3522-07-4

Basic information

• Product Name: 6-Methoxy-1H-indazole
• Synonyms: 6-Methoxy-1H-indazole;6-methoxyindazole;6-Methyloxy-indazole
• CAS NO: 3522-07-4
• Molecular Formula: C₈H₈N₂O
• Molecular Weight: 148.16192
• Mol File: 3522-07-4.mol

Chemical Properties

• Melting Point: 97-99 °C
• Boiling Point: 312.497 °C at 760 mmHg
• Flash Point: 114.568 °C
• Appearance: /
• Density: 1.244 g/cm³
• Vapor Pressure: 0.001mmHg at 25°C
• Refractive Index: 1.647
• Storage Temp.: 2-8°C
• PKA: 14.29±0.40(Predicted)
• CAS DataBase Reference: 6-Methoxy-1H-indazole(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Methoxy-1H-indazole(3522-07-4)
• EPA Substance Registry System: 6-Methoxy-1H-indazole(3522-07-4)

Safety Data

• Hazardous Substances Data: 3522-07-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Development:
6-Methoxy-1H-indazole is used as a pharmaceutical precursor for the development of drugs with various biological activities. Its indazole derivatives have been studied for their anticancer, anti-inflammatory, and antimicrobial properties, making it a promising candidate for the creation of new therapeutic agents.
Used in Medicinal Chemistry Research:
6-Methoxy-1H-indazole is utilized as a research compound in medicinal chemistry to explore its potential as a lead molecule for drug discovery. Its unique chemical structure and biological activities provide valuable insights into the design and synthesis of novel pharmaceuticals.
Used in Synthetic Chemistry:
6-Methoxy-1H-indazole is used as a building block in synthetic chemistry for the synthesis of other indazole derivatives with potential pharmacological activities. Its versatile chemical properties allow for the creation of a wide range of compounds with diverse therapeutic applications.

InChI:InChI=1/C8H8N2O/c1-11-7-3-2-6-5-9-10-8(6)4-7/h2-5H,1H3,(H,9,10)

Upstream product

• 23244-88-4 1H-indazol-6-ol 
• 77-78-1 dimethyl sulfate 
• 343773-70-6 1-(6-Methoxy-indazol-1-yl)-ethanone 
• 331-64-6 2-fluoro-4-methoxy-benzaldehyde 
• 43192-31-0 2-bromo-4-methoxybenzaldehyde 
• 74-88-4 methyl iodide 
• 459-60-9 1-fluoro-4-methoxybenzene 
• 50868-72-9 5-methoxy-o-toluidine 

Downstream Products

• 1150618-46-4 3-iodo-6-methoxy-1H-indazole 
• 885278-53-5 methyl 6-methoxy-1H-indazole-3-carboxylate 
• 1431163-17-5 3-iodo-6-methoxy-1-methyl-1H-indazole 
• 1354030-86-6 6-(4-(4-(2-methoxyphenyl)piperazin-1-yl)butoxy)-1H-indazole 
• 1354030-85-5 6-(3-(4-(2-methoxyphenyl)piperazin-1-yl)propoxy)-1H-indazole 
• 1354030-82-2 6-(4-(4-(2,3-dichlorophenyl)-1,4-diazepan-1-yl)butoxy)-1H-indazole 
• 1354030-81-1 6-(3-(4-(2,3-dichlorophenyl)-1,4-diazepan-1-yl)propoxy)-1H-indazole 
• 1354030-80-0 6-(4-(4-(2,3-dichlorophenyl)piperidin-1-yl)butoxy)-1H-indazole 
• 1354030-79-7 6-(3-(4-(2,3-dichlorophenyl)piperidin-1-yl)propoxy)-1H-indazole 
• 1354030-60-6 6-(4-(4-(2,3-dichlorophenyl)piperazin-1-yl)butoxy)-1H-indazole 
• 1354030-46-8 6-(3-(4-(2,3-dichlorophenyl)piperazin-1-yl)propoxy)-1H-indazole 
• 23244-88-4 1H-indazol-6-ol 
• 1178903-48-4 6-methoxy-2-(4-methoxybenzyl)-2H-indazole 
• 1178903-37-1 6-methoxy-1-(4-methoxybenzyl)-1H-indazole 

Relevant articles and documents

A novel copper-catalyzed, hydrazine-free synthesis of N-1 unsubstituted 1H-indazoles using stable guanylhydrazone salts as substrates

A CuI-catalyzed, hydrazine-free transformation of 2-(2-bromoarylidene)guanylhydrazone hydrochlorides using Cs2CO3 as a base and DMEDA as a ligand at 120 °C for 5 h delivers substituted 1H-indazoles with yields up to 75%. The C,N double bond configuration of the substrates was determined by NMR experiments and quantum chemical calculations. The reaction mechanism was studied using quantum chemical calculations.

