Cas no 860297-14-9 (3-formyl-1-methyl-1H-indole-5-carbonitrile)

3-Formyl-1-methyl-1H-indole-5-carbonitrile is a versatile heterocyclic compound featuring both formyl and nitrile functional groups on an indole scaffold. Its structural properties make it a valuable intermediate in organic synthesis, particularly for the preparation of pharmaceuticals, agrochemicals, and functional materials. The presence of the formyl group allows for further derivatization via condensation or nucleophilic addition reactions, while the nitrile moiety offers opportunities for cyclization or hydrolysis. The methyl substitution at the 1-position enhances stability and influences reactivity. This compound is particularly useful in medicinal chemistry for constructing indole-based frameworks, offering a balance of reactivity and selectivity for targeted applications.
3-formyl-1-methyl-1H-indole-5-carbonitrile structure
860297-14-9 structure
Product Name:3-formyl-1-methyl-1H-indole-5-carbonitrile
CAS No:860297-14-9
MF:C11H8N2O
MW:184.19402217865
CID:1011910
PubChem ID:71551582
Update Time:2025-08-03

3-formyl-1-methyl-1H-indole-5-carbonitrile Chemical and Physical Properties

Names and Identifiers

    • 1H-Indole-5-carbonitrile,3-formyl-1-methyl-
    • 3-formyl-1-methyl-1H-indole-5-carbonitrile
    • 1H-Indole-5-carbonitrile, 3-formyl-1-methyl-
    • 3-formyl-1-methylindole-5-carbonitrile
    • CS-0456506
    • 860297-14-9
    • VBMKHTWSSPQKCR-UHFFFAOYSA-N
    • SCHEMBL5440329
    • DB-339368
    • Inchi: 1S/C11H8N2O/c1-13-6-9(7-14)10-4-8(5-12)2-3-11(10)13/h2-4,6-7H,1H3
    • InChI Key: VBMKHTWSSPQKCR-UHFFFAOYSA-N
    • SMILES: O=CC1=CN(C)C2C=CC(C#N)=CC=21

Computed Properties

  • Exact Mass: 184.063662883g/mol
  • Monoisotopic Mass: 184.063662883g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 14
  • Rotatable Bond Count: 1
  • Complexity: 280
  • 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: 1.2
  • Topological Polar Surface Area: 45.8?2

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Additional information on 3-formyl-1-methyl-1H-indole-5-carbonitrile

3-Formyl-1-Methyl-1H-Indole-5-Carbonitrile: A Comprehensive Overview

3-formyl-1-methyl-1H-indole-5-carbonitrile (CAS No. 860297-14-9) is a fascinating compound that has garnered significant attention in the fields of organic chemistry, pharmacology, and materials science. This compound, often abbreviated as FMI-Cy, belongs to the indole family of heterocyclic compounds, which are known for their versatile applications in drug discovery and advanced materials. The indole core of this molecule serves as a platform for various functional groups, making it highly customizable for specific applications.

The structure of 3-formyl-1-methyl-1H-indole-5-carbonitrile consists of an indole ring system with a formyl group at position 3, a methyl group at position 1, and a cyano group at position 5. This unique combination of substituents imparts distinctive electronic and steric properties to the molecule. The formyl group introduces electron-withdrawing effects, while the methyl group provides steric bulk and enhances lipophilicity. The cyano group, being highly electronegative, contributes to the overall polarity of the molecule and can participate in hydrogen bonding interactions.

Recent studies have highlighted the potential of 3-formyl-1-methyl-1H-indole-5-carbonitrile as a building block in drug design. Its ability to act as a scaffold for bioactive molecules has been explored in various therapeutic areas, including anticancer, antiviral, and anti-inflammatory agents. For instance, researchers have reported that derivatives of this compound exhibit potent inhibitory activity against key enzymes involved in cancer progression, such as cyclin-dependent kinases (CDKs) and histone deacetylases (HDACs). These findings underscore its potential as a lead compound in drug discovery pipelines.

In addition to its pharmacological applications, 3-formyl-1-methyl-1H-indole-5-carbonitrile has also found use in materials science. Its ability to form stable coordination complexes with metal ions has made it a valuable component in the synthesis of metalloorganic frameworks (MOFs) and other porous materials. These materials hold promise for applications in gas storage, catalysis, and sensing technologies. Recent advancements in this area have demonstrated that incorporating FMI-Cy into MOFs can significantly enhance their adsorption capacities for gases such as CO2 and CH4.

The synthesis of 3-formyl-1-methyl-1H-indole-5-carbonitrile typically involves multi-step organic reactions. A common approach involves the condensation of an appropriate indole derivative with aldehyde or ketone groups followed by cyanation at the desired position. Researchers have also explored alternative methods, such as microwave-assisted synthesis and enzymatic catalysis, to improve the efficiency and sustainability of the synthesis process. These developments align with the growing emphasis on green chemistry principles in modern organic synthesis.

From a structural standpoint, the indole ring system in 3-formyl-1-methyl-1H-indole-5-carbonitrile is highly conjugated, which contributes to its strong absorption properties in the ultraviolet-visible (UV-vis) spectrum. This characteristic makes it an attractive candidate for applications in optoelectronics and fluorescence sensing. Recent studies have demonstrated that derivatives of this compound can serve as sensitive probes for detecting metal ions or small biomolecules in complex biological environments.

In terms of biological activity, 3-formyl-1-methyl-1H-indole-5-carbonitrile has shown promising results in preclinical models. For example, it has been reported to exhibit selective cytotoxicity against cancer cells while sparing normal cells, indicating its potential as an anticancer agent with reduced side effects. Additionally, its ability to modulate cellular signaling pathways makes it a valuable tool for studying disease mechanisms at the molecular level.

Looking ahead, the versatility of 3-formyl-1-methyl-1H-indole

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