4-AMINO-5-BROMO-3-METHYLPYRIDINE Chemical Properties

Melting point:

115.0 °C

Boiling point:

290.0±35.0 °C(Predicted)

Density 

1.593±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

pka

7.34±0.24(Predicted)

Appearance

White to off-white Solid

InChI

InChI=1S/C6H7BrN2/c1-4-2-9-3-5(7)6(4)8/h2-3H,1H3,(H2,8,9)

InChIKey

GUAFGBUKLIFASX-UHFFFAOYSA-N

SMILES

C1=NC=C(C)C(N)=C1Br

Safety Information

HS Code 

2933399990

4-AMINO-5-BROMO-3-METHYLPYRIDINE Usage And Synthesis

Synthesis

The general procedure for the synthesis of 3-methyl-4-amino-5-bromopyridine from 3-methyl-4-aminopyridine is as follows: Step 1: To a solution of 4-amino-3-methylpyridine (97, 10 g, 0.092 mol) and hydrobromic acid (HBr, 50 mL) heated to 70 °C was slowly added 15% hydrogen peroxide (H2O2, 16 mL) over a period of 1 hour. The reaction mixture was continued to be stirred at 70 °C for 1 h. The reaction was subsequently quenched by pouring into ice (100 g). The pH of the reaction mixture was adjusted to about 5 with 50% sodium hydroxide (NaOH) solution and the resulting red precipitate was collected by filtration. Subsequently, the pH of the filtrate was adjusted to about 9 and the resulting white precipitate was collected by filtration to afford 3-methyl-4-amino-5-bromopyridine (98, 13.5 g, 78% yield).

References

[1] Patent: WO2005/16892, 2005, A1. Location in patent: Page/Page column 104
[2] Journal fuer Praktische Chemie (Leipzig), 1989, vol. 331, # 3, p. 369 - 374
[3] Journal fuer Praktische Chemie (Leipzig), 1989, vol. 331, # 3, p. 369 - 374
[4] Patent: US2013/5705, 2013, A1

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