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1,3-Bis(4-chlorophenyl)-1H-imidazol-3-ium chloride

  • CAS No. 141556-46-9

  • Cat. No. CS-0035204
  • Purity≥97%
  • MDL No.MFCD03788924

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

1,3-Bis(4-chlorophenyl)-1H-imidazol-3-ium chloride|CS-0035204

Structure of 141556-46-9

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General Information

  • CAS No. 141556-46-9
  • Cat. No. CS-0035204
  • Purity ≥97%
  • MDL No. MFCD03788924
  • Storage 4°C, protect from light, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₅H₁₁Cl₃N₂
  • Molecular Weight 325.62
  • Synonym(s) 1,3-BIS-(4-CHLORPHENYL)-IMIDAZOLIUM CHLORIDE
  • SMILES ClC1=CC=C(C=C1)[N+]2=CN(C=C2)C3=CC=C(C=C3)Cl.[Cl-]

Description

1,3-Bis(4-chlorophenyl)-1H-imidazol-3-ium chloride features a rigid, electron-deficient imidazolium core flanked by two 4-chlorophenyl groups, enhancing its stability and solubility in polar solvents. This charged scaffold serves as a robust building block for ionic liquids and catalytic systems requiring strong cationic character and steric protection.

Application

1,3-Bis(4-chlorophenyl)-1H-imidazol-3-ium chloride serves as a stable, bench-ready imidazolium salt widely employed in transition-metal-catalyzed cross-coupling reactions. Its ortho-chloroaryl substituents enable facile functionalization and serve as versatile handles for downstream derivatization. The salt exhibits excellent solubility in polar aprotic solvents, facilitates catalyst activation in Pd-catalyzed processes, and demonstrates robust stability under standard laboratory conditions, making it a reliable building block for synthesizing complex heterocyclic scaffolds and functionalized aryl systems.

Synthesis

  • Route1
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      24978-44-7
    • null|null
      3188-13-4
    • ~65%
    • In-stock
      1,3-Bis(4-chlorophenyl)-1H-imidazol-3-ium chloride|CS-0035204
      141556-46-9

    References

    • Solovyev, Andrey; Ueng, Shau-Hua; Monot, Julien; Fensterbank, Louis; Malacria, Max; Lacote, Emmanuel; Curran, Dennis P. Organic Letters, 2010 , vol. 12, # 13 p. 2998 - 3001

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-H312-H332
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362+P364-P501

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Computational Chemistry Data

  • TPSA   8.81
  • LogP   1.0648
  • H_Acceptors   1
  • H_Donors   0
  • Rotatable_Bonds   2

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