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9-Phenanthryl iodide

  • CAS No. 17024-12-3

  • Cat. No. CS-0098534
  • Purity≥97%
  • MDL No.None

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

9-Phenanthryl iodide|CS-0098534

Structure of 17024-12-3

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General Information

  • CAS No. 17024-12-3
  • Cat. No. CS-0098534
  • Purity ≥97%
  • MDL No. None
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₄H₉I
  • Molecular Weight 304.13
  • Synonym(s) Phenanthrene, 9-iodo-
  • SMILES IC1=CC2=CC=CC=C2C3=CC=CC=C31

Description

9-Phenanthryl iodide serves as a highly reactive aryl iodide handle for transition-metal-catalyzed cross-coupling reactions. The phenanthryl scaffold imparts enhanced stability and solubility, while the iodine moiety enables efficient coupling under standard conditions. This compound integrates readily into complex molecular architectures.

Application

9-Phenanthryl iodide serves as a versatile aryl halide building block in transition-metal-catalyzed coupling reactions, enabling efficient C–C bond formation via palladium- or nickel-mediated cross-coupling. Its rigid, polycyclic structure imparts excellent stability and predictable reactivity, facilitating the synthesis of conjugated biaryls and functionalized phenanthrene derivatives with high regiocontrol. The iodide moiety offers superior reactivity compared to bromides or chlorides, enabling mild reaction conditions and broad functional group tolerance. This compound is particularly valuable for constructing advanced scaffolds in materials chemistry and medicinal research.

Synthesis

  • Route1

    References

    • Stark, Tina; Suhartono, Marcel; Goebel, Michael W.; Lautens, Mark Synlett, 2013 , vol. 24, # 20 art. no. ST-2013-S0604-L, p. 2730 - 2734
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    • In-stock
      9-Phenanthryl iodide|CS-0098534
      17024-12-3

    References

    • Chemische Berichte, , vol. 61, p. 270

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H315-H319-H335
Precautionary Statements : P261-P264-P271-P280-P302+P352-P304+P340-P362-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   0
  • LogP   4.5976
  • H_Acceptors   0
  • H_Donors   0
  • Rotatable_Bonds   0

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