2-Bromo-5-trifluoromethoxypyridine Chemical Properties

Boiling point:

63-66 °C(Press: 11 Torr)

Density 

1.737±0.06 g/cm3(Predicted)

storage temp. 

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

pka

-3.55±0.10(Predicted)

form 

liquid

color 

Clear, almost colourless

InChI

InChI=1S/C6H3BrF3NO/c7-5-2-1-4(3-11-5)12-6(8,9)10/h1-3H

InChIKey

RKXYQQVLVNEAFB-UHFFFAOYSA-N

SMILES

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

Safety Information

Risk Statements 

43

Safety Statements 

36/37

RIDADR 

2810

HazardClass 

6.1

PackingGroup 

Ⅲ

HS Code 

2933399990

2-Bromo-5-trifluoromethoxypyridine Usage And Synthesis

Synthesis

General procedure for the synthesis of 2-bromo-5-trifluoromethoxypyridine: 2-chloro-5-(trifluoromethoxy)pyridine (6, 7.0 g, 35.4 mmol) and bromotrimethylsilane (10.8 g, 9.3 mL, 70.8 mmol, 2 eq.) were dissolved in propionitrile (35 mL) and heated to reflux for 24 hours. The reaction process was monitored by gas chromatography (GC) to confirm 100% conversion. Upon completion of the reaction, the mixture was vacuum distilled to afford pure 2-bromo-5-trifluoromethoxypyridine (31, 7.0 g, 28.7 mmol, 81% yield) as a colorless oil. Boiling point: 63-66°C (14 mbar). NMR data: 1H NMR (CDCl3, 300 MHz): δ= 8.34 (d, J = 2.8 Hz, 1H), 7.56 (d, J = 8.7 Hz, 1H), 7.45 (dd, J = 8.7, 2.8 Hz, 1H). 19F NMR (CDCl3, 282 MHz): δ= -58.8. 13C NMR (CDCl3, 75 MHz): δ= 145.6, 143.1, 139.2, 131.4, 129.0, 120.1 (q, J = 260 Hz). Elemental analysis: C6H3BrF3NO (molecular weight 241) Calculated value (%): C 29.78, H 1.25, N 5.79; measured value: C 29.96, H 1.41, N 5.64.

References

[1] Patent: WO2010/40461, 2010, A1. Location in patent: Page/Page column 38-39
[2] European Journal of Organic Chemistry, 2010, # 31, p. 6043 - 6066

2-Bromo-5-trifluoromethoxypyridine(888327-36-4)Related Product Information

• 4-Bromopyridine hydrochloride
• Pyridinium tribromide
• 3-Pyridyl bromide
• 2-Bromopyridine
• 2-Chloro-5-trifluoromethylpyridine