5-Bromo-2-chloro-3-cyanopyridine Chemical Properties

Melting point:

138.0 to 142.0 °C

Boiling point:

272.7±35.0 °C(Predicted)

Density 

1.85±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

pka

-4.56±0.10(Predicted)

form 

Solid

color 

White to Yellow to Green

Water Solubility 

Slightly soluble in water.

InChI

InChI=1S/C6H2BrClN2/c7-5-1-4(2-9)6(8)10-3-5/h1,3H

InChIKey

MQOHJAYYYVQBSH-UHFFFAOYSA-N

SMILES

C1(Cl)=NC=C(Br)C=C1C#N

Safety Information

Hazard Codes 

Xi,T

Risk Statements 

25-37/38-41

Safety Statements 

26-39

RIDADR 

UN 2811 6.1 / PGIII

WGK Germany 

3

HazardClass 

6.1

HazardClass 

IRRITANT

PackingGroup 

III

HS Code 

2933399990

5-Bromo-2-chloro-3-cyanopyridine Usage And Synthesis

Uses

5-Bromo-2-chloro-3-cyanopyridine is used as pharmaceutical intermediate.

Synthesis

Synthesis of 5-bromo-2-chloronicotinonitrile (13): 5-bromo-2-oxo-1,2-dihydropyridine-3-carbonitrile (12) (69 mg, 0.35 mmol) was mixed with phosphorus pentachloride (PCl5) (109 mg, 0.52 mmol) in phosphorus oxychloride (POCl3) (5 mL), and the reaction was carried out at reflux overnight. Upon completion of the reaction, the reaction mixture was cooled to room temperature and slowly added dropwise to ice water. The pH was adjusted to 8 with 4 M sodium hydroxide (NaOH) solution and then extracted with dichloromethane (CH2Cl2) (3 x 30 mL). The organic phases were combined, washed sequentially with aqueous sodium bicarbonate (NaHCO3) and saturated saline, dried over anhydrous sodium sulfate (Na2SO4), and concentrated under reduced pressure. Purification by column chromatography (petroleum ether/ethyl acetate=20:1) afforded the target product 5-bromo-2-chloronicotinonitrile (13) (63 mg, 84% yield) as a yellow solid. Melting point: 138~139°C. 1H NMR (400MHz, CDCl3): δ8.66 (d, J=2.4Hz, 1H), 8.12 (d, J=2.4Hz, 1H).

References

[1] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 9, p. 1577 - 1580
[2] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 20, p. 5578 - 5585
[3] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 16, p. 3251 - 3255
[4] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 23, p. 6578 - 6581
[5] Patent: US2004/19052, 2004, A1. Location in patent: Page/Page column 17

5-Bromo-2-chloro-3-cyanopyridine(405224-23-9)Related Product Information

• BROMOCHLORODIFLUOROMETHANE
• 5-Bromo-2-chloronicotinic acid
• Chlorobromoisocyanurate
• 2-Chloro-3-cyanopyridine
• 5-BROMO-2-CHLORO-4,6-DIMETHYLNICOTINONITRILE
• SPECS AO-801/41077570
• 5-Bromo-2-chloro-3-cyanopyridine
• 2-Chloro-3-methyl-5-bromopyridine
• 5-Bromonicotinonitrile