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3-Formyl-1H-indole-2-carboxylic acid

  • CAS No. 28737-34-0

  • Cat. No. CS-0182626
  • Purity≥98%
  • MDL No.MFCD06809647

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

3-Formyl-1H-indole-2-carboxylic acid|CS-0182626

Structure of 28737-34-0

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General Information

  • CAS No. 28737-34-0
  • Cat. No. CS-0182626
  • Purity ≥98%
  • MDL No. MFCD06809647
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₀H₇NO₃
  • Molecular Weight 189.17
  • Synonym(s) 1H-Indole-3-carboxaldehyde,dimethylhydrazone
  • SMILES O=C(C(N1)=C(C=O)C2=C1C=CC=C2)O

Description

3-Formyl-1H-indole-2-carboxylic acid integrates a reactive aldehyde and carboxylic acid group on the indole scaffold, enabling direct conjugation in peptide coupling and heterocyclic synthesis. This bifunctional motif supports efficient derivatization under mild conditions, delivering high yields in medicinal chemistry campaigns.

Application

3-Formyl-1H-indole-2-carboxylic acid serves as a versatile bifunctional building block for the synthesis of indole-based pharmaceuticals and functional materials. The aldehyde and carboxylic acid groups enable sequential transformations, including reductive amination, amidation, and condensation reactions, with high chemoselectivity under standard conditions. Its bench-stable crystalline form facilitates handling and purification, making it well-suited for iterative synthetic workflows in medicinal chemistry and process development.

Synthesis

  • Route1

    References

    • Font, M.; Monge, A.; Cuartero, A.; Ellorriaga, A.; Martinez-Irujo, J.J.; et al. European Journal of Medicinal Chemistry, 1995 , vol. 30, # 12 p. 963 - 972
  • Route2

    References

    • Fischer; Pistor Chemische Berichte, 1923 , vol. 56, p. 2317
  • Route3

    References

    • Fischer; Pistor Chemische Berichte, 1923 , vol. 56, p. 2317

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-H312-H315-H319-H332-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   70.16
  • LogP   1.6786
  • H_Acceptors   2
  • H_Donors   2
  • Rotatable_Bonds   2

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