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CS-W001157 4
Total: USD 88.00

4-Hydroxy-1H-indole-3-carbaldehyde

  • CAS No. 81779-27-3

  • Cat. No. CS-0136886
  • Purity≥96%
  • MDL No.MFCD05864721

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

4-Hydroxy-1H-indole-3-carbaldehyde|CS-0136886

Structure of 81779-27-3

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General Information

  • CAS No. 81779-27-3
  • Cat. No. CS-0136886
  • Purity ≥96%
  • MDL No. MFCD05864721
  • Storage 4°C, protect from light, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₇NO₂
  • Molecular Weight 161.16
  • Synonym(s) 4-Hydroxyindole-3-carboxaldehyde
  • SMILES O=CC1=CNC2=C1C(O)=CC=C2

Description

4-Hydroxy-1H-indole-3-carbaldehyde features a hydroxyl group at the 4-position and an aldehyde function at the 3-position of the indole core, enabling direct conjugation in C–C coupling reactions. The electron-rich aromatic system enhances reactivity in transition-metal-catalyzed transformations, while the carbonyl moiety serves as a key handle for derivatization. This scaffold supports rapid access to functionalized heterocycles in medicinal chemistry campaigns.

Application

4-Hydroxy-1H-indole-3-carbaldehyde serves as a versatile building block for heterocyclic synthesis, enabling efficient access to indole-based scaffolds through standard coupling and functionalization reactions. Its ortho-hydroxyl and aldehyde groups offer complementary reactivity for late-stage derivatization, while demonstrating sufficient bench stability for routine handling in medicinal chemistry workflows.

Synthesis

  • Route1
    • In-stock
      4-Hydroxyindole|CS-D1727
      2380-94-1
    • null|null
      68-12-2
    • ~79%
    • In-stock
      4-Hydroxy-1H-indole-3-carbaldehyde|CS-0136886
      81779-27-3

    References

    • Fukui, Yoshikazu; Adachi, Makoto; Sasatani, Takashi Patent: US2003/236295 A1, 2003 ; Location in patent: Page 9 ;
  • Route2

    References

    • Yamada, Fumio; Tamura, Mayumi; Hasegawa, Atsuko; Somei, Masanori Chemical and pharmaceutical bulletin, 2002 , vol. 50, # 1 p. 92 - 99
  • Route3

    References

    • EP1325909 A1, ; EP 1325909 A1

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   53.09
  • LogP   1.686
  • H_Acceptors   2
  • H_Donors   2
  • Rotatable_Bonds   1

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