Cas no 28165-58-4 (3-Bromo-2,6-diiodophenol)

3-Bromo-2,6-diiodophenol structure
3-Bromo-2,6-diiodophenol structure
Product Name:3-Bromo-2,6-diiodophenol
CAS No:28165-58-4
MF:C6H3BrI2O
MW:424.800365686417
CID:4976963
Update Time:2025-11-02

3-Bromo-2,6-diiodophenol Chemical and Physical Properties

Names and Identifiers

    • 3-Bromo-2,6-diiodophenol
    • BrC=1C(=C(C(=CC1)I)O)I
    • Inchi: 1S/C6H3BrI2O/c7-3-1-2-4(8)6(10)5(3)9/h1-2,10H
    • InChI Key: KTNMLAQHPDRRTA-UHFFFAOYSA-N
    • SMILES: IC1C(=CC=C(C=1O)I)Br

Computed Properties

  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 1
  • Heavy Atom Count: 10
  • Rotatable Bond Count: 0
  • Complexity: 122
  • XLogP3: 3.6
  • Topological Polar Surface Area: 20.2

3-Bromo-2,6-diiodophenol Pricemore >>

Related Categories No. Product Name Cas No. Purity Specification Price update time Inquiry
Alichem
A013017016-250mg
3-Bromo-2,6-diiodophenol
28165-58-4 97%
250mg
$480.00 2023-09-02
Alichem
A013017016-500mg
3-Bromo-2,6-diiodophenol
28165-58-4 97%
500mg
$855.75 2023-09-02
Alichem
A013017016-1g
3-Bromo-2,6-diiodophenol
28165-58-4 97%
1g
$1460.20 2023-09-02

Additional information on 3-Bromo-2,6-diiodophenol

Chemical Profile of 3-Bromo-2,6-diiodophenol (CAS No. 28165-58-4)

3-Bromo-2,6-diiodophenol, identified by its Chemical Abstracts Service (CAS) number 28165-58-4, is a halogenated aromatic compound that has garnered significant attention in the field of medicinal chemistry and materials science. This compound features a phenolic core substituted with bromine and iodine atoms at the 3rd and 2,6-positions, respectively, which endows it with unique electronic and steric properties. The strategic placement of halogen atoms makes it a valuable intermediate in the synthesis of various bioactive molecules, including pharmaceuticals and functional materials.

The structural motif of 3-Bromo-2,6-diiodophenol is highly versatile, enabling its incorporation into complex molecular frameworks through nucleophilic aromatic substitution, cross-coupling reactions, and other palladium-catalyzed transformations. Its dual halogenation enhances reactivity while providing stability, making it an attractive building block for drug discovery campaigns. In recent years, this compound has been explored in the development of novel therapeutic agents targeting diverse biological pathways.

One of the most compelling applications of 3-Bromo-2,6-diiodophenol lies in its role as a precursor for small-molecule inhibitors. Researchers have leveraged its scaffold to design molecules with potent activity against enzymes implicated in cancer progression. For instance, studies have demonstrated its utility in generating derivatives that selectively inhibit tyrosine kinases, which are critical drivers of tumor growth and metastasis. The bromo and iodo substituents facilitate further functionalization, allowing chemists to fine-tune pharmacokinetic properties such as solubility and metabolic stability.

Moreover, the electronic properties of 3-Bromo-2,6-diiodophenol make it a promising candidate for applications in organic electronics. Its extended conjugation system and strong electron-withdrawing effects contribute to its utility as an electron transport material in organic light-emitting diodes (OLEDs) and photovoltaic devices. Recent advancements in this area have highlighted its potential in enhancing device efficiency through optimized molecular design.

In the realm of medicinal chemistry, the synthesis of 3-Bromo-2,6-diiodophenol has been refined to achieve high yields and purity using modern catalytic methods. Transition-metal-catalyzed reactions, particularly those involving palladium and copper complexes, have enabled efficient functionalization at the aromatic ring. These methodologies align with green chemistry principles by minimizing waste and reducing reliance on hazardous reagents.

The biological activity of derivatives derived from 3-Bromo-2,6-diiodophenol has been extensively investigated. Notably, researchers have reported its incorporation into kinase inhibitors that exhibit nanomolar potency in cellular assays. The phenolic hydroxyl group serves as a hydrogen bond acceptor or a site for coordination with metal ions in biological targets, enhancing binding affinity. Structural modifications around this core have revealed insights into ligand-receptor interactions that could inform future drug design strategies.

Recent computational studies have further elucidated the mechanistic aspects of reactions involving 3-Bromo-2,6-diiodophenol. Quantum mechanical calculations have provided detailed insights into transition state geometries and reaction energetics for various transformations. These findings not only aid in optimizing synthetic routes but also contribute to a deeper understanding of how structural features influence chemical reactivity.

The versatility of 3-Bromo-2,6-diiodophenol extends to its application in material science beyond pharmaceuticals. Its ability to undergo cross-coupling reactions with a wide range of substrates has been exploited to create novel polymers with tailored properties. For example, polymeric materials derived from this compound have shown promise as conductive films or sensors due to their ability to form stable π-conjugated networks.

In conclusion,3-Bromo-2,6-diiodophenol (CAS No. 28165-58-4) represents a cornerstone compound in synthetic chemistry with broad implications for drug discovery and advanced materials development. Its unique structural features enable diverse functionalization strategies while maintaining chemical robustness under various reaction conditions. As research continues to uncover new applications for this versatile intermediate,3-Bromo-2,6-diiodophenol is poised to remain at the forefront of innovation across multiple scientific disciplines.

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