5334-39-4

Basic information

• Product Name: 3-Methyl-4-nitropyrazole
• Synonyms: 3-Methyl-4-Nitro-1H-Pyrazole;at-7519-lua2-3-261-156g;1H-Pyrazole,3-methyl-4-nitro-(9CI);3-Methyl-4-nitropyrazole;3-Methyl-4-nitropyra;3-Methyl-4-Nitro-1H-Pyrazole
• CAS NO: 5334-39-4
• Molecular Formula: C₄H₅N₃O₂
• Molecular Weight: 127.1
• Product Categories: NITRO
• Mol File: 5334-39-4.mol
• Article Data: 12

Chemical Properties

• Melting Point: 131-134℃
• Boiling Point: 325℃
• Flash Point: 142.854 °C
• Appearance: /
• Density: 1.427 g/cm³
• Vapor Pressure: 0.000962mmHg at 25°C
• Refractive Index: 1.591
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 10.19±0.50(Predicted)
• Water Solubility: Slightly soluble in water.
• CAS DataBase Reference: 3-Methyl-4-nitropyrazole(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Methyl-4-nitropyrazole(5334-39-4)
• EPA Substance Registry System: 3-Methyl-4-nitropyrazole(5334-39-4)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-37
• RTECS: UQ7435000
• Hazardous Substances Data: 5334-39-4(Hazardous Substances Data)

Usage

Description

3-Methyl-4-nitropyrazole is an organic compound characterized by its molecular structure that features a methyl group at the 3rd position and a nitro group at the 4th position of the pyrazole ring. It is a versatile intermediate in the synthesis of various chemical compounds and has demonstrated potential applications in the pharmaceutical and chemical industries.

Uses

Used in Pharmaceutical Industry:
3-Methyl-4-nitropyrazole is used as a reactant for the preparation of aminopyrazole derivatives, which are potent, selective, and brain-penetrant small molecule inhibitors of Leucine-rich repeat kinase 2 (LRRK2). These inhibitors play a crucial role in the development of therapeutic agents for the treatment of neurodegenerative disorders, such as Parkinson's disease, by targeting the LRRK2 enzyme and modulating its activity.

InChI:InChI=1/C4H5N3O2/c1-3-4(7(8)9)2-5-6-3/h2H,1H3,(H,5,6)

Upstream product

• 13808-64-5 4-bromo-3-methyl-1H-pyrazole 
• 15802-75-2 4-iodo-3-methyl-1H-pyrazole 
• 1453-58-3 3-Methylpyrazole 
• 21901-41-7 4-methyl-5-nitropyridin-2(1H)-one 

Downstream Products

• 90946-24-0 3-methyl-4-nitro-1-phenyl-1H-pyrazole 
• 1795275-33-0 tert-butyl 4-(4-amino-3-methyl-1H-pyrazol-1-yl)piperidine-1-carboxylate 
• 64517-88-0 1,3-dimethyl-1H-pyrazol-4-amine 
• 121983-36-6 4-amino-1,5-dimethyl-1H-pyrazole 
• 847139-22-4 tert-butyl 3-methyl-4-nitro-1H-pyrazole-1-carboxylate 
• 1566543-93-8 C₉H₁₃N₃O₄ 
• 1006955-98-1 (3-methyl-4-nitro-1H-pyrazol-1-yl)acetonitrile 
• 1374829-39-6 3-methyl-1-(4-(methylsulfonyl)phenyl)-4-amino-1H-pyrazole 
• 1374830-19-9 5-methyl-1-(4-(methylsulfonyl)phenyl)-4-amino-1H-pyrazole 

Relevant articles and documents

Structure of 3(5)-Methyl-4-nitropyrazole in the Solid State: Tautomerism, Crystallography and the Problem of Desmotropy

The first example of desmotropy in azoles has been found concerning 3-methyl-4-nitropyrazole and its tautomer, 5-methyl-4-nitropyrazole: the crystal and molecular structure of both tautomers has been determined by X-ray analysis, 13C CPMAS NMR spectroscopy has been used for studying the isomerization processes in the solid state.

Chiral phosphoric acid-catalyzed enantioselective three- component aza-diels-alder reactions of aminopyrroles and aminopyrazoles

A highly stereoselective three-component Povarov reaction, catalyzed by (R)- and (S)-BINOL hydrogen phosphate, was achieved for the first time with aminopyrroles and aminopyrazoles as 2-azadiene precursors. A variety of aldehydes, enecarbamates, amino-substituted azines participated in the reaction to afford the tetrahydropyrrolopyridines and tetrahydropyrazolopyridines in good yields with excellent diatereo- and enantioselectivities. A stereochemical model is proposed to account for the observed absolute stereochemistry.

A simple and environmentally benign nitration of pyrazoles by impregnated bismuth nitrate

We report herein a facile, rapid, and environmentally friendly synthesis of nitropyrazoles in good yields using silica-bismuth nitrate and silica-sulfuric acid-bismuth nitrate at room temperature for the first time. The relatively non-toxic nature, ease o