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CS-W001157 4
Total: USD 88.00

1,3,5-Triiodobenzene

  • CAS No. 626-44-8

  • Cat. No. CS-W005324
  • Purity≥97%
  • MDL No.MFCD02690052

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

1,3,5-Triiodobenzene|CS-W005324

Structure of 626-44-8

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General Information

  • CAS No. 626-44-8
  • Cat. No. CS-W005324
  • Purity ≥97%
  • MDL No. MFCD02690052
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₃I₃
  • Molecular Weight 455.80
  • Synonym(s) 5-Triiodobenzene
  • SMILES IC1=CC(I)=CC(I)=C1

Description

1,3,5-Triiodobenzene serves as a highly iodinated aromatic scaffold for constructing complex molecular architectures. This electron-deficient benzene derivative features three iodine atoms positioned at the 1,3,5-axial sites, enabling selective cross-coupling reactions under mild conditions. The molecule exhibits enhanced stability and solubility in organic media, facilitating its use in palladium-catalyzed transformations and materials synthesis.

Application

1,3,5-Triiodobenzene serves as a versatile building block in transition-metal-catalyzed cross-coupling reactions, enabling the efficient construction of complex aromatic architectures. Its three iodine substituents provide orthogonal reactivity for sequential functionalization, facilitating the synthesis of multi-substituted arenes and heterocyclic scaffolds. The compound exhibits excellent bench stability and is compatible with standard palladium-catalyzed coupling protocols, offering predictable regioselectivity and straightforward purification.

Synthesis

  • Route1

    References

    • Schoeberl, Ulrich; Magnera, Thomas F.; Harrison, Robin M.; Fleischer, Frank; Pflug, Jodi L.; Schwab, Peter F. H.; Meng, Xiangsheng; Lipiak, Dariusz; Noll, Bruce C.; Allured, Viloya S.; Rudalevige, Trevor; Lee, Stephen; Michl, Josef Journal of the American Chemical Society, 1997 , vol. 119, # 17 p. 3907 - 3917
  • Route2
    • 1,3,5-Tris(trimethylsilyl)benzene|CS-0213752
      5624-60-2
    • ~94%
    • In-stock
      1,3,5-Triiodobenzene|CS-W005324
      626-44-8

    References

    • Banno, Motonori; Yamaguchi, Tomoko; Nagai, Kanji; Kaiser, Christian; Hecht, Stefan; Yashima, Eiji Journal of the American Chemical Society, 2012 , vol. 134, # 20 p. 8718 - 8728
  • Route3

    References

    • Vatsadze; Titanyuk; Chernikov; Zyk Russian Chemical Bulletin, 2004 , vol. 53, # 2 p. 471 - 473

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   0
  • LogP   3.5004
  • H_Acceptors   0
  • H_Donors   0
  • Rotatable_Bonds   0

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