3-Bromo-5-methylpyridine Chemical Properties

Melting point:

16.5-16.7 °C

Boiling point:

110°C/25mmHg(lit.)

Density 

1.4869 g/mL at 25 °C

refractive index 

1.5618

Flash point:

91 °C

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

pka

3.16±0.20(Predicted)

form 

powder to lump to clear liquid

color 

White or Colorless to Almost white or Almost colorless

CAS DataBase Reference

3430-16-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-41-22

Safety Statements 

26-36/37/39-39

RIDADR 

NA 1993 / PGIII

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

2933399990

3-Bromo-5-methylpyridine Usage And Synthesis

Chemical Properties

Light yellow liquid

Uses

5-Bromo-3-picoline is an intermediate of pyridinyl pyrrole compounds as proton pump inhibitors with improved gastric acid secretion suppressive activity

Synthesis

The general procedure for the synthesis of 3-bromo-5-methylpyridine from 3,5-dibromopyridine and trimethylcyclotriboroxane was as follows: under nitrogen protection, cesium carbonate (1.38 g, 4.22 mmol), trimethylcyclotriboroxane (0.2 mL, 1.47 mmol), and tetrakis(triphenylphosphine)palladium(0) (0.488 g, 0.42 mmol ). Subsequently, a solution of 3,5-dibromopyridine (1.0 g, 4.22 mmol) dissolved in a 9:1 solvent mixture of dioxane and water (10 mL) was added. The reaction mixture was stirred at 110 °C for 16 hours. Upon completion of the reaction, trimethylcyclotriboroxane (0.2 mL, 1.47 mmol) was added again and the reaction temperature was lowered to 100 °C and the reaction continued to be stirred for 16 hours. At the end of the reaction, the reaction mixture was cooled to room temperature, filtered through diatomaceous earth and the filter cake was washed with ethyl acetate. The filtrate was concentrated and the resulting residue was purified by silica gel column chromatography with the eluent being a 80:20 solvent mixture of hexane and ethyl acetate, resulting in 3-bromo-5-methylpyridine as a colorless oil (0.654 g, 90% yield). The product was identified by 1H NMR (300 MHz, CDCl3): δ 2.34 (s, 3H), 7.66 (s, 1H), 8.36 (s, 1H), 8.49 (s, 1H).GC-MS (EI) analysis showed: m/z = 171.0, 173.0 [M].

References

[1] Patent: WO2005/94822, 2005, A1. Location in patent: Page/Page column 25

3-Bromo-5-methylpyridine(3430-16-8)Related Product Information

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• 2,5-DIBROMO-6-METHYLPYRIDINE
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