Production Method 1

360575-28-6

914311-50-5

186407-74-9

Reaction Conditions

1.1 Reagents: Potassium carbonate ,  Hydroxyamine hydrochloride Solvents: 1,2-Dimethoxyethane ;  4 - 5 h, 40 °C
1.2 Reagents: Hydrazine ;  5 - 25 h, reflux

Reference

New Practical Synthesis of Indazoles via Condensation of o-Fluorobenzaldehydes and Their O-Methyloximes with Hydrazine

Lukin, Kirill; et al, Journal of Organic Chemistry, 2006, 71(21), 8166-8172

Production Method 2

79544-27-7

914311-50-5

Reaction Conditions

1.1 Reagents: Hydrazine hydrate (1:1) Solvents: 1-Butanol ;  7 h, reflux

Reference

3-[(Imidazolidin-2-yl)imino]indazole ligands with selectivity for the α2-adrenoceptor compared to the imidazoline I1 receptor

Saczewski, Franciszek; et al, Bioorganic & Medicinal Chemistry, 2011, 19(1), 321-329

4-Bromo-1H-indazol-3-amine Raw materials

• 2-Bromo-6-fluorobenzonitrile
• 2-Bromo-6-fluorobenzaldehyde

4-Bromo-1H-indazol-3-amine Preparation Products

• 4-Bromo-1H-indazol-3-amine (914311-50-5)
• 4-Bromo-1H-indazole (186407-74-9)

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• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Benzopyrazoles Indazoles

4-Bromo-1H-indazol-3-amine (CAS No. 914311-50-5): A Versatile Building Block in Medicinal Chemistry

4-Bromo-1H-indazol-3-amine (CAS No. 914311-50-5) is a highly valuable heterocyclic compound that has gained significant attention in pharmaceutical research and organic synthesis. This brominated indazole derivative serves as a crucial intermediate in the development of various biologically active molecules, particularly in the field of kinase inhibitor drug discovery and cancer therapeutics.

The molecular structure of 4-Bromo-1H-indazol-3-amine features a bromine atom at the 4-position and an amino group at the 3-position of the indazole core, making it an excellent substrate for palladium-catalyzed cross-coupling reactions. This characteristic has made it particularly valuable in modern medicinal chemistry, where researchers frequently search for "indazole-based drug candidates" or "brominated heterocycle building blocks".

Recent studies have highlighted the importance of 4-Bromo-1H-indazol-3-amine derivatives in addressing current medical challenges. With growing interest in "targeted cancer therapies" and "precision medicine approaches", this compound has emerged as a key player in developing inhibitors for various protein kinases. The pharmaceutical industry has shown particular interest in its potential applications for "tyrosine kinase inhibitor development" and "JAK-STAT signaling pathway modulation".

From a synthetic chemistry perspective, 4-Bromo-1H-indazol-3-amine offers multiple sites for functionalization, allowing medicinal chemists to create diverse molecular libraries. This aligns well with current trends in "fragment-based drug design" and "combinatorial chemistry approaches". The presence of both bromine and amino groups enables various transformations, including Buchwald-Hartwig aminations, Suzuki-Miyaura couplings, and nucleophilic aromatic substitutions.

The compound's physicochemical properties make it particularly suitable for drug discovery applications. With a molecular weight of 212.05 g/mol and moderate lipophilicity, 4-Bromo-1H-indazol-3-amine derivatives often exhibit favorable drug-like properties, addressing the pharmaceutical industry's need for "bioavailable small molecules" and "orally active compounds". These characteristics explain why searches for "indazole pharmacokinetics" and "heterocycle ADME properties" have increased significantly in recent years.

Beyond its pharmaceutical applications, 4-Bromo-1H-indazol-3-amine has found use in material science as a precursor for organic electronic materials. The indazole core's electron-rich nature and the bromine atom's reactivity make it suitable for creating conjugated systems, responding to growing interest in "organic semiconductors" and "molecular electronics".

The synthesis and handling of 4-Bromo-1H-indazol-3-amine require specialized knowledge in heterocyclic chemistry. Researchers often search for "indazole synthesis protocols" and "brominated heterocycle purification methods", reflecting the technical challenges associated with working with this class of compounds. Proper characterization techniques, including NMR spectroscopy and mass spectrometry, are essential for quality control.

Market analysis indicates growing demand for 4-Bromo-1H-indazol-3-amine and related indazole derivatives, driven by increased pharmaceutical R&D investment. The compound's versatility aligns with current trends toward "multitarget drug discovery" and "polypharmacology approaches", explaining why it remains a popular choice among medicinal chemists.

In conclusion, 4-Bromo-1H-indazol-3-amine (CAS No. 914311-50-5) represents a strategically important building block in modern drug discovery and materials science. Its unique structural features and reactivity profile continue to make it valuable for researchers working on "next-generation therapeutics" and "advanced functional materials". As the scientific community's understanding of indazole chemistry deepens, the applications of this compound are likely to expand further.

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