4-Nitropyrazole-3-carboxylic acid

Base Information

• Chemical Name: 4-Nitropyrazole-3-carboxylic acid
• CAS No.: 5334-40-7
• Molecular Formula: C4H3N3O4
• Molecular Weight: 157.086
• Hs Code.: 29339900
• Mol file: 5334-40-7.mol

Synonyms:4-nitro pyrazole-3-carboxylic acid;Pyrazole-3(or5)-carboxylic acid, 4-nitro- (6CI);Pyrazole-3-carboxylic acid, 4-nitro- (8CI);4-Nitro-1H-pyrazol-3-carboxylic acid;4-Nitro-1H-pyrazole-3-carboxylic acid;4-Nitropyrazole-3-carboxylic acid;4-Nitropyrazole-5-carboxylic acid;NSC 1411;

Chemical Property of 4-Nitropyrazole-3-carboxylic acid

Chemical Property:

• Appearance/Colour: White to off-white crystalline powder
• Vapor Pressure: 3.3E-11mmHg at 25°C
• Melting Point: 195°C
• Refractive Index: 1.679
• Boiling Point: 509.596 °C at 760 mmHg
• PKA: 1.41±0.35(Predicted)
• Flash Point: 261.995 °C
• PSA: 111.80000
• Density: 1.84 g/cm³
• LogP: 0.53930
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature

Purity/Quality:

98% ^*data from raw suppliers

4-Nitro-1H-pyrazole-3-carboxylicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 22-36/37/39-37/39-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• General Description: 4-Nitropyrazole-3-carboxylic acid is a key intermediate used in the synthesis of 4-benzoylamino-1H-pyrazole-3-carboxamide derivatives, which were designed as potent and selective CDK2 inhibitors for cancer therapy. Its role in the synthetic pathway contributes to the development of compounds like DC-K2in212, which exhibit high CDK2 inhibition, antiproliferative effects, and low toxicity, demonstrating potential as anticancer agents.

Technology Process of 4-Nitropyrazole-3-carboxylic acid

There total 4 articles about 4-Nitropyrazole-3-carboxylic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 82.0%

4-amino-1H-pyrazole-5-carboxylic acid (116008-52-7) → 4-nitro-1H-pyrazole-5-carboxylic acid (5334-40-7)

Guidance literature:

With oxone||potassium monopersulfate triple salt; In water; at 40 ℃; for 18h; Green chemistry;

DOI:10.1021/op5000754

Reference yield:

3-Methylpyrazole (1453-58-3) → 4-nitro-1H-pyrazole-3-carboxylic acid (5334-40-7)

Guidance literature:

With sodium dichromate; sulfuric acid; nitric acid; Yield given. Multistep reaction; 1.) 100 deg C, 4 h, 2.) 60 deg C, 10 h;

DOI:10.1007/BF00699004

Reference yield:

→ 4-nitro-1H-pyrazole-3-carboxylic acid (5334-40-7)

Guidance literature:

3-Methyl-4-nitropyrazole, KMnO4;

DOI:10.1007/BF00474885

upstream raw materials:

3-methyl-4-nitro-1H-pyrazole

4-amino-1H-pyrazole-5-carboxylic acid

3-Methylpyrazole

Downstream raw materials:

4-nitro-1H-pyrazole-5-carbonyl chloride

4-nitro-2H-pyrazole-3-carboxylic acid methyl ester

N-(2,3-dichlorobenzyl)-4-nitro-1H-pyrazole-5-carboxamide

N-benzyl-4-nitro-1H-pyrazole-5-carboxamide

Refernces

Design, synthesis, and biological evaluation of 4-benzoylamino-1H-pyrazole-3-carboxamide derivatives as potent CDK2 inhibitors

10.1016/j.ejmech.2021.113281

The research focuses on the development of selective CDK2 inhibitors for cancer therapy. CDK2 is a promising target due to its role in cell cycle progression and tumorigenesis. The study involves the design and synthesis of a series of 4-benzoylamino-1H-pyrazole-3-carboxamide derivatives, starting from the pan-CDK inhibitor AT7519. Key chemicals used in the synthesis include 4-nitro-1H-pyrazole-3-carboxylic acid, various amines, EDCI, HOBt, and different acylating agents like 3-bromo-2,6-difluorobenzoic acid. The most selective compound, DC-K2in212, demonstrated high potency against CDK2, effective antiproliferative activity against cancer cell lines A2058 and MV4-11, and low toxicity towards normal cell lines MRC5 and LX2. Molecular modeling showed that DC-K2in212 binds to CDK2 similarly to C-73, a highly selective CDK2 inhibitor. Biological studies revealed that DC-K2in212 inhibits CDK2-associated signaling pathways, induces cell cycle arrest, and promotes apoptosis, highlighting its potential as a therapeutic agent for further development.