58514-96-8

Basic information

• Product Name: 5-methoxy-1H-indazol-3-amine
• Synonyms: 5-methoxy-1H-indazol-3-amine;(5-Methoxy-1H-indazol-3-yl)amine;3-Amino-5-methoxyindazole;5-(Methyloxy)-1H-indazol-3-amine
• CAS NO: 58514-96-8
• Molecular Formula: C₈H₉N₃O
• Molecular Weight: 163.17656
• Mol File: 58514-96-8.mol
• Article Data: 8

Chemical Properties

• Melting Point: 170-172 °C
• Boiling Point: 406.3 °C at 760 mmHg
• Flash Point: 199.5 °C
• Appearance: /
• Density: 1.344
• Vapor Pressure: 8.21E-07mmHg at 25°C
• Refractive Index: 1.712
• PKA: 14.51±0.40(Predicted)
• CAS DataBase Reference: 5-methoxy-1H-indazol-3-amine(CAS DataBase Reference)
• NIST Chemistry Reference: 5-methoxy-1H-indazol-3-amine(58514-96-8)
• EPA Substance Registry System: 5-methoxy-1H-indazol-3-amine(58514-96-8)

Safety Data

• Hazardous Substances Data: 58514-96-8(Hazardous Substances Data)

Usage

General Description

5-methoxy-1H-indazol-3-amine is a chemical compound with the molecular formula C8H8N2O. It is a derivative of indazole, a heterocyclic aromatic organic compound. 5-methoxy-1H-indazol-3-amine has a methoxy group (-OCH3) attached to the 5th carbon atom of the indazole ring, and an amine group (-NH2) attached to the 3rd carbon atom. 5-methoxy-1H-indazol-3-amine has potential applications in medicinal chemistry and pharmaceutical research, as it may exhibit biological activities such as anti-inflammatory, antimicrobial, or anticancer properties. Overall, 5-methoxy-1H-indazol-3-amine is a versatile and interesting chemical compound that has potential uses in various fields of science and technology.

InChI:InChI=1/C8H9N3O/c1-12-5-2-3-7-6(4-5)8(9)11-10-7/h2-4H,1H3,(H3,9,10,11)

Upstream product

• 1219024-61-9 2-[2-(diphenylmethylene)hydrazino]-5-methoxybenzonitrile 
• 127667-01-0 2-fluoro 5-methoxybenzonitrile 

Downstream Products

• 1041612-50-3 2-fluoro-N-(5-methoxy-1H-indazol-3-yl)benzenesulfonamide 
• 1041612-45-6 5-methoxy-1-(4-methoxybenzyl)-1H-indazol-3-ylamine 
• 1426854-82-1 5-methoxy-1-phenyl-1H-indazol-3-ylamine 

Relevant articles and documents

Lewis-acid Promoted Chemoselective Condensation of 2-Aminobenzimidazoles or 3-Aminoindazoles with 3-Ethoxycyclobutanones to Construct Fused Nitrogen heterocycles

A Lewis-acid promoted chemoselective condensation of 2-aminobenzimidazoles or 3-aminoindazoles with 3-ethoxycyclobutanones is presented. Diverse fused heterocycles benzo[4,5]-imidazo[1,2-a]pyrimidine and pyrimido[1,2-b]-indazole derivatives were obtained in moderate to high yields under mild conditions, the reaction mechanism of which was in sharp contrast to previous [3+3] annulation reaction of 3-ethoxycyclobutanones. (Figure presented.).

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.

Two-step synthesis of substituted 3-aminoindazoles from 2-bromobenzonitriles

A general two-step synthesis of substituted 3-aminoindazoles from 2-bromobenzonitriles involving a palladium-catalyzed arylation of benzophenone hydrazone followed by an acidic deprotection/cyclization sequence is described. This procedure offers a general and efficient alternative to the typical S NAr reaction of hydrazine with o-fluorobenzonitriles.