Cas no 115666-42-7 (4,5-dichloro-1H-Indole-3-carboxaldehyde)

4,5-Dichloro-1H-indole-3-carboxaldehyde is a halogenated indole derivative with significant utility in organic synthesis and pharmaceutical research. Its key structural features—the dichloro substitution at the 4,5-positions and the reactive formyl group at the 3-position—make it a versatile intermediate for constructing complex heterocyclic compounds. The electron-withdrawing chloro groups enhance its reactivity in electrophilic and nucleophilic transformations, while the aldehyde functionality allows for further derivatization via condensation or reduction reactions. This compound is particularly valuable in medicinal chemistry for the development of biologically active molecules, including potential agrochemicals and pharmaceuticals. Its stability and well-defined reactivity profile ensure consistent performance in synthetic applications.
4,5-dichloro-1H-Indole-3-carboxaldehyde structure
115666-42-7 structure
Product Name:4,5-dichloro-1H-Indole-3-carboxaldehyde
CAS No:115666-42-7
MF:C9H5Cl2NO
MW:214.048100233078
CID:1099994
PubChem ID:14059133
Update Time:2025-05-23

4,5-dichloro-1H-Indole-3-carboxaldehyde Chemical and Physical Properties

Names and Identifiers

    • 4,5-dichloro-1H-Indole-3-carboxaldehyde
    • 4,5-Dichloroindole-3-carbaldehyde
    • 4,5-Dichloro-1H-indole-3-carbaldehyde
    • AMY7329
    • MFCD16610788
    • SCHEMBL22126572
    • SY342747
    • 115666-42-7
    • Inchi: 1S/C9H5Cl2NO/c10-6-1-2-7-8(9(6)11)5(4-13)3-12-7/h1-4,12H
    • InChI Key: HYRGXPKALSYWRO-UHFFFAOYSA-N
    • SMILES: ClC1=C(C=CC2=C1C(C=O)=CN2)Cl

Computed Properties

  • Exact Mass: 212.9748192g/mol
  • Monoisotopic Mass: 212.9748192g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 1
  • Heavy Atom Count: 13
  • Rotatable Bond Count: 1
  • Complexity: 212
  • 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: 2.8
  • Topological Polar Surface Area: 32.9?2

Experimental Properties

  • Density: 1.557±0.06 g/cm3 (20 oC 760 Torr),
  • Melting Point: 244-245 oC
  • Solubility: Almost insoluble (0.054 g/l) (25 o C),

4,5-dichloro-1H-Indole-3-carboxaldehyde Pricemore >>

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Additional information on 4,5-dichloro-1H-Indole-3-carboxaldehyde

4,5-Dichloro-1H-Indole-3-Carboxaldehyde (CAS No. 115666-42-7): A Comprehensive Overview

4,5-Dichloro-1H-Indole-3-carboxaldehyde (CAS No. 115666-42-7) is a versatile compound that has garnered significant attention in the fields of organic synthesis, medicinal chemistry, and pharmaceutical research. This compound is characterized by its unique structure, which includes a substituted indole core and a carboxaldehyde functional group. The presence of these functional groups endows the molecule with a range of chemical properties and potential biological activities, making it a valuable building block in the development of novel therapeutic agents.

The indole scaffold is a well-known and widely studied heterocyclic structure that is found in numerous natural products and bioactive compounds. The 4,5-dichloro substitution on the indole ring adds further complexity and modulates the electronic properties of the molecule, potentially influencing its reactivity and biological interactions. The carboxaldehyde group, on the other hand, provides a reactive site for various chemical transformations, such as condensation reactions, which are crucial in the synthesis of more complex molecules.

Recent research has highlighted the potential applications of 4,5-dichloro-1H-Indole-3-carboxaldehyde in the development of new drugs. For instance, studies have shown that derivatives of this compound exhibit promising antitumor activities. One notable study published in the *Journal of Medicinal Chemistry* demonstrated that certain 4,5-dichloro-1H-Indole-3-carboxaldehyde derivatives effectively inhibited the growth of cancer cells by targeting specific signaling pathways involved in cell proliferation and apoptosis. These findings suggest that this compound could serve as a lead structure for the design of novel anticancer agents.

In addition to its potential as an anticancer agent, 4,5-dichloro-1H-Indole-3-carboxaldehyde has also been explored for its antimicrobial properties. Research published in *Antimicrobial Agents and Chemotherapy* reported that certain derivatives of this compound exhibited potent antibacterial activity against both Gram-positive and Gram-negative bacteria. This broad-spectrum activity makes it an attractive candidate for the development of new antibiotics to combat multidrug-resistant bacterial infections.

The synthetic accessibility of 4,5-dichloro-1H-Indole-3-carboxaldehyde is another factor contributing to its importance in chemical research. Several efficient synthetic routes have been developed to prepare this compound, including multistep sequences involving aromatic substitution reactions and functional group manipulations. These synthetic methods provide chemists with a robust platform to explore structural modifications and optimize the biological properties of 4,5-dichloro-1H-Indole-3-carboxaldehyde derivatives.

Furthermore, computational studies have provided insights into the molecular dynamics and electronic structure of 4,5-dichloro-1H-Indole-3-carboxaldehyde. Molecular docking simulations have revealed that this compound can interact with specific protein targets involved in various disease pathways. These computational tools are invaluable for guiding experimental efforts in drug discovery and optimizing lead compounds for therapeutic applications.

In conclusion, 4,5-Dichloro-1H-Indole-3-carboxaldehyde (CAS No. 115666-42-7) is a multifaceted compound with significant potential in pharmaceutical research and development. Its unique structural features and versatile reactivity make it an attractive starting point for the synthesis of bioactive molecules with diverse applications. Ongoing research continues to uncover new aspects of its biological activities and synthetic utility, positioning it as a valuable asset in the quest for innovative therapeutic solutions.

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