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CS-W001157 4
Total: USD 88.00

2-(2,5-Dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

  • CAS No. 356570-53-1

  • Cat. No. CS-0189089
  • Purity≥96%
  • MDL No.None

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

2-(2,5-Dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane|CS-0189089

Structure of 356570-53-1

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General Information

  • CAS No. 356570-53-1
  • Cat. No. CS-0189089
  • Purity ≥96%
  • MDL No. None
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₄H₂₁BO₂
  • Molecular Weight 232.13
  • Synonym(s) 2-(2,5-Dimethyl-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane
  • SMILES CC1(C)C(C)(C)OB(C2=CC(C)=CC=C2C)O1

Description

This boronate ester features a sterically shielded tetramethyl-1,3,2-dioxaborolane ring paired with a 2,5-dimethylphenyl group, delivering enhanced stability and reactivity in cross-coupling transformations. The electron-rich aryl moiety enables efficient palladium-catalyzed coupling under standard conditions, while the bulky substituents minimize protodeboronation and side reactions. Ideal for constructing complex biaryl architectures with high functional group tolerance.

Application

2-(2,5-Dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane serves as a stable, bench-ready boron building block for Suzuki-Miyaura cross-coupling reactions. Its sterically shielded dioxaborolane ring enhances air and moisture tolerance, enabling reliable coupling with aryl halides and triflates under standard conditions. The 2,5-dimethylphenyl group provides a robust, electron-rich aryl handle suitable for constructing complex biaryl scaffolds in medicinal chemistry and materials science applications.

Synthesis

  • Route1
    • 2-Chloro-1,4-dimethylbenzene|CS-W016448
      95-72-7
    • In-stock
      Bis(pinacolato)diborane|CS-D1216
      73183-34-3
    • ~87%
    • In-stock
      2-(2,5-Dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane|CS-0189089
      356570-53-1

    References

    • Billingsley, Kelvin L.; Barder, Timothy E.; Buchwald, Stephen L. Angewandte Chemie - International Edition, 2007 , vol. 46, # 28 p. 5359 - 5363
  • Route2
    • null|null
      106-42-3
    • In-stock
      Bis(pinacolato)diborane|CS-D1216
      73183-34-3
    • ~64%
    • In-stock
      2-(2,5-Dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane|CS-0189089
      356570-53-1

    References

    • Yan, Guobing; Jiang, Yubo; Kuang, Chunxiang; Wang, Shuai; Liu, Haichao; Zhang, Yan; Wang, Jianbo Chemical Communications, 2010 , vol. 46, # 18 p. 3170 - 3172
  • Route3
    • null|null
      61676-62-8
    • In-stock
      2,5-Dimethylbromobenzene|CS-W016967
      553-94-6
    • ~91%
    • In-stock
      2-(2,5-Dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane|CS-0189089
      356570-53-1

    References

    • Jin, Sung-Ho; Jeong, Hwan-Hee; Hwang, Chan-Koo; Moon, Seong-Bae; Lee, Jae Wook; Hwang, Jin-Taek; Gal, Yeong-Soon; Lee, Jin-Kook Molecular Crystals and Liquid Crystals, 2006 , vol. 444, p. 1 - 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 : 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   2.60264
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   1

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