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CS-W001157 4
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2-Hexyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

  • CAS No. 86308-26-1

  • Cat. No. CS-0139357
  • Purity≥97%
  • MDL No.MFCD08457665

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

2-Hexyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane|CS-0139357

Structure of 86308-26-1

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General Information

  • CAS No. 86308-26-1
  • Cat. No. CS-0139357
  • Purity ≥97%
  • MDL No. MFCD08457665
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₂H₂₅BO₂
  • Molecular Weight 212.14
  • Synonym(s) None
  • SMILES CC1(C)C(C)(C)OB(CCCCCC)O1

Description

2-Hexyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane offers enhanced stability and solubility in organic media, enabling efficient Suzuki-Miyaura coupling reactions. The bulky tetramethyl substitution minimizes protodeboronation, while the hexyl chain improves compatibility with nonpolar solvents. This boronate ester delivers reliable performance under standard conditions.

Application

2-Hexyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane serves as a stable, bench-ready boron reagent for Suzuki-Miyaura cross-coupling reactions. Its sterically protected dioxaborolane ring enhances shelf life and minimizes protodeboronation, while the hexyl group provides solubility in organic media. Functions reliably in diverse coupling protocols with aryl, heteroaryl, and vinyl halides, enabling efficient C–C bond formation under standard conditions.

Synthesis

  • Route1
    • null|null
      592-41-6
    • null|null
      25015-63-8
    • ~94%
    • In-stock
      2-Hexyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane|CS-0139357
      86308-26-1

    References

    • Zhu, Yinghuai; Jang, Shi Hui Agnes; Tham, Yue Hao; Algin, Oh Biying; Maguire, John A.; Hosmane, Narayan S. Organometallics, 2012 , vol. 31, # 7 p. 2589 - 2596
  • Route2
    • null|null
      111-25-1
    • In-stock
      Bis(pinacolato)diborane|CS-D1216
      73183-34-3
    • ~89%
    • In-stock
      2-Hexyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane|CS-0139357
      86308-26-1

    References

    • Yang, Chu-Ting; Zhang, Zhen-Qi; Tajuddin, Hazmi; Wu, Chen-Cheng; Liang, Jun; Liu, Jing-Hui; Fu, Yao; Czyzewska, Maria; Steel, Patrick G.; Marder, Todd B.; Liu, Lei Angewandte Chemie - International Edition, 2012 , vol. 51, # 2 p. 528 - 532
  • Route3
    • null|null
      592-41-6
    • In-stock
      Bis(pinacolato)diborane|CS-D1216
      73183-34-3
    • ~96%
    • In-stock
      2-Hexyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane|CS-0139357
      86308-26-1

    References

    • Cano, Rafael; Ramon, Diego J.; Yus, Miguel Journal of Organic Chemistry, 2010 , vol. 75, # 10 p. 3458 - 3460

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   18.46
  • LogP   3.6589
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   5

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