CAS 14047-29-1 4-Carboxyphenylboronic acid - Materials / Alfa Chemistry

NAVIGATION

4-Carboxyphenylboronic acid

PRICE INQUIRY

Catalog Number

ACM14047291

CAS Number

14047-29-1

Product Name

4-Carboxyphenylboronic acid

Structure

Category

Salt

Synonyms

Benzeneboronic acid, p-carboxy-

IUPAC Name

4-boronobenzoic acid

Molecular Weight

165.94

Molecular Formula

C7H7BO4

Canonical SMILES

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

InChI

InChI=1S/C7H7BO4/c9-7(10)5-1-3-6(4-2-5)8(11)12/h1-4,11-12H,(H,9,10)

InChI Key

SIAVMDKGVRXFAX-UHFFFAOYSA-N

Boiling Point

406.4±47.0 °C

Melting Point

220 °C (dec.)(lit.)

Purity

99.5%+

Density

1.40±0.1 g/ml

Application

4-Carboxyphenylboronic acid serves as a versatile reagent with a broad range of applications, particularly in the synthesis and functionalization of various chemical compounds. It plays a key role in condensation reactions with stabilizer chains on polystyrene latex surfaces and is essential in Suzuki-Miyaura cross-coupling reactions, which are crucial for forming carbon-carbon bonds. This reagent is also employed in esterification processes, the derivatization of polyvinylamine, and the synthesis of isotopically labeled mercury. Additionally, it facilitates the functionalization of poly-SiNW for dopamine detection and plays a part in inducing pH sensitivity on the fluorescence lifetime of quantum dots with NIR fluorescent dyes. The application of 4-Carboxyphenylboronic acid extends to bio-supported palladium nanoparticles acting as a phosphine-free catalyst for Suzuki reactions in aqueous environments and enabling Chan-Lam-type Copper-catalyzed S-arylation at room temperature. It aids in preparing isoquinolones through regioselective Suzuki-Miyaura cross-coupling, followed by tandem palladium-catalyzed aminocarbonylation and annulation, as well as developing ultra-potent HIV-1 protease inhibitors based on amprenavir. Furthermore, it is involved in the visible-light initiated aerobic oxidative hydroxylation of arylboronic acids, the creation of glucose-sensitive boronic acid-bearing block copolymers, and forming trisulfonated calixarene derivatives for complexation with the trimethyllysine epigenetic mark. In addition to these applications, 4-Carboxyphenylboronic acid can function as a corrosion inhibitor for steel.

Complexity

163

Covalently-Bonded Unit Count

Exact Mass

166.043739g/mol

Formal Charge

Heavy Atom Count

Monoisotopic Mass

166.043739g/mol

NSC Number

221170

Rotatable Bond Count