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CS-W001157 4
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6-Bromo-3-isopropyl-[1,2,4]triazolo[4,3-a]pyridine

  • CAS No. 459448-06-7

  • Cat. No. CS-W007094
  • Purity≥97%
  • MDL No.MFCD08272050

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

6-Bromo-3-isopropyl-[1,2,4]triazolo[4,3-a]pyridine|CS-W007094

Structure of 459448-06-7

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General Information

  • CAS No. 459448-06-7
  • Cat. No. CS-W007094
  • Purity ≥97%
  • MDL No. MFCD08272050
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₁₀BrN₃
  • Molecular Weight 240.10
  • Synonym(s) 6-Bromo-3-(propan-2-yl)-[1,2,4]triazolo[4,3-a]pyridine
  • SMILES CC(C1=NN=C2C=CC(Br)=CN21)C

Description

6-Bromo-3-isopropyl-[1,2,4]triazolo[4,3-a]pyridine features a fused triazolopyridine core with a bromine at the 6-position and a sterically hindered isopropyl group at the 3-position. This combination imparts enhanced stability and directs regioselective functionalization in cross-coupling reactions. The electron-deficient heterocycle facilitates efficient palladium-catalyzed transformations, making it a valuable scaffold for medicinal chemistry and materials science applications.

Application

6-Bromo-3-isopropyl-[1,2,4]triazolo[4,3-a]pyridine serves as a versatile building block in medicinal chemistry, enabling palladium-catalyzed cross-coupling reactions due to its well-defined bromine handle. The isopropyl group enhances steric and electronic stability, improving shelf life and facilitating purification. This scaffold functions effectively in the synthesis of triazolopyridine-based heterocycles, commonly found in kinase inhibitors and other bioactive molecules, with broad compatibility in standard coupling protocols.

Synthesis

  • Route1
    • In-stock
      (5-Bromopyridin-2-yl)hydrazine|CS-D0767
      77992-44-0
    • null|null
      79-30-1
    • ~95%
    • In-stock
      6-Bromo-3-isopropyl-[1,2,4]triazolo[4,3-a]pyridine|CS-W007094
      459448-06-7

    References

    • PFIZER PRODUCTS INC. Patent: WO2004/20440 A1, 2004 ; Location in patent: Page 55 ; WO 2004/020440 A1
  • Route2
    • null|null
      459448-05-6
    • ~72%
    • In-stock
      6-Bromo-3-isopropyl-[1,2,4]triazolo[4,3-a]pyridine|CS-W007094
      459448-06-7

    References

    • Mathias, John Paul; Millan, David Simon; Lewthwaite, Russell Andrew; Phillips, Christopher Patent: US2006/35922 A1, 2006 ; Location in patent: Page/Page column 31 ; US 20060035922 A1
  • Route3
    • null|null
      1344738-15-3
    • ~%
    • In-stock
      6-Bromo-3-isopropyl-[1,2,4]triazolo[4,3-a]pyridine|CS-W007094
      459448-06-7

    References

    • Millan, David S.; Bunnage, Mark E.; Burrows, Jane L.; Butcher, Kenneth J.; Dodd, Peter G.; Evans, Timothy J.; Fairman, David A.; Hughes, Samantha J.; Kilty, Iain C.; Lemaitre, Arnaud; Lewthwaite, Russell A.; Mahnke, Axel; Mathias, John P.; Philip, James; Smith, Robert T.; Stefaniak, Mark H.; Yeadon, Michael; Phillips, Christopher Journal of Medicinal Chemistry, 2011 , vol. 54, # 22 p. 7797 - 7814

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   30.19
  • LogP   2.6152
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   1

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