Palladium catalyzed hydrodefluorination of fluoro-(hetero)arenes

Palladium catalyzed hydrodefluorination was developed for fine-tuning the properties of fluoro-(hetero)aromatic compounds. The robust reaction can be set up in air, requires only commercially available components, and tolerates a variety of heterocycles and functionalities relevant to drug discovery. Given the prevalence of fluorine incorporation around metabolic hotspots, the corresponding deuterodefluorination reaction may prove useful for converting fluorinated libraries to deuterated analogues to suppress the oxidative metabolism by kinetic isotope effects.

HURAT1 (human urate anion transporter 1) inhibitors and application thereof

The invention belongs to the field of medicinal chemistry and particularly relates to hURAT1 (human urate anion transporter 1) inhibitors and an application thereof. Specifically, the hURAT1 inhibitors are compounds with structure shown as formula (I) or (II) in the description or pharmaceutically acceptable salts of the compounds. Experiments prove that the compounds have good inhibition effect on uric acid transport of the hURAT1 in an HEK293 transfection cell, which shows that the compounds have good application prospect in treatment of hyperuricemia or gout.

MUSCARINIC AGONISTS

Compounds of formula (I) and methods are provided for the treatment of disease or conditions in which modification of cholinergic, especially muscarinic receptor activity, has a beneficial effect.

FUNCTIONALLY SELECTIVE LIGANDS OF DOPAMINE D2 RECEPTORS

The present invention relates to novel functionally selective ligands of dopamine D2 receptors, including agonists, antagonists, and inverse agonists. The invention further relates to the use of these compounds for treating central nervous system disorders related to D2 receptors.

Scaffold-hopping strategy: Synthesis and biological evaluation of 5,6-fused bicyclic heteroaromatics to identify orally bioavailable anticancer agents

Utilizing scaffold-hopping drug-design strategy, we sought to identify a backup drug candidate for BPR0L075 (1), an indole-based anticancer agent. For this purpose, 5,6-fused bicyclic heteroaromatic scaffolds were designed and synthesized through shufflin

A general, one-step synthesis of substituted indazoles using a flow reactor

Flow chemistry is a rapidly emerging technology within the pharmaceutical industry, both within medicinal and development chemistry groups. The advantages of flow chemistry, increased safety, improved reproducibility, enhanced scalability, are readily apparent, and we aimed to exploit this technology in order to provide small amounts of pharmaceutically interesting fragments via a safe and scalable route, which would enable the rapid synthesis of multigram quantities on demand. Here we report a general and versatile route which utilises flow chemistry to deliver a range of known and novel indazoles, including 3-amino and 3-hydroxy analogues.

Toward biophysical probes for the 5-HT3 receptor: Structure-activity relationship study of granisetron derivatives

This report describes the synthesis and biological characterization of novel granisetron derivatives that are antagonists of the human serotonin (5-HT3A) receptor. Some of these substituted granisetron derivatives showed low nanomolar binding affinity and allowed the identification of positions on the granisetron core that might be used as attachment points for biophysical tags. A BODIPY fluorophore was appended to one such position and specifically bound to 5-HT3A receptors in mammalian cells.

Indazoles: Regioselective protection and subsequent amine coupling reactions

(Chemical Equation Presented) Indazoles are unselectively protected under strongly basic conditions to give a mixture at N-1 and N-2. Under mildly acidic conditions, regioselective protection at N-2 takes place. Thermodynamic conditions lead to regioselective protection at N-1. This trend applies to various substituted indazoles. Protected 5-bromoindazoles participate in Buchwald reactions with a range of amines to generate novel derivatives.