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

  • CAS No. 253342-48-2

  • Cat. No. CS-0094693
  • Purity≥97%
  • MDL No.MFCD05864303

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

4,4,5,5-Tetramethyl-2-(m-tolyl)-1,3,2-dioxaborolane|CS-0094693

Structure of 253342-48-2

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General Information

  • CAS No. 253342-48-2
  • Cat. No. CS-0094693
  • Purity ≥97%
  • MDL No. MFCD05864303
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₃H₁₉BO₂
  • Molecular Weight 218.10
  • Synonym(s) m-Tolylboronic Acid Pinacol Ester
  • SMILES CC1=CC(B2OC(C)(C)C(C)(C)O2)=CC=C1

Description

This boronate ester features a sterically protected tetramethylcyclopentadione core paired with an m-tolyl group, delivering enhanced stability and reactivity in Suzuki-Miyaura cross-coupling. The electron-rich boron center enables efficient palladium-catalyzed transformations under mild conditions, while the bulky substituents minimize protodeboronation and side reactions.

Application

4,4,5,5-Tetramethyl-2-(m-tolyl)-1,3,2-dioxaborolane serves as a stable, bench-ready boron reagent for Suzuki-Miyaura cross-coupling reactions. Its sterically hindered dioxaborolane ring enhances shelf stability and minimizes protodeboronation, while the m-tolyl group provides a well-defined aryl coupling partner. The compound exhibits excellent functional group tolerance and facilitates efficient C–C bond formation under mild reaction conditions, making it a reliable building block in medicinal chemistry and materials synthesis workflows.

Synthesis

  • Route1
    • null|null
      591-17-3
    • null|null
      25015-63-8
    • ~98%
    • In-stock
      4,4,5,5-Tetramethyl-2-(m-tolyl)-1,3,2-dioxaborolane|CS-0094693
      253342-48-2

    References

    • THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; CLARY, Jacob, W.; SINGARAM, Bakthan Patent: WO2013/16185 A1, 2013 ; Location in patent: Paragraph 0075; 0077 ;
  • Route2
    • null|null
      28987-79-3
    • null|null
      25015-63-8
    • ~80%
    • In-stock
      4,4,5,5-Tetramethyl-2-(m-tolyl)-1,3,2-dioxaborolane|CS-0094693
      253342-48-2

    References

    • THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; CLARY, Jacob, W.; SINGARAM, Bakthan Patent: WO2013/16185 A1, 2013 ; Location in patent: Paragraph 0062; 0065 ;
  • Route3
    • null|null
      74497-02-2
    • In-stock
      2-(3-Chloro-5-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane|CS-0368938
      502630-89-9
    • ~17%
    • null|null
      651014-84-5
    • In-stock
      4,4,5,5-Tetramethyl-2-(m-tolyl)-1,3,2-dioxaborolane|CS-0094693
      253342-48-2

    References

    • US2004/24237 A1, ; Page 7-11 ;

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H315-H319-H335
Precautionary Statements : P261-P264-P271-P280-P302+P352-P304+P340-P362+P364-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   18.46
  • LogP   2.29422
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   1

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