4-Carboxyphenylboronic acid

Catalog Number	ACM14047291
CAS Number	14047-29-1
Structure
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.