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CS-W001157 4
Total: USD 88.00

4-Iodo-1-methyl-1H-imidazole

  • CAS No. 71759-87-0

  • Cat. No. CS-W003987
  • Purity≥97%
  • MDL No.MFCD01632214

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

4-Iodo-1-methyl-1H-imidazole|CS-W003987

Structure of 71759-87-0

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General Information

  • CAS No. 71759-87-0
  • Cat. No. CS-W003987
  • Purity ≥97%
  • MDL No. MFCD01632214
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₄H₅IN₂
  • Molecular Weight 208.00
  • Synonym(s) 4-iodo-1-methyl-imidazole hydrochloride
  • SMILES Cn1cc(nc1)I

Description

4-Iodo-1-methyl-1H-imidazole is a bench-stable, moisture-tolerant heterocyclic reagent featuring a reactive iodide at the C4 position and a methyl group at nitrogen. This combination enables efficient coupling in palladium-catalyzed cross-coupling reactions, particularly Suzuki-Miyaura and Buchwald-Hartwig transformations. The electron-deficient imidazole ring enhances electrophilicity, facilitating selective functionalization.

Application

4-Iodo-1-methyl-1H-imidazole serves as a versatile building block in transition-metal-catalyzed cross-coupling reactions, enabling efficient construction of biaryl and heteroaryl architectures. Its iodine atom facilitates reliable Suzuki, Stille, and Negishi couplings under standard conditions. The methyl-substituted imidazole core provides enhanced bench stability and improved solubility compared to unsubstituted analogs, simplifying handling and purification in medicinal chemistry workflows.

Synthesis

  • Route1

    References

    • Kunz, Peter C.; Thiel, Indre; Noffke, Anna Louisa; Reiss, Guido J.; Mohr, Fabian; Spingler, Bernhard Journal of Organometallic Chemistry, 2012 , vol. 697, # 1 p. 33 - 40
  • Route2

    References

    • Tetrahedron Letters, , vol. 45, # 28 p. 5529 - 5532
  • Route3
    • In-stock
      4,5-Diiodo-1-methyl-1H-imidazole|CS-0186914
      37067-96-2
    • null|null
      870-63-3
    • ~%
    • null|null
      213179-97-6
    • In-stock
      4-Iodo-1-methyl-1H-imidazole|CS-W003987
      71759-87-0

    References

    • Tetrahedron Letters, , vol. 39, # 33 p. 5963 - 5964

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

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Computational Chemistry Data

  • TPSA   17.82
  • LogP   1.0247
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   0

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