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CS-W001157 4
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Methyl 3-oxo-3,4-dihydro-2H-1,4-benzoxazine-7- carboxylate

  • CAS No. 142166-00-5

  • Cat. No. CS-W000707
  • Purity≥97%
  • MDL No.MFCD07774184

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

Methyl 3-oxo-3,4-dihydro-2H-1,4-benzoxazine-7- carboxylate|CS-W000707

Structure of 142166-00-5

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General Information

  • CAS No. 142166-00-5
  • Cat. No. CS-W000707
  • Purity ≥97%
  • MDL No. MFCD07774184
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₀H₉NO₄
  • Molecular Weight 207.18
  • Synonym(s) methyl 3-oxo-3,4-dihydro-2H-1,4-benzoxazine-7-carboxylate
  • SMILES COC(=O)c1ccc2c(c1)OCC(=O)N2

Description

Methyl 3-oxo-3,4-dihydro-2H-1,4-benzoxazine-7-carboxylate features a fused benzoxazine core with a ketone at C3 and a methyl ester at C7, delivering enhanced stability and reactivity in heterocyclic synthesis. This bench-stable scaffold integrates readily into complex molecular architectures via nucleophilic addition or transition-metal-catalyzed coupling, enabling efficient access to bioactive analogs and functionalized materials.

Application

Methyl 3-oxo-3,4-dihydro-2H-1,4-benzoxazine-7-carboxylate serves as a versatile building block for the synthesis of substituted benzoxazines and related heterocyclic scaffolds. Its functionality enables facile derivatization at the C3 carbonyl and C7 ester positions, supporting diverse transformations including nucleophilic additions, reductive aminations, and coupling reactions. The compound exhibits good bench stability and ease of purification, making it well-suited for iterative synthesis in medicinal chemistry and process development workflows.

Synthesis

  • Route1
    • null|null
      1268818-20-7
    • ~55%
    • In-stock
      Methyl 3-oxo-3,4-dihydro-2H-1,4-benzoxazine-7- carboxylate|CS-W000707
      142166-00-5

    References

    • Ramesh, Chintakunta; Raju, B. Rama; Kavala, Veerababurao; Kuo, Chun-Wei; Yao, Ching-Fa Tetrahedron, 2011 , vol. 67, # 6 p. 1187 - 1192
  • Route2
    • null|null
      79-04-9
    • In-stock
      Methyl 4-amino-3-hydroxybenzenecarboxylate|CS-W000706
      63435-16-5
    • ~%
    • In-stock
      Methyl 3-oxo-3,4-dihydro-2H-1,4-benzoxazine-7- carboxylate|CS-W000707
      142166-00-5

    References

    • US5597820 A1, ;
  • Route3

    References

    • Yamamoto, Takeshi; Hori, Manabu; Watanabe, Ikuo; Tsutsui, Hisayoshi; Harada, Kengo; Ikeda, Shoji; Maruo, Joji; Morita, Tominori; Ohtaka, Hiroshi Chemical and Pharmaceutical Bulletin, 1997 , vol. 45, # 12 p. 1975 - 1983

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
Precautionary Statements : P264-P270-P330

Quality Control

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Computational Chemistry Data

  • TPSA   64.63
  • LogP   0.8041
  • H_Acceptors   4
  • H_Donors   1
  • Rotatable_Bonds   1

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