2 - Formylphenylboronic acid pinacol ester, CAS No. 380151-85-9

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380151-85-9

Catalog No. EBD8479

CAS 380151-85-9

Name 2 - Formylphenylboronic acid pinacol ester

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Basic Information

Synonyms: 2-Formylbenzeneboronicacidpinacolester 2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde Benzaldehyde,2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- 2-Formylphenylboronicacidpinacolester 2-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzaldehyde

Molecular Formula: C13H17BO3

Molecular Weight: 232.08

MDL Number: MFCD07363841

Categories: Synthetic Chemistry > Organic Building Blocks > Boronic Acids and Boronic Esters Synthetic Chemistry > Organic Building Blocks > Aldehydes and Ketones

Product Description:

2-Formylphenylboronic acid pinacol ester is an organoboron compound featuring both a formyl (aldehyde) group and a boronic acid pinacol ester group on an aromatic ring. This bifunctional structure makes it a versatile building block in synthetic organic chemistry. Its primary application is as a key intermediate in Suzuki-Miyaura cross-coupling reactions. The boronic ester moiety readily participates in palladium-catalyzed coupling with aryl or vinyl halides to form biaryl or styryl derivatives. Simultaneously, the aldehyde group serves as a reactive handle for further transformations, such as reductive amination, condensation, or oxidation. This dual functionality allows for the efficient synthesis of complex molecules, particularly in medicinal chemistry for constructing drug-like scaffolds and in materials science for creating conjugated organic frameworks. The pinacol ester protecting group enhances the stability and handling properties of the boronic acid derivative compared to its free acid form, making it a preferred reagent in multi-step syntheses.

Physical Properties

Boiling Point: 345.894 °C at 760 mmHg

Flash Point: >110 °C

Density: 1.0532 g/mL at 25 °C

Refractivity: n20/D 1.5143

Storage: 2-8°C