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6-Methyl-2-(p-tolyl)imidazo[1,2-a]pyridine

  • CAS No. 88965-00-8

  • Cat. No. CS-0172131
  • Purity≥98%
  • MDL No.None

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

6-Methyl-2-(p-tolyl)imidazo[1,2-a]pyridine|CS-0172131

Structure of 88965-00-8

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General Information

  • CAS No. 88965-00-8
  • Cat. No. CS-0172131
  • Purity ≥98%
  • MDL No. None
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₅H₁₄N₂
  • Molecular Weight 222.29
  • Synonym(s) 6-Methyl-2-p-tolyl-imidazo[1,2-a]pyridine
  • SMILES CC1=CC=C(C=C1)C2=CN3C=C(C)C=CC3=N2

Description

6-Methyl-2-(p-tolyl)imidazo[1,2-a]pyridine is a sterically hindered heteroaromatic scaffold featuring a fused imidazo[1,2-a]pyridine core with methyl and para-tolyl substituents. This electron-deficient system enables robust coupling in transition metal catalysis and serves as a key ligand component in photoredox and organocatalytic systems.

Application

6-Methyl-2-(p-tolyl)imidazo[1,2-a]pyridine serves as a versatile heterocyclic building block in medicinal chemistry, enabling efficient construction of bioactive scaffolds. Its fused imidazopyridine core exhibits enhanced metabolic stability and favorable π-stacking interactions. The methyl and p-tolyl substituents provide steric and electronic modulation, facilitating functionalization at C6 and C2 positions. This compound demonstrates bench stability, compatibility with standard coupling reactions, and ease of purification—making it well-suited for iterative synthesis campaigns in drug discovery.

Synthesis

  • Route1

    References

    • George; Rossey; Depoortere; Mompon; Allen Farmaco, 1991 , vol. 46, # SUPPL. 1 p. 277 - 288
  • Route2
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    • In-stock
      6-Methyl-2-(p-tolyl)imidazo[1,2-a]pyridine|CS-0172131
      88965-00-8

    References

    • MALLINCKRODT INC. Patent: WO2007/64444 A1, 2007 ; Location in patent: Page/Page column 13 ;
  • Route3

    References

    • Zhang, Yuhong; Zhang, Yuanfei; Chen, Zhengkai; Wu, Wenliang; Su, Weiping Journal of Organic Chemistry, 2013 , vol. 78, # 24 p. 12494 - 12504

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   17.3
  • LogP   3.61814
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   1

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