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CS-W001157 4
Total: USD 88.00

4,4,5,5-Tetramethyl-2-(4-methyl-1-cyclohexen-1-yl)-1,3,2-dioxaborolane

  • CAS No. 865869-26-7

  • Cat. No. CS-0055060
  • Purity≥95%
  • MDL No.None

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

4,4,5,5-Tetramethyl-2-(4-methyl-1-cyclohexen-1-yl)-1,3,2-dioxaborolane|CS-0055060

Structure of 865869-26-7

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General Information

  • CAS No. 865869-26-7
  • Cat. No. CS-0055060
  • Purity ≥95%
  • MDL No. None
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₃H₂₃BO₂
  • Molecular Weight 222.13
  • Synonym(s) 4-Methylcyclohexene-1-boronic Acid Pinacol Ester
  • SMILES CC1CCC(=CC1)B1OC(C)(C)C(C)(C)O1

Description

This boronate ester features a sterically hindered tetramethylcyclopentadione core paired with a conjugated cyclohexenyl group, enabling robust coupling in Suzuki-Miyaura reactions. The electron-rich boronate moiety enhances reactivity while maintaining bench-stable handling under standard conditions.

Application

4,4,5,5-Tetramethyl-2-(4-methyl-1-cyclohexen-1-yl)-1,3,2-dioxaborolane serves as a stable, bench-friendly boronate building block for palladium-catalyzed cross-coupling reactions. Its cyclohexenyl moiety enables efficient incorporation into complex molecular frameworks, while the tetramethyl-substituted dioxaborolane core ensures high chemical stability and predictable reactivity in Suzuki-Miyaura coupling protocols. The product facilitates rapid assembly of functionalized cyclic scaffolds with excellent functional group tolerance and ease of purification.

Synthesis

  • Route1
    • null|null
      119472-66-1
    • In-stock
      Bis(pinacolato)diborane|CS-D1216
      73183-34-3
    • ~%
    • In-stock
      4,4,5,5-Tetramethyl-2-(4-methyl-1-cyclohexen-1-yl)-1,3,2-dioxaborolane|CS-0055060
      865869-26-7

    References

    • WO2005/92863 A1, ; Page/Page column 65 ;
  • Route2
    • null|null
      589-92-4
    • ~%
    • In-stock
      4,4,5,5-Tetramethyl-2-(4-methyl-1-cyclohexen-1-yl)-1,3,2-dioxaborolane|CS-0055060
      865869-26-7

    References

    • WO2011/32277 A1, ; WO 2011/032277 A1
  • Route3
    • null|null
      108-94-1
    • ~%
    • In-stock
      4,4,5,5-Tetramethyl-2-(4-methyl-1-cyclohexen-1-yl)-1,3,2-dioxaborolane|CS-0055060
      865869-26-7

    References

    • WO2012/83105 A1, ; WO 2012/083105 A1

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   3.3642
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   1

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