Cas no 1823899-58-6 (6-Bromo-3-chloro-2,4-dimethylpyridine)

6-Bromo-3-chloro-2,4-dimethylpyridine is a halogenated pyridine derivative with a molecular formula of C7H7BrClN. This compound features a bromo and chloro substituent on a dimethylpyridine scaffold, making it a versatile intermediate in organic synthesis and pharmaceutical applications. Its distinct substitution pattern enhances reactivity in cross-coupling reactions, such as Suzuki or Buchwald-Hartwig couplings, facilitating the construction of complex heterocyclic systems. The electron-withdrawing effects of the halogens and steric influence of the methyl groups contribute to selective functionalization. This compound is particularly valuable in medicinal chemistry for the development of bioactive molecules, offering precise control over molecular architecture. High purity and stability ensure consistent performance in synthetic workflows.
6-Bromo-3-chloro-2,4-dimethylpyridine structure
1823899-58-6 structure
Product Name:6-Bromo-3-chloro-2,4-dimethylpyridine
CAS No:1823899-58-6
MF:C7H7BrClN
MW:220.494179964066
CID:4828298
PubChem ID:72710364
Update Time:2026-02-27

6-Bromo-3-chloro-2,4-dimethylpyridine Chemical and Physical Properties

Names and Identifiers

    • 6-Bromo-3-chloro-2,4-dimethylpyridine
    • G68245
    • 1823899-58-6
    • Inchi: 1S/C7H7BrClN/c1-4-3-6(8)10-5(2)7(4)9/h3H,1-2H3
    • InChI Key: XXSBBPPYPGCKDD-UHFFFAOYSA-N
    • SMILES: BrC1=CC(C)=C(C(C)=N1)Cl

Computed Properties

  • Exact Mass: 218.94504g/mol
  • Monoisotopic Mass: 218.94504g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 1
  • Heavy Atom Count: 10
  • Rotatable Bond Count: 0
  • Complexity: 120
  • 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: 3.3
  • Topological Polar Surface Area: 12.9

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Additional information on 6-Bromo-3-chloro-2,4-dimethylpyridine

Introduction to 6-Bromo-3-chloro-2,4-dimethylpyridine (CAS No. 1823899-58-6)

6-Bromo-3-chloro-2,4-dimethylpyridine, identified by the Chemical Abstracts Service Number (CAS No.) 1823899-58-6, is a significant intermediate in the field of pharmaceutical and agrochemical research. This compound belongs to the pyridine family, a heterocyclic aromatic structure that has garnered considerable attention due to its versatile reactivity and biological potential. The presence of both bromo and chloro substituents, along with methyl groups at the 2 and 4 positions, enhances its utility as a building block in synthetic chemistry, enabling the construction of more complex molecules with tailored properties.

The synthesis and application of 6-Bromo-3-chloro-2,4-dimethylpyridine have been extensively explored in recent years, particularly in the development of novel therapeutic agents. Its structural features make it an attractive precursor for medicinal chemists seeking to design molecules with enhanced binding affinity and selectivity. For instance, the bromo and chloro atoms serve as versatile handles for further functionalization via cross-coupling reactions, such as Suzuki-Miyaura or Buchwald-Hartwig couplings, which are pivotal in constructing biaryl frameworks found in many bioactive compounds.

In the realm of drug discovery, 6-Bromo-3-chloro-2,4-dimethylpyridine has been utilized in the synthesis of kinase inhibitors, a class of compounds that play a crucial role in targeting cancer and inflammatory diseases. Recent studies have highlighted its role in generating substituted pyridines that exhibit potent activity against tyrosine kinases. The dimethyl groups at the 2 and 4 positions contribute to steric hindrance, which can be fine-tuned to optimize binding interactions within the active site of target enzymes. This structural flexibility has allowed researchers to develop inhibitors with improved pharmacokinetic profiles.

Moreover, the compound’s halogenated nature makes it a valuable scaffold for exploring structure-activity relationships (SAR). By systematically varying or modifying these substituents, scientists can gain insights into how different functional groups influence biological activity. For example, comparative studies have demonstrated that introducing electron-withdrawing groups at specific positions can modulate receptor binding affinity. Such insights are critical for rational drug design, where understanding the molecular interactions at a substructure level is paramount.

The agrochemical industry has also leveraged 6-Bromo-3-chloro-2,4-dimethylpyridine in the development of novel pesticides and herbicides. Pyridine derivatives are well-known for their efficacy in crop protection due to their ability to interact with biological targets in pests and weeds. Researchers have synthesized analogs of this compound that exhibit herbicidal activity by inhibiting key enzymatic pathways involved in plant growth regulation. The bromo and chloro substituents facilitate further derivatization into more potent agrochemicals with improved environmental profiles.

From a synthetic chemistry perspective, 6-Bromo-3-chloro-2,4-dimethylpyridine serves as a versatile precursor for accessing nitrogen-containing heterocycles through various cyclization reactions. For instance, it can be converted into pyrimidines or triazines through condensation reactions with appropriate reagents. These heterocycles are fundamental components in many pharmaceuticals and agrochemicals due to their broad spectrum of biological activities. The ability to efficiently synthesize such derivatives from readily available starting materials like 6-Bromo-3-chloro-2,4-dimethylpyridine underscores its importance in synthetic methodologies.

Recent advances in flow chemistry have further expanded the utility of 6-Bromo-3-chloro-2,4-dimethylpyridine by enabling scalable and controlled synthesis under mild conditions. Flow systems allow for precise manipulation of reaction parameters such as temperature and pressure, leading to higher yields and purities compared to traditional batch processing. This approach is particularly advantageous when dealing with sensitive intermediates or when large quantities are required for industrial applications.

The compound’s role in material science is another emerging area of interest. Pyridine-based molecules are known for their electronic properties, making them suitable candidates for organic semiconductors or ligands in catalytic systems. Researchers have explored its derivatives as components in light-emitting diodes (LEDs) and photovoltaic cells due to their ability to form stable conjugated systems. The halogen substituents can also be used to tune electron transport properties, which is critical for optimizing device performance.

In conclusion,6-Bromo-3-chloro-2,4-dimethylpyridine (CAS No. 1823899-58-6) is a multifaceted compound with broad applications across pharmaceuticals, agrochemicals, and materials science. Its unique structural features—combining bromo and chloro substituents with methyl groups—make it an indispensable intermediate for synthetic chemists aiming to develop novel bioactive molecules. As research continues to uncover new methodologies and applications,6-Bromo-3-chloro-2,4-dimethylpyridine will undoubtedly remain at the forefront of chemical innovation.

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