Cas no 4147-43-7 (6-methoxy-2-methyl-1H-Indole-3-carboxaldehyde)

6-Methoxy-2-methyl-1H-indole-3-carboxaldehyde is a versatile heterocyclic compound featuring a methoxy-substituted indole core with a formyl group at the 3-position. This structural motif is valuable in organic synthesis, particularly in the preparation of pharmaceuticals, agrochemicals, and functional materials. The methoxy and methyl substituents enhance its reactivity and selectivity in condensation and cyclization reactions, making it a useful intermediate for constructing complex indole derivatives. Its well-defined crystalline form ensures consistent purity and handling stability. The compound is commonly employed in the synthesis of bioactive molecules, including alkaloids and receptor-targeting ligands, due to its electron-rich aromatic system and functional group compatibility.
6-methoxy-2-methyl-1H-Indole-3-carboxaldehyde structure
4147-43-7 structure
Product Name:6-methoxy-2-methyl-1H-Indole-3-carboxaldehyde
CAS No:4147-43-7
MF:C11H11NO2
MW:189.210542917252
CID:1112282
PubChem ID:13874128
Update Time:2025-08-05

6-methoxy-2-methyl-1H-Indole-3-carboxaldehyde Chemical and Physical Properties

Names and Identifiers

    • 6-methoxy-2-methyl-1H-Indole-3-carboxaldehyde
    • 6-Methoxy-2-methyl-1H-indole-3-carbaldehyde
    • 6-Methoxy-2-Methylindole-3-carboxaldehyde
    • 4147-43-7
    • AT15968
    • Inchi: 1S/C11H11NO2/c1-7-10(6-13)9-4-3-8(14-2)5-11(9)12-7/h3-6,12H,1-2H3
    • InChI Key: AVSMDSQJQCPESI-UHFFFAOYSA-N
    • SMILES: O(C)C1C=CC2C(C=O)=C(C)NC=2C=1

Computed Properties

  • Exact Mass: 189.078978594g/mol
  • Monoisotopic Mass: 189.078978594g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 14
  • Rotatable Bond Count: 2
  • Complexity: 219
  • 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: 1.9
  • Topological Polar Surface Area: 42.1?2

6-methoxy-2-methyl-1H-Indole-3-carboxaldehyde Pricemore >>

Related Categories No. Product Name Cas No. Purity Specification Price update time Inquiry
SHANG HAI HAO HONG Biomedical Technology Co., Ltd.
1735589-1g
6-Methoxy-2-methyl-1h-indole-3-carbaldehyde
4147-43-7 98%
1g
¥4868.00 2024-05-14

Additional information on 6-methoxy-2-methyl-1H-Indole-3-carboxaldehyde

Introduction to 6-methoxy-2-methyl-1H-Indole-3-carboxaldehyde (CAS No. 4147-43-7) and Its Emerging Applications in Chemical Biology

6-methoxy-2-methyl-1H-Indole-3-carboxaldehyde, identified by the chemical compound identifier CAS No. 4147-43-7, is a heterocyclic aldehyde that has garnered significant attention in the field of chemical biology and pharmaceutical research due to its unique structural properties and versatile reactivity. This compound belongs to the indole family, a class of molecules widely recognized for their biological significance and pharmacological potential. The presence of both methoxy and methyl substituents, along with the aldehyde functional group, endows this molecule with distinct chemical characteristics that make it a valuable scaffold for drug discovery and synthetic chemistry.

The indole core is a privileged structure in medicinal chemistry, frequently appearing in natural products and bioactive molecules. Its aromatic system can interact with biological targets through various mechanisms, including hydrogen bonding, π-stacking, and hydrophobic interactions. The aldehyde group in 6-methoxy-2-methyl-1H-Indole-3-carboxaldehyde serves as a reactive handle, enabling further functionalization through condensation reactions, oxidation, or reduction processes. These attributes have positioned this compound as a key intermediate in the synthesis of more complex molecules with potential therapeutic applications.

Recent advancements in synthetic methodologies have enhanced the accessibility of 6-methoxy-2-methyl-1H-Indole-3-carboxaldehyde, allowing for scalable production and modification. These improvements have fueled interest in exploring its utility in diverse chemical biology applications. For instance, researchers have leveraged this compound to develop novel inhibitors targeting enzymes involved in metabolic pathways relevant to diseases such as cancer and inflammation.

One notable area of investigation involves the use of 6-methoxy-2-methyl-1H-Indole-3-carboxaldehyde as a precursor in the synthesis of indole-based scaffolds that mimic natural products known for their bioactivity. By strategically modifying the indole core, scientists have generated derivatives with enhanced binding affinity to protein targets. Such derivatives are being evaluated in preclinical studies for their potential as therapeutic agents.

The aldehyde functionality of 6-methoxy-2-methyl-1H-Indole-3-carboxaldehyde also facilitates its role as a building block in cross-coupling reactions, which are cornerstone techniques in modern organic synthesis. These reactions enable the formation of carbon-carbon bonds under mild conditions, allowing for the construction of intricate molecular architectures. The ability to incorporate this compound into larger frameworks has opened new avenues for designing molecules with tailored biological activities.

In addition to its synthetic utility, 6-methoxy-2-methyl-1H-Indole-3-carboxaldehyde has been explored for its potential role in modulating biological pathways. Studies have suggested that derivatives of this compound may interact with transcription factors and signaling proteins, influencing cellular processes such as proliferation and differentiation. These findings highlight its significance as a tool for dissecting molecular mechanisms underlying disease states.

The growing body of research on 6-methoxy-2-methyl-1H-Indole-3-carboxaldehyde underscores its importance as a versatile intermediate in chemical biology. As synthetic methods continue to evolve, the accessibility and applicability of this compound are expected to expand further, driving innovation in drug discovery and molecular medicine.

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