2 - Hydroxyphenylboronic acid pinacol ester, CAS No. 269409-97-4

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269409-97-4

Catalog No. EBD6598

CAS 269409-97-4

Name 2 - Hydroxyphenylboronic acid pinacol ester

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Basic Information

Synonyms: 2-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenol 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol phenol,2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- 2-Hydroxyphenylboronicacidpinacolester 2-hydroxyphenylboronicacid,pinacolester 2-hydroxybenzeneboronicacid,pinacolester 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2yl)

Molecular Formula: C12H17BO3

Molecular Weight: 220.07

MDL Number: MFCD02093754

Categories: Synthetic Chemistry > Organic Building Blocks > Boronic Acids and Boronic Esters Synthetic Chemistry > Catalysts and Ligands > Oxygen Ligands

Product Description:

2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenol is an organoboron compound featuring a phenol group ortho-substituted with a pinacol boronate ester moiety. This bifunctional structure combines the reactivity of a boronic ester, commonly used in Suzuki-Miyaura cross-coupling reactions, with the coordinating and acidic properties of a phenol. Its primary application is as a versatile building block in organic synthesis and materials science. The boronate ester enables the introduction of the phenolic aryl group into complex molecules via palladium-catalyzed coupling. More specifically, the compound serves as a key precursor or ligand in catalytic systems. For instance, it is utilized in the synthesis of salen-type ligands and as a component in the preparation of novel catalysts for polymerization reactions, such as nickel-based complexes for ethylene oligomerization. The presence of both the boron and oxygen donor sites makes it a valuable synthon for constructing chelating ligands and functional organic materials. It is typically handled under inert atmosphere to prevent hydrolysis of the boronate ester.

Physical Properties

Boiling Point: 282 °C(lit.)

Flash Point: >110 °C

Density: 1.05 g/mL at 25 °C(lit.)

Refractivity: n20/D 1.506(lit.)

Storage: Refrigerator

Analytical Data

Appearance: pale yellow to brown liquid