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CS-W001157 4
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4,5-Dibromo-1,2-dimethyl-1H-imidazole

  • CAS No. 16954-05-5

  • Cat. No. CS-0152843
  • Molecule weight253.92
  • Purity≥98%
  • MDL No.MFCD02179518

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

4,5-Dibromo-1,2-dimethyl-1H-imidazole|CS-0152843

Structure of 16954-05-5

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General Information

  • CAS No. 16954-05-5
  • Cat. No. CS-0152843
  • Purity ≥98%
  • MDL No. MFCD02179518
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₅H₆Br₂N₂
  • Molecular Weight 253.92
  • Synonym(s) None
  • SMILES CC1=NC(=C(Br)N1C)Br

Description

4,5-Dibromo-1,2-dimethyl-1H-imidazole features two bromine atoms at the 4 and 5 positions of the imidazole ring, flanked by methyl groups at the 1 and 2 positions. This electron-deficient heterocycle serves as a stable, bench-accessible building block for transition metal-catalyzed cross-coupling reactions. The sterically protected core enables selective functionalization in complex molecule synthesis.

Application

4,5-Dibromo-1,2-dimethyl-1H-imidazole serves as a versatile building block for the synthesis of brominated heterocyclic scaffolds. Its dual bromine substituents enable efficient cross-coupling reactions, while the methyl groups provide steric and electronic modulation. The compound exhibits excellent bench stability and facilitates straightforward purification, making it well-suited for iterative functionalization in medicinal chemistry and materials science applications.

Synthesis

  • Route1
    • In-stock
      4,5-Dibromo-2-methyl-1H-imidazole|CS-0112306
      4002-81-7
    • null|null
      77-78-1
    • ~91%
    • In-stock
      4,5-Dibromo-1,2-dimethyl-1H-imidazole|CS-0152843
      16954-05-5

    References

    • Bahnous, Mebarek; Bouraiou, Abdelmalek; Chelghoum, Meryem; Bouacida, Sofiane; Roisnel, Thierry; Smati, Farida; Bentchouala, Chafia; Gros, Philippe C.; Belfaitah, Ali Bioorganic and Medicinal Chemistry Letters, 2013 , vol. 23, # 5 p. 1274 - 1278
  • Route2

    References

    • Bahnous, Mebarek; Mouats, Chabane; Fort, Yves; Gros, Philippe C. Tetrahedron Letters, 2006 , vol. 47, # 12 p. 1949 - 1951
  • Route3
    • (1,2-Dimethyl-1H-imidazol-5-yl)methanol|CS-0378520
      24021-93-0
    • ~%
    • In-stock
      5-Bromo-1,2-dimethyl-1H-imidazole|CS-0036019
      24134-09-6
    • In-stock
      4,5-Dibromo-1,2-dimethyl-1H-imidazole|CS-0152843
      16954-05-5

    References

    • Webel, Matthias; Palmer, Andreas Marc; Scheufler, Christian; Haag, Dieter; Mueller, Bernd Organic Process Research and Development, 2010 , vol. 14, # 1 p. 142 - 151

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   17.82
  • LogP   2.25352
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   0

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