(4-Nitro-pyrazol-1-yl)-acetic acid

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(4-Nitro-pyrazol-1-yl)-acetic acid Basic information
Product Name:(4-Nitro-pyrazol-1-yl)-acetic acid
Synonyms:(4-nitro-1H-pyrazol-1-yl)acetic acid(SALTDATA: FREE);ART-CHEM-BB B000219;CHEMBRDG-BB 5913009;(4-NITRO-1H-PYRAZOL-1-YL)ACETIC ACID;AKOS B000219;AKOS PAO-0916;TIMTEC-BB SBB000166;2-(4-nitro-1-pyrazolyl)acetic acid
CAS:6645-69-8
MF:C5H5N3O4
MW:171.11
EINECS:
Product Categories:
Mol File:6645-69-8.mol
(4-Nitro-pyrazol-1-yl)-acetic acid Structure
(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
pka3.33±0.10(Predicted)
AppearanceWhite to light yellow Solid
Safety Information
Hazard Codes Xi
HazardClass IRRITANT
MSDS Information
(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
4-Nitropyrazole

2075-46-9

Bromoacetic acid

79-08-3

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

6645-69-8

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
(4-Nitro-pyrazol-1-yl)-acetic acid Preparation Products And Raw materials
Raw materialsEthyl 2-(1H-pyrazol-1-yl)acetate-->4-Nitropyrazole-->Bromoacetic acid-->Water-->Potassium hydroxide-->Acetone
Preparation Products1H-Pyrazole-1-acetamide, 4-amino-N-(1-methylethyl)-
Tag:(4-Nitro-pyrazol-1-yl)-acetic acid(6645-69-8) Related Product Information
(3-Methoxy-4-nitro-pyrazol-1-yl)-acetic acid ethyl ester 2-(3,5-Dimethyl-4-nitro-pyrazol-1-yl)-propionic acid (4-Nitro-pyrazol-1-yl)-acetic acid ethyl ester (3-Nitro-pyrazol-1-yl)-acetic acid 2-Methyl-2-(4-nitro-pyrazol-1-yl)-propionic acid ethyl ester 2-(3-Methoxy-4-nitro-pyrazol-1-yl)-propionic acid methyl ester (5-Methyl-4-nitro-pyrazol-1-yl)-acetic acid 2-(3,5-Dimethyl-4-nitro-pyrazol-1-yl)-propionic acid ethyl ester (4-Nitro-pyrazol-1-yl)-acetic acid (5-Methyl-3-nitro-pyrazol-1-yl)-acetic acid (3,5-Dimethyl-4-nitro-pyrazol-1-yl)-acetic acid hydrazide (3,5-Dimethyl-4-nitro-pyrazol-1-yl)-acetic acid (4-Chloro-5-methyl-3-nitro-pyrazol-1-yl)-acetic acid ethyl ester (3-Methyl-4-nitro-pyrazol-1-yl)-acetic acid (3-Methyl-4-nitro-pyrazol-1-yl)-acetic acid hydrazide (3-Difluoromethyl-5-methyl-4-nitro-pyrazol-1-yl)-acetic acid (4-Chloro-3-nitro-pyrazol-1-yl)-acetic acid hydrazide 2-Methyl-2-(4-nitro-pyrazol-1-yl)-propionic acid