CAS 5720-05-8 4-Methylphenylboronic Acid (contains varying amounts of Anhydride)

NAVIGATION

4-Methylphenylboronic Acid (contains varying amounts of Anhydride)

PRICE INQUIRY

Catalog Number

ACM5720058-1

CAS Number

5720-05-8

Product Name

4-Methylphenylboronic Acid (contains varying amounts of Anhydride)

Structure

Category

Liquid Crystal (LC) Building Blocks

IUPAC Name

(4-methylphenyl)boronic acid

Molecular Weight

135.96g/mol

Molecular Formula

C7H9BO2;C7H9BO2

Canonical SMILES

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

InChI

InChI=1S/C7H9BO2/c1-6-2-4-7(5-3-6)8(9)10/h2-5,9-10H,1H3

InChI Key

BIWQNIMLAISTBV-UHFFFAOYSA-N

Application

4-Methylphenylboronic Acid, which may contain varying amounts of anhydride, is a versatile reagent primarily used to facilitate numerous palladium (Pd)-catalyzed processes. Its applications include the Pd-catalyzed direct arylation, the direct Palladium(II)-catalyzed synthesis, and the renowned Suzuki-Miyaura cross-coupling in water, which is essential for aryl bond formation. Additionally, it plays a crucial role in cyclopalladation, the tandem-type Pd(II)-catalyzed oxidative Heck reaction, and intramolecular C-H amidation sequences. Beyond palladium, it is also employed in reactions catalyzed by ruthenium and rhodium, such as ruthenium-catalyzed direct arylation and rhodium-catalyzed asymmetric conjugate addition. Notably, 4-Methylphenylboronic Acid is effective in ligand-free copper-catalyzed cross-coupling reactions, as well as in regioselective arylation and alkynylation via Suzuki-Miyaura and Sonogashira cross-coupling reactions. It supports ligand-free Suzuki, Sonogashira, and Heck cross-coupling reactions, and is essential in the preparation of catalysts, particularly those used for the Suzuki-Miyaura cross-coupling of aryl bromides. Furthermore, it contributes to the development of recyclable palladium nanoparticle catalysts, which are immobilized by click ionic copolymers for efficient cross-coupling reactions in water, underscoring its pivotal role in modern synthetic chemistry.

Complexity

97.8

Covalently-Bonded Unit Count

Exact Mass

136.06956g/mol

Formal Charge

Heavy Atom Count

MeSH Entry Terms

para-tolylboronic acid;tolylboronic acid

Monoisotopic Mass

136.06956g/mol

NSC Number