Date published: 2025-12-18

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4,6-Dimethoxyindole (CAS 23659-87-2)

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Application:
4,6-Dimethoxyindole is a useful indole derivative
CAS Number:
23659-87-2
Molecular Weight:
177.20
Molecular Formula:
C10H11NO2
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

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4,6-Dimethoxyindole, a derivative of the indole family, features a core indole structure—a fused system comprising a benzene and a pyrrole ring—with methoxy groups attached to the 4 and 6 positions. This substitution pattern significantly enhances the electron density of the indole ring through the electron-donating effects of the methoxy groups, which influences its chemical reactivity, particularly in electrophilic substitution reactions. In the realm of research, this compound is prized for its versatility as a building block in the synthesis of complex natural products and various heterocyclic compounds. Its utility extends to facilitating a range of transformations including alkylation, acylation, and palladium-catalyzed cross-coupling reactions, positioning it as a fundamental precursor for creating biologically active molecules and advanced materials. The electron-rich nature of 4,6-Dimethoxyindole makes it an attractive candidate for studies focused on the development of new synthetic methodologies in organic chemistry, particularly for pharmaceuticals, dyes, and electronic materials, thereby contributing to significant advancements in these fields without direct therapeutic implications.


4,6-Dimethoxyindole (CAS 23659-87-2) References

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  2. Methoxycamalexins and related compounds: Syntheses, antifungal activity and inhibition of brassinin oxidase.  |  Pedras, MSC. and Abdoli, A. 2018. Bioorg Med Chem. 26: 4461-4469. PMID: 30078606
  3. Synthesis and reactions of 4, 6‐dimethoxyindole, an unusual indole system.  |  Brown, Vernon H., et al. 1969. Journal of Heterocyclic Chemistry. 6.4: 539-543.
  4. Electrophilic substitution in indoles. Part 10. The mechanism of substitution in 4, 6-and 5, 6-dimethoxyindoles.  |  Ibaceta-Lizana, Juana SL, et al. 1978. Journal of the Chemical Society, Perkin Transactions. 2 8: 733-742.
  5. Metal template reactions. XX. Macrocyclic metal complexes derived from 4, 6-Dimethoxy-3-methylindole-2, 7-dicarbaldehyde and some primary diamines with additional nitrogen donor atoms.  |  Black, D. St C., et al. 1983. Australian journal of chemistry. 36.12: 2407-2412.
  6. A flexible approach to pyrido [4, 3-b] carbazoles. The syntheses of 8, 10-dimethoxy-5-methyl-, 5, 11-dimethoxy-7, 10-dimethyl-and 9-fluoro-5, 11-dimethylpyrido [4, 3-b] carbazoles by variations of the 'type D'route.  |  Maria-Joao, R. P. and V. R. Patrick. 1993. Journal of the Chemical Society, Perkin Transactions 1. 16: 1879-1889.
  7. Synthesis of indolo [3, 2-b] carbazoles from 4, 6-dimethoxyindole and aryl aldehydes 1.  |  Black, David StC, et al. 1995. Tetrahedron. 51.43: 11801-11808.
  8. SYNTHESIS OF NEW ACTIVATED INDOLES; 3-(4'-BROMOPHENYL)-4, 6-DIMETHOXY-2-METHYLINDOLE.  |  Wahyuningsih, Tutik Dwi. 2004. Indonesian Journal of Chemistry. 4.3: 197-200.
  9. Wilson, Zoe E., Amanda M. Heapy, and Margaret A. Brimble. 'Synthesis of indole analogues of the anti-Helicobacter pylori compounds CJ-13,015, CJ-13,102, CJ-13,104 and CJ-13,108.  |  Wilson, Zoe E., et al. 2007. Tetrahedron. 63.25: 5379-5385.
  10. The design of novel 4, 6-dimethoxyindole based hydrazide-hydrazones: Molecular modeling, synthesis and anticholinesterase activity.  |  Bingul, Murat, et al. 2020. Journal of Molecular Structure. 1213: 128202.

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

4,6-Dimethoxyindole, 1 g

sc-256841
1 g
$154.00