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CS-W001157 4
Total: USD 88.00

1-Fluoro-2-vinylbenzene

  • CAS No. 394-46-7

  • Cat. No. CS-W016578
  • Purity≥98%
  • MDL No.MFCD00013550

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

1-Fluoro-2-vinylbenzene|CS-W016578

Structure of 394-46-7

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General Information

  • CAS No. 394-46-7
  • Cat. No. CS-W016578
  • Purity ≥98%
  • MDL No. MFCD00013550
  • Storage -20°C, sealed storage, away from moisture
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₇F
  • Molecular Weight None
  • Synonym(s) Benzene, 1-ethenyl-2-fluoro-
  • SMILES C=CC1=CC=CC=C1F

Description

1-Fluoro-2-vinylbenzene features a conjugated vinyl group adjacent to a fluorinated aromatic ring, enabling efficient coupling in palladium-catalyzed cross-coupling reactions. The electron-withdrawing fluorine stabilizes the intermediate aryl radical, enhancing reactivity in cascade cyclizations and functionalization sequences. This bench-stable, moisture-tolerant reagent integrates seamlessly into synthetic pathways requiring selective C–C bond formation under mild conditions.

Application

1-Fluoro-2-vinylbenzene serves as a versatile building block for transition-metal-catalyzed cross-coupling reactions, enabling the efficient construction of biaryl and styrenyl architectures. The vinyl group facilitates Heck and Suzuki-Miyaura couplings, while the ortho-fluorine supports directed functionalization and palladium-catalyzed C–H activation. Its bench-stable nature and compatibility with diverse reaction conditions make it a practical choice for synthesizing complex aromatic scaffolds in medicinal chemistry and materials science applications.

Synthesis

  • Route1

    References

    • Solomon,I.J.; Filler,R. Journal of the American Chemical Society, 1963 , vol. 85, p. 3492 - 3496
  • Route2
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      54509-73-8
    • In-stock
      1-Fluoro-2-iodobenzene|CS-D1738
      348-52-7
    • ~%
    • In-stock
      1-Fluoro-2-vinylbenzene|CS-W016578
      394-46-7

    References

    • Bourne, Samuel L.; O'Brien, Matthew; Kasinathan, Sivarajan; Koos, Peter; Tolstoy, Paeivi; Hu, Dennis X.; Bates, Roderick W.; Martin, Benjamin; Schenkel, Berthold; Ley, Steven V. ChemCatChem, 2013 , vol. 5, # 1 p. 159 - 172
  • Route3

    References

    • Redeuilh,G. et al. Bulletin de la Societe Chimique de France, 1973 , p. 2667 - 2668

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS02
Signal Word : Warning
UN#: 1993
Class : 3
Packing Group : Ⅲ
Hazard Statements : H226
Precautionary Statements : P210-P233-P240-P241-P242-P243-P280-P370+P378-P501

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Computational Chemistry Data

  • TPSA   0
  • LogP   2.4687
  • H_Acceptors   0
  • H_Donors   0
  • Rotatable_Bonds   1

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