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6-Nitro-1H-indole-2-carboxylic acid

  • CAS No. 10242-00-9

  • Cat. No. CS-0100036
  • Purity≥95%
  • MDL No.MFCD02664466

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

6-Nitro-1H-indole-2-carboxylic acid|CS-0100036

Structure of 10242-00-9

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General Information

  • CAS No. 10242-00-9
  • Cat. No. CS-0100036
  • Purity ≥95%
  • MDL No. MFCD02664466
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₆N₂O₄
  • Molecular Weight 206.15
  • Synonym(s) 6-Nitroindole-2-carboxylicacid
  • SMILES O=C(C(N1)=CC2=C1C=C([N+]([O-])=O)C=C2)O

Description

6-Nitro-1H-indole-2-carboxylic acid features a nitro group at the 6-position and a carboxylic acid at the 2-position, creating a highly electron-deficient indole scaffold. This combination enables direct functionalization in C–H activation reactions and facilitates conjugation to biomolecules via amide coupling. The molecule exhibits enhanced solubility in polar solvents compared to non-substituted analogs, streamlining purification and handling in synthetic workflows.

Application

6-Nitro-1H-indole-2-carboxylic acid serves as a versatile building block in medicinal chemistry, enabling direct functionalization at the C2 position via standard carboxylic acid transformations. Its electron-deficient indole core enhances reactivity in nucleophilic substitution and transition-metal-catalyzed coupling reactions. The nitro group provides orthogonal handle for selective reduction or further derivatization, while the bench-stable, crystalline nature facilitates straightforward isolation and purification.

Synthesis

  • Route1

    References

    • Botyanszki, Janos; Shi, Dong-Fang; Roberts, Christopher Don; Gezginci, Mikail Hakan; Valdez, Stephen Corey; Sattarzadeh, Sherwin Patent: US2004/63645 A1, 2004 ; Location in patent: Page/Page column 46; 65 ;
  • Route2
    • In-stock
      Ethyl 6-nitro-1H-indole-2-carboxylate|CS-0434773
      16792-45-3
    • Ethyl 4-nitro-1H-indole-2-carboxylate|CS-0453049
      4993-93-5
    • ~%
    • 4-Nitro-1h-indole-2-carboxylic acid|CS-0216118
      16732-60-8
    • In-stock
      6-Nitro-1H-indole-2-carboxylic acid|CS-0100036
      10242-00-9

    References

    • Hadida Ruah, Sara S.; Grootenhuis, Peter D.J.; Van Goor, Frederick; Zhou, Jinglan; Bear, Brian; Miller, Mark T.; McCartney, Jason; Numa, Mehdi Michel Jamel Patent: US2007/244159 A1, 2007 ; Location in patent: Page/Page column 139 ;
  • Route3
    • null|null
      134747-25-4
    • ~%
    • 4-Nitro-1h-indole-2-carboxylic acid|CS-0216118
      16732-60-8
    • In-stock
      6-Nitro-1H-indole-2-carboxylic acid|CS-0100036
      10242-00-9

    References

    • Vertex Pharmaceuticals Incorporated Patent: US2012/309758 A1, 2012 ; Location in patent: Page/Page column 68 ; US 20120309758 A1

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-P280-P302+P352

Quality Control

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Computational Chemistry Data

  • TPSA   96.23
  • LogP   1.7743
  • H_Acceptors   3
  • H_Donors   2
  • Rotatable_Bonds   2

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