Cas no 1186398-35-5 ((5-Formyl-2-methylphenyl)boronic acid)

(5-Formyl-2-methylphenyl)boronic acid is a versatile boronic acid derivative commonly employed in Suzuki-Miyaura cross-coupling reactions, a key methodology in organic synthesis for constructing biaryl and heteroaryl structures. The formyl (–CHO) and methyl (–CH?) substituents on the phenyl ring enhance its reactivity and selectivity in palladium-catalyzed transformations, making it valuable for pharmaceutical and materials science applications. Its stability under typical reaction conditions and compatibility with diverse functional groups contribute to its utility in complex molecule synthesis. The compound is typically handled under inert conditions to preserve its boronic acid functionality. Proper storage in a cool, dry environment is recommended to maintain its integrity for synthetic use.
(5-Formyl-2-methylphenyl)boronic acid structure
1186398-35-5 structure
Product Name:(5-Formyl-2-methylphenyl)boronic acid
CAS No:1186398-35-5
MF:C8H9BO3
MW:163.966262578964
MDL:MFCD16295249
CID:1026290
PubChem ID:57497297
Update Time:2025-05-21

(5-Formyl-2-methylphenyl)boronic acid Chemical and Physical Properties

Names and Identifiers

    • (5-Formyl-2-methylphenyl)boronic acid
    • MDL: MFCD16295249
    • Inchi: 1S/C8H9BO3/c1-6-2-3-7(5-10)4-8(6)9(11)12/h2-5,11-12H,1H3
    • InChI Key: VBQDWWUYMAWKHV-UHFFFAOYSA-N
    • SMILES: OB(C1C=C(C=O)C=CC=1C)O

Computed Properties

  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 12
  • Rotatable Bond Count: 2

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(5-Formyl-2-methylphenyl)boronic acid Related Literature

Additional information on (5-Formyl-2-methylphenyl)boronic acid

1186398-35-5: (5-Formyl-2-methylphenyl)boronic Acid

The compound with CAS No. 1186398-35-5, commonly referred to as (5-Formyl-2-methylphenyl)boronic Acid, is a significant molecule in the field of organic chemistry and materials science. This compound is characterized by its unique structure, which combines a boronic acid group with a substituted aromatic ring containing a formyl and methyl substituent. The boronic acid functional group is particularly valuable due to its reactivity in cross-coupling reactions, making it a key component in the synthesis of various complex molecules.

Recent advancements in chemical synthesis have highlighted the importance of (5-Formyl-2-methylphenyl)boronic Acid in the development of advanced materials and pharmaceutical compounds. Its structure, featuring a formyl group at the 5-position and a methyl group at the 2-position of the phenyl ring, provides a versatile platform for further functionalization. Researchers have demonstrated that this compound can be effectively utilized in Suzuki-Miyaura coupling reactions, enabling the construction of biaryl structures with high precision and efficiency.

The synthesis of (5-Formyl-2-methylphenyl)boronic Acid typically involves multi-step processes, including aromatic substitution reactions and subsequent boronation. These methods have been optimized to ensure high yields and purity, making the compound readily available for various applications. The stability of the boronic acid group under mild conditions further enhances its utility in large-scale production processes.

In terms of applications, (5-Formyl-2-methylphenyl)boronic Acid has found significant use in the pharmaceutical industry as an intermediate in drug discovery programs. Its ability to participate in cross-coupling reactions allows for the creation of diverse molecular frameworks, which are essential for exploring new therapeutic targets. Additionally, this compound has been employed in the development of advanced materials, such as organic light-emitting diodes (OLEDs), where its electronic properties contribute to enhanced device performance.

Recent studies have also explored the potential of (5-Formyl-2-methylphenyl)boronic Acid in bioconjugation chemistry. By leveraging its reactivity, researchers have successfully incorporated this compound into bioactive molecules, paving the way for innovative applications in diagnostics and therapeutics. The integration of this compound into peptide and nucleic acid systems has demonstrated promising results, underscoring its versatility across multiple disciplines.

The growing interest in (5-Formyl-2-methylphenyl)boronic Acid is driven by its unique combination of chemical stability and reactivity. As research continues to uncover new synthetic pathways and applications, this compound is poised to play an increasingly important role in both academic and industrial settings. Its contribution to the advancement of organic synthesis techniques further solidifies its position as a cornerstone molecule in modern chemistry.

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