Cas no 57826-36-5 (6-Methoxy-2-phenyl-1H-indole)

6-Methoxy-2-phenyl-1H-indole is a heterocyclic organic compound featuring an indole core substituted with a methoxy group at the 6-position and a phenyl ring at the 2-position. This structure imparts unique electronic and steric properties, making it a valuable intermediate in pharmaceutical and agrochemical research. Its indole scaffold is particularly significant in the synthesis of bioactive molecules, including serotonin receptor modulators and kinase inhibitors. The methoxy and phenyl substituents enhance its reactivity and selectivity in cross-coupling and electrophilic substitution reactions. With high purity and stability, it is suitable for use in medicinal chemistry, material science, and as a building block for complex organic frameworks.
6-Methoxy-2-phenyl-1H-indole structure
6-Methoxy-2-phenyl-1H-indole structure
Product Name:6-Methoxy-2-phenyl-1H-indole
CAS No:57826-36-5
MF:C15H13NO
MW:223.269823789597
CID:344031
PubChem ID:10751571
Update Time:2025-10-28

6-Methoxy-2-phenyl-1H-indole Chemical and Physical Properties

Names and Identifiers

    • 6-Methoxy-2-phenyl-1H-indole
    • 1H-Indole, 6-methoxy-2-phenyl-
    • 1H-Indole,6-methoxy-2-phenyl
    • 2-Phenyl-6-methoxyindol
    • 2-phenyl-6-methoxyindole
    • 6-methoxy-2-phenylindole
    • methyl 2-phenyl-1H-indol-6-yl ether
    • 57826-36-5
    • 1h-indole,6-methoxy-2-phenyl-
    • Oprea1_099169
    • MFCD01464079
    • SCHEMBL3699661
    • FT-0732954
    • JLVHJFKZSFKVHO-UHFFFAOYSA-N
    • DTXSID00444389
    • DB-072380
    • HS-7818
    • G68987
    • AE-562/12222939
    • MDL: MFCD01464079
    • Inchi: 1S/C15H13NO/c1-17-13-8-7-12-9-14(16-15(12)10-13)11-5-3-2-4-6-11/h2-10,16H,1H3
    • InChI Key: JLVHJFKZSFKVHO-UHFFFAOYSA-N
    • SMILES: O(C)C1C=CC2C=C(C3C=CC=CC=3)NC=2C=1

Computed Properties

  • Exact Mass: 223.10000
  • Monoisotopic Mass: 223.099714038g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 17
  • Rotatable Bond Count: 2
  • Complexity: 249
  • 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: 3.7
  • Topological Polar Surface Area: 25?2

Experimental Properties

  • PSA: 25.02000
  • LogP: 3.84350

6-Methoxy-2-phenyl-1H-indole Customs Data

  • HS CODE:2933990090
  • Customs Data:

    China Customs Code:

    2933990090

    Overview:

    2933990090. Other heterocyclic compounds containing only nitrogen heteroatoms. VAT:17.0%. Tax refund rate:13.0%. Regulatory conditions:nothing. MFN tariff:6.5%. general tariff:20.0%

    Declaration elements:

    Product Name, component content, use to, Please indicate the appearance of Urotropine, 6- caprolactam please indicate the appearance, Signing date

    Summary:

    2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

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Additional information on 6-Methoxy-2-phenyl-1H-indole

Recent Advances in the Study of 6-Methoxy-2-phenyl-1H-indole (CAS: 57826-36-5) in Chemical Biology and Pharmaceutical Research

6-Methoxy-2-phenyl-1H-indole (CAS: 57826-36-5) is a structurally unique indole derivative that has garnered significant attention in recent years due to its potential applications in medicinal chemistry and drug discovery. This compound, characterized by a methoxy group at the 6-position and a phenyl ring at the 2-position of the indole scaffold, exhibits a range of biological activities, making it a promising candidate for further investigation. Recent studies have explored its synthesis, pharmacological properties, and mechanisms of action, shedding light on its therapeutic potential.

One of the key areas of research involving 6-Methoxy-2-phenyl-1H-indole is its role as a building block for the development of novel bioactive molecules. A 2023 study published in the Journal of Medicinal Chemistry demonstrated its utility in the synthesis of indole-based kinase inhibitors, which showed potent activity against cancer cell lines. The researchers highlighted the compound's ability to modulate key signaling pathways, including the PI3K/AKT/mTOR axis, suggesting its potential as a lead compound for anticancer drug development.

In addition to its anticancer properties, 6-Methoxy-2-phenyl-1H-indole has been investigated for its anti-inflammatory and neuroprotective effects. A recent preprint article on bioRxiv reported that derivatives of this compound exhibited significant inhibition of pro-inflammatory cytokines such as TNF-α and IL-6 in vitro. The study also suggested that these derivatives could cross the blood-brain barrier, opening new avenues for the treatment of neurodegenerative diseases like Alzheimer's and Parkinson's.

The synthetic routes to 6-Methoxy-2-phenyl-1H-indole have also been optimized in recent years. A 2022 paper in Organic Letters described a novel one-pot synthesis method using palladium-catalyzed C-H activation, which significantly improved the yield and scalability of the compound. This advancement is particularly relevant for industrial-scale production, as it reduces the cost and complexity of manufacturing.

Despite these promising developments, challenges remain in the clinical translation of 6-Methoxy-2-phenyl-1H-indole-based therapeutics. Issues such as bioavailability, metabolic stability, and off-target effects need to be addressed through further structural optimization and preclinical studies. Nevertheless, the growing body of research underscores the compound's versatility and potential as a cornerstone for future drug discovery efforts.

In conclusion, 6-Methoxy-2-phenyl-1H-indole (CAS: 57826-36-5) represents a compelling case study in the intersection of chemical biology and pharmaceutical research. Its diverse biological activities, coupled with recent advancements in synthesis and mechanistic understanding, position it as a valuable tool for scientists exploring new therapeutic strategies. Future research should focus on translating these findings into clinically viable treatments, leveraging the compound's unique properties to address unmet medical needs.

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