3-Bromo-2-methylpyridine Chemical Properties

Boiling point:

76°C/17mm

Density 

1.495

refractive index 

1.5604

Flash point:

174°F

storage temp. 

Inert atmosphere,Room Temperature

pka

3.59±0.10(Predicted)

form 

Liquid

color 

Clear, colorless to brown

InChI

InChI=1S/C6H6BrN/c1-5-6(7)3-2-4-8-5/h2-4H,1H3

InChIKey

AIPWPTPHMIYYOX-UHFFFAOYSA-N

SMILES

C1(C)=NC=CC=C1Br

CAS DataBase Reference

38749-79-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

22-37/38-41-36/37/38-20/21/22

Safety Statements 

26-36/39-36-36/37/39

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29333990

3-Bromo-2-methylpyridine Usage And Synthesis

Chemical Properties

colorless liquid

Uses

Conversion to the corresponding pyridine carboxaldehyde via peroxide initiated NBS gem-dibromination followed by hydrolysis.

Synthesis

The general procedure for synthesizing 2-methyl-3-bromopyridine from 2-methylpyridine was as follows: 2-methylpyridine (46.6 g) was slowly added dropwise to aluminum chloride (200 g) with reference to the method of Example 182, and the mixture was stirred continuously at 100°C. Maintaining the same temperature, bromine (40.0 g) was slowly added dropwise to the mixture over a period of 1 hour, followed by continued stirring for 30 minutes. Upon completion of the reaction, the mixture was cooled and poured into ice water, followed by addition of concentrated hydrochloric acid until the mixture was acidified. The resulting solution was washed with ethyl acetate and the aqueous layer was alkalized with 8 mol/L aqueous sodium hydroxide. The alkalized aqueous layer was extracted with ether and the extract was washed with saturated brine and dried with anhydrous sodium sulfate. Subsequently, the extract was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ether=10:1) to afford 2-methyl-3-bromopyridine as a colorless oil (yield 5.09 g, 12% yield). The structure of the product was confirmed by 1H-NMR (CDCl3): δ 2.67 (3H, s), 6.98-7.03 (1H, m), 7.78-7.82 (1H, m), 8.40-8.44 (1H, m).

References

[1] Patent: US2007/60623, 2007, A1. Location in patent: Page/Page column 50

3-Bromo-2-methylpyridine(38749-79-0)Related Product Information

• 1-Hexadecylpyridinium bromide
• 2-Picoline
• 2,4,6-Collidine
• 3-Pyridyl bromide
• 4-Methylpyridine
• Azamethiphos
• 2,6-Lutidine
• 2-Chloro-5-chloromethylpyridine
• 3-Bromoanisole
• 2-AMINO-3,5-DIBROMO-6-METHYLPYRIDINE
• 2,6-Dimethyl-3,5-dibromopyridine
• 6-AMINO-3-BROMO-2-METHYLPYRIDINE,2-AMINO-5-BROMO-6-METHYLPYRIDINE
• 3-Bromo-2,6-dimethylpyridine
• 3-Bromo-2,5-lutidine
• 3,5-Dibromo-2-methylpyridine
• 3-Bromo-2,4,6-trimethylpyridine
• 3,5-DIBROMO-2,4,6-TRIMETHYLPYRIDINE
• Bromine