58706-36-8

Basic information

• Product Name: 1-METHYL-7-NITROINDAZOLE
• Synonyms: 1-METHYL-7-NITROINDAZOLE;1-Methyl-7-nitro-1H-indazole
• CAS NO: 58706-36-8
• Molecular Formula: C₈H₇N₃O₂
• Molecular Weight: 177.16
• Mol File: 58706-36-8.mol
• Article Data: 12

Chemical Properties

• Melting Point: 99-100 °C
• Boiling Point: 332.9°Cat760mmHg
• Flash Point: 155.1°C
• Appearance: /
• Density: 1.42g/cm³
• Vapor Pressure: 0.000274mmHg at 25°C
• Refractive Index: 1.676
• PKA: -1.14±0.30(Predicted)
• CAS DataBase Reference: 1-METHYL-7-NITROINDAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-METHYL-7-NITROINDAZOLE(58706-36-8)
• EPA Substance Registry System: 1-METHYL-7-NITROINDAZOLE(58706-36-8)

Safety Data

• Hazardous Substances Data: 58706-36-8(Hazardous Substances Data)

Usage

General Description

1-Methyl-7-nitroindazole is a chemical compound with the molecular formula C8H7N3O2. It is a derivative of indazole, a heterocyclic compound containing a five-membered ring with two nitrogen atoms. 1-METHYL-7-NITROINDAZOLE is used in research as a selective inhibitor of neuronal nitric oxide synthase, an enzyme involved in the production of nitric oxide in the central nervous system. Inhibition of this enzyme can have implications for studying the role of nitric oxide in various physiological and pathological processes, including neurotransmission, inflammation, and neurodegenerative diseases. Additionally, 1-Methyl-7-nitroindazole has been investigated for its potential therapeutic applications in conditions such as ischemic stroke and traumatic brain injury, where nitric oxide levels play a significant role in the pathological process.

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

Upstream product

• 77-78-1 dimethyl sulfate 
• 2942-42-9 7-Nitroindazole 
• 74-88-4 methyl iodide 
• 570-24-1 2-Methyl-6-nitroaniline 

Downstream Products

• 41926-06-1 7-amino-1-methyl-1H-indazole 
• 864724-72-1 4-methoxy-N-(1-methyl-1H-7-indazolyl)-benzenesulfonamide 
• 369652-64-2 2-[(1-methyl-1H-indazol-7-yl)amino]-3-nitrobenzoic acid 
• 1620816-63-8 1‐methyl‐7‐nitro‐3‐phenyl‐1H‐indazole 
• 874297-18-4 3‐(4‐methoxyphenyl)‐1‐methyl‐7‐nitro‐1H‐indazole 

Relevant articles and documents

“On Water” Palladium Catalyzed Direct Arylation of 1H‐Indazole and 1H‐7‐Azaindazole

The C3 direct arylation of 1H-indazole and 1H-7-azaindazole has been a significant challenge due to the lack of the reactivity at this position. In this paper, we describe a mild and an efficient synthesis of new series of C3-aryled 1H-indazoles and C3-aryled 1H-7-azaindazoles via a C3 direct arylation using water as solvent. On water, PPh3 was effective as a ligand along with a lower charge of the catalyst Pd(OAc)2 (5 mol%) at 100 oC, leading to C3-aryled 1H-indazoles or C3-aryled 1H-7-azaindazoles in moderate to good yields.

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.