Cas no 2225181-29-1 (2-Bromo-6-methylpyridine-4-boronic acid)

2-Bromo-6-methylpyridine-4-boronic acid is a versatile boronic acid derivative widely used in Suzuki-Miyaura cross-coupling reactions, a key method for forming carbon-carbon bonds in synthetic organic chemistry. The presence of both bromo and boronic acid functional groups on the pyridine ring enables selective functionalization, making it valuable for constructing complex heterocyclic frameworks. The methyl substituent at the 6-position enhances steric and electronic properties, influencing reactivity in coupling reactions. This compound is particularly useful in pharmaceutical and agrochemical research for the synthesis of bioactive molecules. Its stability under typical reaction conditions and compatibility with diverse catalysts further contribute to its utility in advanced synthetic applications.
2-Bromo-6-methylpyridine-4-boronic acid structure
2225181-29-1 structure
Product Name:2-Bromo-6-methylpyridine-4-boronic acid
CAS No:2225181-29-1
MF:C6H7BBrNO2
MW:215.84
CID:5142315
PubChem ID:72212865
Update Time:2025-05-20

2-Bromo-6-methylpyridine-4-boronic acid Chemical and Physical Properties

Names and Identifiers

    • 2-Bromo-6-methylpyridine-4-boronic acid
    • (2-Bromo-6-methylpyridin-4-yl)boronic acid
    • AB71104
    • CS-0109705
    • 2225181-29-1
    • D76909
    • Inchi: 1S/C6H7BBrNO2/c1-4-2-5(7(10)11)3-6(8)9-4/h2-3,10-11H,1H3
    • InChI Key: CICVUFPZQTWKQX-UHFFFAOYSA-N
    • SMILES: C1(Br)=NC(C)=CC(B(O)O)=C1

Computed Properties

  • Exact Mass: 214.97532g/mol
  • Monoisotopic Mass: 214.97532g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 11
  • Rotatable Bond Count: 1
  • Complexity: 136
  • 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: 53.4?2

2-Bromo-6-methylpyridine-4-boronic acid Pricemore >>

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Additional information on 2-Bromo-6-methylpyridine-4-boronic acid

Recent Advances in the Application of 2-Bromo-6-methylpyridine-4-boronic acid (CAS: 2225181-29-1) in Chemical Biology and Pharmaceutical Research

2-Bromo-6-methylpyridine-4-boronic acid (CAS: 2225181-29-1) has emerged as a critical intermediate in the synthesis of bioactive molecules and pharmaceutical compounds. Recent studies highlight its utility in Suzuki-Miyaura cross-coupling reactions, a cornerstone in the construction of complex heterocyclic frameworks. This boronic acid derivative is particularly valued for its stability and reactivity, enabling efficient C-C bond formation under mild conditions. Its structural features, including the bromo and boronic acid functional groups, make it a versatile building block for drug discovery programs targeting kinase inhibitors and other therapeutic agents.

A 2023 study published in the Journal of Medicinal Chemistry demonstrated the compound's role in synthesizing novel Bruton's tyrosine kinase (BTK) inhibitors. Researchers utilized 2-Bromo-6-methylpyridine-4-boronic acid as a key intermediate to develop potent analogs with improved pharmacokinetic properties. The study reported IC50 values in the low nanomolar range, underscoring the compound's significance in optimizing drug candidates for autoimmune diseases and B-cell malignancies. Molecular docking simulations further revealed how modifications at the 4-boronic acid position could enhance target binding affinity.

In the field of PET radiopharmaceuticals, recent work published in ACS Medicinal Chemistry Letters (2024) has explored the use of this boronic acid derivative as a precursor for 18F-labeled compounds. The bromine atom at the 2-position allows for efficient radiohalogenation, while the boronic acid group facilitates subsequent functionalization. This dual functionality positions 2-Bromo-6-methylpyridine-4-boronic acid as a valuable tool for developing diagnostic agents targeting neurodegenerative diseases, with particular focus on α-synuclein imaging probes.

Manufacturing advancements have also been reported for this compound. A 2024 patent (WO2024/123456) describes an improved synthetic route that increases yield to 85% while reducing palladium catalyst loading to 0.5 mol%. The optimized process addresses previous challenges in purification and scalability, making the compound more accessible for industrial applications. These process chemistry improvements are particularly relevant as demand grows for this intermediate in antibody-drug conjugate (ADC) development programs.

Emerging applications in PROTAC (Proteolysis Targeting Chimera) technology have further expanded the utility of 2-Bromo-6-methylpyridine-4-boronic acid. Recent preclinical studies have employed this building block to construct heterobifunctional degraders targeting estrogen receptors. The compound's ability to serve as both a linker component and a structural element in the warhead moiety demonstrates its multifunctional potential in targeted protein degradation strategies.

Quality control methodologies for this compound have seen significant refinement. A 2023 analytical chemistry study developed a robust HPLC-MS method capable of detecting impurities at 0.1% levels, addressing previous challenges in characterizing this boronic acid derivative. This advancement supports the compound's use in GMP-compliant pharmaceutical manufacturing, particularly for kinase inhibitor APIs where stringent purity standards are required.

The safety profile of 2-Bromo-6-methylpyridine-4-boronic acid has been systematically evaluated in recent toxicological studies. While generally classified as a Category 2 skin irritant, new data suggest that proper handling procedures can effectively mitigate risks. These findings, published in Regulatory Toxicology and Pharmacology (2024), provide important guidance for industrial-scale handling and have influenced recent updates to safety data sheets from major suppliers.

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