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CS-W001157 4
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5-Nitro-1H-indole-3-carbonitrile

  • CAS No. 7147-14-0

  • Cat. No. CS-0043006
  • Purity≥97%
  • MDL No.MFCD02090219

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

5-Nitro-1H-indole-3-carbonitrile|CS-0043006

Structure of 7147-14-0

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General Information

  • CAS No. 7147-14-0
  • Cat. No. CS-0043006
  • Purity ≥97%
  • MDL No. MFCD02090219
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₅N₃O₂
  • Molecular Weight None
  • Synonym(s) 5-Nitroindole-3-carbonitrile
  • SMILES N#CC1=CNC2=C1C=C([N+]([O-])=O)C=C2

Description

5-Nitro-1H-indole-3-carbonitrile features a fused bicyclic indole core bearing a nitro group at the 5-position and a nitrile at the 3-position. This electron-deficient scaffold enables direct incorporation into heterocyclic architectures, serving as a key building block for bioactive molecule synthesis under standard conditions.

Application

5-Nitro-1H-indole-3-carbonitrile serves as a versatile building block for the synthesis of functionalized indole scaffolds. Its dual electron-withdrawing groups—nitro at C5 and cyano at C3—enhance electrophilicity for nucleophilic substitution and facilitate downstream transformations such as reduction, coupling reactions, and heterocycle elaboration. The compound exhibits good bench stability and is compatible with standard synthetic workflows, enabling efficient access to medicinally relevant indole derivatives in medicinal chemistry and process development.

Synthesis

  • Route1
    • In-stock
      5-Nitroindole|CS-D1052
      6146-52-7
    • null|null
      140-29-4
    • ~90%
    • In-stock
      5-Nitro-1H-indole-3-carbonitrile|CS-0043006
      7147-14-0

    References

    • Zhang, Lianpeng; Wen, Qiaodong; Jin, Jisong; Wang, Chen; Lu, Ping; Wang, Yanguang Tetrahedron, 2013 , vol. 69, # 21 p. 4236 - 4240
  • Route2
    • 5-nitro-1H-indole-3-carboxamide|CS-0062164
      128200-32-8
    • ~44%
    • In-stock
      5-Nitro-1H-indole-3-carbonitrile|CS-0043006
      7147-14-0

    References

    • Swain; Baker; Kneen; Herbert; Moseley; Saunders; Seward; Stevenson; Beer; Stanton; Watling; Ball Journal of Medicinal Chemistry, 1992 , vol. 35, # 6 p. 1019 - 1031
  • Route3
    • null|null
      110-18-9
    • In-stock
      5-Nitroindole|CS-D1052
      6146-52-7
    • ~62%
    • In-stock
      5-Nitro-1H-indole-3-carbonitrile|CS-0043006
      7147-14-0

    References

    • Liu, Bin; Wang, Jiehui; Zhang, Bo; Sun, Yang; Wang, Lei; Chen, Jianbin; Cheng, Jiang Chemical Communications, 2014 , vol. 50, # 18 p. 2315 - 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-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   82.72
  • LogP   1.94778
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   1

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