Cas no 885520-37-6 (4,6-Diiodo-1H-indole)

4,6-Diiodo-1H-indole is a halogenated indole derivative characterized by the presence of iodine atoms at the 4 and 6 positions of the indole ring. This compound serves as a versatile intermediate in organic synthesis, particularly in the preparation of pharmaceuticals, agrochemicals, and advanced materials. Its iodine substituents enhance reactivity, enabling selective cross-coupling reactions such as Sonogashira, Suzuki, or Buchwald-Hartwig transformations. The electron-rich indole core further facilitates functionalization, making it valuable for constructing complex heterocyclic systems. With high purity and stability under standard conditions, 4,6-Diiodo-1H-indole is a reliable building block for researchers in medicinal chemistry and material science. Proper handling under inert atmospheres is recommended to preserve its integrity.
4,6-Diiodo-1H-indole structure
4,6-Diiodo-1H-indole structure
Product Name:4,6-Diiodo-1H-indole
CAS No:885520-37-6
MF:C8H5I2N
MW:368.940946340561
MDL:MFCD07781706
CID:840670
PubChem ID:24728297
Update Time:2025-05-24

4,6-Diiodo-1H-indole Chemical and Physical Properties

Names and Identifiers

    • 4,6-Diiodo-1H-indole
    • 1H-Indole, 4,6-diiodo-
    • 4,6-Diiodo indole
    • SB15281
    • DTXSID30646334
    • 4,6-Diiodoindole
    • AKOS022173027
    • 885520-37-6
    • DB-184272
    • MDL: MFCD07781706
    • Inchi: 1S/C8H5I2N/c9-5-3-7(10)6-1-2-11-8(6)4-5/h1-4,11H
    • InChI Key: ZITYWKTZRRHYBA-UHFFFAOYSA-N
    • SMILES: IC1=CC(=CC2=C1C=CN2)I

Computed Properties

  • Exact Mass: 368.85114g/mol
  • Monoisotopic Mass: 368.85114g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 1
  • Heavy Atom Count: 11
  • Rotatable Bond Count: 0
  • Complexity: 151
  • 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: 3.3
  • Topological Polar Surface Area: 15.8?2

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Additional information on 4,6-Diiodo-1H-indole

4,6-Diiodo-1H-indole: A Comprehensive Overview

4,6-Diiodo-1H-indole (CAS No. 885520-37-6) is a fascinating compound that has garnered significant attention in the fields of organic chemistry, pharmacology, and materials science. This compound is a derivative of indole, a heterocyclic aromatic compound with a nitrogen atom in its structure. The presence of two iodine atoms at the 4 and 6 positions of the indole ring introduces unique electronic and structural properties, making it a valuable molecule for various applications.

Chemical Structure and Properties

The molecular formula of 4,6-Diiodo-1H-indole is C8H5I2N. Its molecular weight is approximately 359.8 g/mol. The compound consists of an indole ring system with two iodine atoms attached at the 4 and 6 positions. The indole ring is aromatic and consists of a six-membered benzene ring fused to a five-membered pyrrole ring. The iodine atoms at positions 4 and 6 are in the para positions relative to each other on the benzene ring.

Synthesis and Characterization

The synthesis of 4,6-Diiodo-1H-indole typically involves iodination reactions. One common method involves the reaction of indole with an iodinating agent such as iodine monochloride (ICl) or iodine in the presence of a suitable catalyst. The reaction conditions are carefully controlled to ensure selective iodination at the desired positions. Advanced characterization techniques such as nuclear magnetic resonance (NMR) spectroscopy, mass spectrometry (MS), and X-ray crystallography are employed to confirm the structure and purity of the compound.

Applications in Pharmacology

Recent studies have highlighted the potential of 4,6-Diiodo-1H-indole in drug discovery. The compound has shown promising activity in various biological assays, including anti-inflammatory, antioxidant, and anticancer activities. Its unique electronic properties make it a potential candidate for designing novel therapeutic agents.

One area where 4,6-Diiodo-1H-indole has shown significant promise is in cancer research. Studies have demonstrated that this compound can induce apoptosis in cancer cells by modulating key signaling pathways. Additionally, its ability to inhibit enzyme activities associated with inflammation makes it a potential candidate for anti-inflammatory drug development.

Applications in Materials Science

Beyond pharmacology, 4,6-Diiodo-1H-indole has found applications in materials science. Its electronic properties make it suitable for use in organic electronics, such as organic light-emitting diodes (OLEDs) and field-effect transistors (FETs). Researchers have explored its use as a building block for constructing advanced materials with tailored electronic properties.

Recent advancements in materials science have focused on incorporating 4,6-Diiodo-1H-indole into self-assembled monolayers (SAMs) and supramolecular assemblies. These structures have potential applications in sensing devices and nanotechnology.

Environmental Considerations

As with any chemical compound, understanding the environmental impact of 4,6-Diiodo-1H-indole is crucial. Studies have been conducted to assess its biodegradability and toxicity levels. Preliminary results suggest that the compound exhibits moderate biodegradability under aerobic conditions. However, further research is needed to fully understand its environmental fate and potential risks.

Efforts are also being made to develop sustainable synthesis methods for 4,6-Diiodo-1H-indole, reducing its environmental footprint while maintaining its high-quality standards.

Future Prospects

The future of 4,6-Diiodo-1H-indole looks promising as researchers continue to explore its diverse applications. Ongoing studies aim to uncover new biological targets and optimize its pharmacokinetic properties for drug development.

In materials science,
researchers are exploring novel ways to integrate
this compound into advanced materials systems.
Additionally,
collaborations between chemists,
biologists,

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