1048925-02-5

Basic information

• Product Name: 3-methyl-5-nitro-1H-pyrazole
• Synonyms: 3-methyl-5-nitro-1H-pyrazole;1H-Pyrazole, 5-methyl-3-nitro-;3(5)-methyl-5(3)-nitropyrazole;3-methyl-5-nitropyrazole
• CAS NO: 1048925-02-5
• Molecular Formula: C₄H₅N₃O₂
• Molecular Weight: 127.1014
• Mol File: 1048925-02-5.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 335.7±22.0 °C(Predicted)
• Appearance: /
• Density: 1.426±0.06 g/cm3(Predicted)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 8.88±0.10(Predicted)
• CAS DataBase Reference: 3-methyl-5-nitro-1H-pyrazole(CAS DataBase Reference)
• NIST Chemistry Reference: 3-methyl-5-nitro-1H-pyrazole(1048925-02-5)
• EPA Substance Registry System: 3-methyl-5-nitro-1H-pyrazole(1048925-02-5)

Safety Data

• Hazardous Substances Data: 1048925-02-5(Hazardous Substances Data)

Usage

Description

3-methyl-5-nitro-1H-pyrazole is an organic compound characterized by its pyrazole ring structure, which features a methyl group at the 3rd position and a nitro group at the 5th position. 3-methyl-5-nitro-1H-pyrazole is known for its potential applications in various chemical and pharmaceutical processes due to its unique structural properties.

Uses

Used in Pharmaceutical Industry:
3-methyl-5-nitro-1H-pyrazole is used as a reagent for the preparation of sulfonylpyridine inhibitors of Interleukin-2 inducible T-cell kinase. These inhibitors play a crucial role in regulating the immune system and have potential applications in treating autoimmune diseases and other immune-related conditions.
Used in Chemical Synthesis:
3-methyl-5-nitro-1H-pyrazole serves as a valuable scaffold for the synthesis of various complex organic compounds, such as 7-trifluoromethyl-substituted pyrazolo[1,5-a]pyrimidine. This scaffold's unique structural features enable the development of novel molecules with potential applications in various fields, including pharmaceuticals, agrochemicals, and materials science.

Upstream product

• 31230-17-8 3-methyl-5-aminopyrazole 

Downstream Products

• 1006950-51-1 2-(5-methyl-3-nitro-1H-pyrazol-1-yl)ethanol 
• 151588-03-3 1-amino-3-nitro-5-methylpyrazole 

Relevant articles and documents

A green and facile approach for synthesis of nitro heteroaromatics in water

A convenient and green method for the oxidation of nitrogen-rich heterocyclic amines to nitro-substituted heteroaromatics using potassium peroxymonosulfate (2KHSO5·KHSO4·K 2SO4, Oxone) in water was developed. This method has several advantages over previous methods: operational simplicity, safety, inexpensive reagents, the use of H2O as the sole solvent, and mild conditions. The utility of the present oxidative system was demonstrated by the synthesis of the important energetic compounds 3,4,5-trinitro-1H-pyrazole (TNP) and 5-amino-3-nitro-1H-1,2,4-triazole (ANTA).

N-benzoylpyrazoles are novel small-molecule inhibitors of human neutrophil elastase

Human neutrophil elastase (NE) plays an important role in the pathogenesis of pulmonary disease. Using high-throughput chemolibrary screening, we identified 10 N-benzoylpyrazole derivatives that were potent NE inhibitors. Nine additional NE inhibitors were identified through further screening of N-benzoylpyrazole analogues. Evaluation of inhibitory activity against a range of proteases showed high specificity for NE, although several derivatives were also potent inhibitors of chymotrypsin. Analysis of reaction kinetics and inhibitor stability revealed that N-benzoylpyrazoles were pseudoirreversible competitive inhibitors of NE. Structure-activity relationship (SAR) analysis demonstrated that modification of N-benzoylpyrazole ring substituents modulated enzyme selectivity and potency. Furthermore, molecular modeling of the binding of selected active and inactive compounds to the NE active site revealed that active compounds fit well into the catalytic site, whereas inactive derivatives contained substituents or conformations that hindered binding or accessibility to the catalytic residues. Thus, N-benzoylpyrazole derivatives represent novel structural templates that can be utilized for further development of efficacious NE inhibitors.