Cas no 2244428-33-7 ((4-ethyl-2,6-difluorophenyl)boronic acid)

(4-Ethyl-2,6-difluorophenyl)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 organic synthesis. Its electron-withdrawing fluorine substituents enhance reactivity while the ethyl group contributes to steric stability, making it particularly valuable in the preparation of complex biaryl structures. This compound exhibits good solubility in common organic solvents and demonstrates consistent performance under mild reaction conditions. Its stability and selectivity make it a preferred intermediate in pharmaceutical and materials science research, particularly for constructing fluorinated aromatic frameworks. The compound is typically handled under inert conditions to preserve its reactivity.
(4-ethyl-2,6-difluorophenyl)boronic acid structure
2244428-33-7 structure
Product Name:(4-ethyl-2,6-difluorophenyl)boronic acid
CAS No:2244428-33-7
MF:C8H9BF2O2
MW:185.96
CID:5073025
PubChem ID:135395616
Update Time:2025-06-14

(4-ethyl-2,6-difluorophenyl)boronic acid Chemical and Physical Properties

Names and Identifiers

    • 4-ethyl-2, 6-difluorobenzene boric acid
    • (4-ethyl-2,6-difluorophenyl)boronic acid
    • 4-ethyl-2,6-difluorophenylboronic acid
    • 2244428-33-7
    • EN300-33332230
    • G67859
    • Inchi: 1S/C8H9BF2O2/c1-2-5-3-6(10)8(9(12)13)7(11)4-5/h3-4,12-13H,2H2,1H3
    • InChI Key: DHUHTTQSXYKAAH-UHFFFAOYSA-N
    • SMILES: C1=C(F)C(B(O)O)=C(F)C=C1CC

Computed Properties

  • Exact Mass: 186.0663660g/mol
  • Monoisotopic Mass: 186.0663660g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 13
  • Rotatable Bond Count: 2
  • Complexity: 156
  • 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: 40.5?2

(4-ethyl-2,6-difluorophenyl)boronic acid Pricemore >>

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(4-ethyl-2,6-difluorophenyl)boronic acid Related Literature

Additional information on (4-ethyl-2,6-difluorophenyl)boronic acid

Recent Advances in the Application of (4-ethyl-2,6-difluorophenyl)boronic acid (CAS: 2244428-33-7) in Chemical Biology and Pharmaceutical Research

The compound (4-ethyl-2,6-difluorophenyl)boronic acid (CAS: 2244428-33-7) has recently emerged as a promising building block in chemical biology and pharmaceutical research. This boronic acid derivative has garnered significant attention due to its unique physicochemical properties and versatile reactivity, making it a valuable tool in drug discovery, materials science, and bioconjugation strategies. Recent studies have demonstrated its potential in various applications, ranging from the development of novel therapeutics to the design of advanced biomaterials.

One of the most notable applications of (4-ethyl-2,6-difluorophenyl)boronic acid is in the field of targeted drug delivery. Researchers have exploited its ability to form reversible covalent bonds with diols and other nucleophiles, enabling the development of pH-responsive drug carriers. A 2023 study published in the Journal of Medicinal Chemistry demonstrated its use in creating tumor-targeting prodrugs that selectively release active compounds in the acidic microenvironment of cancer cells. The ethyl and difluoro substitutions on the phenyl ring were found to significantly enhance the stability and selectivity of these prodrugs compared to simpler boronic acid derivatives.

In the realm of materials science, (4-ethyl-2,6-difluorophenyl)boronic acid has shown remarkable potential in the development of self-healing polymers. Its ability to form dynamic boronate ester bonds has been utilized to create materials with tunable mechanical properties and responsiveness to environmental stimuli. A recent breakthrough published in Advanced Materials highlighted its incorporation into hydrogel networks that can undergo reversible gel-sol transitions in response to glucose concentration changes, opening new possibilities for glucose-sensing applications in diabetes management.

The compound has also found applications in proteomics research, particularly in the selective enrichment and identification of glycoproteins. The unique electronic effects conferred by the 4-ethyl and 2,6-difluoro substitutions enhance its binding affinity for cis-diol-containing biomolecules while maintaining excellent specificity. This property has been leveraged in several recent studies to develop novel affinity chromatography matrices for glycoproteome analysis, as reported in a 2024 Nature Methods paper.

From a synthetic chemistry perspective, (4-ethyl-2,6-difluorophenyl)boronic acid serves as a valuable intermediate in cross-coupling reactions. Its steric and electronic properties make it particularly suitable for Suzuki-Miyaura couplings with challenging substrates. Recent work in Organic Letters has demonstrated its effectiveness in the synthesis of complex biaryl structures found in many pharmaceutical compounds, with the difluoro substitution pattern proving crucial for controlling regioselectivity in these transformations.

Looking forward, researchers are exploring the potential of (4-ethyl-2,6-difluorophenyl)boronic acid in emerging areas such as covalent organic frameworks (COFs) and bioorthogonal chemistry. Preliminary results suggest that its unique substitution pattern may enable the development of COFs with unprecedented stability and functionality. Additionally, its reactivity profile appears promising for the design of new bioorthogonal reactions that could expand the toolkit for live-cell labeling and imaging.

In conclusion, (4-ethyl-2,6-difluorophenyl)boronic acid (CAS: 2244428-33-7) represents a versatile and valuable compound with diverse applications across chemical biology and pharmaceutical research. Its unique structural features continue to inspire innovative solutions to challenges in drug development, materials science, and biological research. As synthetic methodologies advance and our understanding of boronic acid chemistry deepens, we can anticipate even more groundbreaking applications of this compound in the coming years.

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