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Benzoic acid, 2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-, methyl ester

  • CAS No. 955929-54-1

  • Cat. No. CS-0029505
  • Purity≥97%
  • MDL No.None

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

Benzoic acid, 2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-, methyl ester|CS-0029505

Structure of 955929-54-1

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General Information

  • CAS No. 955929-54-1
  • Cat. No. CS-0029505
  • Purity ≥97%
  • MDL No. None
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₅H₂₁BO₄
  • Molecular Weight 276.14
  • Synonym(s) (3-(METHOXYCARBONYL)-2-METHYLPHEN
  • SMILES O=C(OC)C1=CC=CC(B2OC(C)(C)C(C)(C)O2)=C1C

Description

Methyl 2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate delivers a boronate ester functionality compatible with palladium-catalyzed cross-coupling reactions. The tetramethyl-substituted dioxaborolane moiety enhances stability and reactivity under standard conditions. This bench-stable reagent integrates readily into synthetic sequences requiring arylboron building blocks.

Application

Methyl 2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate serves as a versatile boronate building block in palladium-catalyzed cross-coupling reactions. Its stability under ambient conditions and tolerance to diverse functional groups enable reliable incorporation into complex molecular architectures. The methyl ester moiety provides a handle for downstream derivatization, while the pinacol boronate group facilitates efficient Suzuki-Miyaura coupling, making it ideal for constructing biaryl motifs and heterocyclic scaffolds in medicinal chemistry and materials science applications.

Synthesis

  • Route1

    References

    • EP2011788 A1, ; Page/Page column 19 ;
  • Route2

    References

    • US2012/35196 A1, ;

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   44.76
  • LogP   2.08082
  • H_Acceptors   4
  • H_Donors   0
  • Rotatable_Bonds   2

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