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5-(Trifluoromethyl)-1H-imidazole-2-carbaldehyde

  • CAS No. 102808-02-6

  • Cat. No. CS-0044861
  • Purity≥95%
  • MDL No.MFCD10696737

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

5-(Trifluoromethyl)-1H-imidazole-2-carbaldehyde|CS-0044861

Structure of 102808-02-6

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General Information

  • CAS No. 102808-02-6
  • Cat. No. CS-0044861
  • Purity ≥95%
  • MDL No. MFCD10696737
  • Storage -20°C, sealed storage, away from moisture
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₅H₃F₃N₂O
  • Molecular Weight 164.09
  • Synonym(s) 4-(TRIFLUOROMETHYL)-1H-IMIDAZOLE-2-CARBALDEHYDE
  • SMILES O=CC1=NC=C(C(F)(F)F)N1

Description

5-(Trifluoromethyl)-1H-imidazole-2-carbaldehyde features a trifluoromethyl group at the C5 position and an aldehyde function at C2, creating a highly electron-deficient imidazole scaffold. This combination enhances reactivity in nucleophilic addition and cycloaddition processes. The molecule exhibits excellent bench stability and solubility in common organic solvents, enabling straightforward incorporation into synthetic workflows for pharmaceutical intermediates and functional materials.

Application

5-(Trifluoromethyl)-1H-imidazole-2-carbaldehyde serves as a versatile building block in medicinal chemistry, enabling the synthesis of imidazole-based pharmacophores. Its trifluoromethyl group enhances metabolic stability and lipophilicity, while the aldehyde functionality facilitates efficient coupling reactions via reductive amination, condensation, or nucleophilic addition. The compound exhibits good bench stability and is compatible with standard purification methods, making it well-suited for high-throughput library synthesis and API development.

Synthesis

  • Route1
    • 2-(Dimethoxymethyl)-4-(trifluoromethyl)-1H-imidazole|CS-0056190
      1171125-25-9
    • ~68%
    • In-stock
      5-(Trifluoromethyl)-1H-imidazole-2-carbaldehyde|CS-0044861
      102808-02-6

    References

    • Daiichi Sankyo Company, Limited Patent: EP2226322 A1, 2010 ; Location in patent: Page/Page column 57 ;

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-P280-P302+P352

Quality Control

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Computational Chemistry Data

  • TPSA   45.75
  • LogP   1.241
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   1

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