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CS-W001157 4
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4,5-Dichloro-2-nitroaniline

  • CAS No. 6641-64-1

  • Cat. No. CS-W015295
  • Purity≥96%
  • MDL No.MFCD00007770

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

4,5-Dichloro-2-nitroaniline|CS-W015295

Structure of 6641-64-1

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General Information

  • CAS No. 6641-64-1
  • Cat. No. CS-W015295
  • Purity ≥96%
  • MDL No. MFCD00007770
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₄Cl₂N₂O₂
  • Molecular Weight 207.01
  • Synonym(s) 4,5-DICHLORO-2-NITROBENZENAMINE; 4,5-Dichloro-2-nitroaniline
  • SMILES NC1=CC(Cl)=C(Cl)C=C1[N+]([O-])=O

Description

4,5-Dichloro-2-nitroaniline features a nitro group at the ortho position relative to the amino functionality, creating a strongly electron-deficient aromatic system. This configuration enhances reactivity in coupling processes, particularly in Pd-catalyzed cross-couplings and electrophilic substitutions. The molecule exhibits high thermal stability and moisture tolerance under standard bench conditions, enabling reliable handling in synthetic workflows.

Application

4,5-Dichloro-2-nitroaniline serves as a versatile building block in heterocyclic synthesis and medicinal chemistry, enabling efficient access to substituted anilines and nitroaromatics. Its dual chloro substituents facilitate selective electrophilic substitution and palladium-catalyzed coupling reactions, while the nitro group provides a handle for reduction to amine intermediates. The compound exhibits good bench stability and is compatible with standard purification methods, making it well-suited for scalable synthesis workflows.

Synthesis

  • Route1
    • null|null
      99-54-7
    • ~13%
    • 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
  • Route2
    • 2,4,5-Trichloronitrobenzene|CS-0204672
      89-69-0
    • ~47%
    • In-stock
      4,5-Dichloro-2-nitroaniline|CS-W015295
      6641-64-1

    References

    • Wollweber; Kolling; Niemers; et al. Arzneimittel-Forschung/Drug Research, 1984 , vol. 34, # 5 p. 531 - 542
  • Route3

    References

    • Journal of the Chemical Society, , p. 1842

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS06,GHS08,GHS09
Signal Word : Danger
UN#: 2811
Class : 6.1
Packing Group : Ⅲ
Hazard Statements : H300+H310+H330-H373-H411
Precautionary Statements : P260-P262-P264-P270-P271-P273-P280-P284-P302+P352-P304+P340-P330-P361+P364-P391-P405-P501

Quality Control

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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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