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CS-W001157 4
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3-Formyl-1H-indole-4-carbonitrile

  • CAS No. 53269-35-5

  • Cat. No. CS-0112929
  • Purity≥98%
  • MDL No.None

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

3-Formyl-1H-indole-4-carbonitrile|CS-0112929

Structure of 53269-35-5

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General Information

  • CAS No. 53269-35-5
  • Cat. No. CS-0112929
  • Purity ≥98%
  • MDL No. None
  • Storage 4°C, protect from light, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₀H₆N₂O
  • Molecular Weight 170.17
  • Synonym(s) 3-Formyl-indol-4-carbonitril
  • SMILES N#CC1=CC=CC2=C1C(C=O)=CN2

Description

3-Formyl-1H-indole-4-carbonitrile features a strategically positioned aldehyde and nitrile group on the indole scaffold, enabling direct functionalization in transition-metal-catalyzed couplings and multicomponent reactions. This electron-deficient heterocycle serves as a key building block for bioactive molecule synthesis, particularly in medicinal chemistry and materials science.

Application

3-Formyl-1H-indole-4-carbonitrile serves as a versatile building block in medicinal chemistry, enabling efficient access to indole-based scaffolds through classic C–H functionalization and transition-metal-catalyzed coupling reactions. The ortho-functionalized structure supports sequential transformations, with the formyl group amenable to reductive amination, condensation, or oxidation, while the nitrile offers a handle for hydrolysis or cycloaddition. Bench-stable and readily purified by recrystallization, it facilitates scalable synthesis of bioactive heterocycles and API intermediates.

Synthesis

  • Route1
    • In-stock
      4-Cyanoindole|CS-W007669
      16136-52-0
    • null|null
      68-12-2
    • ~85%
    • In-stock
      3-Formyl-1H-indole-4-carbonitrile|CS-0112929
      53269-35-5

    References

    • Zheng, Jing; Deng, Lijuan; Chen, Minfeng; Xiao, Xuzhi; Xiao, Shengwei; Guo, Cuiping; Xiao, Gaokeng; Bai, Liangliang; Ye, Wencai; Zhang, Dongmei; Chen, Heru European Journal of Medicinal Chemistry, 2013 , vol. 65, p. 158 - 167
  • Route2
    • 4-Iodo-1H-indole-3-carbaldehyde|CS-0468937
      72527-73-2
    • null|null
      544-92-3
    • ~68%
    • In-stock
      3-Formyl-1H-indole-4-carbonitrile|CS-0112929
      53269-35-5

    References

    • Somei; Wakida; Ohta Chemical and Pharmaceutical Bulletin, 1988 , vol. 36, # 3 p. 1162 - 1168
  • Route3
    • In-stock
      4-Cyanoindole|CS-W007669
      16136-52-0
    • null|null
      93-61-8
    • ~%
    • In-stock
      3-Formyl-1H-indole-4-carbonitrile|CS-0112929
      53269-35-5

    References

    • Uhle; Harris Journal of the American Chemical Society, 1957 , vol. 79, p. 102,108

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+P364-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   56.65
  • LogP   1.85208
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   1

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