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CS-W001157 4
Total: USD 88.00

1-Ethynyl-4-iodobenzene

  • CAS No. 766-99-4

  • Cat. No. CS-0148277
  • Molecule weight228.03
  • Purity≥95%
  • MDL No.None

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

1-Ethynyl-4-iodobenzene|CS-0148277

Structure of 766-99-4

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General Information

  • CAS No. 766-99-4
  • Cat. No. CS-0148277
  • Purity ≥95%
  • MDL No. None
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₅I
  • Molecular Weight 228.03
  • Synonym(s) 1-iodo-4-ethynylbenzene
  • SMILES IC1=CC=C(C#C)C=C1

Description

1-Ethynyl-4-iodobenzene serves as a key building block in transition-metal-catalyzed coupling reactions, featuring a terminal alkyne and iodide handle for efficient C–C and C–heteroatom bond formation. This bench-stable, moisture-tolerant aryl-iodide integrates seamlessly into Sonogashira and Suzuki-Miyaura protocols, enabling rapid access to conjugated biaryls and functionalized alkynes under standard conditions.

Application

1-Ethynyl-4-iodobenzene serves as a versatile building block in transition-metal-catalyzed cross-coupling reactions, particularly in Sonogashira and Suzuki-Miyaura protocols. The terminal alkyne functionality enables efficient C–C bond formation, while the iodide group provides high reactivity in palladium-catalyzed coupling processes. Its bench-stable nature and compatibility with diverse functional groups make it ideal for constructing complex aryl-alkynyl architectures in medicinal chemistry and materials science applications.

Synthesis

  • Route1

    References

    • Aakeroey, Christer B.; Baldrighi, Michele; Desper, John; Metrangolo, Pierangelo; Resnati, Giuseppe Chemistry - A European Journal, 2013 , vol. 19, # 48 p. 16240 - 16247
  • Route2
    • null|null
      90965-06-3
    • In-stock
      4-Iodobenzaldehyde|CS-W002179
      15164-44-0
    • ~93%
    • In-stock
      1-Ethynyl-4-iodobenzene|CS-0148277
      766-99-4

    References

    • MacHin, Ben P.; Pagenkopf, Brian L. Synlett, 2011 , # 19 art. no. S07111ST, p. 2799 - 2802
  • Route3
    • null|null
      116815-00-0
    • ~82%
    • In-stock
      1-Ethynyl-4-iodobenzene|CS-0148277
      766-99-4

    References

    • Goeb, Sebastien; Ziessel, Raymond Tetrahedron Letters, 2008 , vol. 49, # 16 p. 2569 - 2574

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

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Computational Chemistry Data

  • TPSA   0
  • LogP   2.2725
  • H_Acceptors   0
  • H_Donors   0
  • Rotatable_Bonds   0

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