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CS-W001157 4
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2-(9,9-Dioctyl-9H-fluoren-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

  • CAS No. 302554-81-0

  • Cat. No. CS-0152269
  • Purity≥97%
  • MDL No.None

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

2-(9,9-Dioctyl-9H-fluoren-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane|CS-0152269

Structure of 302554-81-0

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General Information

  • CAS No. 302554-81-0
  • Cat. No. CS-0152269
  • Purity ≥97%
  • MDL No. None
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₃₅H₅₃BO₂
  • Molecular Weight 516.61
  • Synonym(s) 9,9-Di-n-octylfluorene-2-boronic Acid Pinacol Ester
  • SMILES CCCCCCCCC1(CCCCCCCC)C2=CC=CC=C2C3=C1C=C(C=C3)B4OC(C)(C)C(C)(C)O4

Description

This boronate ester features a fluorene core functionalized with two octyl chains, enhancing solubility in organic media. The tetramethyl-1,3,2-dioxaborolane moiety enables stable coupling under Suzuki-Miyaura conditions. Designed for efficient cross-coupling applications in complex molecular architectures.

Application

2-(9,9-Dioctyl-9H-fluoren-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane serves as a stable, bench-ready boronate building block for Suzuki-Miyaura cross-coupling reactions. Its sterically protected boronate moiety exhibits excellent functional group tolerance and compatibility with diverse aryl and vinyl halides. The fluorenyl core provides enhanced stability and solubility in organic media, facilitating purification and scalable synthesis of complex biaryl architectures.

Synthesis

  • Route1

    References

    • Wang, Yafei; Tan, Hua; Liu, Yu; Jiang, Chenxian; Hu, Zhengyong; Zhu, Meixiang; Wang, Lei; Zhu, Weiguo; Cao, Yong Tetrahedron, 2010 , vol. 66, # 7 p. 1483 - 1488
  • Route2
    • null|null
      61676-62-8
    • In-stock
      2-Bromo-9,9-di-n-octylfluorene|CS-0168390
      302554-80-9
    • ~66%
    • In-stock
      2-(9,9-Dioctyl-9H-fluoren-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane|CS-0152269
      302554-81-0

    References

    • Belletete, Michel; Beaupre, Serge; Bouchard, Jimmy; Blondin, Pierre; Leclerc, Mario; Durocher, Gilles Journal of Physical Chemistry B, 2000 , vol. 104, # 39 p. 9118 - 9125
  • Route3

    References

    • Cocherel, Nicolas; Poriel, Cyril; Rault-Berthelot, Joelle; Barriere, Frederic; Audebrand, Nathalie; Slawin, Alexandra M. Z.; Vignau, Laurence Chemistry - A European Journal, 2008 , vol. 14, # 36 p. 11328 - 11342

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   18.46
  • LogP   9.7535
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   15

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