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CS-W001157 4
Total: USD 88.00

2,5-Dibromo-4-nitro-1H-imidazole

  • CAS No. 6154-30-9

  • Cat. No. CS-0060033
  • Purity≥98%
  • MDL No.MFCD11877989

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

2,5-Dibromo-4-nitro-1H-imidazole|CS-0060033

Structure of 6154-30-9

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General Information

  • CAS No. 6154-30-9
  • Cat. No. CS-0060033
  • Purity ≥98%
  • MDL No. MFCD11877989
  • Storage 4°C, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₃HBr₂N₃O₂
  • Molecular Weight 270.87
  • Synonym(s) 2,4-Dibromo-5-nitro-1H-imidazole
  • SMILES C1(=C(NC(=N1)Br)[N+](=O)[O-])Br

Description

2,5-Dibromo-4-nitro-1H-imidazole features a rigid imidazole core bearing two bromine substituents and a nitro group at the 4-position, enabling efficient coupling in cross-coupling reactions. The electron-deficient nature of the ring enhances reactivity in palladium-catalyzed transformations, while the bench-stable crystalline form simplifies handling and storage.

Application

2,5-Dibromo-4-nitro-1H-imidazole serves as a versatile building block for heterocyclic synthesis, enabling direct functionalization at C2 and C5 positions via palladium-catalyzed cross-coupling reactions. The nitro group at C4 provides a handle for selective reduction or substitution, while the dibromo substitution pattern ensures high reactivity in iterative coupling sequences. Its bench-stable crystalline form facilitates handling and purification, making it ideal for constructing complex imidazole-based scaffolds in 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-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

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Computational Chemistry Data

  • TPSA   71.82
  • LogP   1.8429
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   1

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