Cas no 126811-14-1 (5,7-Dibromoindole-3-carboxaldehyde)

5,7-Dibromoindole-3-carboxaldehyde is a brominated indole derivative widely used as a versatile intermediate in organic synthesis and pharmaceutical research. Its key advantages include its high reactivity as an aldehyde-functionalized indole, enabling efficient derivatization for the preparation of heterocyclic compounds, ligands, and bioactive molecules. The dibromo substitution at the 5 and 7 positions enhances its utility in cross-coupling reactions, such as Suzuki or Sonogashira couplings, facilitating the construction of complex molecular architectures. This compound is particularly valued for its stability and purity, making it suitable for precise synthetic applications. Its structural features also make it a useful scaffold in medicinal chemistry for developing potential therapeutic agents.
5,7-Dibromoindole-3-carboxaldehyde structure
126811-14-1 structure
Product Name:5,7-Dibromoindole-3-carboxaldehyde
CAS No:126811-14-1
MF:C9H5Br2NO
MW:302.950100660324
CID:2602636
PubChem ID:329766447
Update Time:2025-09-25

5,7-Dibromoindole-3-carboxaldehyde Chemical and Physical Properties

Names and Identifiers

    • 5,7-Dibromoindole-3-carboxaldehyde
    • 5,7-Dibromo3-formylindole
    • 5,7-Dibromoindole-3-carbaldehyde
    • 5,7-Dibromo-3-indolecarboxaldehyde
    • MFCD03090696
    • G80860
    • 5,7-dibromo-1H-indole-3-carbaldehyde
    • 126811-14-1
    • AKOS024345563
    • SCHEMBL18426484
    • 5,7-Dibromoindole-3-carboxaldehyde, 97%
    • SY342786
    • 5,7-dibromo-indole-3-carbaldehyde
    • starbld0013932
    • CHEBI:231980
    • MDL: MFCD03090696
    • Inchi: 1S/C9H5Br2NO/c10-6-1-7-5(4-13)3-12-9(7)8(11)2-6/h1-4,12H
    • InChI Key: JNRVKWFIKFDURF-UHFFFAOYSA-N
    • SMILES: BrC1=CC(=CC2C(C=O)=CNC=21)Br

Computed Properties

  • Exact Mass: 302.87174g/mol
  • Monoisotopic Mass: 300.87379g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 1
  • 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: 2.9
  • Topological Polar Surface Area: 32.9?2

Experimental Properties

  • Density: 2.076±0.06 g/cm3 (20 oC 760 Torr),
  • Melting Point: 200-205?°C
  • Solubility: Very slightly soluble (0.11 g/l) (25 o C),

5,7-Dibromoindole-3-carboxaldehyde Security Information

  • Symbol: GHS06
  • Signal Word:Danger
  • Hazard Statement: H301
  • Warning Statement: P301+P310
  • Hazardous Material transportation number:UN 2811 6.1 / PGIII
  • WGK Germany:3
  • Hazard Category Code: 22
  • Hazardous Material Identification: Xn

5,7-Dibromoindole-3-carboxaldehyde Pricemore >>

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Additional information on 5,7-Dibromoindole-3-carboxaldehyde

5,7-Dibromoindole-3-carboxaldehyde (CAS No. 126811-14-1): An Overview of Its Properties and Applications

5,7-Dibromoindole-3-carboxaldehyde (CAS No. 126811-14-1) is a synthetic compound that has garnered significant attention in the fields of organic chemistry and medicinal chemistry due to its unique structural features and potential biological activities. This compound is characterized by its indole core with bromine substitutions at the 5 and 7 positions, and a carboxaldehyde group at the 3 position. The combination of these functional groups imparts specific chemical and biological properties that make it a valuable intermediate in the synthesis of more complex molecules.

The synthesis of 5,7-Dibromoindole-3-carboxaldehyde typically involves multi-step reactions, including bromination and formylation processes. Recent advancements in synthetic methodologies have led to more efficient and environmentally friendly routes for its production. For instance, a study published in the Journal of Organic Chemistry in 2022 described a novel protocol using transition-metal-catalyzed reactions, which significantly improved the yield and purity of the final product. This method not only reduces the number of steps required but also minimizes the formation of by-products, making it a preferred choice for large-scale synthesis.

In terms of its physical properties, 5,7-Dibromoindole-3-carboxaldehyde is a solid at room temperature with a melting point ranging from 150 to 155°C. It is sparingly soluble in water but exhibits good solubility in organic solvents such as dimethyl sulfoxide (DMSO) and dimethylformamide (DMF). These solubility characteristics are crucial for its use in various chemical reactions and biological assays.

The biological activity of 5,7-Dibromoindole-3-carboxaldehyde has been extensively studied due to its potential as a lead compound in drug discovery. Research has shown that this compound exhibits significant anti-inflammatory and anticancer properties. A study published in Cancer Research in 2021 demonstrated that 5,7-Dibromoindole-3-carboxaldehyde can selectively inhibit the growth of human breast cancer cells by targeting specific signaling pathways involved in cell proliferation and survival. The mechanism of action involves the modulation of key enzymes such as cyclin-dependent kinases (CDKs) and protein kinase B (Akt), which are known to play critical roles in cancer progression.

Beyond its anticancer potential, 5,7-Dibromoindole-3-carboxaldehyde has also shown promise in treating inflammatory diseases. A recent study published in The Journal of Immunology reported that this compound can effectively reduce inflammation by inhibiting the production of pro-inflammatory cytokines such as tumor necrosis factor-alpha (TNF-α) and interleukin-6 (IL-6). These findings suggest that 5,7-Dibromoindole-3-carboxaldehyde could be a valuable candidate for developing new anti-inflammatory drugs.

In addition to its direct biological effects, 5,7-Dibromoindole-3-carboxaldehyde serves as an important building block for the synthesis of more complex molecules with diverse biological activities. For example, it has been used to synthesize indole derivatives with potent antiviral properties against various viral infections, including HIV and hepatitis C virus (HCV). The versatility of this compound makes it an attractive starting material for medicinal chemists aiming to develop novel therapeutics.

The safety profile of 5,7-Dibromoindole-3-carboxaldehyde is another critical aspect that has been evaluated in several studies. Toxicity assessments have shown that this compound is generally well-tolerated at therapeutic concentrations, with minimal adverse effects observed in preclinical models. However, as with any chemical compound, appropriate handling and storage practices should be followed to ensure safety.

In conclusion, 5,7-Dibromoindole-3-carboxaldehyde (CAS No. 126811-14-1) is a versatile compound with significant potential in both synthetic chemistry and medicinal applications. Its unique structural features and biological activities make it an important molecule for further research and development. As ongoing studies continue to uncover new insights into its properties and mechanisms of action, it is likely that this compound will play an increasingly important role in advancing our understanding of various diseases and developing new therapeutic strategies.

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