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CS-W001157 4
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4,6-Dichloro-1-methyl-1H-imidazo[4,5-c]pyridine

  • CAS No. 887147-19-5

  • Cat. No. CS-0097767
  • Purity≥97%
  • MDL No.MFCD21603853

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

4,6-Dichloro-1-methyl-1H-imidazo[4,5-c]pyridine|CS-0097767

Structure of 887147-19-5

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General Information

  • CAS No. 887147-19-5
  • Cat. No. CS-0097767
  • Purity ≥97%
  • MDL No. MFCD21603853
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₅Cl₂N₃
  • Molecular Weight 202.04
  • Synonym(s) None
  • SMILES CN1C=NC2=C1C=C(Cl)N=C2Cl

Description

4,6-Dichloro-1-methyl-1H-imidazo[4,5-c]pyridine is a sterically hindered, bench-stable heterocycle featuring two electron-deficient chlorine substituents at the 4- and 6-positions. This configuration enhances electrophilicity at the imidazopyridine core, enabling efficient coupling in cross-coupling reactions. The methyl group at N1 improves solubility and reduces basicity, facilitating handling in synthetic workflows.

Application

4,6-Dichloro-1-methyl-1H-imidazo[4,5-c]pyridine serves as a versatile building block for constructing biologically relevant heterocyclic scaffolds. The dichloro substitution enables regioselective cross-coupling reactions, while the methylated imidazopyridine core offers enhanced stability and favorable solubility. It functions as a key intermediate in the synthesis of kinase inhibitors and other pharmaceutical candidates, with predictable reactivity under standard Suzuki-Miyaura and Buchwald-Hartwig conditions.

Synthesis

  • Route1
    • 4,6-Dichloro-1-methyl-1H-imidazo[4,5-c]pyridin-7-amine|CS-0552865
      805316-72-7
    • ~99%
    • In-stock
      4,6-Dichloro-1-methyl-1H-imidazo[4,5-c]pyridine|CS-0097767
      887147-19-5

    References

    • Kempson, James; Guo, Junqing; Das, Jagabandhu; Moquin, Robert V.; Spergel, Steven H.; Watterson, Scott H.; Langevine, Charles M.; Dyckman, Alaric J.; Pattoli, Mark; Burke, James R.; Yang, XiaoXia; Gillooly, Kathleen M.; McIntyre, Kim W.; Chen, Laishun; Dodd, John H.; McKinnon, Murray; Barrish, Joel C.; Pitts, William J. Bioorganic and Medicinal Chemistry Letters, 2009 , vol. 19, # 10 p. 2646 - 2649
  • Route2
    • null|null
      149-73-5
    • ~99%
    • In-stock
      4,6-Dichloro-1-methyl-1H-imidazo[4,5-c]pyridine|CS-0097767
      887147-19-5

    References

    • BRISTOL-MYERS SQUIBB COMPANY Patent: WO2006/53166 A1, 2006 ; Location in patent: Page/Page column 59 ;
  • Route3
    • 2,6-dichloro-4-N-methylpyridine-3,4-diamine|CS-0061784
      914942-86-2
    • null|null
      122-51-0
    • ~75%
    • In-stock
      4,6-Dichloro-1-methyl-1H-imidazo[4,5-c]pyridine|CS-0097767
      887147-19-5

    References

    • BRISTOL-MYERS SQUIBB COMPANY Patent: WO2006/122137 A1, 2006 ; Location in patent: Page/Page column 74 ; WO 2006/122137 A1

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   30.71
  • LogP   2.2751
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   0

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