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CS-W001157 4
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ethyl 3,4-dihydro-2H-1,4-benzoxazine-2-carboxylate

  • CAS No. 22244-22-0

  • Cat. No. CS-0038273
  • Purity≥96%
  • MDL No.None

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

ethyl 3,4-dihydro-2H-1,4-benzoxazine-2-carboxylate|CS-0038273

Structure of 22244-22-0

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General Information

  • CAS No. 22244-22-0
  • Cat. No. CS-0038273
  • Purity ≥96%
  • MDL No. None
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₁H₁₃NO₃
  • Molecular Weight 207.23
  • Synonym(s) 3,4-DIHYDRO-2H-BENZO[1,4]OXAZINE-2-CARBOXYLIC ACID ETHYL ESTER
  • SMILES CCOC(=O)C1CNC2=C(C=CC=C2)O1

Description

Ethyl 3,4-dihydro-2H-1,4-benzoxazine-2-carboxylate features a fused heterocyclic core with a bench-stable oxazine ring and an ester-functionalized C2 position. This structural motif enables direct incorporation into synthetic sequences requiring nitrogen-rich, electron-deficient scaffolds. The compound serves as a versatile intermediate in the construction of bioactive molecules and functional polymers.

Application

Ethyl 3,4-dihydro-2H-1,4-benzoxazine-2-carboxylate serves as a versatile scaffold for the synthesis of bioactive heterocycles and pharmaceutical intermediates. Its fused benzoxazine core enables selective functionalization at the C2 position, while the ester group supports transformations such as reduction, hydrolysis, or coupling reactions. The compound exhibits good bench stability and facilitates efficient purification, making it well-suited for iterative synthetic sequences in medicinal chemistry and process development workflows.

Synthesis

  • Route1
    • null|null
      95-55-6
    • In-stock
      Ethyl 2,3-Dibromopropionate|CS-W012517
      3674-13-3
    • ~66%
    • In-stock
      ethyl 3,4-dihydro-2H-1,4-benzoxazine-2-carboxylate|CS-0038273
      22244-22-0

    References

    • Touzeau, Frederique; Arrault, Axelle; Guillaumet, Gerald; Scalbert, Elizabeth; Pfeiffer, Bruno; Rettori, Marie-Claire; Renard, Pierre; Merour, Jean-Yves Journal of Medicinal Chemistry, 2003 , vol. 46, # 10 p. 1962 - 1979
  • Route2
    • null|null
      95-55-6
    • In-stock
      Ethyl 2,3-Dibromopropionate|CS-W012517
      3674-13-3
    • ~78%
    • Ethyl 3,4-dihydro-2H-benzo[b][1,4]oxazine-3-carboxylate|CS-0737437
      177202-60-7
    • In-stock
      ethyl 3,4-dihydro-2H-1,4-benzoxazine-2-carboxylate|CS-0038273
      22244-22-0

    References

    • Journal of Heterocyclic Chemistry, , vol. 38, # 1 p. 221 - 225
  • Route3

    References

    • US5474988 A1, ;

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07,GHS09
Signal Word : Warning
UN#: 3077
Class : 9
Packing Group : Ⅲ
Hazard Statements : H302-H411
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   1.4226
  • H_Acceptors   4
  • H_Donors   1
  • Rotatable_Bonds   2

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