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CS-W001157 4
Total: USD 88.00

1,3-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene

  • CAS No. 196212-27-8

  • Cat. No. CS-W000894
  • Purity≥95%
  • MDL No.MFCD09864185

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

1,3-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene|CS-W000894

Structure of 196212-27-8

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General Information

  • CAS No. 196212-27-8
  • Cat. No. CS-W000894
  • Purity ≥95%
  • MDL No. MFCD09864185
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₈H₂₈B₂O₄
  • Molecular Weight 330.04
  • Synonym(s) 4,4,5,5-tetramethyl-2-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1,3,2-dioxaborolane
  • SMILES CC1(C)OB(OC1(C)C)c1cccc(c1)B1OC(C(O1)(C)C)(C)C

Description

This boronate-functionalized benzene derivative features two tetramethyl-1,3,2-dioxaborolane groups at the 1,3-positions, enabling efficient Suzuki-Miyaura cross-coupling reactions. The sterically shielded dioxaborolane moieties enhance stability under ambient conditions while maintaining high reactivity in palladium-catalyzed transformations. Ideal for constructing complex biaryl architectures with precise spatial control.

Application

1,3-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene serves as a versatile bisboronate building block for Suzuki-Miyaura cross-coupling reactions. Its ortho-diboryl substitution enables efficient construction of biaryl and polyaryl architectures with high regiocontrol. The sterically protected boronate groups exhibit excellent stability under ambient conditions, facilitating handling and purification. This reagent functions reliably in diverse coupling protocols, supporting scalable synthesis of complex scaffolds relevant to pharmaceutical and materials research.

Synthesis

  • Route1

    References

    • NITTO DENKO CORPORATION Patent: US2012/226046 A1, 2012 ; Location in patent: Page/Page column 18; 19 ;
  • Route2

    References

    • Tse; Cho; Smith 3rd. Organic letters, 2001 , vol. 3, # 18 p. 2831 - 2833
  • Route3

    References

    • Journal of the American Chemical Society, , vol. 127, # 30 p. 10539 - 10544

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

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Computational Chemistry Data

  • TPSA   36.92
  • LogP   2.285
  • H_Acceptors   4
  • H_Donors   0
  • Rotatable_Bonds   2

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