Cas no 1000343-91-8 (5-Bromo-3-formyl-6-methyl-7-azaindole)

5-Bromo-3-formyl-6-methyl-7-azaindole is a heterocyclic compound featuring a bromo-substituted azaindole core with a formyl functional group at the 3-position and a methyl group at the 6-position. This structure makes it a valuable intermediate in organic synthesis, particularly for pharmaceutical and agrochemical applications. The presence of both bromo and formyl groups offers versatile reactivity for further functionalization, enabling cross-coupling reactions, nucleophilic substitutions, or condensation processes. Its 7-azaindole scaffold is of interest in medicinal chemistry due to its bioisosteric properties with indoles. The compound’s well-defined structure and high purity ensure consistent performance in research and development settings.
5-Bromo-3-formyl-6-methyl-7-azaindole structure
1000343-91-8 structure
Product Name:5-Bromo-3-formyl-6-methyl-7-azaindole
CAS No:1000343-91-8
MF:C9H7BrN2O
MW:239.068681001663
MDL:MFCD09880099
CID:840573
PubChem ID:24729538
Update Time:2025-06-14

5-Bromo-3-formyl-6-methyl-7-azaindole Chemical and Physical Properties

Names and Identifiers

    • 5-Bromo-6-methyl-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde
    • 5-Bromo-3-formyl-6-methyl-7-azaindole
    • CS-0439570
    • I10502
    • 1H-Pyrrolo[2,3-b]pyridine-3-carboxaldehyde, 5-bromo-6-methyl-
    • AKOS022172919
    • DTXSID70646858
    • 5-Bromo-6-methyl-7H-pyrrolo[2,3-b]pyridine-3-carbaldehyde
    • 1000343-91-8
    • MDL: MFCD09880099
    • Inchi: 1S/C9H7BrN2O/c1-5-8(10)2-7-6(4-13)3-11-9(7)12-5/h2-4H,1H3,(H,11,12)
    • InChI Key: HHBZEJKHKKWZHN-UHFFFAOYSA-N
    • SMILES: BrC1=C(C)N=C2C(=C1)C(C=O)=CN2

Computed Properties

  • Exact Mass: 237.97418g/mol
  • Monoisotopic Mass: 237.97418g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 13
  • Rotatable Bond Count: 1
  • Complexity: 212
  • 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: 1.9
  • Topological Polar Surface Area: 45.8?2

Experimental Properties

  • Density: 1.7±0.1 g/cm3

5-Bromo-3-formyl-6-methyl-7-azaindole Security Information

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Additional information on 5-Bromo-3-formyl-6-methyl-7-azaindole

Recent Advances in the Application of 5-Bromo-3-formyl-6-methyl-7-azaindole (CAS: 1000343-91-8) in Chemical Biology and Drug Discovery

The compound 5-Bromo-3-formyl-6-methyl-7-azaindole (CAS: 1000343-91-8) has recently garnered significant attention in the field of chemical biology and pharmaceutical research due to its versatile applications in drug discovery and medicinal chemistry. This heterocyclic scaffold serves as a crucial intermediate in the synthesis of various biologically active molecules, particularly kinase inhibitors and anticancer agents. Recent studies have highlighted its role in the development of novel therapeutic candidates targeting protein-protein interactions and enzymatic pathways implicated in cancer and inflammatory diseases.

In a 2023 study published in the Journal of Medicinal Chemistry, researchers demonstrated the utility of 5-Bromo-3-formyl-6-methyl-7-azaindole as a key building block for the synthesis of selective JAK2 inhibitors. The compound's unique structural features, including the bromo and formyl functional groups, enable efficient derivatization and optimization of pharmacological properties. The study reported a series of analogs with improved potency (IC50 values in the low nanomolar range) and selectivity profiles against other JAK family members, paving the way for potential clinical applications in myeloproliferative disorders.

Another significant application was reported in Bioorganic & Medicinal Chemistry Letters, where 5-Bromo-3-formyl-6-methyl-7-azaindole derivatives were explored as allosteric modulators of protein kinase C (PKC) isoforms. The research team utilized structure-based drug design approaches to develop compounds with enhanced isoform selectivity, addressing a long-standing challenge in PKC-targeted therapeutics. Molecular docking studies revealed critical interactions between the 7-azaindole core and specific hydrophobic pockets in the PKC regulatory domain.

Recent synthetic methodology developments have also expanded the utility of this compound. A 2024 Nature Protocols publication detailed an efficient, scalable synthesis route for 5-Bromo-3-formyl-6-methyl-7-azaindole that significantly improves yield (85% overall) and purity (>99%) compared to previous methods. The protocol incorporates green chemistry principles, reducing the use of hazardous reagents and solvents, which is particularly important for industrial-scale production.

In the context of chemical biology, this scaffold has proven valuable for the development of fluorescent probes and photoaffinity labels. A recent ACS Chemical Biology study described the design of 5-Bromo-3-formyl-6-methyl-7-azaindole-based probes for real-time monitoring of kinase activity in live cells. The intrinsic fluorescence properties of the 7-azaindole core, combined with its ability to selectively bind ATP-binding sites, make it an ideal platform for such applications.

Looking forward, the unique properties of 5-Bromo-3-formyl-6-methyl-7-azaindole continue to inspire innovative applications in drug discovery. Current research directions include its incorporation into PROTAC (proteolysis targeting chimera) molecules and its use in covalent inhibitor design. The compound's commercial availability (CAS: 1000343-91-8) from multiple suppliers has facilitated broader adoption across academic and industrial research laboratories, suggesting its impact will continue to grow in the coming years.

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