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CS-W001157 4
Total: USD 88.00

6-Cyano-7-azaindole

  • CAS No. 189882-33-5

  • Cat. No. CS-0004098
  • Purity≥95%
  • MDL No.MFCD06659673

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

6-Cyano-7-azaindole|CS-0004098

Structure of 189882-33-5

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General Information

  • CAS No. 189882-33-5
  • Cat. No. CS-0004098
  • Purity ≥95%
  • MDL No. MFCD06659673
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₅N₃
  • Molecular Weight 143.15
  • Synonym(s) PYRROLO[2,3-B]PYRIDINE-6-CARBONITRILE
  • SMILES N#CC1=CC=C2C(NC=C2)=N1

Description

6-Cyano-7-azaindole is a nitrogen-rich heterocycle featuring a cyano group at the 6-position and an azaindole core, offering enhanced electron-withdrawing character. This scaffold integrates readily into medicinal chemistry libraries, providing improved solubility and metabolic stability in drug discovery programs.

Application

6-Cyano-7-azaindole serves as a versatile heterocyclic building block in medicinal chemistry, enabling efficient access to bioactive scaffolds through palladium-catalyzed cross-coupling and electrophilic functionalization. The nitrile group enhances solubility and provides a handle for downstream derivatization, while the 7-azaindole core offers favorable π-stacking and hydrogen-bonding interactions in target binding. Bench-stable and readily purified by chromatography, it functions effectively in standard synthetic workflows.

Synthesis

  • Route1
    • null|null
      557-21-1
    • In-stock
      6-Bromo-7-azaindole|CS-D0071
      143468-13-7
    • ~%
    • In-stock
      6-Cyano-7-azaindole|CS-0004098
      189882-33-5

    References

    • WO2012/95463 A1, ; Page/Page column 80 ;
  • Route2
    • null|null
      7677-24-9
    • In-stock
      1H-Pyrrolo[2,3-b]pyridine 7-oxide|CS-B0511
      55052-24-9
    • ~88%
    • In-stock
      6-Cyano-7-azaindole|CS-0004098
      189882-33-5

    References

    • Pillard, Christelle; Bassene, Carine Ekambome; Suzenet, Franck; Guillaumet, Gerald Synthesis, 2008 , # 13 p. 2049 - 2054
  • Route3
    • null|null
      143468-08-0
    • ~76%
    • In-stock
      6-Cyano-7-azaindole|CS-0004098
      189882-33-5

    References

    • Minakata, Satoshi; Hamada, Takayuki; Komatsu, Mitsuo; Tsuboi, Hiroyuki; Kikuta, Hiroshige; Ohshiro, Yoshiki Journal of Agricultural and Food Chemistry, 1997 , vol. 45, # 6 p. 2345 - 2348

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   52.47
  • LogP   1.43458
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   0

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