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CS-W001157 4
Total: USD 88.00

5-Bromoimidazo[1,2-a]pyridine-2-carbaldehyde

  • CAS No. 878197-68-3

  • Cat. No. CS-0041955
  • Purity≥95%
  • MDL No.MFCD11226918

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

5-Bromoimidazo[1,2-a]pyridine-2-carbaldehyde|CS-0041955

Structure of 878197-68-3

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General Information

  • CAS No. 878197-68-3
  • Cat. No. CS-0041955
  • Purity ≥95%
  • MDL No. MFCD11226918
  • Storage -20°C, sealed storage, away from moisture
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₅BrN₂O
  • Molecular Weight 225.04
  • Synonym(s) 5-BROMOIMIDAZO[1,2-A]PYRIDINE-2-CARBOXALDEHYDE
  • SMILES O=CC1=CN2C(Br)=CC=CC2=N1

Description

5-Bromoimidazo[1,2-a]pyridine-2-carbaldehyde features a fused heterocyclic core with a bromine substituent and a formyl group at adjacent positions. This combination enables direct functionalization in transition-metal-catalyzed cross-coupling reactions, facilitating rapid access to complex imidazopyridine scaffolds for medicinal chemistry applications. The molecule exhibits robust stability under standard bench conditions and tolerates diverse reaction environments.

Application

5-Bromoimidazo[1,2-a]pyridine-2-carbaldehyde serves as a versatile building block for heterocyclic synthesis, enabling efficient construction of imidazo[1,2-a]pyridine scaffolds via palladium-catalyzed cross-coupling. The aldehyde functionality facilitates direct derivatization through reductive amination or Grignard addition, while the bromo group supports further functionalization via Suzuki-Miyaura or Negishi coupling. Bench-stable and compatible with standard purification methods, it functions effectively in medicinal chemistry campaigns requiring nitrogen-rich, rigid frameworks.

Synthesis

  • Route1
    • In-stock
      2-Amino-6-bromopyridine|CS-D1448
      19798-81-3
    • null|null
      921-03-9
    • ~74%
    • In-stock
      5-Bromoimidazo[1,2-a]pyridine-2-carbaldehyde|CS-0041955
      878197-68-3

    References

    • SMITHKLINE BEECHAM CORPORATION Patent: WO2007/87549 A2, 2007 ; Location in patent: Page/Page column 49 ; WO 2007/087549 A2

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   34.37
  • LogP   1.9093
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   1

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