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Ethyl 5-(hydroxymethyl)isoxazole-3-carboxylate

  • CAS No. 123770-62-7

  • Cat. No. CS-0043770
  • Purity≥95%
  • MDL No.MFCD08273501

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

Ethyl 5-(hydroxymethyl)isoxazole-3-carboxylate|CS-0043770

Structure of 123770-62-7

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General Information

  • CAS No. 123770-62-7
  • Cat. No. CS-0043770
  • Purity ≥95%
  • MDL No. MFCD08273501
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₉NO₄
  • Molecular Weight 171.15
  • Synonym(s) ethyl 5-(hydroxymethyl)-1,2-oxazole-3-carboxylate
  • SMILES O=C(C1=NOC(CO)=C1)OCC

Description

Ethyl 5-(hydroxymethyl)isoxazole-3-carboxylate features a bench-stable isoxazole core bearing a pendant hydroxymethyl group, enabling direct functionalization at the side chain. This polar, moisture-tolerant scaffold integrates readily into synthetic sequences requiring regioselective derivatization. The ethyl ester facilitates downstream transformations while maintaining stability under standard conditions.

Application

Ethyl 5-(hydroxymethyl)isoxazole-3-carboxylate serves as a versatile building block in heterocyclic synthesis, enabling efficient access to isoxazole-based scaffolds. The hydroxymethyl group facilitates direct functionalization via oxidation, protection, or substitution, while the ester moiety supports further derivatization. Its bench-stable nature and compatibility with standard reaction conditions make it well-suited for medicinal chemistry campaigns and process-scale applications.

Synthesis

  • Route1
    • null|null
      107-19-7
    • In-stock
      Ethyl 2-chloro-2-(hydroxyimino)acetate|CS-D1024
      14337-43-0
    • ~70%
    • In-stock
      Ethyl 5-(hydroxymethyl)isoxazole-3-carboxylate|CS-0043770
      123770-62-7

    References

    • European Journal of Medicinal Chemistry, , vol. 27, # 6 p. 581 - 593
  • Route2
    • In-stock
      Ethyl nitroacetate|CS-0000037
      626-35-7
    • null|null
      107-19-7
    • ~98%
    • In-stock
      Ethyl 5-(hydroxymethyl)isoxazole-3-carboxylate|CS-0043770
      123770-62-7

    References

    • European Journal of Organic Chemistry, , # 26 p. 4352 - 4359
  • Route3
    • null|null
      107-19-7
    • null|null
      861135-87-7
    • ~%
    • In-stock
      Ethyl 5-(hydroxymethyl)isoxazole-3-carboxylate|CS-0043770
      123770-62-7

    References

    • WO2005/68432 A1, ; Page/Page column 221 ;

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

Quality Control

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Computational Chemistry Data

  • TPSA   72.56
  • LogP   0.3436
  • H_Acceptors   5
  • H_Donors   1
  • Rotatable_Bonds   3

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