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CS-W001157 4
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Methyl 3,4-dihydro-2H-benzo[b][1,4]oxazine-6-carboxylate

  • CAS No. 758684-29-6

  • Cat. No. CS-W006856
  • Purity≥96%
  • MDL No.MFCD08544342

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

Methyl 3,4-dihydro-2H-benzo[b][1,4]oxazine-6-carboxylate|CS-W006856

Structure of 758684-29-6

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General Information

  • CAS No. 758684-29-6
  • Cat. No. CS-W006856
  • Purity ≥96%
  • MDL No. MFCD08544342
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₀H₁₁NO₃
  • Molecular Weight 193.20
  • Synonym(s) Methyl 3,4-dihydro-2H-benzo[1,4]oxazine-6-carboxylate
  • SMILES O=C(C1=CC=C(OCCN2)C2=C1)OC

Description

Methyl 3,4-dihydro-2H-benzo[b][1,4]oxazine-6-carboxylate is a bench-stable heterocyclic ester featuring a fused oxazine ring system with a para-substituted carboxylate handle. This scaffold integrates readily into medicinal chemistry campaigns, offering enhanced solubility and metabolic stability in bioactive molecule design.

Application

Methyl 3,4-dihydro-2H-benzo[b][1,4]oxazine-6-carboxylate serves as a versatile heterocyclic building block for medicinal chemistry and synthetic organic applications. The oxazine scaffold provides a rigid, planar core with moderate electron-rich character, enabling selective functionalization at the C6 position. The ester group facilitates downstream transformations such as hydrolysis, reduction, or coupling reactions. Bench-stable and compatible with standard reaction conditions, it functions effectively in multistep syntheses involving transition metal catalysis or nucleophilic substitution.

Synthesis

  • Route1
    • null|null
      106-93-4
    • In-stock
      Orthocaine|CS-W005637
      536-25-4
    • ~74%
    • In-stock
      Methyl 3,4-dihydro-2H-benzo[b][1,4]oxazine-6-carboxylate|CS-W006856
      758684-29-6

    References

    • Ackermann, Jean; Bleicher, Konrad; Ceccarelli, Simona M.; Chomienne, Odile; Mattei, Patrizio; Sander, Ulrike Obst Patent: US2007/191603 A1, 2007 ; Location in patent: Page/Page column 25 ;
  • Route2

    References

    • US2007/10670 A1, ; Page/Page column 97 ;
  • 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   47.56
  • LogP   1.2775
  • H_Acceptors   4
  • H_Donors   1
  • Rotatable_Bonds   1

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