Cas no 2096333-35-4 (3-Bromo-5-T-butyl-2-fluorophenylboronic acid)

3-Bromo-5-T-butyl-2-fluorophenylboronic acid is a specialized boronic acid derivative featuring a bromo and fluoro-substituted phenyl ring with a sterically hindered tert-butyl group at the meta position. This compound is particularly valuable in Suzuki-Miyaura cross-coupling reactions due to its stability and reactivity, enabling the synthesis of complex biaryl structures. The presence of both bromo and boronic acid functional groups allows for sequential functionalization, enhancing its utility in multi-step synthetic routes. The tert-butyl group improves solubility in organic solvents and may influence regioselectivity in coupling reactions. Its well-defined structure makes it a reliable intermediate for pharmaceutical and materials science applications.
3-Bromo-5-T-butyl-2-fluorophenylboronic acid structure
2096333-35-4 structure
Product Name:3-Bromo-5-T-butyl-2-fluorophenylboronic acid
CAS No:2096333-35-4
MF:C10H13BBrFO2
MW:274.922425985336
MDL:MFCD18783155
CID:4637934
Update Time:2025-05-20

3-Bromo-5-T-butyl-2-fluorophenylboronic acid Chemical and Physical Properties

Names and Identifiers

    • 3-BROMO-5-T-BUTYL-2-FLUOROPHENYLBORONIC ACID
    • (3-bromo-5-tert-butyl-2-fluorophenyl)boronic acid
    • C10H13BBrFO2
    • Y2492
    • (3-Bromo-5-(tert-butyl)-2-fluorophenyl)boronic acid
    • 3-Bromo-5-T-butyl-2-fluorophenylboronic acid
    • MDL: MFCD18783155
    • Inchi: 1S/C10H13BBrFO2/c1-10(2,3)6-4-7(11(14)15)9(13)8(12)5-6/h4-5,14-15H,1-3H3
    • InChI Key: KFIDBWNQEIABRB-UHFFFAOYSA-N
    • SMILES: BrC1C(=C(B(O)O)C=C(C=1)C(C)(C)C)F

Computed Properties

  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 15
  • Rotatable Bond Count: 2
  • Complexity: 220
  • Topological Polar Surface Area: 40.5

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Additional information on 3-Bromo-5-T-butyl-2-fluorophenylboronic acid

3-Bromo-5-T-butyl-2-fluorophenylboronic Acid: A Comprehensive Overview

The compound 3-Bromo-5-T-butyl-2-fluorophenylboronic acid, with the CAS number 2096333-35-4, is a highly specialized aromatic boronic acid derivative. This compound has garnered significant attention in the fields of organic synthesis, materials science, and drug discovery due to its unique structural features and versatile reactivity. The molecule consists of a phenyl ring substituted with bromine, fluorine, and a tert-butyl group, along with a boronic acid moiety. These substituents not only enhance the compound's stability but also make it an ideal precursor for various cross-coupling reactions.

Recent advancements in cross-coupling chemistry have underscored the importance of boronic acids like 3-Bromo-5-T-butyl-2-fluorophenylboronic acid in constructing complex molecular architectures. The presence of the boronic acid group enables this compound to participate in Suzuki-Miyaura coupling reactions, which are widely used in the synthesis of biaryl compounds. The bulky tert-butyl group at the 5-position of the phenyl ring provides steric protection, ensuring high regioselectivity during these reactions. This feature is particularly valuable in the synthesis of heterocyclic compounds and bioactive molecules.

In addition to its role in cross-coupling reactions, 3-Bromo-5-T-butyl-2-fluorophenylboronic acid has been explored as a building block in the development of advanced materials. Its ability to form stable covalent bonds with other organic moieties makes it a promising candidate for the synthesis of high-performance polymers and organic semiconductors. Recent studies have demonstrated its utility in creating self-healing polymers, where the boronic acid group plays a critical role in dynamic covalent bonding networks.

The synthesis of 3-Bromo-5-T-butyl-2-fluorophenylboronic acid involves a multi-step process that typically begins with bromination or fluorination of an aromatic precursor followed by boronate ester formation and subsequent hydrolysis to yield the final product. The choice of reagents and reaction conditions is crucial to ensure high yields and purity. For instance, the use of palladium catalysts in certain steps has been shown to significantly improve reaction efficiency, as highlighted in recent publications on catalytic methods for boronic acid synthesis.

The application of 3-Bromo-5-T-butyl-2-fluorophenylboronic acid extends into medicinal chemistry, where it serves as an intermediate in the synthesis of potential drug candidates. Its ability to undergo various transformations while retaining key functional groups makes it an invaluable tool for medicinal chemists. For example, recent research has focused on its use in developing inhibitors for kinase enzymes, which are implicated in various disease states such as cancer and inflammatory disorders.

In conclusion, 3-Bromo-5-T-butyl-2-fluorophenylboronic acid is a versatile compound with a wide range of applications across multiple disciplines. Its unique structure and reactivity make it an essential building block in modern organic synthesis. As research continues to uncover new methods for its preparation and utilization, this compound is poised to play an even greater role in advancing scientific discoveries and technological innovations.

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