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Ethyl 5-bromoisoxazole-3-carboxylate

  • CAS No. 1914946-33-0

  • Cat. No. CS-0473448
  • Molecule weight220.02
  • Purity≥97%
  • MDL No.None

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

Ethyl 5-bromoisoxazole-3-carboxylate|CS-0473448

Structure of 1914946-33-0

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General Information

  • CAS No. 1914946-33-0
  • Cat. No. CS-0473448
  • Purity ≥97%
  • MDL No. None
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₆BrNO₃
  • Molecular Weight 220.02
  • Synonym(s) 5-Bromo-isoxazole-3-carboxylic acid ethyl ester
  • SMILES CCOC(=O)C1C=C(Br)ON=1

Description

Ethyl 5-bromoisoxazole-3-carboxylate features a brominated isoxazole core that enables direct functionalization in cross-coupling reactions. The ethyl ester group provides enhanced solubility and reactivity, while the electron-deficient heterocycle facilitates nucleophilic substitution. This bench-stable reagent integrates efficiently into synthetic sequences requiring regioselective halogenation or transition-metal-catalyzed transformations.

Application

Ethyl 5-bromoisoxazole-3-carboxylate serves as a versatile building block in heterocyclic synthesis, enabling direct functionalization at the 5-position via palladium-catalyzed cross-coupling. The bromine moiety exhibits high reactivity in Suzuki, Stille, and Negishi reactions, while the isoxazole core provides excellent stability under standard reaction conditions. Its ethyl ester group allows for selective transformations, facilitating downstream derivatization in medicinal chemistry and agrochemical development.

Safety Information

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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

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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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