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5-Bromo-2-nitro-1H-imidazole

  • CAS No. 121816-84-0

  • Cat. No. CS-0054329
  • Purity≥97%
  • MDL No.MFCD09028957

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

5-Bromo-2-nitro-1H-imidazole|CS-0054329

Structure of 121816-84-0

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General Information

  • CAS No. 121816-84-0
  • Cat. No. CS-0054329
  • Purity ≥97%
  • MDL No. MFCD09028957
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₃H₂BrN₃O₂
  • Molecular Weight 191.97
  • Synonym(s) 4-bromo-2-nitro-1H-imidazole
  • SMILES O=[N+](C1=NC=C(Br)N1)[O-]

Description

5-Bromo-2-nitro-1H-imidazole features a bromine substituent at C5 and a nitro group at C2, delivering a highly electron-deficient imidazole core. This combination enables direct functionalization in cross-coupling reactions and facilitates incorporation into bioactive scaffolds requiring strong electrophilic character. The compound exhibits excellent stability under standard bench conditions and is compatible with palladium-catalyzed transformations.

Application

5-Bromo-2-nitro-1H-imidazole serves as a versatile building block for the synthesis of substituted imidazoles and heterocyclic scaffolds. The bromine at C5 enables palladium-catalyzed cross-coupling reactions, while the nitro group at C2 provides a handle for selective reduction or further functionalization. Its bench-stable nature and compatibility with common reaction conditions facilitate efficient access to biologically relevant imidazole derivatives in medicinal chemistry and materials science workflows.

Synthesis

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      121816-85-1

    References

    • Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), , p. 95 - 99

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   71.82
  • LogP   1.0804
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   1

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