20925-60-4

Basic information

• Product Name: 4-CHLORO-1H-INDAZOL-3-AMINE
• Synonyms: 4-CHLORO-1H-INDAZOL-3-AMINE;4-CHLORO-1H-INDAZOL-3-YLAMINE;3-Amino-4-chloro-1H-indazole;3-Amino-4-chloro-1H-indazole 95%;1H-Indazol-3-aMine, 4-chloro;1H-Indazol-3-aMine, 4-chloro-Mes
• CAS NO: 20925-60-4
• Molecular Formula: C₇H₆ClN₃
• Molecular Weight: 167.6
• Mol File: 20925-60-4.mol
• Article Data: 6

Chemical Properties

• Melting Point: 159-162
• Boiling Point: 408.7 °C at 760 mmHg
• Flash Point: 201 °C
• Appearance: /
• Density: 1.533 g/cm³
• Vapor Pressure: 6.86E-07mmHg at 25°C
• Refractive Index: 1.777
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 13.72±0.40(Predicted)
• CAS DataBase Reference: 4-CHLORO-1H-INDAZOL-3-AMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-CHLORO-1H-INDAZOL-3-AMINE(20925-60-4)
• EPA Substance Registry System: 4-CHLORO-1H-INDAZOL-3-AMINE(20925-60-4)

Safety Data

• Hazard Codes: Xi
• Safety Statements: 24/25
• HazardClass: IRRITANT
• Hazardous Substances Data: 20925-60-4(Hazardous Substances Data)

Usage

General Description

4-Chloro-1H-indazol-3-amine is a specialized chemical compound belonging to the class of organic compounds known as indazoles. It is distinguished by its indazole ring system that has a nitrogen atom at position 1 and an amino group at position 3. 4-Chloro-1H-indazol-3-amine also possesses a chlorine atom at the 4th position in the indazole ring. Indazoles are aromatic structures analogous to indoles but with a second nitrogen atom replacing a carbon atom in the benzene ring. As of present scientific knowledge, the specific uses, benefits, or hazards of 4-Chloro-1H-indazol-3-amine aren't particularly documented, indicating it's mainly used for research or industrial purposes.

InChI:InChI=1/C7H6ClN3/c8-4-2-1-3-5-6(4)7(9)11-10-5/h1-3H,(H3,9,10,11)

Upstream product

• 1194-65-6 2,6-dichloro-benzonitrile 
• 387-45-1 2-chloro-6-fluorobenzaldehyde 
• 668-45-1 2-chloro-6-fluorobenzonitrile 
• 914311-51-6 2-chloro-6-hydrazinobenzonitrile 

Downstream Products

• 796967-16-3 linifanib 

Relevant articles and documents

The discovery and development of a safe, practical synthesis of ABT-869

The discovery, development and implementation of two chemical routes to ABT-869 is reported. Optimization of the first-generation heterocycle formation and Suzuki coupling is briefly described. Key features of the second-generation synthesis include the development of a safe hydrazine condensation by utilizing an inorganic base to increase the onset temperature of exothermic decomposition. The second-generation Suzuki reaction is discussed in detail, culminating in the use of an oxygen monitor as a PAT to maximize reproducibility on scale.

Synthesis and structure-activity relationships of indazole arylsulfonamides as allosteric CC-chemokine receptor 4 (CCR4) antagonists

A series of indazole arylsulfonamides were synthesized and examined as human CCR4 antagonists. Methoxy- or hydroxyl- containing groups were the more potent indazole C4 substituents. Only small groups were tolerated at C5, C6, or C7, with the C6 analogues being preferred. The most potent N3-substituent was 5-chlorothiophene-2-sulfonamide. N1 meta-substituted benzyl groups possessing an α-amino-3-[(methylamino)acyl]- group were the most potent N1-substituents. Strongly basic amino groups had low oral absorption in vivo. Less basic analogues, such as morpholines, had good oral absorption; however, they also had high clearance. The most potent compound with high absorption in two species was analogue 6 (GSK2239633A), which was selected for further development. Aryl sulfonamide antagonists bind to CCR4 at an intracellular allosteric site denoted site II. X-ray diffraction studies on two indazole sulfonamide fragments suggested the presence of an important intramolecular interaction in the active conformation.

NOVEL COMPOUNDS

Indazole compounds, processes for their preparation, intermediates usable in these processes, pharmaceutical compositions containing such compounds and their use in therapy.