CAS 5720-05-8 4-Tolylboronic acid - Materials / Alfa Chemistry

NAVIGATION

4-Tolylboronic acid

PRICE INQUIRY

Catalog Number

ACM5720058

CAS Number

5720-05-8

Product Name

4-Tolylboronic acid

Category

Organic Light-Emitting Diode (OLED) Materials

Synonyms

AKOS BRN-0019;4-TOLYLBORONIC ACID;4-TOLYBORONIC ACID;4-METHYLBENZENEBORONIC ACID;4-METHYLPHENYLBORIC ACID;4-METHYLPHENYLBORONIC ACID;P-METHYLPHENYLBORONIC ACID;P-TOLYLBORONIC ACID

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-Tolylboronic acid is a versatile reagent appearing as a white to light yellow crystal powder, primarily employed in a variety of catalytic processes. It serves an essential role in palladium-catalyzed reactions, including direct arylation and the direct synthesis utilizing Palladium (II). This reagent is pivotal in Suzuki-Miyaura cross-coupling in water, providing a pathway for effective palladium-catalyzed arylation. It is also crucial in cyclopalladation, a tandem-type Pd(II)-catalyzed oxidative Heck reaction, as well as intramolecular C-H amidation sequences. Beyond palladium applications, 4-Tolylboronic acid is utilized in ruthenium-catalyzed direct arylation, rhodium-catalyzed asymmetric conjugate addition, and ligand-free copper-catalyzed cross-coupling reactions. Its role extends to regioselective arylation and alkynylation by Suzuki-Miyaura and Sonogashira cross-coupling reactions, including ligand-free versions of Suzuki, Sonogashira, and Heck cross-coupling reactions. Moreover, it is a crucial component in the preparation of catalysts for the Suzuki-Miyaura cross-coupling of aryl bromides and in the development of recyclable palladium nanoparticle catalysts, which are immobilized by click ionic copolymers for efficient 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