CAS 83947-56-2 Trans-2-phenylvinylboronic acid pinacol ester

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Trans-2-phenylvinylboronic acid pinacol ester

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Catalog Number

ACM83947562-1

CAS Number

83947-56-2

Product Name

Trans-2-phenylvinylboronic acid pinacol ester

Category

Salt

Synonyms

570214_ALDRICH, BM056, trans-Styrylboronic acid pinacol ester, trans-2-Styreneboronic acid pinacol ester, ST5408452, trans-2-Phenylvinylboronic acid pinacol ester, trans-2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)styrene, 83947-56-2

IUPAC Name

4,4,5,5-tetramethyl-2-[(E)-2-phenylethenyl]-1,3,2-dioxaborolane

Molecular Weight

230.11

Molecular Formula

C₁₄H₁₉BO₂

Canonical SMILES

B1(OC(C(O1)(C)C)(C)C)C=CC2=CC=CC=C2

InChI Key

ARAINKADEARZLZ-ZHACJKMWSA-N

Boiling Point

128ºC/4mm

Melting Point

27-33ºC(lit.)

Flash Point

>230 °F

Purity

N/A

Density

0.99g/cm³

Application

Trans-2-phenylvinylboronic acid pinacol ester is a versatile chemical compound widely used as a reactant in various organic synthesis processes. Its applications encompass oxidative coupling reactions that are areneruthenium-catalyzed and cycloaddition reactions, making it valuable for creating complex molecular structures. Additionally, it plays a crucial role in the preparation of allyl vinyl ethers through copper-catalyzed coupling with alcohols and contributes to the synthesis of 5-vinyl-3-pyridinecarbonitriles, known as inhibitors of protein kinase C theta (PKCθ). The compound also facilitates diastereoselective addition to zincated hydrazones and aids in the stereospecific trapping of boron/zinc bimetallic intermediates by carbon electrophiles. Moreover, it enables regioselective and stereoselective chelate-controlled intermolecular oxidative Heck reactions, which are palladium-catalyzed, enhancing the precision and efficiency of chemical transformations.

Exact Mass

230.14800

WGK Germany

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