CAS 6783-05-7 Boronic acid,B-[(1E)-2-phenylethenyl]-

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Boronic acid,B-[(1E)-2-phenylethenyl]-

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Catalog Number

ACM6783057-1

CAS Number

6783-05-7

Product Name

Boronic acid,B-[(1E)-2-phenylethenyl]-

Category

Salt

Synonyms

2-Phenylvinylboronic Acid, (E)-Phenylethenylboronic acid, 473790_ALDRICH, trans-2-Phenylvinylboronic acid, P4986G1, ST5412060, TL8007171, 6783-05-7

IUPAC Name

[(E)-2-phenylethenyl]boronic acid

Molecular Weight

147.97

Molecular Formula

C8H9BO2

Canonical SMILES

B(C=CC1=CC=CC=C1)(O)O

InChI Key

VKIJXFIYBAYHOE-VOTSOKGWSA-N

Boiling Point

315.9ºC at 760 mmHg

Melting Point

146-156ºC(lit.)

Flash Point

144.9ºC

Purity

96%

Density

1.13 g/cm³

Appearance

Brown granular powder

Application

Boronic acid, B-[(1E)-2-phenylethenyl]-, is a versatile brown granular powder that serves as a crucial reagent in a variety of advanced chemical reactions. It plays a key role in the palladium-catalyzed Suzuki-Miyaura coupling reactions, which are fundamental to building carbon-carbon bonds in organic synthesis. Additionally, it supports the rhodium-catalyzed intramolecular amination of aryl azides, enhancing the formation of nitrogen-containing compounds. This compound is involved in diastereoselective synthesis through palladium-catalyzed Heck-Suzuki cascade reactions, as well as in copper-mediated cyanation processes. Furthermore, it facilitates rhodium-catalyzed asymmetric additions and the diastereoselective synthesis via iridium-catalyzed additions, broadening its application in stereochemical reactions. Boronic acid, B-[(1E)-2-phenylethenyl]- also enables palladium-catalyzed cascade cyclizations and is indispensable in producing optically active unsaturated amino acids through the diastereoselective Petasis borono-Mannich reaction. Moreover, it is instrumental in synthesizing amino alcohol dienes using the Petasis 3-component reaction, which is complemented by ruthenium-catalyzed ring-closing metathesis and isomerization, showcasing its significant versatility and importance in modern organic synthesis strategies.

Exact Mass

148.07000

Hazard Statements

Safety Description

S26-S37-S39

WGK Germany

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