13436-58-3

Basic information

• Product Name: 2-methyl-7-nitro-2H-indazole
• Synonyms: 2-methyl-7-nitro-2H-indazole;2H-INDAZOLE, 2-METHYL-7-NITRO-;7-Nitro-2-methylindazole;2-Methyl-7-nitro-1H-indazole
• CAS NO: 13436-58-3
• Molecular Formula: C₈H₇N₃O₂
• Molecular Weight: 177.162
• Mol File: 13436-58-3.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 364.5 °C at 760 mmHg
• Flash Point: 174.2 °C
• Appearance: /
• Density: 1.42g/cm³
• Vapor Pressure: 3.51E-05mmHg at 25°C
• Refractive Index: 1.676
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2-methyl-7-nitro-2H-indazole(CAS DataBase Reference)
• NIST Chemistry Reference: 2-methyl-7-nitro-2H-indazole(13436-58-3)
• EPA Substance Registry System: 2-methyl-7-nitro-2H-indazole(13436-58-3)

Safety Data

• Hazardous Substances Data: 13436-58-3(Hazardous Substances Data)

Usage

General Description

2-methyl-7-nitro-2H-indazole is a chemical compound with the molecular formula C8H7N3O2. It is a nitro-substituted indazole derivative that is commonly used in organic synthesis and medicinal chemistry. 2-methyl-7-nitro-2H-indazole has a nitro group at the 7-position and a methyl group at the 2-position of the indazole ring. It is known for its potential pharmacological properties and is the subject of research for its potential use in the development of new drugs. 2-methyl-7-nitro-2H-indazole is a yellow crystalline solid that is sparingly soluble in water but more soluble in organic solvents. Its chemical structure and properties make it a valuable building block in the synthesis of diverse molecules for various applications in the fields of pharmaceuticals, agrochemicals, and material science.

InChI:InChI=1/C8H7N3O2/c1-10-5-6-3-2-4-7(11(12)13)8(6)9-10/h2-5H,1H3

Upstream product

• 77-78-1 dimethyl sulfate 
• 2942-42-9 7-Nitroindazole 
• 2533-69-9 methyl 2,2,2-trichloroacetimidate 
• 570-24-1 2-Methyl-6-nitroaniline 
• 74-88-4 methyl iodide 
• 420-37-1 trimethoxonium tetrafluoroborate 

Downstream Products

• 90223-02-2 7-amino-2-methyl-2H-indazole 

Relevant articles and documents

SnCl2/RSH: A versatile catalytic system for the synthesis of 4-Alkylsulfanyl-indazole derivatives

The treatment of alkylated nitro derivatives of indazole with stannous chloride in alkanethiol gave after coupling of the obtained amines with 4-methoxybenzenesulfonyl chloride in pyridine the new N-(4-Alkylsulfanylindazol-7-yl)-4-methoxybenzene sulfonamides via the nucleophilic substitution of hydrogen in position 4 of indazole, together with the expected 4-methoxy-N-(indazol-7-yl)-benzenesulfonamides. All the newly synthesized compounds have been characterized by elemental analysis and spectroscopic data.

New nitroindazolylacetonitriles: Efficient synthetic access: Via vicarious nucleophilic substitution and tautomeric switching mediated by anions

New N-Alkyl-nitroindazolylacetonitriles were efficiently obtained via vicarious nucleophilic substitution of N-methyl-nitroindazoles with 4-chlorophenoxyacetonitrile. All compounds were fully characterized by NMR and mass spectroscopy techniques and the structures of some of them were additionally confirmed by X-ray diffraction analysis data. Tautomeric switching was observed in this series of nitroindazolylacetonitriles upon addition of basic anions followed by UV-Vis spectrophotometric and 1H-NMR titrations. The formation of tautomeric species induced by anionic species was endorsed by Density Functional Theory calculations.

Fluorinated indazoles as novel selective inhibitors of nitric oxide synthase (NOS): Synthesis and biological evaluation

In order to find new compounds with neuroprotective activity and NOS-I/NOS-II selectivity, we have designed, synthesized, and characterized 14 new NOS inhibitors with an indazole structure. The first group corresponds to 4,5,6,7-tetrahydroindazoles (4-8), the second to the N-methyl derivatives (9-12) of 7-nitro-1H-indazole (1) and 3-bromo-7-nitro-1H-indazole (2), and the latter to 4,5,6,7-tetrafluoroindazoles (13-17). Compound 13 (4,5,6,7-tetrafluoro-3-methyl-1H-indazole) inhibited NOS-I by 63% and NOS-II by 83%. Interestingly, compound 16 (4,5,6,7-tetrafluoro-3-perfluorophenyl-1H-indazole) inhibited NOS-II activity by 80%, but it did not affect to NOS-I activity. Structural comparison between these new indazoles further supports the importance of the aromatic indazole skeleton for NOS inhibition and indicate that bulky groups or N-methylation of 1 and 2 diminish their effect on NOS activity. The fluorination of the aromatic ring increased the inhibitory potency and NOS-II selectivity, suggesting that this is a promising strategy for NOS selective inhibitors.