21443-96-9

Basic information

• Product Name: 1H-INDAZOL-7-AMINE
• Synonyms: 7-AMINO (1H)INDAZOLE;1H-INDAZOL-7-AMINE;1H-Indazol-5-ylamine;1H-Indazol-7-amine ,97%;7-Amino-1H-indazole ,97%;1H-indazol-7-amine(SALTDATA: FREE);1H-Indazol-7-ylaMine;7-AMinoindazole
• CAS NO: 21443-96-9
• Molecular Formula: C₇H₇N₃
• Molecular Weight: 133.15
• EINECS: 244-391-8
• Product Categories: pharmacetical;Amines;Building Blocks;Indazole;Fused Ring Systems;Indazoles
• Mol File: 21443-96-9.mol
• Article Data: 18

Chemical Properties

• Melting Point: 156-159°C
• Boiling Point: 376.6 °C at 760 mmHg
• Flash Point: 209.5 °C
• Appearance: Tan/Crystalline Solid
• Density: 1.367 g/cm³
• Vapor Pressure: 7.16E-06mmHg at 25°C
• Refractive Index: 1.78
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 14.89±0.40(Predicted)
• CAS DataBase Reference: 1H-INDAZOL-7-AMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-INDAZOL-7-AMINE(21443-96-9)
• EPA Substance Registry System: 1H-INDAZOL-7-AMINE(21443-96-9)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 34-36/37/38-22
• Safety Statements: 26-36/37/39
• RIDADR: 3259
• WGK Germany: 3
• RTECS: NK7713000
• HazardClass: IRRITANT
• Hazardous Substances Data: 21443-96-9(Hazardous Substances Data)

Usage

Description

1H-Indazol-7-amine, also known as a substituted-indazole, is an organic compound characterized by its light yellow solid appearance. It is a derivative of the indazole family, which is a fused ring system consisting of a benzene and a pyrazole. 1H-Indazol-7-amine is known for its ability to inhibit nitric oxide synthases, making it a potential candidate for various applications in different industries.

Uses

Used in Pharmaceutical Industry:
1H-Indazol-7-amine is used as a pharmaceutical agent for its nitric oxide synthase inhibitory properties. Nitric oxide synthases are enzymes that catalyze the production of nitric oxide, which plays a crucial role in various physiological processes. However, excessive nitric oxide production can lead to inflammation and other health issues. By inhibiting these enzymes, 1H-Indazol-7-amine can help regulate nitric oxide levels and potentially be used in the treatment of conditions related to nitric oxide dysregulation.
Used in Research and Development:
1H-Indazol-7-amine is used as a research compound for studying the role of nitric oxide synthases in various biological processes. Its inhibitory properties make it a valuable tool for understanding the mechanisms behind nitric oxide production and its impact on cellular functions. This knowledge can contribute to the development of new therapeutic strategies and drug candidates targeting nitric oxide-related conditions.
Used in Chemical Synthesis:
1H-Indazol-7-amine can be used as a starting material or intermediate in the synthesis of other organic compounds. Its unique chemical structure allows for further functionalization and modification, enabling the creation of new molecules with potential applications in various industries, such as pharmaceuticals, agrochemicals, and materials science.

InChI:InChI=1/C7H7N3/c8-6-3-1-2-5-4-9-10-7(5)6/h1-4H,8H2,(H,9,10)

Upstream product

• 2942-42-9 7-Nitroindazole 
• 112698-24-5 methyl-4 dihydro-3,7 pyrazolo<1,5,4-ef>benzodiazepine-1,5 one-6 
• 112698-22-3 phenyl-4 dihydro-3,7 pyrazolo <1,5,4-ef>benzodiazepine-1,5 one-6 
• 119-26-6 (2,4-dinitro-phenyl)-hydrazine 
• 570-24-1 2-Methyl-6-nitroaniline 
• 64-17-5 ethanol 

Downstream Products

• 857621-48-8 N-acetyl-sulfanilic acid-(1⁽²⁾H-indazol-7-ylamide) 
• 81382-46-9 7-hydroxy-1H-indazole 
• 112698-22-3 phenyl-4 dihydro-3,7 pyrazolo <1,5,4-ef>benzodiazepine-1,5 one-6 
• 112698-18-7 N-(1H-Indazol-7-yl)-3-oxo-3-phenyl-propionamide 
• 150-60-7 dibenzyl disulphide 
• 369652-62-0 2-(1H-indazol-7-ylamino)-3-nitrobenzoic acid 
• 165668-35-9 4-methoxy-N-(7-indazolyl)benzenesulfonamide 
• 945761-94-4 7-iodo-1H-indazole 
• 945761-95-5 3-bromo-7-iodo-1H-indazole 
• 256228-64-5 1H-indazole-7-carbonitrile 
• 945761-98-8 7-((trimethylsilyl)ethynyl)-1H-indazole 
• 945761-99-9 7-ethynyl-1H-indazole 
• 945762-00-5 3-bromo-7-cyano-1H-indazole 

Relevant articles and documents

Efficient synthesis of 7-substituted or 3,7-disubstituted 1H-indazoles

This work reports on the synthesis of the novel indazole scaffolds 7-OTf-1H-indazole (trifluoromethanesulfonic acid 1H-indazol-7-yl ester), 7-iodo-1H-indazole and 3-bromo-7-iodo-1H-indazole. These new compounds are potent building blocks in divergent syntheses of indazoles via palladium cross-coupling reactions. Georg Thieme Verlag Stuttgart.

Synthesis of new α-amino-1H indazolyl-phosphonate derivatives: Crystal structure, Hirshfeld surface analysis and DFT studies

A new α-amino-1H Indazolyl-phosphonates derivative 3a–e were synthesized and subjected to solid state characterization by single-crystal X-ray diffraction analysis, and to study their NMR and Hirshfeld surface analysis. The P atom exhibits tetrahedral geometry involving two O-ethyl groups, a C atom and a double-bonded O atom. The P–C bond has an approximately staggered conformation, with the aniline and substituted groups in gauche positions with respect to the P[dbnd]O double bond. The molecules are arranged as centrosymmetric or pseudocentrosymmetric dimers connected by two N–H?O[dbnd]P hydrogen bonds and also by C–H … π interaction in the case of structures 3a–e, which are responsible for the formation and stability of the molecular assemblies. Hirshfeld surface analysis (dnorm surface and two-dimensional (2D) fingerprint plots) revealed the nature of intermolecular contacts. The most important contributions for the crystal packing are from H?H, H?C/C?H, O?H/H?O, and H?N/N?H interactions. In addition, frontier molecular orbitals and Molecular Electrostatic Potential map of the compounds was produced by using the optimized structures.

Synthesis and molecular modeling studies of N-Hydroxyindazolecarboximidamides as novel indoleamine 2,3-Dioxygenase 1 (IDO1) inhibitors

Indoleamine 2,3-dioxygenase 1 (IDO1) is an immunosuppressive enzyme that is highly overexpressed in various cancer cells and antigen-presenting cells. It has emerged as an attractive therapeutic target for cancer immunotherapy, which has prompted high interest in the development of small-molecule inhibitors. To discover novel IDO1 inhibitors, we designed and synthesized a series of N-hydroxyindazolecarboximidamides. Among the compounds synthesized, compound 8a inhibited both tryptophan depletion and kynurenine production through the IDO1 enzyme. Molecular docking studies revealed that 8a binds to IDO1 with the same binding mode as the analog, epacadostat (INCB24360). Here, we report the synthesis and biological evaluation of these hydroxyindazolecarboximidamides and present the molecular docking study of 8a with IDO1.