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CS-W001157 4
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2,3,3-Trimethyl-5-nitro-3H-indole

  • CAS No. 3484-22-8

  • Cat. No. CS-W018934
  • Molecule weight204.23
  • Purity≥97%
  • MDL No.MFCD00447544

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

2,3,3-Trimethyl-5-nitro-3H-indole|CS-W018934

Structure of 3484-22-8

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General Information

  • CAS No. 3484-22-8
  • Cat. No. CS-W018934
  • Purity ≥97%
  • MDL No. MFCD00447544
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₁H₁₂N₂O₂
  • Molecular Weight 204.23
  • Synonym(s) 5-Nitro-2,3,3-trimethylindoleninez
  • SMILES CC1=NC2=CC=C(C=C2C1(C)C)[N+]([O-])=O

Description

2,3,3-Trimethyl-5-nitro-3H-indole features a sterically hindered indole core with a nitro group at the 5-position, enhancing electronic withdrawal and stability. This electron-deficient scaffold integrates readily into synthetic routes requiring robust heterocyclic intermediates under standard conditions.

Application

2,3,3-Trimethyl-5-nitro-3H-indole serves as a versatile building block for nitrogen-containing heterocycles, featuring a stable indole core with defined substituent positioning. The nitro group at C5 enables subsequent reduction or coupling reactions, while the trimethyl substitution enhances steric shielding and bench stability. Its predictable reactivity facilitates incorporation into pharmaceutical intermediates and agrochemical scaffolds, offering reliable performance in standard synthetic workflows.

Synthesis

  • Route1

    References

    • LABORATOIRES SYNTH-INNOVE Patent: US2012/45851 A1, 2012 ; Location in patent: Page/Page column 14; 18 ;
  • Route2
    • null|null
      91337-77-8
    • ~%
    • In-stock
      2,3,3-Trimethyl-5-nitro-3H-indole|CS-W018934
      3484-22-8

    References

    • Journal of the American Chemical Society, , vol. 75, p. 1877,1880
  • Route3
    • null|null
      563-80-4
    • null|null
      100-16-3
    • ~74%
    • In-stock
      2,3,3-Trimethyl-5-nitro-3H-indole|CS-W018934
      3484-22-8

    References

    • Mancois, Fabien; Pozzo, Jean-Luc; Pan, Jianfeng; Adamietz, Frederic; Rodriguez, Vincent; Ducasse, Laurent; Castet, Frederic; Plaquet, Aurelie; Champagne, Benoit Chemistry - A European Journal, 2009 , vol. 15, # 11 p. 2560 - 2571

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   55.5
  • LogP   2.9784
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   1

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