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CS-W001157 4
Total: USD 88.00

5-Nitrobenzo[d]isoxazole

  • CAS No. 39835-28-4

  • Cat. No. CS-W022419
  • Purity≥97%
  • MDL No.MFCD06659648

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

5-Nitrobenzo[d]isoxazole|CS-W022419

Structure of 39835-28-4

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General Information

  • CAS No. 39835-28-4
  • Cat. No. CS-W022419
  • Purity ≥97%
  • MDL No. MFCD06659648
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₄N₂O₃
  • Molecular Weight 164.12
  • Synonym(s) 5-Nitro-1,2-benzisoxazole
  • SMILES O=[N+](C1=CC2=C(ON=C2)C=C1)[O-]

Description

5-Nitrobenzo[d]isoxazole is a heterocyclic scaffold featuring an electron-deficient isoxazole ring fused to a nitro-substituted benzene. This configuration imparts enhanced reactivity in transition-metal-catalyzed couplings and enables direct functionalization at the 5-position. The nitro group stabilizes adjacent negative charge, facilitating nucleophilic substitution under mild conditions. Its robustness under standard bench protocols supports use in complex molecule assembly.

Application

5-Nitrobenzo[d]isoxazole serves as a versatile heterocyclic building block in medicinal chemistry and materials science, offering a robust scaffold with predictable reactivity. The nitro group enables further functionalization via reduction or coupling reactions, while the benzo[d]isoxazole core provides metabolic stability and favorable electronic properties. Its bench-stable nature and compatibility with standard cross-coupling protocols facilitate integration into complex molecular architectures.

Synthesis

  • Route1

    References

    • Zamri; Schalk; Pattus; Abdallah Bioorganic and Medicinal Chemistry Letters, 2003 , vol. 13, # 6 p. 1147 - 1150
  • Route2
    • null|null
      1595-15-9
    • ~61%
    • In-stock
      5-Nitrobenzo[d]isoxazole|CS-W022419
      39835-28-4

    References

    • Stokker, Gerald Journal of Organic Chemistry, 1983 , vol. 48, # 15 p. 2613 - 2615
  • Route3

    References

    • Caronna; Palazzo Gazzetta Chimica Italiana, 1959 , vol. 89, p. 1009,1013

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

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Computational Chemistry Data

  • TPSA   69.17
  • LogP   1.736
  • H_Acceptors   4
  • H_Donors   0
  • Rotatable_Bonds   1

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