion of the reaction, the reaction was quenched with aqueous sodium bicarbonate (50 mL) and subsequently extracted with ethyl acetate (3 x 100 mL). The organic layers were combined, washed with brine (2 x 50 mL), dried over anhydrous sodium sulfate, filtered and concentrated. Purification by silica gel column chromatography (100-200 mesh) using a hexane solution of 5% ethyl acetate as eluent afforded 4-bromo-2-(difluoromethyl)pyridine (3.0 g, 14.492 mmol, 54% yield).1H NMR (400 MHz, CDCl3) δ= 8.48 (d, J = 4.9 Hz, 1H), 7.82 (d, J = 1.5 Hz, 1H), 7.66-7.50 (m, 1H), 6.60 (t, 1H).LCMS: 207.9 [M + H]+.

References

[1] Patent: WO2016/161160, 2016, A1. Location in patent: Paragraph 0207
[2] Patent: US2015/152108, 2015, A1. Location in patent: Paragraph 0480; 0481
[3] Patent: WO2016/79709, 2016, A1. Location in patent: Page/Page column 179
[4] Patent: US2010/125082, 2010, A1. Location in patent: Page/Page column 24; 25
[5] Patent: WO2015/180612, 2015, A1. Location in patent: Page/Page column 78