Cas no 1379328-62-7 (6-BROMO-1H-INDAZOLE-3-CARBOXAMIDE)

6-Bromo-1H-indazole-3-carboxamide is a heterocyclic organic compound featuring a brominated indazole core with a carboxamide functional group at the 3-position. This structure makes it a valuable intermediate in pharmaceutical and agrochemical synthesis, particularly for the development of bioactive molecules. The bromine substituent enhances reactivity for further functionalization, while the carboxamide group offers versatility in forming hydrogen bonds, aiding in target binding. Its high purity and stability under standard conditions ensure reliable performance in cross-coupling reactions, such as Suzuki or Buchwald-Hartwig couplings. The compound is commonly utilized in medicinal chemistry research for constructing kinase inhibitors and other therapeutic agents.
6-BROMO-1H-INDAZOLE-3-CARBOXAMIDE structure
1379328-62-7 structure
Product Name:6-BROMO-1H-INDAZOLE-3-CARBOXAMIDE
CAS No:1379328-62-7
MF:C8H6BrN3O
MW:240.056740283966
CID:4595215
PubChem ID:75412341
Update Time:2025-05-23

6-BROMO-1H-INDAZOLE-3-CARBOXAMIDE Chemical and Physical Properties

Names and Identifiers

    • 1H-Indazole-3-carboxamide, 6-bromo-
    • 6-BROMO-1H-INDAZOLE-3-CARBOXAMIDE
    • Inchi: 1S/C8H6BrN3O/c9-4-1-2-5-6(3-4)11-12-7(5)8(10)13/h1-3H,(H2,10,13)(H,11,12)
    • InChI Key: QWCFPVXXLJQESR-UHFFFAOYSA-N
    • SMILES: N1C2=C(C=CC(Br)=C2)C(C(N)=O)=N1

Computed Properties

  • Exact Mass: 238.96942g/mol
  • Monoisotopic Mass: 238.96942g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 13
  • Rotatable Bond Count: 1
  • Complexity: 223
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 1.5
  • Topological Polar Surface Area: 71.8?2

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Additional information on 6-BROMO-1H-INDAZOLE-3-CARBOXAMIDE

6-Bromo-1H-indazole-3-carboxamide: A Comprehensive Overview

6-Bromo-1H-indazole-3-carboxamide (CAS No. 1379328-62-7) is a fascinating compound that has garnered significant attention in the fields of organic chemistry, pharmacology, and materials science. This compound belongs to the indazole family, a class of heterocyclic aromatic compounds known for their unique electronic properties and versatile applications. The presence of the bromine atom at the 6-position and the carboxamide group at the 3-position introduces distinct chemical and biological characteristics, making it a subject of intense research.

Recent studies have highlighted the potential of 6-bromo-1H-indazole-3-carboxamide as a promising candidate in drug discovery. Its structural features, including the indazole core and substituents, contribute to its ability to interact with various biological targets. For instance, researchers have explored its role as a modulator of protein kinases, which are critical in cellular signaling pathways. The bromine atom at the 6-position is particularly significant as it enhances the molecule's electron-withdrawing properties, potentially improving its binding affinity to target proteins.

The synthesis of 6-bromo-1H-indazole-3-carboxamide involves a multi-step process that typically begins with the preparation of indazole derivatives. One common approach is the condensation of o-phenylenediamine with carbonyl compounds under acidic conditions, followed by bromination and amidation steps. Recent advancements in catalytic methods have enabled more efficient and selective syntheses, reducing production costs and improving yields.

In terms of applications, 6-bromo-1H-indazole-3-carboxamide has shown potential in several areas. In pharmaceuticals, it has been investigated for its anti-inflammatory and antioxidant properties. Preclinical studies suggest that it may offer therapeutic benefits in conditions such as neurodegenerative diseases and cardiovascular disorders. Additionally, its photochemical properties make it a candidate for use in optoelectronic materials, such as organic light-emitting diodes (OLEDs) and photovoltaic cells.

One of the most intriguing aspects of 6-bromo-1H-indazole-3-carboxamide is its ability to act as a scaffold for further chemical modifications. Researchers have explored substituent effects on its electronic properties, leading to derivatives with enhanced bioavailability and efficacy. For example, introducing electron-donating groups at specific positions has been shown to improve solubility and stability, which are critical factors in drug design.

From an environmental perspective, 6-bromo-1H-indazole-3-carboxamide has been studied for its biodegradability and toxicity profiles. Initial assessments indicate that it is not acutely toxic to aquatic organisms under standard test conditions. However, long-term ecological impacts require further investigation to ensure sustainable use.

In conclusion, 6-bromo-1H-indazole-3-carboxamide (CAS No. 1379328-62-7) is a versatile compound with diverse applications across multiple disciplines. Its unique structure, combined with recent advancements in synthesis and application studies, positions it as a valuable tool in both academic research and industrial development. As research continues to unfold, this compound is expected to contribute significantly to innovative solutions in medicine, materials science, and beyond.

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