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2,6-Difluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid

  • CAS No. 1008119-07-0

  • Cat. No. CS-0041162
  • Purity≥97%
  • MDL No.MFCD16996277

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

2,6-Difluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid|CS-0041162

Structure of 1008119-07-0

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General Information

  • CAS No. 1008119-07-0
  • Cat. No. CS-0041162
  • Purity ≥97%
  • MDL No. MFCD16996277
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₃H₁₅BF₂O₄
  • Molecular Weight 284.06
  • Synonym(s) benzoic acid,2,6-difluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)
  • SMILES O=C(O)C1=C(F)C=C(B2OC(C)(C)C(C)(C)O2)C=C1F

Description

This boronic acid ester features a difluorinated aryl core paired with a tetramethyl-1,3,2-dioxaborolane handle, enabling reliable Suzuki-Miyaura cross-coupling under standard conditions. The carboxylic acid group provides a polar anchor for downstream conjugation and enhances solubility in aqueous-organic mixtures.

Application

2,6-Difluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid serves as a versatile boronate building block for Suzuki-Miyaura cross-coupling reactions. The difluorophenyl moiety enhances metabolic stability and modulates electronic properties, while the pinacol boronate group ensures excellent bench stability and compatibility with a broad range of reaction conditions. This reagent facilitates efficient construction of substituted biaryl scaffolds in medicinal chemistry and materials science applications.

Synthesis

  • Route1

    References

    • Bristol-Myers Squibb Company Patent: US2009/75995 A1, 2009 ; Location in patent: Page/Page column 67 ;

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   55.76
  • LogP   1.9622
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   2

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