Cas no 29735-85-1 (5-hydroxybenzofuran-3-carboxylic acid)

5-Hydroxybenzofuran-3-carboxylic acid is a heterocyclic organic compound featuring a benzofuran core substituted with a hydroxyl group at the 5-position and a carboxylic acid moiety at the 3-position. This structure imparts unique reactivity, making it a valuable intermediate in pharmaceutical and agrochemical synthesis. The hydroxyl and carboxyl groups offer versatile functionalization sites for further derivatization, enabling applications in drug discovery and material science. Its rigid benzofuran scaffold contributes to enhanced stability and binding affinity in molecular design. The compound is typically synthesized via controlled cyclization and oxidation steps, ensuring high purity for research and industrial use.
5-hydroxybenzofuran-3-carboxylic acid structure
29735-85-1 structure
Product Name:5-hydroxybenzofuran-3-carboxylic acid
CAS No:29735-85-1
MF:C9H6O4
MW:178.14154291153
CID:1110473
PubChem ID:68619366
Update Time:2025-05-20

5-hydroxybenzofuran-3-carboxylic acid Chemical and Physical Properties

Names and Identifiers

    • 5-hydroxy-3-Benzofurancarboxylic acid
    • 5-hydroxybenzofuran-3-carboxylic acid
    • 3-Benzofurancarboxylic acid, 5-hydroxy-
    • F73602
    • 3-carboxy-5-hydroxybenzofuran
    • 5-hydroxy-1-benzofuran-3-carboxylic acid
    • AKOS022910293
    • 5-hydroxy-1-benzofuran-3-carboxylicacid
    • GWWDURABERRAPL-UHFFFAOYSA-N
    • Z1255392768
    • DB-427945
    • MFCD15144229
    • 29735-85-1
    • EN300-749485
    • SCHEMBL3377499
    • Inchi: 1S/C9H6O4/c10-5-1-2-8-6(3-5)7(4-13-8)9(11)12/h1-4,10H,(H,11,12)
    • InChI Key: GWWDURABERRAPL-UHFFFAOYSA-N
    • SMILES: O1C=C(C(=O)O)C2C=C(C=CC1=2)O

Computed Properties

  • Exact Mass: 178.02658
  • Monoisotopic Mass: 178.02660867g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 13
  • Rotatable Bond Count: 1
  • Complexity: 216
  • 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: 1.5
  • Topological Polar Surface Area: 70.7?2

Experimental Properties

  • PSA: 70.67

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Additional information on 5-hydroxybenzofuran-3-carboxylic acid

Introduction to 5-hydroxybenzofuran-3-carboxylic acid (CAS No. 29735-85-1)

5-hydroxybenzofuran-3-carboxylic acid, identified by the Chemical Abstracts Service Number (CAS No.) 29735-85-1, is a significant organic compound that has garnered considerable attention in the field of pharmaceutical chemistry and bioorganic synthesis. This heterocyclic aromatic compound belongs to the benzofuran family, characterized by a fused benzene and furan ring system. The presence of both hydroxyl and carboxylic acid functional groups on the benzofuran core enhances its reactivity and makes it a versatile intermediate in the synthesis of various biologically active molecules.

The structural features of 5-hydroxybenzofuran-3-carboxylic acid contribute to its unique chemical properties, which are highly valued in medicinal chemistry. The hydroxyl group at the 5-position and the carboxylic acid at the 3-position provide multiple sites for functionalization, enabling the construction of more complex scaffolds through esterification, amidation, or other transformations. These modifications are crucial for developing novel therapeutic agents with improved pharmacokinetic profiles and target-specific interactions.

In recent years, 5-hydroxybenzofuran-3-carboxylic acid has been extensively studied for its potential applications in drug discovery. Its benzofuran core is a common motif in natural products and pharmacologically active compounds, including several FDA-approved drugs. The compound’s ability to serve as a precursor for synthesizing heterocyclic derivatives has made it a focal point in academic and industrial research.

One of the most compelling aspects of 5-hydroxybenzofuran-3-carboxylic acid is its role in developing inhibitors targeting specific biological pathways. For instance, derivatives of this compound have been explored as potential antitumor agents due to their ability to modulate enzyme activity involved in cell proliferation and apoptosis. The hydroxyl group at the 5-position can be further functionalized to enhance binding affinity to protein targets, making it an attractive scaffold for rational drug design.

Recent advancements in computational chemistry have further accelerated the exploration of 5-hydroxybenzofuran-3-carboxylic acid derivatives. Molecular modeling studies have revealed that subtle modifications to its structure can significantly alter its biological activity. For example, computational screening has identified novel analogs with enhanced potency against certain kinases, which are key enzymes in cancer signaling pathways. These findings highlight the importance of 5-hydroxybenzofuran-3-carboxylic acid as a building block for next-generation therapeutics.

The synthesis of 5-hydroxybenzofuran-3-carboxylic acid itself is an area of active interest. Traditional synthetic routes often involve multi-step sequences starting from readily available aromatic precursors. However, recent reports have demonstrated more efficient one-pot or catalytic methods that improve yield and reduce environmental impact. These innovations align with the growing emphasis on sustainable chemistry practices in pharmaceutical manufacturing.

The pharmacological profile of 5-hydroxybenzofuran-3-carboxylic acid derivatives continues to be a subject of intense investigation. Preclinical studies have shown promising results in models of inflammation, neurodegeneration, and metabolic disorders. The compound’s ability to interact with various biological targets suggests its broad applicability across multiple therapeutic areas. Researchers are particularly interested in exploring its potential as an antioxidant or anti-inflammatory agent, given the structural similarities to known bioactive molecules.

In conclusion, 5-hydroxybenzofuran-3-carboxylic acid (CAS No. 29735-85-1) represents a valuable chemical entity with significant implications for drug development. Its unique structural features and reactivity make it an ideal candidate for generating novel therapeutic agents. As research progresses, it is anticipated that new synthetic methodologies and pharmacological applications will continue to emerge, further solidifying its importance in modern medicinal chemistry.

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