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CS-W001157 4
Total: USD 88.00

4-Iodo-2-nitroaniline

  • CAS No. 20691-72-9

  • Cat. No. CS-W007996
  • Purity≥96%
  • MDL No.MFCD06808526

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

4-Iodo-2-nitroaniline|CS-W007996

Structure of 20691-72-9

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General Information

  • CAS No. 20691-72-9
  • Cat. No. CS-W007996
  • Purity ≥96%
  • MDL No. MFCD06808526
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₅IN₂O₂
  • Molecular Weight 264.02
  • Synonym(s) 4-Iodo-2-nitrophenylamine
  • SMILES NC1=CC=C(I)C=C1[N+]([O-])=O

Description

4-Iodo-2-nitroaniline features a para-iodo and ortho-nitro substitution pattern on an aniline scaffold, delivering high reactivity in cross-coupling transformations. The electron-deficient aromatic ring facilitates palladium-catalyzed coupling, while the iodide serves as a reliable handle for C–C bond formation. This compound integrates readily into complex molecular architectures under standard conditions.

Application

4-Iodo-2-nitroaniline serves as a versatile building block in medicinal chemistry and materials science, enabling palladium-catalyzed cross-coupling reactions due to its iodine substituent. The nitro group facilitates subsequent reduction to an amine or participation in electrophilic substitution, while the molecule exhibits good bench stability and straightforward purification, making it well-suited for multi-step synthesis workflows.

Synthesis

  • Route1
    • null|null
      88-74-4
    • ~99%
    • In-stock
      4-Iodo-2-nitroaniline|CS-W007996
      20691-72-9

    References

    • Monatshefte fur Chemie, , vol. 133, # 10 p. 1325 - 1330
  • Route2

    References

    • Tetrahedron, , vol. 66, # 38 p. 7642 - 7650
  • Route3
    • N-(2-Nitrophenyl)acetamide|CS-0137350
      552-32-9
    • ~45%
    • In-stock
      4-Iodo-2-nitroaniline|CS-W007996
      20691-72-9

    References

    • Journal of Chemical Research - Part S, , # 4 p. 204 - 205

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-H317
Precautionary Statements : P261-P264-P270-P272-P280-P302+P352-P330-P362+P364-P501

Quality Control

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Computational Chemistry Data

  • TPSA   69.16
  • LogP   1.7816
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   1

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