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CS-W001157 4
Total: USD 88.00

2,3-Dichloro-6-nitroaniline

  • CAS No. 65078-77-5

  • Cat. No. CS-0060318
  • Purity≥96%
  • MDL No.MFCD00110529

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

2,3-Dichloro-6-nitroaniline|CS-0060318

Structure of 65078-77-5

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General Information

  • CAS No. 65078-77-5
  • Cat. No. CS-0060318
  • Purity ≥96%
  • MDL No. MFCD00110529
  • Storage RT, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₄Cl₂N₂O₂
  • Molecular Weight 207.02
  • Synonym(s) None
  • SMILES C1=CC(=C(C(=C1Cl)Cl)N)[N+](=O)[O-]

Description

2,3-Dichloro-6-nitroaniline features a nitro group at the para position relative to the amino functionality, creating a strongly electron-deficient aromatic system. This configuration enhances reactivity in electrophilic substitution and facilitates coupling reactions. The presence of two chlorine atoms at adjacent positions provides sites for palladium-catalyzed cross-coupling transformations. The compound exhibits bench-stable handling characteristics and serves as a key intermediate in the synthesis of advanced pharmaceuticals and agrochemicals.

Application

2,3-Dichloro-6-nitroaniline serves as a valuable building block in heterocyclic synthesis and medicinal chemistry, offering orthogonal reactivity through its nitro group and two chloro substituents. The molecule exhibits good bench stability and facilitates direct electrophilic substitution or nucleophilic displacement reactions, enabling efficient access to substituted anilines and complex aromatic scaffolds. Its functional group tolerance supports integration into multi-step synthetic sequences for API intermediates.

Synthesis

  • Route1

    References

    • Saluja; Zou; Drach; Townsend Journal of Medicinal Chemistry, 1996 , vol. 39, # 4 p. 881 - 891
  • Route2
    • null|null
      99-54-7
    • ~75%
    • In-stock
      2,3-Dichloro-6-nitroaniline|CS-0060318
      65078-77-5
    • In-stock
      4,5-Dichloro-2-nitroaniline|CS-W015295
      6641-64-1

    References

    • Journal of the Chemical Society - Perkin Transactions 1, , # 11 p. 1437 - 1444
  • Route3

    References

    • Bioorganic and Medicinal Chemistry, , vol. 15, # 5 p. 1914 - 1927

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   69.16
  • LogP   2.4838
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   1

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