4-bromo-1-methylpyrazole-3-carboxy acid Chemical Properties

Melting point:

235-236 °C

Boiling point:

347.4±27.0 °C(Predicted)

Density 

1.93±0.1 g/cm3(Predicted)

storage temp. 

2-8°C

pka

1.75±0.37(Predicted)

Appearance

White to off-white Solid

Safety Information

HazardClass 

IRRITANT

4-bromo-1-methylpyrazole-3-carboxy acid Usage And Synthesis

Synthesis

1. 600 ml of anhydrous THF was added to a 2L reaction flask under argon protection. 2. 65.4 g of diisopropylamine was added and the reaction system was subsequently cooled to -78 °C via a dry ice acetone bath. 3. 258 ml of 2.5 M n-butyllithium solution was slowly added dropwise at 0 °C. After the dropwise addition, the reaction temperature was raised to 0 °C and maintained for 0.5 h. The reaction system was then cooled to -78 °C again. 4. 80.0 g of 1-methyl-4-bromopyrazole was slowly added dropwise at -78 °C, and after the dropwise addition was completed, the reaction temperature was maintained at -78 °C for 1 hour. 5. dry carbon dioxide gas was passed into the reaction system until TLC detection showed that the reaction was complete. 6. The pH of the reaction solution was slowly adjusted to 2-3 with 1N HCl, at which time a large amount of white solid was precipitated. 7. The reaction mixture was cooled at 0 °C for 3 h, followed by filtration to collect the white solid. 8. The resulting solid was dried at 40 °C for 16 h to give 77.3 g of white solid compound 22 (4-bromo-1-methyl-1H-pyrazole-5-carboxylic acid).

References

[1] Patent: CN108264520, 2018, A. Location in patent: Paragraph 0261; 0262; 0263; 0264; 0265

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