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CS-W001157 4
Total: USD 88.00

4-Iodo-2-methyl-1H-imidazole

  • CAS No. 73746-45-9

  • Cat. No. CS-D0992
  • Purity≥95%
  • MDL No.MFCD15071119

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

4-Iodo-2-methyl-1H-imidazole|CS-D0992

Structure of 73746-45-9

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General Information

  • CAS No. 73746-45-9
  • Cat. No. CS-D0992
  • Purity ≥95%
  • MDL No. MFCD15071119
  • 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-2-methylimidazole; 5-iodo-2-methyl-1H-imidazole
  • SMILES CC1=NC(I)=CN1

Description

4-Iodo-2-methyl-1H-imidazole features a sterically accessible imidazole core with an iodine atom at the 4-position, enabling efficient coupling in transition-metal-catalyzed reactions. The methyl group enhances solubility and stabilizes the heterocyclic ring under standard conditions. This bench-stable reagent integrates readily into synthetic sequences requiring halogen-directed functionalization.

Application

4-Iodo-2-methyl-1H-imidazole serves as a versatile building block in medicinal chemistry and catalytic cross-coupling reactions. The iodide functionality enables reliable Suzuki, Stille, and Negishi couplings, while the 2-methyl substituent enhances stability and modulates electronic properties. Its bench-stable nature and compatibility with diverse reaction conditions make it a practical choice for constructing imidazole-based scaffolds in drug discovery and materials science.

Synthesis

  • Route1

    References

    • Hendricks, Robert Than; Hermann, Johannes; Kondru, Rama; Lou, Yan; Lynch, Stephen M.; Owens, Timothy D.; Soth, Michael Patent: US2011/230462 A1, 2011 ; Location in patent: Page/Page column 109 ; US 20110230462 A1
  • Route2
    • In-stock
      4,5-Diiodo-2-methyl-1H-imidazole|CS-0188426
      73746-44-8
    • null|null
      109-72-8
    • ~%
    • In-stock
      4-Iodo-2-methyl-1H-imidazole|CS-D0992
      73746-45-9

    References

    • US4728653 A1, ;
  • Route3

    References

    • Journal of Organic Chemistry, , vol. 45, # 15 p. 3108 - 3111

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   28.68
  • LogP   1.32272
  • H_Acceptors   1
  • H_Donors   1
  • Rotatable_Bonds   0

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