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3,4-Dihydro-2H-benzo[b][1,4]oxazine-7-carboxylic acid

  • CAS No. 851202-96-5

  • Cat. No. CS-0051607
  • Purity≥98%
  • MDL No.None

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

3,4-Dihydro-2H-benzo[b][1,4]oxazine-7-carboxylic acid|CS-0051607

Structure of 851202-96-5

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General Information

  • CAS No. 851202-96-5
  • Cat. No. CS-0051607
  • Purity ≥98%
  • MDL No. None
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₉NO₃
  • Molecular Weight 179.17
  • Synonym(s) 3,4-Dihydro-2H-benzo[1,4]oxazine-7-carboxylic acid
  • SMILES OC(=O)C1=CC=C2NCCOC2=C1

Description

This benzo[b][1,4]oxazine scaffold integrates a carboxylic acid at the 7-position, offering a rigid, electron-rich heterocyclic platform for medicinal chemistry. The fused ring system enhances metabolic stability and facilitates hydrogen bonding in target engagement. Its bench-stable, moisture-tolerant nature simplifies handling in synthesis workflows.

Application

3,4-Dihydro-2H-benzo[b][1,4]oxazine-7-carboxylic acid serves as a versatile scaffold for medicinal chemistry and synthetic organic applications. The carboxylic acid functionality enables direct derivatization via amide coupling, esterification, or salt formation, while the fused oxazine ring system provides structural rigidity and favorable pharmacokinetic properties. Bench-stable and compatible with standard protecting group strategies, it facilitates efficient access to heterocyclic libraries and API intermediates through well-established transformations.

Synthesis

  • Route1

    References

    • Walker, Daniel P.; Wishka, Donn G.; Piotrowski, David W.; Jia, Shaojuan; Reitz, Steven C.; Yates, Karen M.; Myers, Jason K.; Vetman, Tatiana N.; Margolis, Brandon J.; Jacobsen, E. Jon; Acker, Brad A.; Groppi, Vincent E.; Wolfe, Mark L.; Thornburgh, Bruce A.; Tinholt, Paula M.; Cortes-Burgos, Luz A.; Walters, Rodney R.; Hester, Matthew R.; Seest, Eric P.; Dolak, Lester A.; Han, Fusen; Olson, Barbara A.; Fitzgerald, Laura; Staton, Brian A.; Raub, Thomas J.; Hajos, Mihaly; Hoffmann, William E.; Li, Kai S.; Higdon, Nicole R.; Wall, Theron M.; Hurst, Raymond S.; Wong, Erik H.F.; Rogers, Bruce N. Bioorganic and Medicinal Chemistry, 2006 , vol. 14, # 24 p. 8219 - 8248
  • Route2
    • Methyl 3-(2-methoxy-2-oxoethoxy)-4-nitrobenzoate|CS-0507170
      138035-71-9
    • ~%
    • In-stock
      3,4-Dihydro-2H-benzo[b][1,4]oxazine-7-carboxylic acid|CS-0051607
      851202-96-5

    References

    • Walker, Daniel P.; Wishka, Donn G.; Piotrowski, David W.; Jia, Shaojuan; Reitz, Steven C.; Yates, Karen M.; Myers, Jason K.; Vetman, Tatiana N.; Margolis, Brandon J.; Jacobsen, E. Jon; Acker, Brad A.; Groppi, Vincent E.; Wolfe, Mark L.; Thornburgh, Bruce A.; Tinholt, Paula M.; Cortes-Burgos, Luz A.; Walters, Rodney R.; Hester, Matthew R.; Seest, Eric P.; Dolak, Lester A.; Han, Fusen; Olson, Barbara A.; Fitzgerald, Laura; Staton, Brian A.; Raub, Thomas J.; Hajos, Mihaly; Hoffmann, William E.; Li, Kai S.; Higdon, Nicole R.; Wall, Theron M.; Hurst, Raymond S.; Wong, Erik H.F.; Rogers, Bruce N. Bioorganic and Medicinal Chemistry, 2006 , vol. 14, # 24 p. 8219 - 8248
  • Route3

    References

    • Walker, Daniel P.; Wishka, Donn G.; Piotrowski, David W.; Jia, Shaojuan; Reitz, Steven C.; Yates, Karen M.; Myers, Jason K.; Vetman, Tatiana N.; Margolis, Brandon J.; Jacobsen, E. Jon; Acker, Brad A.; Groppi, Vincent E.; Wolfe, Mark L.; Thornburgh, Bruce A.; Tinholt, Paula M.; Cortes-Burgos, Luz A.; Walters, Rodney R.; Hester, Matthew R.; Seest, Eric P.; Dolak, Lester A.; Han, Fusen; Olson, Barbara A.; Fitzgerald, Laura; Staton, Brian A.; Raub, Thomas J.; Hajos, Mihaly; Hoffmann, William E.; Li, Kai S.; Higdon, Nicole R.; Wall, Theron M.; Hurst, Raymond S.; Wong, Erik H.F.; Rogers, Bruce N. Bioorganic and Medicinal Chemistry, 2006 , vol. 14, # 24 p. 8219 - 8248

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   58.56
  • LogP   1.1891
  • H_Acceptors   3
  • H_Donors   2
  • Rotatable_Bonds   1

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