3-Bromo-4-cyanopyridine Chemical Properties

Melting point:

92-94℃

Boiling point:

267.5±25.0 °C(Predicted)

Density 

1.72±0.1 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

form 

powder to crystal

pka

-0.48±0.18(Predicted)

color 

White to Gray to Brown

CAS DataBase Reference

13958-98-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

T

Risk Statements 

25

Safety Statements 

45

RIDADR 

UN 2811 6.1 / PGIII

PackingGroup 

III

HS Code 

2933399990

3-Bromo-4-cyanopyridine Usage And Synthesis

Uses

3-Bromo-4-cyanopyridine is used in the synthesis of nicotinic receptor ligands which have application towards diseases such as nicotinic addiction,, neurodegenerative and cognitive disorders. It is al so used in the synthesis of orally bioavailable cannabinoid receptor 2 agonists for use as analgesic and anti-inflammatory agents.

Synthesis

3-Bromopyridine-4-carboxamide (687 mg, 3.4 mmol) was used as a raw material and was slowly added to phosphoryl chloride (5.0 mL) at 0 °C. The reaction mixture was then stirred under reflux conditions for 2 hours. Upon completion of the reaction, the mixture was cooled to room temperature and slowly poured into ice (100 g) under stirring and neutralized with 5 M aqueous sodium hydroxide solution (60 mL). The neutralized mixture was extracted with ether (2 x 50 mL). The organic layers were combined and sequentially washed with saturated aqueous sodium bicarbonate solution, treated with activated carbon and filtered. Subsequently, the solvent was removed by evaporation to give the crude product. The crude product was purified by recrystallization from petroleum ether to afford the target compound 3-bromo-4-cyanopyridine (292 mg, 42% yield) as an off-white powder. The product characterization data were as follows: melting point 79-81 °C (literature value 96.6-98.2 °C); 1H NMR (CDCl3) δ 7.53 (1H, d, J = 4.9 Hz, 5-H), 8.69 (1H, d, J = 4.9 Hz, 6-H), 8.92 (1H, s, 2-H); 13C NMR (CDCl3) (HSQC/HMBC ) δ 114.79 (C≡N), 122.14 (4-C), 124.17 (3-C), 126.75 (5-C), 148.76 (6-C), 152.69 (2-C); MS (ESI) m/z 182.9552 (M + H) (C6H4N2 79Br) Theoretical value 182.9541.

References

[1] Organic Preparations and Procedures International, 1997, vol. 29, # 5, p. 577 - 579
[2] Patent: WO2014/87165, 2014, A1. Location in patent: Page/Page column 132
[3] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 13, p. 3013 - 3032
[4] Patent: US2013/217705, 2013, A1. Location in patent: Paragraph 0184; 0185

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