4-BROMO-PYRIDINE-2-CARBONITRILE Chemical Properties

Melting point:

82-84°C

Boiling point:

265.3±20.0 °C(Predicted)

Density 

1.72±0.1 g/cm3(Predicted)

storage temp. 

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

solubility 

Chloroform (Slightly), Ethyl Acetate (Slightly)

form 

Solid

pka

-2.73±0.10(Predicted)

color 

Off-White to Light Beige

InChI

InChI=1S/C6H3BrN2/c7-5-1-2-9-6(3-5)4-8/h1-3H

InChIKey

CZXDCTUSFIKLIJ-UHFFFAOYSA-N

SMILES

C1(C#N)=NC=CC(Br)=C1

Safety Information

RIDADR 

3439

HazardClass 

6.1

PackingGroup 

Ⅲ

HS Code 

2933399990

Storage Class

11 - Combustible Solids

Hazard Classifications

Acute Tox. 4 Oral

4-BROMO-PYRIDINE-2-CARBONITRILE Usage And Synthesis

Chemical Properties

Off-Solid

Uses

4-Bromopyridine-2-Carbonitrile is a useful synthetic intermediate.

Synthesis

A. 4-Bromopyridine 1-oxide at room temperature. To a suspension of 4-bromopyridine hydrochloride (5.0 g, 25.9 mmol) in dichloromethane (50 mL) was added triethylamine (2.62 g, 25.9 mmol). After stirring for 0.5 h, 3-chloroperoxybenzoic acid (4.46 g, 25.9 mmol) was added in batches, and the reaction mixture was stirred at room temperature for 5 h. The solution was washed with saturated aqueous sodium thiosulfate (30 mL), saturated aqueous sodium carbonate (30 mL), and brine (30 mL), and dried over sodium sulfate. The solvent was removed under reduced pressure to give the crude product, which was purified on silica gel chromatography (eluting with 50-100% ethyl acetate in methanol) to give 4-bromopyridine 1-oxide, solid (2.1 g, 44.8% yield).

B.4-Bromopyridine-2-carbonitrile. A mixture of 4-bromopyridine 1-oxide (2.0 g, 11.56 mmol), trimethylmethylsilyl cyanide (3.43 g, 34.68 mmol) and triethylamine (2.34 g, 23.12 mmol) in acetonitrile (10 mL) was stirred under nitrogen at 110 ??C for 3 h. The reaction mixture was concentrated under reduced pressure and the residue was purified on a silica gel column (with petroleum ether eluting with 20% ethyl acetate in petroleum ether) to afford 4-bromopyridine-2-carbonitrile (1.52 g, 72.4% yield).

4-BROMO-PYRIDINE-2-CARBONITRILE(62150-45-2)Related Product Information

• 2-Fluoro-3-trifluoromethylpyridine
• 3-CHLORO-5-(TRIFLUOROMETHYL)PYRIDINE-2-CARBOXYLIC ACID
• 5-FLUORO-2-HYDROXY-3-NITROPYRIDINE
• 5-Bromo-3-chloropyridine-2-carboxylic acid
• 2-Amino-6-fluoropyridine
• 2-Bromo-5-fluoro-6-methylpyridine
• 2-Cyano-3-chloro-5-(trifluoromethyl)-pyridine
• 3-BROMO-PYRIDINE-2-CARBONITRILE
• 2-CHLORO-3-NITRO-5-(TRIFLUOROMETHYL)PYRIDINE
• 4-BROMO-PYRIDINE-2-CARBONITRILE
• 5-Bromo-2-pyridinecarbonitrile
• 6-BROMO-PYRIDINE-2-CARBONITRILE
• 2-Bromo-4-cyanopyridine
• 4-Bromo-2-methylpyridine
• 2-Cyanopyrimidine
• 3-AMINO-5-BROMO-PYRIDINE-2-CARBONITRILE
• 4-BROMO-3-METHYL-PYRIDINE-2-CARBONITRILE
• 4-BROMO-6-METHYL-PYRIDINE-2-CARBONITRILE