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CS-W001157 4
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3-Bromo-6-nitro-1H-indole

  • CAS No. 126807-09-8

  • Cat. No. CS-0088556
  • Purity≥96%
  • MDL No.MFCD11638212

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

3-Bromo-6-nitro-1H-indole|CS-0088556

Structure of 126807-09-8

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General Information

  • CAS No. 126807-09-8
  • Cat. No. CS-0088556
  • Purity ≥96%
  • MDL No. MFCD11638212
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₅BrN₂O₂
  • Molecular Weight 241.04
  • Synonym(s) 3-Bromo-6-nitroindole
  • SMILES O=[N+](C1=CC2=C(C=C1)C(Br)=CN2)[O-]

Description

3-Bromo-6-nitro-1H-indole features a bromine atom at the 3-position and a nitro group at the 6-position on the indole core, creating a highly electron-deficient aromatic system. This configuration enables efficient cross-coupling reactions and facilitates functionalization in synthetic routes to bioactive heterocycles. The compound exhibits excellent stability under standard bench conditions and is compatible with palladium-catalyzed transformations.

Application

3-Bromo-6-nitro-1H-indole serves as a versatile building block for the synthesis of functionalized indole scaffolds, enabling palladium-catalyzed cross-coupling reactions at the C3 position. The nitro group at C6 facilitates subsequent reduction and cyclization pathways, while the bromine moiety offers orthogonal reactivity for further diversification. Its bench-stable nature and compatibility with standard synthetic protocols make it well-suited for medicinal chemistry and materials science applications.

Safety Information

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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-P330-P362+P364-P405-P501

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Computational Chemistry Data

  • TPSA   58.93
  • LogP   2.8386
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   1

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