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CS-W001157 4
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Benzyl 4-oxo-3,4-dihydropyridine-1(2H)-carboxylate

  • CAS No. 185847-84-1

  • Cat. No. CS-0035499
  • Purity≥95%
  • MDL No.MFCD08437477

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

Benzyl 4-oxo-3,4-dihydropyridine-1(2H)-carboxylate|CS-0035499

Structure of 185847-84-1

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General Information

  • CAS No. 185847-84-1
  • Cat. No. CS-0035499
  • Purity ≥95%
  • MDL No. MFCD08437477
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₃H₁₃NO₃
  • Molecular Weight 231.25
  • Synonym(s) benzyl 4-oxo-2,3-dihydropyridine-1-carboxylate
  • SMILES C1=CC=C(C=C1)COC(=O)N2C=CC(=O)CC2

Description

Benzyl 4-oxo-3,4-dihydropyridine-1(2H)-carboxylate features a reactive dihydropyridine core paired with a benzyl ester handle, enabling direct incorporation into synthetic sequences. The electron-deficient pyridinone scaffold facilitates conjugate addition and cycloaddition reactions under mild conditions. This bench-stable intermediate supports efficient access to nitrogen-containing heterocycles in medicinal chemistry and materials synthesis.

Application

Benzyl 4-oxo-3,4-dihydropyridine-1(2H)-carboxylate serves as a versatile building block in heterocyclic synthesis, enabling efficient access to pyridine and dihydropyridine scaffolds. Its enone functionality facilitates conjugate additions, Michael reactions, and transition-metal-catalyzed couplings. The benzyl ester group offers stability during storage and convenient removal under standard conditions, supporting straightforward downstream functionalization. This compound functions reliably in multistep syntheses requiring controlled reactivity and high purity.

Synthesis

  • Route1
    • In-stock
      4-Methoxypyridine|CS-W007634
      620-08-6
    • null|null
      501-53-1
    • ~80%
    • In-stock
      Benzyl 4-oxo-3,4-dihydropyridine-1(2H)-carboxylate|CS-0035499
      185847-84-1

    References

    • Knapp, Spencer; Yang, Chunhua; Pabbaraja, Srihari; Rempel, Brian; Reid, Steven; Withers, Stephen G. Journal of Organic Chemistry, 2005 , vol. 70, # 19 p. 7715 - 7720
  • Route2
    • null|null
      940925-56-4
    • ~%
    • In-stock
      Benzyl 4-oxo-3,4-dihydropyridine-1(2H)-carboxylate|CS-0035499
      185847-84-1

    References

    • WO2007/64914 A2, ; Page/Page column 111 ;
  • Route3
    • 4-Isopropoxypyridine|CS-0667000
      53708-19-3
    • null|null
      501-53-1
    • ~75%
    • In-stock
      Benzyl 4-oxo-3,4-dihydropyridine-1(2H)-carboxylate|CS-0035499
      185847-84-1

    References

    • Yamada, Hironari; Aoyagi, Sakae; Kibayashi, Chihiro Tetrahedron Letters, 1996 , vol. 37, # 48 p. 8787 - 8790

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   46.61
  • LogP   2.1117
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   2

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