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Methyl 4-[4-(tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]benzoate

  • CAS No. 1381957-27-2

  • Cat. No. CS-0146250
  • Purity≥95%
  • MDL No.None

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

Methyl 4-[4-(tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]benzoate|CS-0146250

Structure of 1381957-27-2

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General Information

  • CAS No. 1381957-27-2
  • Cat. No. CS-0146250
  • Purity ≥95%
  • MDL No. None
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₂₀H₂₃BO₄
  • Molecular Weight 338.21
  • Synonym(s) METHYL 4-[4-(TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PHENYL]BENZ 1G
  • SMILES O=C(OC)C1=CC=C(C2=CC=C(B3OC(C)(C)C(C)(C)O3)C=C2)C=C1

Description

Methyl 4-[4-(tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]benzoate features a boronate ester group that enables reliable Suzuki-Miyaura cross-coupling under mild conditions. The tetramethylcycloborane moiety ensures high stability and moisture tolerance, while the methyl benzoate functionality provides solubility in common organic solvents. This compound serves as a key building block for conjugated aryl systems in pharmaceutical and materials synthesis.

Application

Methyl 4-[4-(tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]benzoate serves as a versatile boron-containing building block for Suzuki-Miyaura cross-coupling reactions. The tetramethylboronate group enables efficient coupling with aryl halides and pseudohalides under mild conditions, offering excellent functional group tolerance and bench stability. This reagent facilitates the construction of biaryl scaffolds commonly found in pharmaceutical intermediates and materials chemistry, with straightforward purification and compatibility across scale-up workflows.

Safety Information

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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   44.76
  • LogP   3.4394
  • H_Acceptors   4
  • H_Donors   0
  • Rotatable_Bonds   3

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