Cas no 1285718-21-9 (4-Iodo-2,3-dihydro-1H-indene)

4-Iodo-2,3-dihydro-1H-indene is a halogenated indane derivative with a molecular formula of C9H9I. This compound serves as a versatile intermediate in organic synthesis, particularly in cross-coupling reactions such as Suzuki-Miyaura and Negishi couplings, due to the reactivity of its iodine substituent. Its fused bicyclic structure provides rigidity, making it useful for constructing complex frameworks in medicinal and materials chemistry. The compound's stability under standard conditions and well-defined reactivity profile enhance its utility in precision synthesis. It is commonly employed in pharmaceutical research for the development of bioactive molecules and in materials science for designing functional organic compounds.
4-Iodo-2,3-dihydro-1H-indene structure
4-Iodo-2,3-dihydro-1H-indene structure
Product Name:4-Iodo-2,3-dihydro-1H-indene
CAS No:1285718-21-9
MF:C9H9I
MW:244.0722
MDL:MFCD22536339
CID:1088898
PubChem ID:57223454
Update Time:2025-05-26

4-Iodo-2,3-dihydro-1H-indene Chemical and Physical Properties

Names and Identifiers

    • 4-Iodo-2,3-dihydro-1H-indene
    • 1H-Indene, 2,3-dihydro-4-iodo-
    • FCH2270247
    • AK138441
    • AX8260044
    • AKOS022174132
    • 1285718-21-9
    • DTXSID60720595
    • CS-0155376
    • DB-138571
    • C9H9I
    • N13267
    • DS-6014
    • SCHEMBL9505658
    • MDL: MFCD22536339
    • Inchi: 1S/C9H9I/c10-9-6-2-4-7-3-1-5-8(7)9/h2,4,6H,1,3,5H2
    • InChI Key: MSVHXIIGNMLZCM-UHFFFAOYSA-N
    • SMILES: IC1=C([H])C([H])=C([H])C2=C1C([H])([H])C([H])([H])C2([H])[H]

Computed Properties

  • Exact Mass: 243.97490g/mol
  • Monoisotopic Mass: 243.97490g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 0
  • Heavy Atom Count: 10
  • Rotatable Bond Count: 0
  • Complexity: 122
  • 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: 0
  • XLogP3: 3.4

Experimental Properties

  • Boiling Point: 270.5±29.0°C at 760 mmHg

4-Iodo-2,3-dihydro-1H-indene Security Information

  • Signal Word:Warning
  • Hazard Statement: H302
  • Warning Statement: P280-P305+P351+P338
  • Storage Condition:Keep in dark place,Sealed in dry,Room Temperature(BD260044)

4-Iodo-2,3-dihydro-1H-indene Pricemore >>

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Additional information on 4-Iodo-2,3-dihydro-1H-indene

Research Briefing on 4-Iodo-2,3-dihydro-1H-indene (CAS: 1285718-21-9) in Chemical Biology and Pharmaceutical Applications

The compound 4-Iodo-2,3-dihydro-1H-indene (CAS: 1285718-21-9) has recently emerged as a significant intermediate in pharmaceutical research, particularly in the development of novel bioactive molecules. This bicyclic aromatic compound, featuring an iodine substituent at the 4-position, has demonstrated remarkable versatility in synthetic organic chemistry and drug discovery applications. Recent studies have highlighted its potential as a key building block for various therapeutic agents, owing to its unique structural characteristics that enable diverse chemical modifications.

In the context of medicinal chemistry, 4-Iodo-2,3-dihydro-1H-indene serves as a crucial precursor for the synthesis of more complex molecular architectures. The iodine moiety provides an excellent handle for various cross-coupling reactions, particularly palladium-catalyzed transformations, which are fundamental to modern drug discovery. Recent publications in journals such as the Journal of Medicinal Chemistry and Bioorganic & Medicinal Chemistry Letters have demonstrated its utility in constructing pharmacologically active indane derivatives with potential applications in central nervous system disorders and inflammatory diseases.

A 2023 study published in ACS Medicinal Chemistry Letters revealed innovative applications of 1285718-21-9 in the development of selective enzyme inhibitors. Researchers successfully employed this compound as a scaffold to create novel inhibitors targeting phosphodiesterase 4 (PDE4), showing promising results in preclinical models of inflammatory conditions. The electron-rich aromatic system combined with the reactive iodo substituent allowed for efficient structure-activity relationship exploration through parallel synthesis approaches.

From a synthetic chemistry perspective, recent advancements have focused on optimizing the preparation and purification of 4-Iodo-2,3-dihydro-1H-indene to meet the growing demand in pharmaceutical research. A 2024 publication in Organic Process Research & Development detailed an improved synthetic protocol that enhances yield and purity while reducing environmental impact through greener solvent systems. These process chemistry improvements are particularly valuable given the compound's increasing importance in high-throughput screening libraries and combinatorial chemistry applications.

The pharmacological potential of derivatives stemming from 1285718-21-9 continues to expand, with recent investigations exploring its incorporation into multitarget-directed ligands. A notable 2023 study in European Journal of Medicinal Chemistry demonstrated how structural modifications of this core could yield compounds with dual activity against serotonin receptors and monoamine transporters, suggesting potential applications in neuropsychiatric disorders. The rigid indane scaffold provides optimal spatial orientation of pharmacophoric elements while maintaining favorable drug-like properties.

Looking forward, the unique chemical properties of 4-Iodo-2,3-dihydro-1H-indene position it as a valuable tool in chemical biology research. Its applications in photoaffinity labeling and bioconjugation chemistry are currently under investigation, as reported in recent Chemical Communications articles. These emerging applications leverage the reactivity of the iodo group for selective biomolecular modifications, opening new avenues for target identification and validation in drug discovery pipelines.

In conclusion, 4-Iodo-2,3-dihydro-1H-indene (1285718-21-9) represents a versatile and increasingly important chemical entity in pharmaceutical research. Its applications span from traditional medicinal chemistry to cutting-edge chemical biology techniques, with recent literature demonstrating continuous innovation in both synthetic methodologies and biological applications. As research progresses, this compound is likely to maintain its prominence in the development of novel therapeutic agents and research tools.

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