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CS-W001157 4
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4-Iodo-3-nitroaniline

  • CAS No. 105752-04-3

  • Cat. No. CS-0102817
  • Molecule weight264.02
  • Purity≥96%
  • MDL No.MFCD08458843

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

4-Iodo-3-nitroaniline|CS-0102817

Structure of 105752-04-3

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General Information

  • CAS No. 105752-04-3
  • Cat. No. CS-0102817
  • Purity ≥96%
  • MDL No. MFCD08458843
  • 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-3-nitrobenzenamine
  • SMILES NC1=CC=C(C([N+]([O-])=O)=C1)I

Description

4-Iodo-3-nitroaniline features a para-iodo and meta-nitro substitution pattern on the benzene ring, delivering a robust platform for cross-coupling reactions. The electron-deficient aromatic core enhances reactivity in palladium-catalyzed transformations, while the bench-stable nature simplifies handling. This compound serves as a direct precursor to functionalized heterocycles and conjugated materials.

Application

4-Iodo-3-nitroaniline serves as a versatile building block in medicinal chemistry and materials science, enabling palladium-catalyzed cross-coupling reactions due to its iodide functionality. The nitro group provides a handle for selective reduction or further functionalization, while the molecule exhibits bench stability and compatibility with standard purification methods, facilitating efficient synthesis of complex heterocycles and API intermediates.

Synthesis

  • Route1
    • null|null
      99-09-2
    • ~77%
    • In-stock
      4-Iodo-3-nitroaniline|CS-0102817
      105752-04-3

    References

    • Shinde, Avinash T.; Zangade, Sainath B.; Chavan, Shivaji B.; Vibhute, Archana Y.; Nalwar, Yogesh S.; Vibhute, Yeshwant B. Synthetic Communications, 2010 , vol. 40, # 23 p. 3506 - 3513
  • Route2

    References

    • Ramana; Malik; Parihar Tetrahedron Letters, 2004 , vol. 45, # 47 p. 8681 - 8683
  • Route3
    • null|null
      99-09-2
    • ~44%
    • In-stock
      2-Iodo-5-nitroaniline|CS-0060328
      5459-50-7
    • In-stock
      4-Iodo-3-nitroaniline|CS-0102817
      105752-04-3

    References

    • Garden, Simon J.; Wardell, James L.; Skakle, Janet M. S.; Low, John N.; Glidewell, Christopher Acta Crystallographica, Section C: Crystal Structure Communications, 2004 , vol. 60, # 5 p. O328 - O330

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-P363-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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