Cas no 71757-16-9 (2-Bromo-4-chloro-6-iodoaniline)

2-Bromo-4-chloro-6-iodoaniline is a halogenated aniline derivative with a highly functionalized aromatic structure, making it a valuable intermediate in organic synthesis and pharmaceutical research. The presence of bromo, chloro, and iodo substituents at the 2, 4, and 6 positions, respectively, provides multiple reactive sites for further chemical modifications, such as cross-coupling reactions or nucleophilic substitutions. This compound is particularly useful in the development of complex molecules, including agrochemicals and bioactive compounds, due to its ability to undergo selective transformations. Its well-defined structure and high purity ensure consistent performance in synthetic applications, making it a reliable choice for researchers requiring precise functionalization of aniline derivatives.
2-Bromo-4-chloro-6-iodoaniline structure
71757-16-9 structure
Product Name:2-Bromo-4-chloro-6-iodoaniline
CAS No:71757-16-9
MF:C6H4BrClIN
MW:332.36413192749
MDL:MFCD24160443
CID:4156117
PubChem ID:20216596
Update Time:2025-05-25

2-Bromo-4-chloro-6-iodoaniline Chemical and Physical Properties

Names and Identifiers

    • Benzenamine, 2-bromo-4-chloro-6-iodo-
    • 2-bromo-4-chloro-6-iodoaniline
    • KGJQFAVZGHPELU-UHFFFAOYSA-N
    • AKOS030628753
    • 71757-16-9
    • DTXSID701297637
    • 2-Bromo-4-chloro-6-iodobenzenamine
    • AS-63051
    • MFCD24160443
    • SCHEMBL10796712
    • 2-Bromo-4-chloro-6-iodoaniline
    • MDL: MFCD24160443
    • Inchi: 1S/C6H4BrClIN/c7-4-1-3(8)2-5(9)6(4)10/h1-2H,10H2
    • InChI Key: KGJQFAVZGHPELU-UHFFFAOYSA-N
    • SMILES: IC1C=C(C=C(C=1N)Br)Cl

Computed Properties

  • Exact Mass: 330.82604g/mol
  • Monoisotopic Mass: 330.82604g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 1
  • Heavy Atom Count: 10
  • Rotatable Bond Count: 0
  • Complexity: 124
  • 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
  • Topological Polar Surface Area: 26
  • XLogP3: 3.2

2-Bromo-4-chloro-6-iodoaniline Pricemore >>

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Additional information on 2-Bromo-4-chloro-6-iodoaniline

Professional Introduction to 2-Bromo-4-chloro-6-iodoaniline (CAS No. 71757-16-9)

2-Bromo-4-chloro-6-iodoaniline, with the chemical formula C?H?BrClIN?, is a halogenated aromatic amine that has garnered significant attention in the field of pharmaceutical and agrochemical research. This compound serves as a versatile intermediate in the synthesis of various biologically active molecules, making it a valuable tool for medicinal chemists and synthetic organic chemists alike. Its unique structural features, comprising bromine, chlorine, and iodine substituents on a benzene ring, contribute to its reactivity and utility in multiple synthetic pathways.

The CAS number 71757-16-9 uniquely identifies this compound in scientific literature and databases, ensuring precise referencing and consistency in research communications. The presence of three halogen atoms on the aromatic ring makes 2-bromo-4-chloro-6-iodoaniline a particularly interesting candidate for cross-coupling reactions, such as Suzuki-Miyaura, Stille, and Buchwald-Hartwig couplings. These reactions are fundamental in constructing complex molecular frameworks, which are often required in the development of novel therapeutic agents.

In recent years, there has been a surge in research focused on halogenated aromatic compounds due to their broad spectrum of biological activities. Studies have demonstrated that such compounds can exhibit antimicrobial, anti-inflammatory, and anticancer properties. The bromo, chloro, and iodo substituents on the benzene ring of 2-bromo-4-chloro-6-iodoaniline can be strategically modified or used in subsequent reactions to tailor the pharmacological profile of derived molecules. For instance, the iodine atom is particularly useful in palladium-catalyzed coupling reactions, while the bromine and chlorine atoms can serve as handles for further functionalization.

One of the most compelling applications of 2-bromo-4-chloro-6-iodoaniline is in the synthesis of kinase inhibitors. Kinases are enzymes that play a crucial role in cell signaling pathways, and their dysregulation is often associated with various diseases, including cancer. By incorporating this compound into drug candidates, researchers aim to develop selective kinase inhibitors that can modulate these pathways effectively. The halogen atoms provide multiple sites for interaction with biological targets, enhancing binding affinity and selectivity.

Moreover, the long-tail keyword "2-bromo-4-chloro-6-iodoaniline" has been increasingly referenced in cutting-edge research related to photodynamic therapy (PDT). Halogenated aromatic compounds have shown promise as photosensitizer precursors due to their ability to form stable complexes with light-absorbing dyes. These complexes can generate reactive oxygen species upon exposure to light, leading to targeted cell destruction. The structural versatility of 2-bromo-4-chloro-6-iodoaniline makes it an ideal candidate for designing novel photosensitizers with improved efficacy and reduced side effects.

Recent advancements in computational chemistry have also highlighted the potential of 2-bromo-4-chloro-6-iodoaniline as a scaffold for drug discovery. Molecular modeling studies suggest that its halogen-rich structure can interact favorably with biological targets through both hydrophobic and electrostatic interactions. This has led to the identification of new lead compounds with enhanced pharmacokinetic properties. The ability to predictively model the behavior of such compounds before experimental synthesis significantly accelerates the drug development process.

The synthesis of 2-bromo-4-chloro-6-iodoaniline typically involves multi-step organic transformations starting from aniline derivatives. Key steps include halogenation using appropriate reagents such as N-bromosuccinimide (NBS) for bromination and phosphorus oxychloride (POCl?) for chlorination. The iodination step is often performed using iodine monochloride (ICl) or molecular iodine (I?) in the presence of a catalyst. These reactions require careful optimization to ensure high yield and purity, which are critical for subsequent applications.

In conclusion, 2-bromo-4-chloro-6-iodoaniline (CAS No. 71757-16-9) is a multifaceted compound with significant potential in pharmaceutical research. Its unique structural features make it an invaluable intermediate for constructing biologically active molecules, particularly kinase inhibitors and photosensitizers. As research continues to uncover new applications for halogenated aromatic compounds, 2-bromo-4-chloro-6-iodoaniline is poised to remain at the forefront of drug discovery efforts.

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