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CS-W001157 4
Total: USD 88.00

4-Bromo-1H-imidazole

  • CAS No. 2302-25-2

  • Cat. No. CS-W002226
  • Purity≥98%
  • MDL No.MFCD00047021

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

4-Bromo-1H-imidazole|CS-W002226

Structure of 2302-25-2

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General Information

  • CAS No. 2302-25-2
  • Cat. No. CS-W002226
  • Purity ≥98%
  • MDL No. MFCD00047021
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₃H₃BrN₂
  • Molecular Weight 146.97
  • Synonym(s) None
  • SMILES BrC1=CN=CN1

Description

4-Bromo-1H-imidazole is a bench-stable heterocyclic reagent featuring a bromine atom at the 4-position of the imidazole ring. This configuration enables direct functionalization in cross-coupling reactions, offering efficient access to substituted imidazoles. The electron-deficient nature of the ring enhances reactivity in palladium-catalyzed transformations.

Application

4-Bromo-1H-imidazole serves as a versatile building block in synthetic organic chemistry, enabling palladium-catalyzed cross-coupling reactions to construct imidazole-based scaffolds. Its bromine substituent provides reliable reactivity in Suzuki, Stille, and Negishi couplings, while the imidazole core offers moderate basicity and hydrogen-bonding capacity. The compound exhibits excellent bench stability and facilitates straightforward purification, making it well-suited for medicinal chemistry campaigns and process-scale synthesis of heterocyclic intermediates.

Synthesis

  • Route1
    • Imidazole Ondansetron Impurity|CS-0229601
      288-32-4
    • ~40%
    • In-stock
      4,5-Dibromo-1H-imidazole|CS-0060722
      2302-30-9
    • null|null
      2034-22-2
    • In-stock
      4-Bromo-1H-imidazole|CS-W002226
      2302-25-2

    References

    • Palmer, Brian D.; Denny, William A. Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1989 , p. 95 - 99
  • Route2
    • null|null
      2034-22-2
    • ~%
    • In-stock
      4-Bromo-1H-imidazole|CS-W002226
      2302-25-2

    References

    • Journal of the Chemical Society, , vol. 121, p. 952
  • Route3

    References

    • Advanced Synthesis and Catalysis, , vol. 355, # 2-3 p. 499 - 507

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS06
Signal Word : Danger
UN#: 2811
Class : 6.1
Packing Group : Ⅲ
Hazard Statements : H301-H315-H319-H335
Precautionary Statements : P264-P270-P330-P405-P501

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Computational Chemistry Data

  • TPSA   28.68
  • LogP   1.1722
  • H_Acceptors   1
  • H_Donors   1
  • Rotatable_Bonds   0

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