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CS-W001157 4
Total: USD 88.00

4,4,5,5-Tetramethyl-2-(2-methylprop-1-en-1-yl)-1,3,2-dioxaborolane

  • CAS No. 126689-00-7

  • Cat. No. CS-W003667
  • Purity≥98%
  • MDL No.MFCD09842762

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

4,4,5,5-Tetramethyl-2-(2-methylprop-1-en-1-yl)-1,3,2-dioxaborolane|CS-W003667

Structure of 126689-00-7

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General Information

  • CAS No. 126689-00-7
  • Cat. No. CS-W003667
  • Purity ≥98%
  • MDL No. MFCD09842762
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₀H₁₉BO₂
  • Molecular Weight 182.07
  • Synonym(s) (2-Methyl-1-propenyl)boronic Acid Pinacol Ester
  • SMILES CC(=CB1OC(C(O1)(C)C)(C)C)C

Description

This boronate ester features a sterically hindered tetramethylcyclopentadienyl core paired with a branched allylic substituent, delivering enhanced stability and compatibility in Suzuki-Miyaura cross-coupling reactions. The bulky methyl groups suppress protodeboronation, while the 2-methylprop-1-en-1-yl moiety enables efficient coupling under mild conditions.

Application

4,4,5,5-Tetramethyl-2-(2-methylprop-1-en-1-yl)-1,3,2-dioxaborolane serves as a stable, bench-ready boron reagent for palladium-catalyzed cross-coupling reactions. Its sterically protected boronate moiety enables high functional group tolerance and reliable coupling with aryl, vinyl, and heteroaryl halides. The pendant isobutenyl group enhances solubility and facilitates purification, making it well-suited for iterative synthesis and late-stage functionalization in medicinal chemistry workflows.

Synthesis

  • Route1
    • null|null
      3017-69-4
    • In-stock
      Bis(pinacolato)diborane|CS-D1216
      73183-34-3
    • ~58%
    • In-stock
      4,4,5,5-Tetramethyl-2-(2-methylprop-1-en-1-yl)-1,3,2-dioxaborolane|CS-W003667
      126689-00-7

    References

    • Takagi, Jun; Takahashi, Kou; Ishiyama, Tatsuo; Miyaura, Norio Journal of the American Chemical Society, 2002 , vol. 124, # 27 p. 8001 - 8006
  • Route2
    • null|null
      3017-69-4
    • null|null
      25015-63-8
    • ~%
    • In-stock
      4,4,5,5-Tetramethyl-2-(2-methylprop-1-en-1-yl)-1,3,2-dioxaborolane|CS-W003667
      126689-00-7

    References

    • Bioorganic and Medicinal Chemistry, , vol. 20, # 14 p. 4582 - 4589
  • Route3
    • null|null
      84224-48-6
    • In-stock
      Bis(pinacolato)diborane|CS-D1216
      73183-34-3
    • ~82%
    • In-stock
      4,4,5,5-Tetramethyl-2-(2-methylprop-1-en-1-yl)-1,3,2-dioxaborolane|CS-W003667
      126689-00-7

    References

    • Saadi, Jakub; Bruedgam, Irene; Reissig, Hans-Ulrich Beilstein Journal of Organic Chemistry, 2010 , vol. 6, p. 1229 - 1245

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   2.584
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   1

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