CAS 14047-29-1 4-Carboxyphenylboronic Acid (contains varying amounts of Anhydride)

NAVIGATION

4-Carboxyphenylboronic Acid (contains varying amounts of Anhydride)

PRICE INQUIRY

Catalog Number

ACM14047291-1

CAS Number

14047-29-1

Product Name

4-Carboxyphenylboronic Acid (contains varying amounts of Anhydride)

Structure

Category

Liquid Crystal (LC) Building Blocks

IUPAC Name

4-boronobenzoic acid

Molecular Weight

165.94g/mol

Molecular Formula

C7H7BO4;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

Application

4-Carboxyphenylboronic Acid, an off-white to light beige powder, serves as a versatile reagent prominently utilized in various chemical reactions and applications. It plays a key role in condensation reactions involving stabilizer chains on polystyrene latex surfaces, and is essential in Suzuki coupling reactions, esterification, and the derivatization of polyvinylamine. Its applications extend to the synthesis of isotopically labeled mercury and the functionalization of poly-SiNW for dopamine detection. This compound is pivotal in Suzuki-Miyaura cross-coupling reactions and allows for the induction of pH sensitivity on quantum dots through NIR fluorescent dyes. Utilizing bio-supported palladium nanoparticles, it acts as a phosphine-free catalyst for conducting Suzuki reactions in water, and it facilitates Chan-Lam-type copper-catalyzed S-arylation with aryl boronic acids at ambient temperature. Furthermore, 4-Carboxyphenylboronic Acid is used in the preparation of isoquinolones via regioselective Suzuki-Miyaura cross-coupling in tandem with palladium-catalyzed intramolecular aminocarbonylation and annulation. It assists in creating amprenavir-based P1-substituted bi-aryl derivatives for potent HIV-1 protease inhibition, and in producing phenols through visible-light initiated aerobic oxidative hydroxylation of arylboronic acids using air, catalyzed by a ruthenium complex. Additionally, it enables the development of glucose-sensitive boronic acid-bearing block copolymers, trisulfonated calixarene upper-rim sulfonamido derivatives and their complexation with trimethyllysine epigenetic marks, and also functions 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