Cas no 958646-67-8 (2-Chloro-6-fluoro-5-hydroxyphenylboronic acid)

2-Chloro-6-fluoro-5-hydroxyphenylboronic acid is a boronic acid derivative commonly employed as a key intermediate in Suzuki-Miyaura cross-coupling reactions, facilitating the synthesis of biaryl compounds. Its hydroxyl and halogen substituents enhance reactivity and selectivity in palladium-catalyzed transformations, making it valuable for pharmaceutical and agrochemical applications. The compound's stability under typical reaction conditions and compatibility with diverse functional groups contribute to its utility in complex molecule construction. Proper handling under inert atmospheres is recommended due to boronic acid sensitivity to protodeboronation. Analytical methods such as NMR and HPLC are typically used for purity verification. Storage in cool, dry conditions is advised to maintain stability.
2-Chloro-6-fluoro-5-hydroxyphenylboronic acid structure
958646-67-8 structure
Product Name:2-Chloro-6-fluoro-5-hydroxyphenylboronic acid
CAS No:958646-67-8
MF:C6H5BClFO3
MW:190.364504575729
MDL:MFCD19105351
CID:4736065
Update Time:2025-11-02

2-Chloro-6-fluoro-5-hydroxyphenylboronic acid Chemical and Physical Properties

Names and Identifiers

    • 2-Chloro-6-fluoro-5-hydroxyphenylboronic acid
    • (6-chloro-2-fluoro-3-hydroxyphenyl)boronic acid
    • BC001752
    • AB0043297
    • Z1202
    • BORONIC ACID, B-(6-CHLORO-2-FLUORO-3-HYDROXYPHENYL)-
    • MDL: MFCD19105351
    • Inchi: 1S/C6H5BClFO3/c8-3-1-2-4(10)6(9)5(3)7(11)12/h1-2,10-12H
    • InChI Key: VHBSCHINLGAFRL-UHFFFAOYSA-N
    • SMILES: ClC1=CC=C(C(=C1B(O)O)F)O

Computed Properties

  • Hydrogen Bond Donor Count: 3
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 12
  • Rotatable Bond Count: 1
  • Complexity: 160
  • Topological Polar Surface Area: 60.7

2-Chloro-6-fluoro-5-hydroxyphenylboronic acid Pricemore >>

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Additional information on 2-Chloro-6-fluoro-5-hydroxyphenylboronic acid

2-Chloro-6-fluoro-5-hydroxyphenylboronic Acid (CAS 958646-67-8): A Versatile Boronic Acid Derivative in Modern Chemistry

2-Chloro-6-fluoro-5-hydroxyphenylboronic acid (CAS 958646-67-8) is an important boronic acid derivative that has gained significant attention in pharmaceutical and material science research. This compound, with its unique halogen-substituted aromatic structure, serves as a valuable building block in Suzuki-Miyaura cross-coupling reactions, one of the most widely used methods for carbon-carbon bond formation in organic synthesis.

The molecular structure of 2-chloro-6-fluoro-5-hydroxyphenylboronic acid features three distinct functional groups: a boronic acid moiety, hydroxyl group, and halogen substituents (chloro and fluoro). This combination makes it particularly useful for creating complex molecular architectures. Recent studies highlight its application in developing PET imaging agents and bioconjugation reagents, addressing current research trends in medical diagnostics and targeted drug delivery systems.

In pharmaceutical applications, CAS 958646-67-8 has shown promise in the synthesis of kinase inhibitors and antibody-drug conjugates (ADCs), two rapidly growing areas in cancer therapeutics. The compound's ability to participate in click chemistry reactions while maintaining stability under physiological conditions makes it particularly valuable for these applications. Researchers are exploring its use in developing next-generation small molecule drugs with improved selectivity and reduced side effects.

The material science field has also benefited from 2-chloro-6-fluoro-5-hydroxyphenylboronic acid, where it serves as a precursor for organic electronic materials and molecular sensors. Its fluorinated aromatic structure contributes to enhanced thermal stability and electronic properties in conjugated polymers, addressing the growing demand for high-performance organic semiconductors in flexible electronics and display technologies.

From a synthetic chemistry perspective, the ortho-hydroxyl group in 958646-67-8 offers unique advantages in chelation-controlled reactions and intramolecular hydrogen bonding, which can influence reaction selectivity and product yields. This characteristic has made it particularly valuable in asymmetric synthesis and the preparation of chiral auxiliaries, topics of high interest in modern organic chemistry.

Recent market analysis shows increasing demand for halogenated boronic acids like 2-chloro-6-fluoro-5-hydroxyphenylboronic acid, driven by expanding applications in medicinal chemistry and material science. The compound's stability, relatively low toxicity, and versatile reactivity profile make it a preferred choice for researchers developing new therapeutic candidates and functional materials.

Quality control of CAS 958646-67-8 typically involves advanced analytical techniques including HPLC purity analysis, NMR spectroscopy, and mass spectrometry. These methods ensure the compound meets the stringent requirements for pharmaceutical and electronic applications, where even minor impurities can significantly impact performance.

Environmental considerations for 2-chloro-6-fluoro-5-hydroxyphenylboronic acid synthesis and handling have become increasingly important. Modern production methods emphasize green chemistry principles, focusing on atom economy, reduced solvent use, and energy efficiency. These approaches align with current industry trends toward sustainable chemical manufacturing processes.

Future research directions for 958646-67-8 include exploring its potential in proteolysis targeting chimeras (PROTACs) and other emerging therapeutic modalities. The compound's ability to serve as a versatile linker in complex molecular systems positions it well for these cutting-edge applications in drug discovery and development.

For researchers working with 2-chloro-6-fluoro-5-hydroxyphenylboronic acid, proper storage conditions (typically cool, dry environments under inert atmosphere) and handling procedures are essential to maintain its reactivity and shelf life. These practical considerations are particularly important given the compound's applications in sensitive bioconjugation reactions and catalytic systems.

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