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CS-W001157 4
Total: USD 88.00

Ethyl 5-cyanoindole-2-carboxylate

  • CAS No. 105191-13-7

  • Cat. No. CS-W022704
  • Purity≥97%
  • MDL No.MFCD04966999

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

Ethyl 5-cyanoindole-2-carboxylate|CS-W022704

Structure of 105191-13-7

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General Information

  • CAS No. 105191-13-7
  • Cat. No. CS-W022704
  • Purity ≥97%
  • MDL No. MFCD04966999
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₂H₁₀N₂O₂
  • Molecular Weight None
  • Synonym(s) 2-Hydroxy-4-Methyl-6-Oxo-1,6-Dihydropyridine-3-Carbonitrile
  • SMILES O=C(C(N1)=CC2=C1C=CC(C#N)=C2)OCC

Description

Ethyl 5-cyanoindole-2-carboxylate features a fused indole core with strategic electron-withdrawing cyano and ester functionalities. This combination enhances reactivity in cross-coupling and heterocycle elaboration, enabling efficient access to complex nitrogen-containing architectures under standard conditions.

Application

Ethyl 5-cyanoindole-2-carboxylate serves as a versatile building block for the synthesis of indole-based heterocycles and pharmaceutical scaffolds. The conjugated cyano and ester groups enable sequential functionalization, while the indole core provides inherent stability and π-conjugation. It facilitates palladium-catalyzed couplings and acts as a precursor in the construction of bioactive molecules, offering excellent bench stability and straightforward purification.

Synthesis

  • Route1
    • null|null
      169463-42-7
    • ~%
    • In-stock
      Ethyl 5-cyanoindole-2-carboxylate|CS-W022704
      105191-13-7

    References

    • Journal of Organic Chemistry, , vol. 18, p. 345,356
  • Route2
    • In-stock
      2-(Ethoxycarbonyl)-5-bromo-indole|CS-W002128
      16732-70-0
    • null|null
      544-92-3
    • ~63%
    • In-stock
      Ethyl 5-cyanoindole-2-carboxylate|CS-W022704
      105191-13-7

    References

    • The Scripps Research Institute Patent: US2005/26987 A1, 2005 ; Location in patent: Page 23 ;
  • Route3
    • null|null
      186392-98-3
    • ~%
    • In-stock
      Ethyl 5-cyanoindole-2-carboxylate|CS-W022704
      105191-13-7

    References

    • US6297269 B1, ;

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

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Computational Chemistry Data

  • TPSA   65.88
  • LogP   2.21628
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   2

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