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CS-W001157 4
Total: USD 88.00

4-Bromo-2-nitroaniline

  • CAS No. 875-51-4

  • Cat. No. CS-W007476
  • Purity≥96%
  • MDL No.MFCD00041312

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

4-Bromo-2-nitroaniline|CS-W007476

Structure of 875-51-4

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General Information

  • CAS No. 875-51-4
  • Cat. No. CS-W007476
  • Purity ≥96%
  • MDL No. MFCD00041312
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₅BrN₂O₂
  • Molecular Weight 217.02
  • Synonym(s) p-Bromo-o-nitroaniline; 4-Bromo-2-nitroaniline
  • SMILES NC1=CC=C(Br)C=C1[N+]([O-])=O

Description

4-Bromo-2-nitroaniline features a bromine substituent at the para position relative to a nitro group on an aniline scaffold, delivering enhanced reactivity in cross-coupling and electrophilic substitution reactions. This bench-stable compound integrates readily into complex molecular architectures requiring electron-deficient aromatic systems.

Application

4-Bromo-2-nitroaniline serves as a versatile building block in medicinal chemistry and materials science, enabling direct functionalization via palladium-catalyzed cross-coupling reactions. Its bromo group facilitates Suzuki, Stille, and Negishi couplings, while the nitro group allows for selective reduction to an amine or participation in electrophilic substitution. The compound exhibits good bench stability and is compatible with standard purification methods, making it a practical reagent for constructing complex heterocyclic scaffolds and API intermediates.

Synthesis

  • Route1
    • null|null
      88-74-4
    • ~97%
    • In-stock
      4-Bromo-2-nitroaniline|CS-W007476
      875-51-4

    References

    • Tetrahedron Letters, , vol. 44, # 21 p. 4085 - 4088
  • Route2
    • null|null
      88-74-4
    • ~80%
    • In-stock
      2-Bromo-6-nitroaniline|CS-W006849
      59255-95-7
    • In-stock
      4-Bromo-2-nitroaniline|CS-W007476
      875-51-4

    References

    • Polyhedron, , vol. 52, p. 246 - 254
  • Route3

    References

    • Journal of Enzyme Inhibition and Medicinal Chemistry, , vol. 29, # 2 p. 281 - 291

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-H317-H319-H335
Precautionary Statements : P261-P264-P270-P271-P272-P280-P302+P352-P304+P340-P330-P362+P364-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   69.16
  • LogP   1.9395
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   1

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