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

  • CAS No. 143825-84-7

  • Cat. No. CS-0099710
  • Molecule weight230.11
  • Purity≥95%
  • MDL No.MFCD06659923

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

4,4,5,5-Tetramethyl-2-(1-phenylvinyl)-1,3,2-dioxaborolane|CS-0099710

Structure of 143825-84-7

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General Information

  • CAS No. 143825-84-7
  • Cat. No. CS-0099710
  • Purity ≥95%
  • MDL No. MFCD06659923
  • Storage -20°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₄H₁₉BO₂
  • Molecular Weight 230.11
  • Synonym(s) PHENYLVINYLBORONICacidPINACOLESTER
  • SMILES C=C(B1OC(C)(C)C(C)(C)O1)C2=CC=CC=C2

Description

This boronate ester features a phenylvinyl substituent flanked by two tetramethyl groups, enhancing stability and solubility. The dioxaborolane ring enables efficient Suzuki-Miyaura coupling under mild conditions, delivering robust cross-coupling outcomes in complex molecule synthesis.

Application

4,4,5,5-Tetramethyl-2-(1-phenylvinyl)-1,3,2-dioxaborolane serves as a stable, bench-ready boronate building block for Suzuki-Miyaura cross-coupling reactions. Its vinyl boronate functionality enables efficient coupling with aryl and heteroaryl halides under mild conditions, facilitating the construction of styrenyl-linked biaryls and conjugated systems. The tetramethyl-substituted dioxaborolane core enhances stability and simplifies purification, making it well-suited for iterative synthesis and late-stage functionalization in medicinal chemistry workflows.

Synthesis

  • Route1
    • null|null
      98-81-7
    • In-stock
      Bis(pinacolato)diborane|CS-D1216
      73183-34-3
    • ~89%
    • In-stock
      4,4,5,5-Tetramethyl-2-(1-phenylvinyl)-1,3,2-dioxaborolane|CS-0099710
      143825-84-7

    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
      28143-79-5
    • In-stock
      Bis(pinacolato)diborane|CS-D1216
      73183-34-3
    • ~99%
    • In-stock
      4,4,5,5-Tetramethyl-2-(1-phenylvinyl)-1,3,2-dioxaborolane|CS-0099710
      143825-84-7

    References

    • Takagi, Jun; Takahashi, Kou; Ishiyama, Tatsuo; Miyaura, Norio Journal of the American Chemical Society, 2002 , vol. 124, # 27 p. 8001 - 8006
  • Route3

    References

    • Jang, Hwanjong; Zhugralin, Adil R.; Lee, Yunmi; Hoveyda, Amir H. Journal of the American Chemical Society, 2011 , vol. 133, # 20 p. 7859 - 7871

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   3.3312
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   2

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