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CS-W001157 4
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4-Iodo-3-nitrobenzonitrile

  • CAS No. 101420-79-5

  • Cat. No. CS-B0300
  • Purity≥98%
  • MDL No.MFCD07783655

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

4-Iodo-3-nitrobenzonitrile|CS-B0300

Structure of 101420-79-5

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General Information

  • CAS No. 101420-79-5
  • Cat. No. CS-B0300
  • Purity ≥98%
  • MDL No. MFCD07783655
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₃IN₂O₂
  • Molecular Weight 274.02
  • Synonym(s) 1-Cyano-3-nitro-4-iodobenzene
  • SMILES N#CC(C=C1[N+]([O-])=O)=CC=C1I

Description

4-Iodo-3-nitrobenzonitrile features a trifunctional aromatic core with iodine, nitro, and nitrile groups positioned for orthogonal reactivity. This configuration enables seamless integration into cross-coupling cascades, where the iodide serves as a reliable coupling handle while the electron-withdrawing nitro and nitrile moieties stabilize intermediates and direct regioselective transformations under standard conditions.

Application

4-Iodo-3-nitrobenzonitrile serves as a versatile building block in cross-coupling chemistry, enabling efficient access to biaryl scaffolds via Pd-catalyzed reactions. The iodine group facilitates reliable coupling under standard conditions, while the nitro and nitrile functionalities offer orthogonal reactivity for downstream transformations. Its bench-stable nature and compatibility with diverse reaction environments support streamlined synthesis of complex heterocycles and functionalized aromatic systems.

Synthesis

  • Route1

    References

    • Sapountzis, Ioannis; Dube, Henry; Lewis, Robert; Gommermann, Nina; Knochel, Paul Journal of Organic Chemistry, 2005 , vol. 70, # 7 p. 2445 - 2454
  • Route2

    References

    • Bioorganic and Medicinal Chemistry Letters, , vol. 21, # 22 p. 6842 - 6851

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

Quality Control

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Computational Chemistry Data

  • TPSA   66.93
  • LogP   2.07108
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   1

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