CAS 5720-05-8 p-Tolylboronic acid - Materials / Alfa Chemistry

NAVIGATION

p-Tolylboronic acid

PRICE INQUIRY

Catalog Number

ACM5720058-2

CAS Number

5720-05-8

Product Name

p-Tolylboronic acid

Category

Salt

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

p-Tolylboronic acid serves as a versatile reagent in a variety of catalytic processes, particularly those involving palladium, including Pd-catalyzed direct arylation and the direct Palladium(II)-catalyzed synthesis. It plays a crucial role in palladium-catalyzed arylation reactions, such as the Suzuki-Miyaura cross-coupling in aqueous solutions, as well as cyclopalladation processes. In addition, it is instrumental in tandem-type Pd(II)-catalyzed oxidative Heck reactions and intramolecular C-H amidation sequences. Beyond palladium catalysis, p-Tolylboronic acid is employed in ruthenium-catalyzed direct arylation and rhodium-catalyzed asymmetric conjugate additions. It also supports ligand-free copper-catalyzed cross-coupling reactions and facilitates regioselective arylation and alkynylation in Suzuki-Miyaura and Sonogashira cross-coupling reactions. Furthermore, it contributes to ligand-free Suzuki, Sonogashira, and Heck cross-coupling reactions. p-Tolylboronic acid is also used in the preparation of catalysts for the Suzuki-Miyaura cross-coupling of aryl bromides and in developing recyclable palladium nanoparticle catalysts immobilized by click ionic copolymers, enhancing the efficiency of Suzuki-Miyaura cross-coupling reactions in water.

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