26120-43-4

Basic information

• Product Name: 1-Methyl-4-nitro-1H-indazole
• Synonyms: 1-Methyl-4-nitro-1H-indazole;1-Methyl-4-nitro-2H-Indazole
• CAS NO: 26120-43-4
• Molecular Formula: C₈H₇N₃O₂
• Molecular Weight: 177.16008
• Product Categories: Indazoles
• Mol File: 26120-43-4.mol
• Article Data: 13

Chemical Properties

• Melting Point: 141-142
• Boiling Point: 332.863 °C at 760 mmHg
• Flash Point: 155.11 °C
• Appearance: /
• Density: 1.425 g/cm³
• Vapor Pressure: 0.000274mmHg at 25°C
• Refractive Index: 1.676
• Storage Temp.: 2-8°C
• PKA: -1.87±0.30(Predicted)
• CAS DataBase Reference: 1-Methyl-4-nitro-1H-indazole(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Methyl-4-nitro-1H-indazole(26120-43-4)
• EPA Substance Registry System: 1-Methyl-4-nitro-1H-indazole(26120-43-4)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 26120-43-4(Hazardous Substances Data)

Usage

General Description

1-Methyl-4-nitro-1H-indazole is a chemical compound with the molecular formula C8H7N3O2. It is a nitro-indazole derivative that is commonly used in organic synthesis and pharmaceutical research. The compound is an important intermediate in the production of various pharmaceuticals and agrochemicals. Its properties and reactivity make it a valuable building block for the synthesis of various biologically active compounds. 1-Methyl-4-nitro-1H-indazole is known for its potential applications in the development of new drugs, particularly in the treatment of various diseases and conditions.

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

Upstream product

• 77-78-1 dimethyl sulfate 
• 2942-40-7 nitro-4 indazole 
• 74-88-4 methyl iodide 
• 603-83-8 3-nitro-o-tolylamine 
• 606-31-5 2,6-dinitrobenzaldehyde 
• 104669-27-4 (2,6-dinitro-benzyliden)-aniline 

Downstream Products

• 77894-69-0 1-methyl-1H-indazol-4-ylamine 
• 82013-51-2 2-methyl-4-amino-2H-indazole 
• 369652-67-5 2-[(1-methyl-1H-indazol-4-yl)amino]-3-nitrobenzoic acid 
• 1395320-25-8 1-methyl-4-nitro-7-[1-(phenylsulfonyl)propyl]-1H-indazole 
• 1415681-50-3 C₁₅H₁₅N₃O₂S 
• 1415681-52-5 N-(1-methyl-7-ethoxy-1H-indazol-4-yl)-4-methylbenzenesulfonamide 
• 1620816-66-1 1-methyl-4-nitro-7-phenyl-1H-indazole 
• 945396-55-4 N²-(3,5-dimorpholinophenyl)-N⁴-(1H-indazol-4-yl)-N⁴-methylpyrimidine-2,4-diamine 
• 581810-84-6 N-(1-methyl-1H-indazol-4-yl)-N'-[4-(1-pyrrolidinyl)benzyl]urea 
• 581810-82-4 N-(1-methyl-1H-indazol-4-yl)-N'-[4-(1-piperidinyl)benzyl]urea 
• 581810-86-8 N-[4-(1-azepanyl)benzyl]-N'-(1-methyl-1H-indazol-4-yl)urea 
• 581810-83-5 N-[3-fluoro-4-(1-piperidinyl)benzyl]-N'-(1-methyl-1H-indazol-4-yl)urea 
• 581810-87-9 N-[4-(1-azepanyl)-3-fluorobenzyl]-N'-(1-methyl-1H-indazol-4-yl)urea 
• 735331-13-2 N-(2,4-dichlorobenzyl)-N'-(1-methyl-1H-indazol-4-yl)urea 

Relevant articles and documents

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.

Palladium-catalyzed direct C7-arylation of substituted indazoles

A novel direct C7-arylation of indazoles with iodoaryls is described using Pd(OAc)2 as catalyst, 1,10-phenanthroline as ligand, and K 2CO3 as base in refluxing DMA. Direct C7-arylation of 3-substituted 1H-indazole containing an EWG on the arene ring gave the expected products in good isolated yields. In addition, a one-pot Suzuki-Miyaura/ arylation procedure leading to C3,C7-diarylated indazoles has been developed.

New hypotheses for the binding mode of 4- and 7-substituted indazoles in the active site of neuronal nitric oxide synthase

Taking into account the potency of 4- and 7-nitro and haloindazoles as nNOS inhibitors previously reported in the literature by our team, a multidisciplinary study, described in this article, has recently been carried out to elucidate their binding mode in the enzyme active site. Firstly, nitrogenous fastening points on the indazole building block have been investigated referring to molecular modeling hypotheses and thanks to the in vitro biological evaluation of N1- and N2-methyl and ethyl-4-substituted indazoles on nNOS. Secondly, we attempted to confirm the importance of the substitution in position 4 or 7 by a hydrogen bond acceptor group thanks to the synthesis and the in vitro biological evaluation of a new analogous 4-substituted derivative, the 4-cyanoindazole. Finally, by opposition to previous hypotheses describing NH function in position 1 of the indazole as a key fastening point, the present work speaks in favour of a crucial role of nitrogen in position 2.