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CS-W001157 4
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4-Methyl-5-nitro-1H-indole

  • CAS No. 165250-69-1

  • Cat. No. CS-0001918
  • Purity≥95%
  • MDL No.MFCD11035915

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

4-Methyl-5-nitro-1H-indole|CS-0001918

Structure of 165250-69-1

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General Information

  • CAS No. 165250-69-1
  • Cat. No. CS-0001918
  • Purity ≥95%
  • MDL No. MFCD11035915
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₈N₂O₂
  • Molecular Weight 176.17
  • Synonym(s) 4-methyl-5-nitro-indole
  • SMILES CC1=C2C=CNC2=CC=C1[N+]([O-])=O

Description

4-Methyl-5-nitro-1H-indole features a fused bicyclic scaffold with complementary electron-deficient and alkylated sites, enabling direct incorporation into heterocyclic architectures. The para-nitro group enhances reactivity in cross-coupling processes, while the methyl substituent provides steric stabilization. This bench-stable compound serves as a key intermediate in medicinal chemistry campaigns targeting kinase inhibitors and bioactive nitrogen heterocycles.

Application

4-Methyl-5-nitro-1H-indole serves as a versatile building block for medicinal chemistry and heterocyclic synthesis, enabling direct functionalization at the C4 position via cross-coupling or electrophilic substitution. The nitro group facilitates subsequent reduction to an amine, while the methyl substituent enhances metabolic stability and modulates electronic properties. This compound exhibits good bench stability and is compatible with standard purification protocols, making it ideal for iterative synthesis of indole-based scaffolds in API development.

Synthesis

  • Route1

    References

    • Synaptic Pharmaceutical Corporation Patent: US5677321 A1, 1997 ; US 5677321 A

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   58.93
  • LogP   2.38452
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   1

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