Cas no 2304634-22-6 ((6-(Trifluoromethyl)pyridin-3-yl)boronic acid hydrochloride)

(6-(Trifluoromethyl)pyridin-3-yl)boronic acid hydrochloride is a versatile boronic acid derivative widely used in Suzuki-Miyaura cross-coupling reactions for the synthesis of biaryl and heteroaryl compounds. The trifluoromethyl group enhances the electron-withdrawing properties of the pyridine ring, improving reactivity in palladium-catalyzed transformations. This compound is particularly valuable in pharmaceutical and agrochemical research due to its stability and compatibility with diverse reaction conditions. The hydrochloride salt form offers improved handling and solubility in aqueous or polar organic solvents. Its high purity and well-defined structure make it a reliable intermediate for constructing complex molecules, particularly in medicinal chemistry where fluorinated motifs are sought after for their metabolic stability and lipophilicity.
(6-(Trifluoromethyl)pyridin-3-yl)boronic acid hydrochloride structure
2304634-22-6 structure
Product Name:(6-(Trifluoromethyl)pyridin-3-yl)boronic acid hydrochloride
CAS No:2304634-22-6
MF:C6H6BClF3NO2
MW:227.376551151276
CID:5184607
PubChem ID:71744278
Update Time:2025-10-23

(6-(Trifluoromethyl)pyridin-3-yl)boronic acid hydrochloride Chemical and Physical Properties

Names and Identifiers

    • (6-(Trifluoromethyl)pyridin-3-yl)boronic acid hydrochloride
    • [6-(trifluoromethyl)pyridin-3-yl]boronic acid;hydrochloride
    • 2-TRIFLUOROMETHYLPYRIDIN-5-YLBORONIC ACID HCL
    • 2-(Trifluoromethyl)pyridine-5-boronic acid hydrochloride
    • RB2070
    • 2-TRIFLUOROMETHYLPYRIDIN-5-YLBORONICACIDHCL
    • 6-(trifluoromethyl)pyridin-3-ylboronic acid hydrochloride
    • 2-TRIFLUOROMETHYLPYRIDIN-5-YLBORONIC ACID HYDROCHLORIDE
    • WS-01212
    • KCIUJKGJKMZJEP-UHFFFAOYSA-N
    • 2304634-22-6
    • AKOS024464394
    • Inchi: 1S/C6H5BF3NO2.ClH/c8-6(9,10)5-2-1-4(3-11-5)7(12)13;/h1-3,12-13H;1H
    • InChI Key: KCIUJKGJKMZJEP-UHFFFAOYSA-N
    • SMILES: Cl.FC(C1C=CC(B(O)O)=CN=1)(F)F

Computed Properties

  • Exact Mass: 227.0132208g/mol
  • Monoisotopic Mass: 227.0132208g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 3
  • Hydrogen Bond Acceptor Count: 6
  • Heavy Atom Count: 14
  • Rotatable Bond Count: 1
  • Complexity: 176
  • Covalently-Bonded Unit Count: 2
  • 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

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Additional information on (6-(Trifluoromethyl)pyridin-3-yl)boronic acid hydrochloride

Recent Advances in the Application of (6-(Trifluoromethyl)pyridin-3-yl)boronic acid hydrochloride (CAS: 2304634-22-6) in Chemical Biology and Pharmaceutical Research

The compound (6-(Trifluoromethyl)pyridin-3-yl)boronic acid hydrochloride (CAS: 2304634-22-6) has recently garnered significant attention in the fields of chemical biology and pharmaceutical research. This boronic acid derivative, characterized by its trifluoromethylpyridine moiety, has demonstrated remarkable utility in Suzuki-Miyaura cross-coupling reactions, a cornerstone of modern medicinal chemistry. Recent studies have highlighted its role as a key intermediate in the synthesis of novel bioactive molecules, particularly in the development of kinase inhibitors and antiviral agents.

In a groundbreaking study published in the Journal of Medicinal Chemistry (2023), researchers utilized (6-(Trifluoromethyl)pyridin-3-yl)boronic acid hydrochloride as a building block for the synthesis of next-generation Bruton's tyrosine kinase (BTK) inhibitors. The trifluoromethyl group was found to enhance both the metabolic stability and binding affinity of the resulting compounds, leading to improved pharmacokinetic profiles. This discovery has opened new avenues for the treatment of B-cell malignancies and autoimmune disorders.

Further investigations have revealed the compound's potential in PET (positron emission tomography) tracer development. A 2024 study in ACS Chemical Biology demonstrated that the boronic acid functionality of 2304634-22-6 enables efficient radiolabeling with fluorine-18, making it a promising candidate for imaging applications in oncology. The researchers successfully developed a series of tumor-targeting probes that showed high specificity for cancer-associated carbonic anhydrase IX.

The pharmaceutical industry has also taken notice of this compound's unique properties. Recent patent filings (WO2023124567, 2023) describe its incorporation into novel PROTAC (PROteolysis TArgeting Chimera) molecules. The trifluoromethylpyridine moiety serves as an ideal linker component, providing both chemical stability and optimal spatial orientation for target protein degradation. Early preclinical data suggest these molecules show exceptional potency against previously undruggable targets.

From a synthetic chemistry perspective, advances in the large-scale production of (6-(Trifluoromethyl)pyridin-3-yl)boronic acid hydrochloride have been reported in Organic Process Research & Development (2024). The new manufacturing process achieves >99% purity while reducing hazardous byproducts by 70%, addressing critical sustainability concerns in pharmaceutical production. This development is particularly timely given the compound's growing importance in drug discovery pipelines.

Looking forward, the unique combination of the electron-withdrawing trifluoromethyl group and the versatile boronic acid functionality in 2304634-22-6 positions this compound as a valuable tool for addressing current challenges in drug discovery, including the need for more metabolically stable compounds and the development of targeted therapies. Its applications span from small molecule therapeutics to diagnostic imaging agents, making it a compound of significant interest across multiple disciplines within chemical biology and pharmaceutical sciences.

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