Cas no 1167055-55-1 (4-Bromo-1H-indazole-3-carbonitrile)

4-Bromo-1H-indazole-3-carbonitrile is a heterocyclic compound featuring a bromo-substituted indazole core with a nitrile functional group at the 3-position. This structure makes it a valuable intermediate in pharmaceutical and agrochemical synthesis, particularly for the development of biologically active molecules. The bromo 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 reliable performance in research and industrial applications. The compound is commonly utilized in medicinal chemistry for the design of kinase inhibitors and other therapeutic agents, demonstrating its significance in drug discovery.
4-Bromo-1H-indazole-3-carbonitrile structure
1167055-55-1 structure
Product Name:4-Bromo-1H-indazole-3-carbonitrile
CAS No:1167055-55-1
MF:C8H4BrN3
MW:222.041460037231
MDL:MFCD11845593
CID:1032201
PubChem ID:53399495
Update Time:2025-08-05

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

Names and Identifiers

    • 4-Bromo-1H-indazole-3-carbonitrile
    • 4-Bromo-3-cyano-1H indazole
    • 1H-Indazole-3-carbonitrile, 4-bromo-
    • 4-Bromo-3-cyano-indazole
    • AK123049
    • KB-240481
    • PB10941
    • SCHEMBL25206592
    • DTXSID80694628
    • AS-50830
    • DB-340080
    • P11206
    • A893530
    • SY020828
    • MFCD11845593
    • 1167055-55-1
    • AKOS016012144
    • MDL: MFCD11845593
    • Inchi: 1S/C8H4BrN3/c9-5-2-1-3-6-8(5)7(4-10)12-11-6/h1-3H,(H,11,12)
    • InChI Key: MWSBWMOOELBNBT-UHFFFAOYSA-N
    • SMILES: BrC1=CC=CC2=C1C(C#N)=NN2

Computed Properties

  • Exact Mass: 220.95886g/mol
  • Monoisotopic Mass: 220.95886g/mol
  • 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
  • XLogP3: 2.3
  • Topological Polar Surface Area: 52.5?2

Experimental Properties

  • Density: 1.85±0.1 g/cm3 (20 oC 760 Torr),
  • Solubility: Very slightly soluble (0.14 g/l) (25 o C),

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

  • Signal Word:Warning
  • Hazard Statement: H302
  • Warning Statement: P280-P305+P351+P338
  • Storage Condition:Sealed in dry,Room Temperature

4-Bromo-1H-indazole-3-carbonitrile Pricemore >>

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Additional information on 4-Bromo-1H-indazole-3-carbonitrile

Research Brief on 4-Bromo-1H-indazole-3-carbonitrile (CAS: 1167055-55-1) in Chemical Biology and Pharmaceutical Applications

4-Bromo-1H-indazole-3-carbonitrile (CAS: 1167055-55-1) is a heterocyclic compound that has garnered significant attention in recent years due to its versatile applications in medicinal chemistry and drug discovery. This indazole derivative serves as a key intermediate in the synthesis of various biologically active molecules, particularly those targeting kinase inhibition and cancer therapeutics. Recent studies have highlighted its role as a privileged scaffold in the development of small-molecule inhibitors for critical signaling pathways.

A 2023 study published in the Journal of Medicinal Chemistry demonstrated the compound's utility in constructing potent and selective inhibitors of cyclin-dependent kinases (CDKs). Researchers utilized 4-Bromo-1H-indazole-3-carbonitrile as a core building block to develop novel CDK4/6 inhibitors with improved pharmacokinetic properties. The bromo-substitution at the 4-position was found to be crucial for maintaining target binding affinity while the nitrile group at the 3-position contributed to favorable metabolic stability.

In the field of antimicrobial research, a 2024 publication in Bioorganic & Medicinal Chemistry Letters reported the synthesis of novel antifungal agents derived from 4-Bromo-1H-indazole-3-carbonitrile. The compound's structure allowed for strategic modifications that enhanced activity against Candida species while maintaining low cytotoxicity. Molecular docking studies revealed that derivatives of this scaffold effectively bind to fungal lanosterol 14α-demethylase, a key enzyme in ergosterol biosynthesis.

Ongoing clinical research has identified 4-Bromo-1H-indazole-3-carbonitrile derivatives as promising candidates for the treatment of inflammatory diseases. A recent patent application (WO2023124567) describes its use in developing IRAK4 inhibitors for autoimmune disorders. The compound's ability to accommodate various pharmacophores while maintaining favorable drug-like properties makes it particularly valuable for structure-activity relationship studies in inflammation pathways.

From a synthetic chemistry perspective, novel methodologies have been developed to improve the efficiency of 4-Bromo-1H-indazole-3-carbonitrile production. A 2023 study in Organic Process Research & Development presented a continuous-flow synthesis approach that increased yield by 35% compared to traditional batch methods, while reducing hazardous waste generation. This advancement addresses the growing demand for this intermediate in pharmaceutical development pipelines.

Future research directions for 4-Bromo-1H-indazole-3-carbonitrile appear promising, with several preclinical studies investigating its derivatives as potential treatments for neurodegenerative diseases and rare genetic disorders. The compound's structural flexibility and demonstrated biological activity across multiple target classes position it as a valuable tool for medicinal chemists addressing unmet medical needs.

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