2-Bromo-5-fluoropyridine Chemical Properties

Melting point:

30-31 °C (lit.)

Boiling point:

80-83 °C/44 mmHg (lit.)

Density 

1.707±0.06 g/cm3(Predicted)

refractive index 

1.5396

Flash point:

167 °F

storage temp. 

Inert atmosphere,Room Temperature

form 

Liquid

pka

-1.63±0.10(Predicted)

color 

Colorless to slightly yellow

BRN 

1561456

InChI

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

InChIKey

UODINHBLNPPDPD-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

41404-58-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn,F

Risk Statements 

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

Safety Statements 

26-36-16

RIDADR 

2811

WGK Germany 

3

Hazard Note 

Irritant

HazardClass 

6.1

PackingGroup 

III

HS Code 

29333990

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

2-Bromo-5-fluoropyridine Usage And Synthesis

Chemical Properties

Light yellow Cryst

Uses

2-Bromo-5-fluoropyridine can be used in the synthesis of the following:

• 5-fluoro-2-phenylpyridine via Suzuki coupling reaction with phenylboronic acid
• 5-fluoro-2-(p-tolyl)pyridine via Suzuki coupling reaction with p-tolylboronic acid

It can undergo palladium-catalyzed homo-coupling reaction to give the corresponding biaryl. It can also be employed in a palladium-catayzed α-arylation of esters leading to 4-pyridylcarboxypiperidines.

Uses

2-Bromo-5-fluoropyridine is used in the synthesis of mGluR5 antagonist for the treatment of neuropathic pain.

Synthesis

Example C Synthesis of 2-bromo-5-fluoropyridine: 2-Amino-5-fluoropyridine (6.5 g, 58 mmol) was added in batches to 48% hydrobromic acid (28.8 mL, 296 mmol) cooled to 0-5 °C. A solution formed from bromine (8.9 mL, 174 mmol) and sodium nitrite (10 g, 145 mmol) dissolved in 20 mL of water was added slowly and dropwise at 0-5 °C (note: nitrogen release). The reaction mixture was stirred for 1 hour and then quenched with concentrated hydrochloric acid. A 32% sodium hydroxide solution (50.5 mL, 0.55 mol) was then added. The reaction mixture was continued to be stirred for 20 minutes at room temperature and then extracted three times with ether. The combined organic phases were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure at 30 °C and 500 mbar (note: the product is volatile). The crude product was purified by rapid chromatography on silica gel with an elution gradient of dichloromethane/pentane (0:100 → 50:50). The final product was 2-bromo-5-fluoropyridine (6.7 g, 66% yield) in light yellow solid form.

References

[1] Patent: US2007/78155, 2007, A1. Location in patent: Page/Page column 29
[2] Patent: WO2016/44323, 2016, A1. Location in patent: Paragraph 0268
[3] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 19, p. 5349 - 5352

2-Bromo-5-fluoropyridine(41404-58-4)Related Product Information

• 1-Hexadecylpyridinium bromide
• Chromium picolinate
• Sulfasalazine
• 2-Bromo-5-chloropyridine
• 2-Bromopyridine
• Flupirtine
• 2-Fluoropyridine
• 2,6-Lutidine
• Ethyl bromodifluoroacetate
• 2-Chloro-3-cyanopyridine
• 2-Bromo-5-fluoropyrimidine
• 2-BROMO-5-METHOXYPYRIDINE
• 2-Bromo-5-methylpyridine
• 2-Bromo-6-(trifluoromethyl)pyridine
• 2-Bromo-6-methylpyridine
• 2-BROMO-5-IODOBENZYL ALCOHOL
• 2-Bromo-5-nitropyridine
• 2-Bromo-5-(trifluoromethyl)pyridine