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Benzyl 5,6-dihydropyridine-1(2H)-carboxylate

  • CAS No. 66207-23-6

  • Cat. No. CS-W022589
  • Purity≥95%
  • MDL No.None

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

Benzyl 5,6-dihydropyridine-1(2H)-carboxylate|CS-W022589

Structure of 66207-23-6

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General Information

  • CAS No. 66207-23-6
  • Cat. No. CS-W022589
  • Purity ≥95%
  • MDL No. None
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₃H₁₅NO₂
  • Molecular Weight 217.26
  • Synonym(s) N-CBZ-1,2,5,6-TETRAHYDROPYRIDINE
  • SMILES O=C(N1CCC=CC1)OCC2=CC=CC=C2

Description

Benzyl 5,6-dihydropyridine-1(2H)-carboxylate features a reducible dihydropyridine core paired with a benzyl ester handle, enabling selective transformations in synthetic routes. The saturated pyridine ring offers enhanced stability compared to aromatic analogs, while the ester group facilitates downstream derivatization. This compound serves as a key intermediate in the construction of nitrogen-containing heterocycles and bioactive scaffolds.

Application

Benzyl 5,6-dihydropyridine-1(2H)-carboxylate serves as a versatile synthetic intermediate for the construction of pyridine-based heterocycles and bioactive molecules. Its dihydropyridine core enables selective oxidation to pyridines or functionalization at the 5- and 6-positions, while the benzyl ester group offers convenient manipulation via hydrogenolysis or acidolysis. The compound exhibits good bench stability and compatibility with common protecting group strategies, facilitating its use in iterative synthesis workflows.

Synthesis

  • Route1
    • null|null
      694-05-3
    • null|null
      501-53-1
    • ~99%
    • In-stock
      Benzyl 5,6-dihydropyridine-1(2H)-carboxylate|CS-W022589
      66207-23-6

    References

    • Hu, X.Eric; Kim, Nick K; Ledoussal, Benoit; Colson, Anny-Odile Tetrahedron Letters, 2002 , vol. 43, # 23 p. 4289 - 4293
  • Route2
    • null|null
      694-05-3
    • In-stock
      N-(Benzyloxycarbonyloxy)succinimide|CS-D0812
      13139-17-8
    • ~99%
    • In-stock
      Benzyl 5,6-dihydropyridine-1(2H)-carboxylate|CS-W022589
      66207-23-6

    References

    • BRISTOL-MYERS SQUIBB COMPANY Patent: WO2005/66176 A1, 2005 ; Location in patent: Page/Page column 62-63 ; WO 2005/066176 A1
  • Route3
    • null|null
      199103-19-0
    • ~36%
    • In-stock
      Benzyl 5,6-dihydropyridine-1(2H)-carboxylate|CS-W022589
      66207-23-6

    References

    • PFIZER INC.; NINKOVIC, Sacha; BRAGANZA, John Frederick; COLLINS, Michael Raymond; KATH, John Charles; LI, Hui; RICHTER, Daniel Tyler Patent: WO2010/16005 A1, 2010 ; Location in patent: Page/Page column 126-127 ; WO 2010/016005 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

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Computational Chemistry Data

  • TPSA   29.54
  • LogP   2.5851
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   2

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