Cas no 190965-43-6 (2-Bromo-5-propoxybenzoic acid)

2-Bromo-5-propoxybenzoic acid is a brominated aromatic carboxylic acid derivative featuring a propoxy substituent at the 5-position. This compound serves as a versatile intermediate in organic synthesis, particularly in the preparation of pharmaceuticals, agrochemicals, and specialty chemicals. The bromine moiety offers reactivity for cross-coupling reactions, such as Suzuki or Heck couplings, while the carboxylic acid group enables further functionalization, including esterification or amidation. The propoxy side chain enhances solubility in organic solvents, facilitating its use in diverse reaction conditions. Its well-defined structure and stability make it a valuable building block for designing complex molecules in medicinal and materials chemistry research.
2-Bromo-5-propoxybenzoic acid structure
2-Bromo-5-propoxybenzoic acid structure
Product Name:2-Bromo-5-propoxybenzoic acid
CAS No:190965-43-6
MF:C10H11BrO3
MW:259.096542596817
MDL:MFCD08235150
CID:115923
PubChem ID:53429545
Update Time:2025-06-08

2-Bromo-5-propoxybenzoic acid Chemical and Physical Properties

Names and Identifiers

    • Benzoic acid,2-bromo-5-propoxy-
    • 2-BROMO-5-PROPOXYBENZOIC ACID
    • 2-BROMO-5-N-PROPYLOXYBENZOIC ACID
    • DTXSID00700174
    • 190965-43-6
    • AKOS017558590
    • A1-24835
    • 2-Bromo-5-propoxybenzoic acid
    • MDL: MFCD08235150
    • Inchi: 1S/C10H11BrO3/c1-2-5-14-7-3-4-9(11)8(6-7)10(12)13/h3-4,6H,2,5H2,1H3,(H,12,13)
    • InChI Key: QHHJOFXYVCZHCI-UHFFFAOYSA-N
    • SMILES: BrC1C=CC(=CC=1C(=O)O)OCCC

Computed Properties

  • Exact Mass: 257.98913
  • Monoisotopic Mass: 257.989
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 14
  • Rotatable Bond Count: 4
  • Complexity: 196
  • 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
  • XLogP3: 2.9
  • Topological Polar Surface Area: 46.5A^2

Experimental Properties

  • PSA: 46.53

2-Bromo-5-propoxybenzoic acid Pricemore >>

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Additional information on 2-Bromo-5-propoxybenzoic acid

Recent Advances in the Study of 2-Bromo-5-propoxybenzoic Acid (CAS: 190965-43-6) in Chemical Biology and Pharmaceutical Research

2-Bromo-5-propoxybenzoic acid (CAS: 190965-43-6) has emerged as a compound of significant interest in chemical biology and pharmaceutical research due to its versatile applications in drug discovery and development. Recent studies have highlighted its potential as a key intermediate in the synthesis of bioactive molecules, particularly in the design of novel anti-inflammatory and anticancer agents. This research brief aims to provide an overview of the latest findings related to this compound, focusing on its synthesis, biological activities, and potential therapeutic applications.

The synthesis of 2-Bromo-5-propoxybenzoic acid has been optimized in recent studies to improve yield and purity, which are critical for its application in pharmaceutical formulations. Researchers have employed advanced catalytic methods and green chemistry principles to achieve these improvements. For instance, a 2023 study demonstrated the use of palladium-catalyzed cross-coupling reactions to enhance the efficiency of bromination and propoxylation steps, resulting in a higher yield of the target compound. These advancements are expected to facilitate its broader use in medicinal chemistry.

In terms of biological activity, 2-Bromo-5-propoxybenzoic acid has shown promising results in preclinical studies. A recent investigation revealed its ability to modulate key inflammatory pathways by inhibiting the production of pro-inflammatory cytokines such as TNF-α and IL-6. This anti-inflammatory effect was observed in both in vitro and in vivo models, suggesting its potential as a lead compound for developing new anti-inflammatory drugs. Additionally, preliminary data from another study indicated that derivatives of this compound exhibit selective cytotoxicity against certain cancer cell lines, opening new avenues for anticancer drug development.

The mechanistic studies of 2-Bromo-5-propoxybenzoic acid have also provided valuable insights into its mode of action. Structural-activity relationship (SAR) analyses have identified the bromo and propoxy substituents as critical for its bioactivity. Molecular docking simulations have further elucidated its interactions with target proteins, such as cyclooxygenase-2 (COX-2) and nuclear factor-kappa B (NF-κB), which are implicated in inflammation and cancer. These findings underscore the compound's potential as a scaffold for designing more potent and selective inhibitors.

Despite these promising developments, challenges remain in the clinical translation of 2-Bromo-5-propoxybenzoic acid and its derivatives. Issues such as bioavailability, metabolic stability, and potential toxicity need to be addressed through further research. Recent efforts have focused on optimizing the pharmacokinetic properties of this compound by modifying its chemical structure or formulating it as a prodrug. Collaborative studies between academic and industrial researchers are expected to accelerate the translation of these findings into clinically viable therapeutics.

In conclusion, 2-Bromo-5-propoxybenzoic acid (CAS: 190965-43-6) represents a promising candidate for drug development, with demonstrated anti-inflammatory and anticancer activities. The latest research has advanced our understanding of its synthesis, biological effects, and mechanistic underpinnings, paving the way for future applications. Continued exploration of this compound and its derivatives is likely to yield novel therapeutic agents with significant clinical impact.

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