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

3-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid is a high-purity borane supplied for industrial and specialty chemical applications. Contact our team for specifications, packaging options and lead times.

1. Suzuki-Miyaura Cross-Coupling Reactions

This compound is primarily used as a building block in Suzuki coupling, where the boronate ester group serves as the organoboron partner.

Facilitates the formation of biaryl compounds, which are common motifs in pharmaceuticals, agrochemicals, and organic materials.

The presence of a carboxylic acid group and a methyl substituent offers site-selective functionalization opportunities and influences the electronic and steric properties of coupling products.

2. Synthesis of Pharmaceuticals and Fine Chemicals

Used in the synthesis of drug candidates and bioactive molecules, especially where the arylbenzoic acid scaffold is important.

The boronate ester moiety enables modular assembly of complex molecules through carbon–carbon bond formation.

The acid functionality allows further derivatization or conjugation to other bioactive groups.

3. Materials Science

Used in the preparation of functional organic materials such as OLEDs, organic semiconductors, and molecular sensors.

The arylboronate ester can be incorporated into π-conjugated systems to modify electronic properties.

4. Chemical Biology and Bioconjugation

The boronate ester group can be exploited for bioconjugation reactions or reversible binding with diols, enabling use in chemical sensors or drug delivery systems.

The carboxylic acid moiety provides a handle for coupling to biomolecules.

1. Versatile Synthetic Intermediate

Boronate esters are stable yet reactive, allowing efficient cross-coupling under mild catalytic conditions.

The compound's structure offers multifunctionality for further chemical transformations.

2. Functional Group Compatibility

Compatible with a wide range of functional groups, enabling incorporation into complex molecules.

The carboxylic acid group is a useful handle for downstream reactions.

3. Facilitates Efficient C–C Bond Formation

Enables rapid and selective construction of biaryl linkages, critical in many chemical and pharmaceutical syntheses.

4. Improves Molecular Design

The methyl substituent and acid group influence solubility, reactivity, and molecular interactions, useful for fine-tuning properties of target compounds.

3-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid (CAS 269409-74-7) is a valuable boronate ester reagent widely employed in cross-coupling chemistry for the synthesis of pharmaceuticals, organic materials, and fine chemicals. Its combination of a boronate ester functional group and carboxylic acid moiety provides versatility for diverse synthetic applications, enabling efficient carbon–carbon bond formation with good functional group tolerance and opportunities for further derivatization.

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