(4-NITRO-PYRAZOL-1-YL)-ACETIC ACID Chemical Properties

Boiling point:

416.4±25.0 °C(Predicted)

Density 

1.71±0.1 g/cm3(Predicted)

storage temp. 

2-8°C

pka

3.33±0.10(Predicted)

Appearance

White to light yellow Solid

Safety Information

Hazard Codes 

Xi

HazardClass 

IRRITANT

(4-NITRO-PYRAZOL-1-YL)-ACETIC ACID Usage And Synthesis

Uses

(4-Nitro-1H-pyrazol-1-yl)acetic Acid is used in pharmacological study of effects of C-nitropyrazoles and C-nitroazoles on ocular blood flow and retinal function recovery after ischemic insult.

Synthesis

An aqueous solution (100 mL) of potassium hydroxide (32.7 g, 0.58 mol) was slowly added to an acetone solution (500 mL) of 4-nitro-1H-pyrazole (30 g, 0.27 mol) under stirring at room temperature. After 30 minutes of reaction, an acetone solution (100 mL) of 2-bromoacetic acid (38.7 g, 0.27 mol) was added dropwise. The reaction mixture was continued to be stirred overnight. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure. The residue was diluted with water and extracted three times with ethyl acetate, the organic phases were combined and concentrated under reduced pressure. Subsequently, the residue was further extracted with a solvent mixture of dichloromethane and methanol, and the organic phases were combined and concentrated again under reduced pressure to give the target product 2-(4-nitro-1H-pyrazol-1-yl)acetic acid (40 g, 88% yield).

References

[1] Patent: WO2013/174895, 2013, A1. Location in patent: Page/Page column 70

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