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CS-W001157 4
Total: USD 88.00

4-Bromo-5-methylisoxazol-3-amine

  • CAS No. 5819-40-9

  • Cat. No. CS-W000691
  • Purity≥96%
  • MDL No.MFCD00052553

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

4-Bromo-5-methylisoxazol-3-amine|CS-W000691

Structure of 5819-40-9

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General Information

  • CAS No. 5819-40-9
  • Cat. No. CS-W000691
  • Purity ≥96%
  • MDL No. MFCD00052553
  • Storage RT, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₄H₅BrN₂O
  • Molecular Weight 177.00
  • Synonym(s) 3-Amino-4-bromo-5-methylisoxazole
  • SMILES CC1=C(C(N)=NO1)Br

Description

4-Bromo-5-methylisoxazol-3-amine features a brominated isoxazole core with a methyl group at the 5-position and a primary amine at the 3-position. This electron-deficient heterocycle integrates readily into pharmaceutical scaffolds, offering high functional group tolerance and stability under standard bench conditions. The pendant amine enables direct coupling for bioconjugation or further derivatization.

Application

4-Bromo-5-methylisoxazol-3-amine serves as a versatile building block for the synthesis of bioactive heterocycles, enabling efficient access to isoxazole-based scaffolds through palladium-catalyzed cross-coupling reactions. Its bromo group facilitates C–C and C–N bond formation under standard conditions, while the pendant amine supports derivatization via acylation or alkylation. The compound exhibits good bench stability and simplifies purification in multi-step sequences, making it well-suited for medicinal chemistry and process development workflows.

Synthesis

  • Route1

    References

    • US2002/95041 A1, ;
  • Route2
    • 5-Methylisoxazol-3-amine Sulfamethoxazole  Impurity|CS-0229023
      1072-67-9
    • ~41%
    • In-stock
      4-Bromo-5-methylisoxazol-3-amine|CS-W000691
      5819-40-9

    References

    • US6342610 B2, ; Page column 142 ; US 6342610 B2
  • Route3
    • 5-Methyl-N-(trimethylsilyl)isoxazol-3-amine|CS-1149830
      99356-57-7
    • ~17%
    • In-stock
      4-Bromo-5-methylisoxazol-3-amine|CS-W000691
      5819-40-9

    References

    • Journal of Organic Chemistry, , vol. 50, # 26 p. 5723 - 5727

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H315-H319
Precautionary Statements : P264-P280-P302+P352-P362

Quality Control

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Computational Chemistry Data

  • TPSA   52.05
  • LogP   1.32772
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   0

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