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CS-W001157 4
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4,4,5,5-Tetramethyl-2-propyl-1,3,2-dioxaborolane

  • CAS No. 67562-19-0

  • Cat. No. CS-0175902
  • Purity≥98%
  • MDL No.MFCD12546187

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

4,4,5,5-Tetramethyl-2-propyl-1,3,2-dioxaborolane|CS-0175902

Structure of 67562-19-0

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General Information

  • CAS No. 67562-19-0
  • Cat. No. CS-0175902
  • Purity ≥98%
  • MDL No. MFCD12546187
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₁₉BO₂
  • Molecular Weight 170.06
  • Synonym(s) n-Propyl boronic acid pinacol
  • SMILES CCCB1OC(C)(C(C)(O1)C)C

Description

4,4,5,5-Tetramethyl-2-propyl-1,3,2-dioxaborolane is a bench-stable boronate reagent featuring a sterically protected boronate moiety and a propyl substituent that enhances solubility in organic solvents. This structure enables efficient coupling in Suzuki-Miyaura reactions under mild conditions, offering reliable performance in complex molecule synthesis.

Application

4,4,5,5-Tetramethyl-2-propyl-1,3,2-dioxaborolane serves as a stable, bench-ready boron building block for Suzuki-Miyaura cross-coupling reactions. Its sterically hindered dioxaborolane core enhances hydrolytic stability and functional group tolerance, enabling reliable coupling with aryl, vinyl, and heteroaryl halides under standard conditions. The propyl substituent improves solubility in organic media, facilitating purification and scalability in complex molecule synthesis.

Synthesis

  • Route1
    • null|null
      590-13-6
    • null|null
      25015-63-8
    • ~82%
    • In-stock
      4,4,5,5-Tetramethyl-2-propyl-1,3,2-dioxaborolane|CS-0175902
      67562-19-0

    References

    • Colin, Sylvie; Vaysse-Ludot, Lucile; Lecouve, Jean-Pierre; Maddaluno, Jacques Journal of the Chemical Society, Perkin Transactions 1, 2000 , # 24 p. 4505 - 4511
  • Route2
    • null|null
      108-86-1
    • In-stock
      2-(3-Bromopropyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane|CS-0174363
      124215-44-7
    • ~0%
    • null|null
      92-52-4
    • In-stock
      4,4,5,5-Tetramethyl-2-propyl-1,3,2-dioxaborolane|CS-0175902
      67562-19-0
    • null|null
      1361022-63-0
    • In-stock
      4,4,5,5-Tetramethyl-2-(3-phenylpropyl)-1,3,2-dioxaborolane|CS-0174530
      329685-40-7
    • null|null
      71-43-2

    References

    • Everson, Daniel A.; Jones, Brittany A.; Weix, Daniel J. Journal of the American Chemical Society, 2012 , vol. 134, # 14 p. 6146 - 6159
  • Route3
    • 4,4,5,5-Tetramethyl-2-(prop-1-yn-1-yl)-1,3,2-dioxaborolane|CS-0175345
      347389-75-7
    • ~%
    • In-stock
      4,4,5,5-Tetramethyl-2-propyl-1,3,2-dioxaborolane|CS-0175902
      67562-19-0

    References

    • Roseblade, Stephen J.; Smilovic, Ivana Gazic; Casar, Zdenko Tetrahedron, 2014 , vol. 70, # 16 p. 2654 - 2660

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS02
Signal Word : Danger
UN#: 3272
Class : 3
Packing Group : Ⅲ
Hazard Statements : H225
Precautionary Statements : P210-P233-P240-P241-P242-P243-P280-P370+P378-P501

Quality Control

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Computational Chemistry Data

  • TPSA   18.46
  • LogP   2.4886
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   2

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