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CS-W001157 4
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Ethyl 3-bromoisoxazole-5-carboxylate

  • CAS No. 105174-97-8

  • Cat. No. CS-W008857
  • Purity≥98%
  • MDL No.MFCD04035587

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

Ethyl 3-bromoisoxazole-5-carboxylate|CS-W008857

Structure of 105174-97-8

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General Information

  • CAS No. 105174-97-8
  • Cat. No. CS-W008857
  • Purity ≥98%
  • MDL No. MFCD04035587
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₆BrNO₃
  • Molecular Weight 220.02
  • Synonym(s) ethyl 3-broMo-1,2-oxazole-5-carboxylate
  • SMILES O=C(C1=CC(Br)=NO1)OCC

Description

Ethyl 3-bromoisoxazole-5-carboxylate features a brominated isoxazole core enabling direct functionalization in late-stage diversification. The ethyl ester group facilitates smooth hydrolysis and coupling reactions, while the electron-deficient heterocycle enhances reactivity in transition-metal-catalyzed transformations. This bench-stable reagent integrates readily into synthetic sequences requiring halogen-directed C–H activation or cross-coupling protocols.

Application

Ethyl 3-bromoisoxazole-5-carboxylate serves as a versatile building block in heterocyclic synthesis, enabling direct functionalization at the C3 position via palladium-catalyzed cross-coupling reactions. Its bromine substituent offers high reactivity and compatibility with standard coupling protocols, while the isoxazole core provides robust stability and favorable polarity for purification. This compound facilitates efficient access to substituted isoxazoles relevant to medicinal chemistry and agrochemical research.

Synthesis

  • Route1
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      944709-38-0
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      623-47-2
    • ~%
    • In-stock
      Ethyl 3-bromoisoxazole-5-carboxylate|CS-W008857
      105174-97-8
    • Ethyl 3-bromoisoxazole-4-carboxylate|CS-0645931
      111303-36-7

    References

    • WO2005/26149 A1, ; Page/Page column 105 ; WO 2005/026149 A1
  • Route2
    • null|null
      74213-24-4
    • null|null
      623-47-2
    • ~%
    • In-stock
      Ethyl 3-bromoisoxazole-5-carboxylate|CS-W008857
      105174-97-8
    • Ethyl 3-bromoisoxazole-4-carboxylate|CS-0645931
      111303-36-7

    References

    • Journal of Heterocyclic Chemistry, , vol. 24, # 1 p. 43 - 46

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   52.33
  • LogP   1.6138
  • H_Acceptors   4
  • H_Donors   0
  • Rotatable_Bonds   2

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