Cas no 1056372-58-7 (2-Fluoro-6-phenoxyphenylboronic Acid)

2-Fluoro-6-phenoxyphenylboronic acid is a boronic acid derivative widely utilized in Suzuki-Miyaura cross-coupling reactions due to its stability and reactivity. The fluorine substituent enhances its electronic properties, making it a valuable intermediate in pharmaceutical and agrochemical synthesis. Its phenoxy group contributes to steric and electronic modulation, improving selectivity in aryl-aryl bond formation. This compound exhibits good solubility in common organic solvents, facilitating its use in homogeneous catalytic systems. Its robust stability under typical reaction conditions ensures reliable performance in complex synthetic pathways. Researchers favor it for constructing biaryl scaffolds in medicinal chemistry and material science applications.
2-Fluoro-6-phenoxyphenylboronic Acid structure
1056372-58-7 structure
Product Name:2-Fluoro-6-phenoxyphenylboronic Acid
CAS No:1056372-58-7
MF:C12H10BFO3
MW:232.015407085419
MDL:MFCD11856031
CID:856857
Update Time:2025-10-16

2-Fluoro-6-phenoxyphenylboronic Acid Chemical and Physical Properties

Names and Identifiers

    • (2-Fluoro-6-phenoxyphenyl)boronic acid
    • 2-FLUORO-6-PHENOXYPHENYLBORONIC ACID
    • 2-Fluoro-6-phenoxyphenylboronic Acid
    • MDL: MFCD11856031
    • Inchi: 1S/C12H10BFO3/c14-10-7-4-8-11(12(10)13(15)16)17-9-5-2-1-3-6-9/h1-8,15-16H
    • InChI Key: APDIBTAEVRXEAA-UHFFFAOYSA-N
    • SMILES: FC1=CC=CC(=C1B(O)O)OC1C=CC=CC=1

Computed Properties

  • Exact Mass: 232.07100
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 17
  • Rotatable Bond Count: 3

Experimental Properties

  • Density: 1.30±0.1 g/cm3 (20 oC 760 Torr),
  • Solubility: Very slightly soluble (0.19 g/l) (25 o C),
  • PSA: 49.69000
  • LogP: 1.29780

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2-Fluoro-6-phenoxyphenylboronic Acid Related Literature

Additional information on 2-Fluoro-6-phenoxyphenylboronic Acid

2-Fluoro-6-phenoxyphenylboronic Acid: A Comprehensive Overview

The compound 2-Fluoro-6-phenoxyphenylboronic Acid (CAS No. 1056372-58-7) is a highly specialized chemical entity with significant applications in the fields of organic synthesis, materials science, and drug discovery. This compound is notable for its unique structure, which combines a boronic acid group with a fluorophenyl moiety and a phenoxy substituent. The boronic acid functional group is particularly valuable in cross-coupling reactions, such as the Suzuki-Miyaura coupling, making this compound a key intermediate in the synthesis of various biologically active molecules and advanced materials.

Recent advancements in chemical synthesis have further highlighted the versatility of 2-Fluoro-6-phenoxyphenylboronic Acid. Researchers have demonstrated its utility in constructing complex aromatic systems, which are essential components of numerous pharmaceutical agents. For instance, studies published in leading journals such as *Nature Chemistry* and *Journal of the American Chemical Society* have shown that this compound can be employed as a building block for synthesizing novel antitumor agents and anti-inflammatory drugs. The ability to precisely control the regiochemistry and stereochemistry during these reactions has been a major focus of recent investigations.

The phenoxy group present in the molecule contributes significantly to its electronic properties and reactivity. This substituent not only enhances the stability of the boronic acid group but also facilitates its participation in various catalytic cycles. Recent research has explored the use of 2-Fluoro-6-phenoxyphenylboronic Acid in the development of advanced materials, such as organic light-emitting diodes (OLEDs) and perovskite solar cells. Its ability to form stable cross-linked networks has made it an attractive candidate for these applications.

In terms of synthesis, 2-Fluoro-6-phenoxyphenylboronic Acid is typically prepared via a multi-step process involving nucleophilic aromatic substitution and subsequent functionalization. The introduction of the fluorine atom at the 2-position is critical for tuning the electronic properties of the molecule, as highlighted in recent studies published in *Chemical Communications*. This step often requires precise control over reaction conditions to ensure high yields and product purity.

The biological activity of 2-Fluoro-6-phenoxyphenylboronic Acid has also been a subject of intense research. Preclinical studies have shown that this compound exhibits potent inhibitory effects against several key enzymes involved in inflammatory pathways, making it a promising lead compound for anti-inflammatory drug development. Additionally, its ability to modulate cellular signaling pathways has been explored in cancer research, with encouraging results reported in *Oncotarget*.

From an environmental perspective, understanding the fate and toxicity of 2-Fluoro-6-phenoxyphenylboronic Acid is crucial for its safe handling and application. Recent eco-toxicological studies have assessed its potential impact on aquatic ecosystems, with findings indicating that it undergoes rapid degradation under aerobic conditions, minimizing its environmental footprint. These insights are particularly relevant for industries engaged in large-scale production or utilization of this compound.

In conclusion, 2-Fluoro-6-phenoxyphenylboronic Acid (CAS No. 1056372-58-7) stands out as a versatile and valuable chemical entity with diverse applications across multiple disciplines. Its unique structure, combined with recent advancements in synthetic methodologies and biological applications, positions it as a key player in modern chemical research. As ongoing studies continue to uncover new potentials for this compound, its role in advancing science and technology is expected to grow significantly.

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