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

  • CAS No. 58960-11-5

  • Cat. No. CS-0188381
  • Purity≥95%
  • MDL No.MFCD08236770

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

6-Methoxy-3,4-dihydro-2H-benzo[b][1,4]oxazine|CS-0188381

Structure of 58960-11-5

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General Information

  • CAS No. 58960-11-5
  • Cat. No. CS-0188381
  • Purity ≥95%
  • MDL No. MFCD08236770
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₁₁NO₂
  • Molecular Weight None
  • Synonym(s) 6-methoxy-3,4-dihydro-2H-1,4-benzoxazine
  • SMILES COC1=CC2=C(C=C1)OCCN2

Description

6-Methoxy-3,4-dihydro-2H-benzo[b][1,4]oxazine is a bench-stable heterocyclic scaffold featuring a methoxy-substituted oxazine ring fused to benzene. This electron-rich system integrates readily into synthetic sequences requiring moderate nucleophilicity and enhanced solubility. The para-methoxy group stabilizes the core through resonance donation, enabling efficient coupling reactions under mild conditions.

Application

6-Methoxy-3,4-dihydro-2H-benzo[b][1,4]oxazine serves as a versatile heterocyclic building block in medicinal chemistry, enabling efficient access to benzoxazine-derived scaffolds. Its methoxy group enhances solubility and modulates electronic properties, while the saturated oxazine ring exhibits good bench stability and functional group tolerance. The compound facilitates diverse transformations, including nucleophilic substitutions and transition-metal-catalyzed couplings, supporting streamlined synthesis of bioactive molecules.

Synthesis

  • Route1

    References

    • Vermeulen, Erik S; van Smeden, Marjan; Schmidt, Anne W; Sprouse, Jeffrey S; Wikstroem, Hakan V; Grol, Cor J Journal of medicinal chemistry, 2004 , vol. 47, # 22 p. 5451 - 5466
  • Route2

    References

    • Journal of medicinal chemistry, , vol. 47, # 22 p. 5451 - 5466
  • Route3
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    • In-stock
      6-Methoxy-3,4-dihydro-2H-benzo[b][1,4]oxazine|CS-0188381
      58960-11-5

    References

    • Tetrahedron Letters, , vol. 47, # 44 p. 7823 - 7826

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-P280-P302+P352

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Computational Chemistry Data

  • TPSA   30.49
  • LogP   1.4995
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   1

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