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CS-W001157 4
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5-Methoxy-1H-indole-2-carbaldehyde

  • CAS No. 21778-81-4

  • Cat. No. CS-0150273
  • Purity≥98%
  • MDL No.MFCD00297147

*For research and further manufacturing use only, not for direct human use.

5-Methoxy-1H-indole-2-carbaldehyde|CS-0150273

Structure of 21778-81-4

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General Information

  • CAS No. 21778-81-4
  • Cat. No. CS-0150273
  • Purity ≥98%
  • MDL No. MFCD00297147
  • Storage -20°C, sealed storage, away from moisture
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₀H₉NO₂
  • Molecular Weight 175.18
  • Synonym(s) 5-METHOXY-1H-INDOLE-2-CARBOXALDEHYDE
  • SMILES COC1=CC2=C(C=C1)NC(=C2)C=O

Description

5-Methoxy-1H-indole-2-carbaldehyde features a strategically positioned aldehyde group at the 2-position and a methoxy substituent at the 5-position, enabling direct functionalization in heterocyclic synthesis. This electron-rich indole scaffold offers enhanced solubility and stability under standard conditions, facilitating its use in medicinal chemistry and materials science applications.

Application

5-Methoxy-1H-indole-2-carbaldehyde serves as a versatile building block in medicinal chemistry and heterocyclic synthesis, enabling efficient access to indole-based scaffolds. Its aldehyde functionality facilitates reductive amination, Grignard additions, and Ugi-type reactions, while the methoxy group enhances solubility and modulates electronic properties. Bench-stable and readily purified by column chromatography, it functions reliably in multi-step syntheses requiring orthogonality and functional group tolerance.

Synthesis

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    References

    • Tsotinis, Andrew; Afroudakis, Pandelis A.; Davidson, Kathryn; Prashar, Anjali; Sugden, David Journal of Medicinal Chemistry, 2007 , vol. 50, # 25 p. 6436 - 6440
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    References

    • Sumitomo Pharmaceuticals Company, Limited Patent: EP1479384 A1, 2004 ;
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    References

    • Meyer; Kruse Journal of Organic Chemistry, 1984 , vol. 49, # 17 p. 3195 - 3199

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H319
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

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Computational Chemistry Data

  • TPSA   42.09
  • LogP   1.989
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   2

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