5-BROMO-3-CHLORO-2-METHYLPYRIDINE Chemical Properties

Boiling point:

208℃

Density 

1.624

Flash point:

80℃

storage temp. 

Inert atmosphere,Room Temperature

pka

1.31±0.20(Predicted)

Appearance

White to off-white Solid

Safety Information

RIDADR 

UN2811

HS Code 

2933399990

5-BROMO-3-CHLORO-2-METHYLPYRIDINE Usage And Synthesis

Uses

5-BROMO-3-CHLORO-2-METHYLPYRIDINE is a heterocyclic compound that belongs to the pyridine family. It is characterized by its unique structure and functional groups, including a bromo and chloro substituent, which make it highly reactive and versatile. It serves as an important intermediate in the synthesis of pharmaceuticals, agrochemicals, and specialty chemicals, and is also used as a reagent in organic synthesis and medicinal chemistry.

Synthesis

General procedure for the synthesis of 2-methyl-3-chloro-5-bromopyridine from diethyl 2-(5-bromo-3-chloropyridin-2-yl)malonate: firstly, impure diethyl 2-(5-bromo-3-chloropyridin-2-yl)malonate (Intermediate 42, 0.41 g, 1.2 mmol) was dissolved in a concentrated aqueous hydrochloric acid solution (3 mL), and heated and refluxed for 3 hours. Upon completion of the reaction, volatiles were removed by vacuum distillation and the residue was co-evaporated with acetonitrile. Subsequently, the resulting monodeoxycarboxylic acid solid was dissolved in dioxane (4.5 mL) and heated to reflux overnight. The volatiles were again removed by vacuum distillation. Finally, the residue was purified by fast chromatography (using 4 g SiO2, heptane/EtOAc gradient elution) to afford the target product 2-methyl-3-chloro-5-bromopyridine (0.12 g, 51% yield). The product was characterized by 1H NMR (500 MHz, CDCl3): δ 2.60 (s, 3H), 7.82 (d, 1H), 8.46 (d, 1H); the mass spectrum (CI) showed m/z 206 [M + H]+.

References

[1] Patent: US2012/165347, 2012, A1. Location in patent: Page/Page column 32

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