Cas no 597562-19-1 (Methyl 4-iodo-1H-indole-6-carboxylate)

Methyl 4-iodo-1H-indole-6-carboxylate is a versatile heterocyclic compound featuring an indole core substituted with an iodine atom at the 4-position and a methyl ester group at the 6-position. This structure makes it a valuable intermediate in organic synthesis, particularly for pharmaceutical and agrochemical applications. The iodine substituent offers reactivity for further functionalization via cross-coupling reactions, while the ester group provides a handle for derivatization. Its high purity and stability under standard conditions ensure reliable performance in synthetic workflows. The compound is commonly used in the development of biologically active molecules, including kinase inhibitors and other therapeutic agents.
Methyl 4-iodo-1H-indole-6-carboxylate structure
597562-19-1 structure
Product Name:Methyl 4-iodo-1H-indole-6-carboxylate
CAS No:597562-19-1
MF:C10H8INO2
MW:301.080494880676
MDL:MFCD03867038
CID:840664
PubChem ID:851585
Update Time:2025-05-24

Methyl 4-iodo-1H-indole-6-carboxylate Chemical and Physical Properties

Names and Identifiers

    • Methyl 4-iodo-1H-indole-6-carboxylate
    • 4-Iodo-6-indole carboxylic acid methyl ester
    • 4-IODO-1H-INDOLE-6-CARBOXYLIC ACID METHYL ESTER
    • 597562-19-1
    • 4-Iodo-6-indole carboxylic acid methyl ester
    • AQ-009/42173809
    • MB03047
    • SCHEMBL3350847
    • DB-072690
    • methyl4-iodo-1H-indole-6-carboxylate
    • MOAJPKHWYSXCSH-UHFFFAOYSA-N
    • CS-0331665
    • DTXSID40357348
    • MDL: MFCD03867038
    • Inchi: 1S/C10H8INO2/c1-14-10(13)6-4-8(11)7-2-3-12-9(7)5-6/h2-5,12H,1H3
    • InChI Key: MOAJPKHWYSXCSH-UHFFFAOYSA-N
    • SMILES: IC1=CC(C(=O)OC)=CC2=C1C=CN2

Computed Properties

  • Exact Mass: 300.96000
  • Monoisotopic Mass: 300.95998g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 14
  • Rotatable Bond Count: 2
  • Complexity: 234
  • 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: 2.6
  • Topological Polar Surface Area: 42.1?2

Experimental Properties

  • PSA: 42.09000
  • LogP: 2.55910

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Additional information on Methyl 4-iodo-1H-indole-6-carboxylate

Comprehensive Overview of Methyl 4-iodo-1H-indole-6-carboxylate (CAS No. 597562-19-1): Properties, Applications, and Industry Insights

Methyl 4-iodo-1H-indole-6-carboxylate (CAS No. 597562-19-1) is a specialized indole derivative with significant relevance in pharmaceutical and organic synthesis. This compound, characterized by its iodo-substituted indole core and methyl ester functional group, serves as a versatile intermediate in drug discovery and material science. Its molecular structure, C10H8INO2, offers unique reactivity patterns, making it invaluable for cross-coupling reactions and heterocyclic chemistry.

In recent years, the demand for functionalized indoles like Methyl 4-iodo-1H-indole-6-carboxylate has surged due to their role in developing targeted therapies and small-molecule inhibitors. Researchers frequently search for "indole-based drug scaffolds" or "iodo-indole synthesis," reflecting its prominence in medicinal chemistry. The compound’s iodine atom enables palladium-catalyzed reactions, such as Suzuki-Miyaura couplings, which are pivotal for creating biaryl structures in oncology and CNS drug candidates.

From a synthetic perspective, Methyl 4-iodo-1H-indole-6-carboxylate is often synthesized via direct iodination of methyl indole-6-carboxylate, followed by purification through column chromatography. Its crystalline solid form and stability under inert conditions make it suitable for high-throughput screening (HTS) workflows. Industry professionals frequently inquire about "scalable indole derivatization" or "CAS 597562-19-1 suppliers," highlighting its commercial importance.

Beyond pharmaceuticals, this compound finds niche applications in agrochemical research and fluorescence probes. Its electron-rich aromatic system allows for modifications to enhance photophysical properties, a topic gaining traction in "organic electronics" forums. Environmental considerations also drive interest in "green synthesis of halogenated indoles," where 597562-19-1 serves as a model for optimizing atom economy.

Analytical characterization of Methyl 4-iodo-1H-indole-6-carboxylate typically involves NMR spectroscopy (1H/13C), mass spectrometry, and HPLC purity assays. Recent publications emphasize its utility in "fragment-based drug design" (FBDD), addressing queries like "how to modify indole C4 position." Regulatory compliance, such as REACH and GMP standards, further underscores its safe handling protocols.

In conclusion, Methyl 4-iodo-1H-indole-6-carboxylate (CAS No. 597562-19-1) exemplifies the intersection of structural complexity and practical utility in modern chemistry. As AI-driven platforms like AlphaFold accelerate molecular modeling, compounds like this will remain pivotal in bridging computational predictions with laboratory validation. Future trends may explore its role in "deuterated pharmaceuticals" or "catalytic C-H activation," ensuring sustained scientific and commercial interest.

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