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CS-W001157 4
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4,4,5,5-Tetramethyl-2-(2-phenylpropyl)-1,3,2-dioxaborolane

  • CAS No. 280559-30-0

  • Cat. No. CS-0174172
  • Purity≥95%
  • MDL No.None

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

4,4,5,5-Tetramethyl-2-(2-phenylpropyl)-1,3,2-dioxaborolane|CS-0174172

Structure of 280559-30-0

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General Information

  • CAS No. 280559-30-0
  • Cat. No. CS-0174172
  • Purity ≥95%
  • MDL No. None
  • Storage -20°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₅H₂₃BO₂
  • Molecular Weight 246.15
  • Synonym(s) 2-Phenyl-1-Propylboronic Acid Pinacol Ester
  • SMILES CC(C1=CC=CC=C1)CB2OC(C)(C(C)(O2)C)C

Description

This boronate ester features a sterically hindered tetramethylcyclopentadione core paired with a 2-phenylpropyl group, delivering enhanced stability and ease of handling. It integrates readily into cross-coupling reactions under standard conditions, enabling efficient access to functionalized biaryl architectures.

Application

4,4,5,5-Tetramethyl-2-(2-phenylpropyl)-1,3,2-dioxaborolane serves as a stable, bench-ready boron reagent enabling efficient Suzuki-Miyaura cross-coupling reactions. Its sterically protected dioxaborolane core enhances air and moisture stability, while the 2-phenylpropyl group provides a versatile aryl coupling handle for constructing biaryl scaffolds in medicinal chemistry and materials science. The compound exhibits excellent functional group tolerance and facilitates straightforward purification, making it ideal for iterative synthesis and high-throughput applications.

Synthesis

  • Route1
    • null|null
      25015-63-8
    • null|null
      98-83-9
    • ~93%
    • In-stock
      4,4,5,5-Tetramethyl-2-(2-phenylpropyl)-1,3,2-dioxaborolane|CS-0174172
      280559-30-0

    References

    • Reichle, Markus A.; Breit, Bernhard Angewandte Chemie - International Edition, 2012 , vol. 51, # 23 p. 5730 - 5734
  • Route2
    • In-stock
      2,3-Dimethylbutane-2,3-diol|CS-0015356
      76-09-5
    • null|null
      98-83-9
    • ~63%
    • null|null
      1085319-31-8
    • In-stock
      4,4,5,5-Tetramethyl-2-(2-phenylpropyl)-1,3,2-dioxaborolane|CS-0174172
      280559-30-0

    References

    • Karatjas, Andrew G.; Vedejs, Edwin Journal of Organic Chemistry, 2008 , vol. 73, # 23 p. 9508 - 9510
  • Route3
    • In-stock
      Bis(pinacolato)diborane|CS-D1216
      73183-34-3
    • null|null
      98-83-9
    • ~85%
    • In-stock
      4,4,5,5-Tetramethyl-2-(2-phenylpropyl)-1,3,2-dioxaborolane|CS-0174172
      280559-30-0

    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-H312-H332
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362+P364-P501

Quality Control

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Computational Chemistry Data

  • TPSA   18.46
  • LogP   3.8823
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   3

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