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2,2'-(1,2-Phenylene)bis[4,4,5,5-tetramethyl-1,3,2-dioxaborolane]

  • CAS No. 269410-07-3

  • Cat. No. CS-B1278
  • Purity≥95%
  • MDL No.MFCD28969469

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

2,2'-(1,2-Phenylene)bis[4,4,5,5-tetramethyl-1,3,2-dioxaborolane]|CS-B1278

Structure of 269410-07-3

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General Information

  • CAS No. 269410-07-3
  • Cat. No. CS-B1278
  • Purity ≥95%
  • MDL No. MFCD28969469
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₈H₂₈B₂O₄
  • Molecular Weight 330.04
  • Synonym(s) 1,2-Phenylenebis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)
  • SMILES CC1(C)C(C)(C)OB(C2=CC=CC=C2B3OC(C)(C)C(C)(C)O3)O1

Description

This boronate reagent features a rigid phenylene bridge linking two tetramethyl-dioxaborolane units, enabling efficient Suzuki-Miyaura coupling. The structure enhances stability and solubility in organic solvents while maintaining high reactivity under standard conditions.

Application

2,2'-(1,2-Phenylene)bis[4,4,5,5-tetramethyl-1,3,2-dioxaborolane] serves as a versatile bis-boronic ester building block for the construction of biaryl scaffolds via palladium-catalyzed cross-coupling reactions. Its ortho-substituted phenylene linkage enables precise spatial control in conjugated systems, while the tetramethyl-substituted dioxaborolane moieties offer enhanced stability, ease of handling, and compatibility with diverse reaction conditions. Ideal for iterative coupling strategies and functional group-tolerant syntheses in medicinal chemistry and materials science applications.

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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