Cas no 885278-24-0 (6-Bromo-1H-indazole-3-carbonitrile)

6-Bromo-1H-indazole-3-carbonitrile is a heterocyclic organic compound featuring a bromo-substituted indazole core with a cyano functional group at the 3-position. This structure makes it a valuable intermediate in pharmaceutical and agrochemical synthesis, particularly in the development of kinase inhibitors and other biologically active molecules. The bromine substituent enhances reactivity for further functionalization via cross-coupling reactions, while the nitrile group offers versatility in derivatization. Its high purity and stability under standard conditions ensure consistent performance in research and industrial applications. The compound is commonly utilized in medicinal chemistry for scaffold modification and lead optimization due to its well-defined reactivity profile.
6-Bromo-1H-indazole-3-carbonitrile structure
885278-24-0 structure
Product Name:6-Bromo-1H-indazole-3-carbonitrile
CAS No:885278-24-0
MF:C8H4BrN3
MW:222.041460037231
MDL:MFCD06659785
CID:69301
PubChem ID:24728894
Update Time:2025-10-20

6-Bromo-1H-indazole-3-carbonitrile Chemical and Physical Properties

Names and Identifiers

    • 6-Bromo-1H-indazole-3-carbonitrile
    • 6-Bromo indzole-3-carbonitrile
    • 6-Bromo-1H-indazole-3-carbonitrile (ACI)
    • CS-0037687
    • SY020629
    • DTXSID70646555
    • AB26304
    • AC-28271
    • AKOS015898368
    • MFCD06659785
    • SCHEMBL11977413
    • 885278-24-0
    • DB-077746
    • BCP11558
    • J-518301
    • FS-3659
    • DTXCID20597306
    • BNMHCHQOAQMIBU-UHFFFAOYSA-N
    • MDL： MFCD06659785
    • Inchi： 1S/C8H4BrN3/c9-5-1-2-6-7(3-5)11-12-8(6)4-10/h1-3H,(H,11,12)
    • InChI Key： BNMHCHQOAQMIBU-UHFFFAOYSA-N
    • SMILES： N#CC1C2C(=CC(=CC=2)Br)NN=1

Computed Properties

  • Exact Mass: 220.95900
  • Monoisotopic Mass: 220.959
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 12
  • Rotatable Bond Count: 0
  • Complexity: 222
  • 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
  • Surface Charge: 0
  • Tautomer Count: 2
  • XLogP3: 2.3
  • Topological Polar Surface Area: 52.5A^2

Experimental Properties

  • Color/Form: No data avaiable
  • Density: 1.9±0.1 g/cm3
  • Melting Point: No data available
  • Boiling Point: 425.3±25.0 °C at 760 mmHg
  • Flash Point: 211.0±23.2 °C
  • PSA: 52.47000
  • LogP: 2.19708
  • Vapor Pressure: 0.0±1.0 mmHg at 25°C

6-Bromo-1H-indazole-3-carbonitrile Security Information

6-Bromo-1H-indazole-3-carbonitrile Customs Data

  • HS CODE：2933990090
  • Customs Data：

    China Customs Code:

    2933990090

    Overview:

    2933990090. Other heterocyclic compounds containing only nitrogen heteroatoms. VAT:17.0%. Tax refund rate:13.0%. Regulatory conditions:nothing. MFN tariff:6.5%. general tariff:20.0%

    Declaration elements:

    Product Name, component content, use to, Please indicate the appearance of Urotropine, 6- caprolactam please indicate the appearance, Signing date

    Summary:

    2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

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6-Bromo-1H-indazole-3-carbonitrile Related Literature

Related Categories

Additional information on 6-Bromo-1H-indazole-3-carbonitrile

Comprehensive Overview of 6-Bromo-1H-indazole-3-carbonitrile (CAS No. 885278-24-0): Properties, Applications, and Research Insights

6-Bromo-1H-indazole-3-carbonitrile (CAS No. 885278-24-0) is a high-value heterocyclic compound widely utilized in pharmaceutical and agrochemical research. This brominated indazole derivative features a nitrile group at the 3-position, making it a versatile intermediate for synthesizing biologically active molecules. Its molecular formula, C8H4BrN3, and unique structural properties have attracted significant attention in medicinal chemistry, particularly in kinase inhibitor development and cancer drug discovery.

The growing demand for indazole-based scaffolds in drug design has positioned 6-Bromo-1H-indazole-3-carbonitrile as a critical building block. Researchers frequently search for "indazole nitrile synthesis" or "6-bromo indazole applications," reflecting its importance in small molecule therapeutics. Recent studies highlight its role in modulating protein-protein interactions, a hot topic in targeted therapy research.

From a synthetic perspective, this compound's bromine substituent enables efficient cross-coupling reactions (e.g., Suzuki-Miyaura), addressing frequent search queries like "functionalized indazole derivatives." Its thermal stability (typically stable below 250°C) and solubility profile (soluble in DMSO, DMF) make it suitable for high-throughput screening platforms. Analytical data shows characteristic HPLC retention times and distinct NMR peaks (δ 8.1-7.5 ppm for aromatic protons), crucial for quality control in preclinical development.

Environmental and regulatory aspects of 6-Bromo-1H-indazole-3-carbonitrile align with green chemistry trends. Queries such as "biodegradable heterocycles" and "sustainable pharmaceutical intermediates" relate to its potential for atom-efficient synthesis. The compound's low ecotoxicity (OECD 201 guidelines) supports its adoption in green synthetic routes, a priority for modern chemical manufacturers.

Emerging applications in material science have expanded the utility of this indazole derivative. Its ability to form coordination complexes with transition metals responds to searches for "nitrile-containing ligands." Recent patents disclose its use in organic electronic materials, particularly as electron-transport layers in OLED devices, demonstrating cross-disciplinary relevance.

Quality specifications for CAS No. 885278-24-0 typically require ≥98% purity (HPLC), with stringent control of residual solvents (ICH Q3C guidelines). This aligns with pharmaceutical industry demands for "high-purity screening compounds." Storage recommendations (-20°C under nitrogen) and handling precautions (use of PPE) address common user concerns about compound stability and laboratory safety.

The global market for 6-Bromo-1H-indazole-3-carbonitrile reflects increasing R&D investment in precision medicine. Market analysis reveals growing procurement by CROs and academic institutions, particularly for fragment-based drug design projects. Custom synthesis services now offer isotope-labeled versions (e.g., 13C- or 15N-labeled), responding to demand for ADME studies and metabolic pathway research.

Future research directions may explore this compound's potential in proteolysis targeting chimeras (PROTACs), a trending topic in drug discovery. Its dual functionality (bromine for conjugation, nitrile for hydrogen bonding) makes it valuable for designing bifunctional degraders. Such applications address frequent queries about "indazole cores in targeted protein degradation," showcasing its evolving scientific relevance.

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