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CS-W001157 4
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1-Methyl-1H-imidazole-4-carbaldehyde

  • CAS No. 17289-26-8

  • Cat. No. CS-0052470
  • Purity≥95%
  • MDL No.None

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

1-Methyl-1H-imidazole-4-carbaldehyde|CS-0052470

Structure of 17289-26-8

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General Information

  • CAS No. 17289-26-8
  • Cat. No. CS-0052470
  • Purity ≥95%
  • MDL No. None
  • Storage -20°C, sealed storage, away from moisture
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₅H₆N₂O
  • Molecular Weight 110.11
  • Synonym(s) N-Methyl-imidazole-4-carbaldehyde
  • SMILES O=CC1=CN(C)C=N1

Description

1-Methyl-1H-imidazole-4-carbaldehyde features a reactive aldehyde group flanked by a methyl-substituted imidazole scaffold, enabling direct incorporation into heterocyclic architectures. This bench-stable derivative offers enhanced solubility in polar solvents and serves as a key intermediate for bioactive molecule synthesis.

Application

1-Methyl-1H-imidazole-4-carbaldehyde serves as a versatile building block in heterocyclic synthesis, enabling efficient access to imidazole-based scaffolds through standard carbonyl transformations. Its aldehyde functionality facilitates nucleophilic additions, reductive aminations, and condensation reactions with amines or hydrazines under mild conditions. The methyl group enhances solubility and stability, while the imidazole core provides favorable electronic properties for further functionalization. This compound functions reliably in multistep syntheses requiring orthogonal reactivity and is amenable to purification by standard chromatographic methods.

Synthesis

  • Route1
    • In-stock
      1H-Imidazole-5-carboxaldehyde|CS-D1058
      3034-50-2
    • null|null
      74-88-4
    • ~%
    • In-stock
      1-Methyl-1H-imidazole-4-carbaldehyde|CS-0052470
      17289-26-8

    References

    • WO2003/87088 A2, ; Page/Page column 28 ; WO 03/087088 A2
  • Route2
    • 1-((2-(Trimethylsilyl)ethoxy)methyl)-1H-imidazole-5-carbaldehyde|CS-0651032
      118004-64-1
    • null|null
      333-27-7
    • ~91%
    • In-stock
      1-Methyl-1H-imidazole-4-carbaldehyde|CS-0052470
      17289-26-8

    References

    • Shapiro, Gideon; Gomez-Lor, Berta Heterocycles, 1995 , vol. 41, # 2 p. 215 - 218
  • Route3

    References

    • Green, Neal; Hu, Yonghan; Janz, Kristin; Li, Huan-Qiu; Kaila, Neelu; Guler, Satenig; Thomason, Jennifer; Joseph-McCarthy, Diane; Tam, Steve Y.; Hotchandani, Rajeev; Wu, Junjun; Huang, Adrian; Wang, Qin; Leung, Louis; Pelker, Jefferey; Marusic, Suzana; Hsu, Sang; Telliez, Jean-Baptiste; Hall, J. Perry; Cuozzo, John W.; Lin, Lih-Ling Journal of Medicinal Chemistry, 2007 , vol. 50, # 19 p. 4728 - 4745

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   34.89
  • LogP   0.2326
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   1

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