Cas no 135586-17-3 (2-Bromo-3-benzyloxy-4-methoxybenzoic Acid)

2-Bromo-3-benzyloxy-4-methoxybenzoic Acid is a substituted benzoic acid derivative featuring bromine, benzyloxy, and methoxy functional groups. This compound is primarily utilized as an intermediate in organic synthesis, particularly in the preparation of pharmaceuticals and fine chemicals. The presence of multiple substituents enhances its reactivity, making it valuable for selective functionalization and cross-coupling reactions. Its well-defined structure ensures consistent performance in synthetic applications, while the bromine atom offers a handle for further derivatization via metal-catalyzed reactions. The compound is typically handled under controlled conditions due to its sensitivity to light and moisture. Its purity and stability make it a reliable choice for research and industrial applications requiring precise molecular modifications.
2-Bromo-3-benzyloxy-4-methoxybenzoic Acid structure
135586-17-3 structure
Product Name:2-Bromo-3-benzyloxy-4-methoxybenzoic Acid
CAS No:135586-17-3
MF:C15H13BrO4
MW:337.165323972702
CID:1059969
Update Time:2025-06-08

2-Bromo-3-benzyloxy-4-methoxybenzoic Acid Chemical and Physical Properties

Names and Identifiers

    • 2-Bromo-3-benzyloxy-4-methoxybenzoic Acid
    • 2-BROMO-3-BENZYLOXY-4-METHOXYBENZOIC ACID,OFF-WHITE SOLID
    • 2-bromo-4-methoxy-3-phenylmethoxybenzoic acid
    • 3-(benzyloxy)-2-bromo-4-methoxybenzoic acid
    • 2-bromo-3-benzylisovanillic acid
    • Inchi: 1S/C15H13BrO4/c1-19-12-8-7-11(15(17)18)13(16)14(12)20-9-10-5-3-2-4-6-10/h2-8H,9H2,1H3,(H,17,18)
    • InChI Key: MNQPGCQOYAYWKT-UHFFFAOYSA-N
    • SMILES: BrC1=C(C(=O)O)C=CC(=C1OCC1C=CC=CC=1)OC

Computed Properties

  • Exact Mass: 336.00000
  • Monoisotopic Mass: 336
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 20
  • Rotatable Bond Count: 5
  • Complexity: 317
  • 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

Experimental Properties

  • Density: 1.486±0.06 g/cm3(Predicted)
  • Melting Point: 159-161 °C
  • Boiling Point: 440.3±45.0 °C(Predicted)
  • PSA: 55.76000
  • LogP: 3.73490

2-Bromo-3-benzyloxy-4-methoxybenzoic Acid Pricemore >>

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2-Bromo-3-benzyloxy-4-methoxybenzoic Acid Production Method

Additional information on 2-Bromo-3-benzyloxy-4-methoxybenzoic Acid

Introduction to 2-Bromo-3-benzyloxy-4-methoxybenzoic Acid (CAS No. 135586-17-3)

2-Bromo-3-benzyloxy-4-methoxybenzoic Acid, identified by its Chemical Abstracts Service (CAS) number 135586-17-3, is a specialized organic compound that has garnered significant attention in the field of pharmaceutical and medicinal chemistry. This benzoic acid derivative, characterized by its bromine, benzyloxy, and methoxy substituents, exhibits a unique structural framework that makes it a valuable intermediate in the synthesis of various bioactive molecules. The compound's distinct chemical profile has positioned it as a subject of interest in both academic research and industrial applications, particularly in the development of novel therapeutic agents.

The molecular structure of 2-Bromo-3-benzyloxy-4-methoxybenzoic Acid consists of a benzoic acid core substituted with a bromine atom at the 2-position, a benzyloxy group at the 3-position, and a methoxy group at the 4-position. This arrangement imparts specific electronic and steric properties to the molecule, which can be exploited in medicinal chemistry for designing compounds with enhanced binding affinity and selectivity. The presence of the bromine atom, for instance, provides a handle for further functionalization via cross-coupling reactions, such as Suzuki or Buchwald-Hartwig couplings, which are widely employed in the construction of complex drug molecules.

In recent years, 2-Bromo-3-benzyloxy-4-methoxybenzoic Acid has been explored as a key intermediate in the synthesis of small-molecule inhibitors targeting various biological pathways. One notable area of research involves its application in the development of kinase inhibitors, which are critical in treating cancers and inflammatory diseases. The benzyloxy and methoxy groups contribute to the compound's ability to interact with specific residues in protein targets, thereby modulating enzymatic activity. For instance, derivatives of this compound have shown promise in inhibiting tyrosine kinases, which play a pivotal role in signal transduction pathways associated with tumor growth and progression.

Furthermore, the compound has been investigated for its potential in antimicrobial applications. The structural features of 2-Bromo-3-benzyloxy-4-methoxybenzoic Acid allow it to disrupt bacterial cell wall synthesis or interfere with essential metabolic processes. Preliminary studies have demonstrated its efficacy against certain resistant strains of bacteria, highlighting its significance as a scaffold for developing novel antibiotics. The bromine substituent is particularly noteworthy, as it can serve as a site for further derivatization to enhance antimicrobial properties while maintaining structural integrity.

The synthetic utility of 2-Bromo-3-benzyloxy-4-methoxybenzoic Acid extends beyond pharmaceutical applications. It has been utilized in material science research, where its aromatic structure and functional groups make it suitable for designing organic semiconductors and liquid crystals. These materials are integral to advanced display technologies and electronic devices, underscoring the compound's versatility across multiple scientific disciplines.

Recent advancements in computational chemistry have also leveraged 2-Bromo-3-benzyloxy-4-methoxybenzoic Acid as a model system for studying molecular interactions. High-throughput virtual screening (HTVS) techniques have been employed to identify potential drug candidates derived from this scaffold. By integrating machine learning algorithms with traditional pharmacophore modeling, researchers have been able to predict binding affinities and optimize lead compounds more efficiently. This synergy between experimental synthesis and computational analysis has accelerated the discovery pipeline for new therapeutic agents.

The industrial production of 2-Bromo-3-benzyloxy-4-methoxybenzoic Acid adheres to stringent quality control measures to ensure consistency and purity. Manufacturers employ advanced purification techniques such as recrystallization and chromatography to isolate the compound from reaction mixtures. These processes are critical in maintaining the integrity of downstream applications where even minor impurities can affect biological activity or material performance.

Future research directions for 2-Bromo-3-benzyloxy-4-methoxybenzoic Acid may focus on expanding its therapeutic applications through structure-activity relationship (SAR) studies. By systematically modifying its substituents, scientists aim to uncover novel bioactivities while minimizing off-target effects. Additionally, green chemistry principles are being incorporated into synthetic protocols to reduce environmental impact without compromising yield or purity.

In conclusion,2-Bromo-3-benzyloxy-4-methoxybenzoic Acid (CAS No. 135586-17-3) represents a versatile and promising compound with diverse applications across pharmaceuticals, materials science, and computational chemistry. Its unique structural features offer opportunities for innovation in drug discovery and material design, making it an indispensable tool for researchers seeking to develop next-generation therapeutics and advanced materials.

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