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CS-W001157 4
Total: USD 88.00

2,4-Dibromo-6-nitroaniline

  • CAS No. 827-23-6

  • Cat. No. CS-0194512
  • Purity≥98%
  • MDL No.None

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

2,4-Dibromo-6-nitroaniline|CS-0194512

Structure of 827-23-6

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General Information

  • CAS No. 827-23-6
  • Cat. No. CS-0194512
  • Purity ≥98%
  • MDL No. None
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₄Br₂N₂O₂
  • Molecular Weight 295.92
  • Synonym(s) Benzenamine, 2,4-dibromo-6-nitro-
  • SMILES C1=C(C=C(C(=C1Br)N)[N+](=O)[O-])Br

Description

2,4-Dibromo-6-nitroaniline features a highly electron-deficient aromatic core due to dual bromine substituents and a nitro group at the para position. This configuration enables direct incorporation into cross-coupling reactions under mild conditions. The molecule exhibits enhanced stability and resistance to premature decomposition, facilitating reliable use in synthetic sequences requiring precise functional group compatibility.

Application

2,4-Dibromo-6-nitroaniline serves as a versatile building block in medicinal chemistry and agrochemical synthesis, enabling direct substitution at the nitro and amino positions. Its bromine atoms facilitate palladium-catalyzed cross-coupling reactions, while the electron-withdrawing nitro group enhances electrophilicity for nucleophilic aromatic substitution. The compound exhibits bench stability and is compatible with standard purification techniques, making it a practical intermediate for constructing complex heterocyclic scaffolds and functionalized aryl systems.

Synthesis

  • Route1
    • null|null
      88-74-4
    • ~99%
    • In-stock
      2,4-Dibromo-6-nitroaniline|CS-0194512
      827-23-6

    References

    • Brown, Neil; Luo, Diheng; Decapo, Joseph A.; Buszek, Keith R. Tetrahedron Letters, 2009 , vol. 50, # 51 p. 7113 - 7115
  • Route2

    References

    • Bagmanov Russian Journal of Applied Chemistry, 2009 , vol. 82, # 9 p. 1570 - 1576
  • Route3
    • null|null
      615-57-6
    • ~95%
    • In-stock
      2,4-Dibromo-6-nitroaniline|CS-0194512
      827-23-6

    References

    • Lemaire, M.; Guy, A.; Boutin, P.; Guette, J. P. Synthesis, 1989 , # 10 p. 761 - 763

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+H312+H332-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362+P364-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   69.16
  • LogP   2.702
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   1

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