Cas no 318292-61-4 (Ethyl 3-hydroxy-5-methoxy-1H-indole-2-carboxylate)

Ethyl 3-hydroxy-5-methoxy-1H-indole-2-carboxylate is a versatile indole derivative with applications in pharmaceutical and organic synthesis. Its structural features, including the hydroxyl and methoxy substituents on the indole core, make it a valuable intermediate for the development of bioactive compounds. The ethyl ester group enhances solubility and reactivity, facilitating further functionalization. This compound is particularly useful in the synthesis of alkaloids and other heterocyclic systems, offering a stable and well-characterized building block for research. High purity and consistent quality ensure reliable performance in synthetic workflows. Its well-defined spectroscopic and chromatographic properties aid in analytical verification and process optimization.
Ethyl 3-hydroxy-5-methoxy-1H-indole-2-carboxylate structure
318292-61-4 structure
Product Name:Ethyl 3-hydroxy-5-methoxy-1H-indole-2-carboxylate
CAS No:318292-61-4
MF:C12H13NO4
MW:235.235923528671
CID:293289
PubChem ID:54734620
Update Time:2025-05-19

Ethyl 3-hydroxy-5-methoxy-1H-indole-2-carboxylate Chemical and Physical Properties

Names and Identifiers

    • Ethyl 3-hydroxy-5-methoxy-1H-indole-2-carboxylate
    • LogP
    • 1H-Indole-2-carboxylicacid, 3-hydroxy-5-methoxy-, ethyl ester
    • FT-0727252
    • A875798
    • 318292-61-4
    • DTXSID40716411
    • AB26276
    • Ethyl3-hydroxy-5-methoxy-1H-indole-2-carboxylate
    • AKOS015898464
    • DB-068533
    • MDL: MFCD06659774
    • Inchi: 1S/C12H13NO4/c1-3-17-12(15)10-11(14)8-6-7(16-2)4-5-9(8)13-10/h4-6,13-14H,3H2,1-2H3
    • InChI Key: FQLSWIFMDRKOJV-UHFFFAOYSA-N
    • SMILES: OC1=C(C(=O)OCC)NC2C=CC(=CC=21)OC

Computed Properties

  • Exact Mass: 234.07666
  • Monoisotopic Mass: 235.084
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 5
  • Heavy Atom Count: 17
  • Rotatable Bond Count: 4
  • Complexity: 284
  • 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
  • Topological Polar Surface Area: 71.6A^2
  • XLogP3: 2.8

Experimental Properties

  • Density: 1.316
  • Boiling Point: 405.583°C at 760 mmHg
  • Flash Point: 199.09°C
  • Refractive Index: 1.629
  • PSA: 68.65

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Additional information on Ethyl 3-hydroxy-5-methoxy-1H-indole-2-carboxylate

Ethyl 3-Hydroxy-5-Methoxy-1H-Indole-2-Carboxylate: A Comprehensive Overview

Ethyl 3-hydroxy-5-methoxy-1H-indole-2-carboxylate (CAS No. 318292-61-4) is a structurally complex organic compound belonging to the class of indole derivatives. This compound has garnered significant attention in recent years due to its unique chemical properties and potential applications in various fields, including pharmacology, materials science, and biotechnology. The molecule consists of an indole ring system with hydroxyl, methoxy, and ester functional groups, which contribute to its versatile reactivity and biological activity.

The indole core of Ethyl 3-hydroxy-5-methoxy-1H-indole-2-carboxylate is a fundamental structural motif found in numerous natural products and bioactive molecules. The presence of the hydroxyl group at position 3 and the methoxy group at position 5 introduces significant electronic and steric effects, which influence the compound's chemical reactivity and biological interactions. The ester group at position 2 further enhances the molecule's solubility and bioavailability, making it an attractive candidate for drug delivery systems.

Recent studies have highlighted the potential of Ethyl 3-hydroxy-5-methoxy-1H-indole-2-carboxylate as a precursor for the synthesis of advanced materials. Researchers have explored its use in the development of self-healing polymers and stimuli-responsive materials, leveraging its unique ability to undergo reversible chemical transformations under specific conditions. These findings underscore the compound's role as a building block for next-generation materials with applications in electronics, healthcare, and environmental technology.

In the field of pharmacology, Ethyl 3-hydroxy-5-methoxy-1H-indole-2-carboxylate has shown promise as a lead compound for drug discovery. Preclinical studies have demonstrated its potential as an anti-inflammatory agent, with research indicating that it can modulate key inflammatory pathways involved in chronic diseases such as arthritis and cardiovascular disorders. Additionally, the compound has exhibited antioxidant properties, suggesting its potential use in combating oxidative stress-related conditions.

The synthesis of Ethyl 3-hydroxy-5-methoxy-1H-indole-2-carboxylate involves a multi-step process that typically begins with the preparation of the indole skeleton. Recent advancements in catalytic asymmetric synthesis have enabled more efficient and environmentally friendly methods for producing this compound. These methods not only improve yield but also reduce waste, aligning with current trends toward sustainable chemistry practices.

From a materials science perspective, Ethyl 3-hydroxy-5-methoxy-1H-indole-2-carboxylate has been investigated for its role in creating bio-inspired materials. Its ability to form supramolecular assemblies through hydrogen bonding and π–π interactions makes it a valuable component in the design of nanomaterials with tailored properties. Such materials hold potential applications in drug delivery systems, sensors, and energy storage devices.

Furthermore, Ethyl 3-hydroxy-5-methoxy-1H-indole-2-carboxylate has been studied for its interactions with biological systems at the molecular level. Computational modeling techniques have provided insights into its binding affinity with various proteins and enzymes, paving the way for its use as a tool in structural biology research. This understanding is critical for designing more effective therapeutic agents based on this compound.

In conclusion, Ethyl 3-hydroxy-5-methoxy-H-indole--carboxy late (CAS No. 318292-) represents a multifaceted compound with diverse applications across multiple disciplines. Its unique chemical structure, combined with recent advancements in synthesis and application research, positions it as a key player in future innovations within pharmacology, materials science, and beyond.

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