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CS-W001157 4
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3-Bromo-5-methylisoxazole

  • CAS No. 25741-97-3

  • Cat. No. CS-W018569
  • Purity≥96%
  • MDL No.MFCD06660140

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

3-Bromo-5-methylisoxazole|CS-W018569

Structure of 25741-97-3

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General Information

  • CAS No. 25741-97-3
  • Cat. No. CS-W018569
  • Purity ≥96%
  • MDL No. MFCD06660140
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₄H₄BrNO
  • Molecular Weight 161.99
  • Synonym(s) Isoxazole, 3-bromo-5-methyl- (6CI,7CI,8CI,9CI)
  • SMILES CC1=CC(Br)=NO1

Description

3-Bromo-5-methylisoxazole is a halogenated isoxazole featuring a methyl group at the 5-position and a bromine substituent at the 3-position. This electron-deficient heterocycle serves as a valuable building block in synthetic organic chemistry, particularly for transition-metal-catalyzed cross-coupling reactions. The molecule combines good stability with reactive handles, enabling efficient integration into complex molecular architectures under mild conditions.

Application

3-Bromo-5-methylisoxazole serves as a versatile building block in medicinal chemistry, enabling efficient late-stage functionalization via palladium-catalyzed cross-coupling reactions. The bromine substituent provides high reactivity in Suzuki, Stille, and Negishi couplings, while the methyl group enhances metabolic stability and modulates electronic properties. Its bench-stable nature and compatibility with diverse reaction conditions make it ideal for constructing complex heterocyclic scaffolds in API development.

Synthesis

  • Route1
    • 4-Nitrobutan-2-one|CS-0668062
      58935-95-8
    • ~%
    • In-stock
      3-Bromo-5-methylisoxazole|CS-W018569
      25741-97-3

    References

    • Chemistry and Industry (London, United Kingdom), , p. 1650
  • Route2
    • null|null
      74213-24-4
    • null|null
      16466-97-0
    • ~%
    • In-stock
      3-Bromo-5-methylisoxazole|CS-W018569
      25741-97-3

    References

    • Gazzetta Chimica Italiana, , vol. 99, p. 1107 - 1114

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   26.03
  • LogP   1.74552
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   0

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