456772

4-Carboxyphenylboronic acid

• Synonym(s): 4-(Dihydroxyboronyl)benzoic acid, 4-(Dihydroxyboryl)benzoic acid, 4-Boronobenzoic acid, 4-Carboxybenzeneboronic acid, 4-Carboxylphenylboronic acid, 4-Hydroxycarbonylphenyl boronic acid, NSC 221170, p-Boronobenzoic acid, p-Carboxybenzeneboronic acid, p-Carboxyphenylboronic acid
• Linear Formula: HO₂CC₆H₄B(OH)₂
• CAS Number: 14047-29-1
• Molecular Weight: 165.94
• Beilstein: 3031088
• MDL number: MFCD00151801
• UNSPSC Code: 12352103
• PubChem Substance ID: 24869234
• EC Index Number: 604-189-6
• NACRES: NA.22

Properties

• Quality Level: 200
• mp: 220 °C (dec.) (lit.)
• SMILES string: OB(O)c1ccc(cc1)C(O)=O
• 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

Description

Application

Reactant involved in:

• Condensation reactions with stabilizer chains at the surface of polystyrene latex
• Suzuki coupling reactions
• Esterification
• Derivatization of polyvinylamine
• Synthesis of isotopically labeled mercury
• Functionalization of poly-SiNW for detection of dopamine

Reagent used for

• Suzuki-Miyaura cross-coupling
• Induction of pH sensitivity on fluorescence lifetime of quantum dots by NIR fluorescent dyes
• Bio-supported palladium nanoparticles as phosphine-free catalyst for Suzuki reaction in water
• Chan-Lam-type Copper (Cu)-catalyzed S-arylation with aryl boronic acids at room temperature

Reagent used in Preparation of

• Isoquinolones via regioselective Suzuki-Miyaura cross-coupling and tandem palladium-catalyzed intramolecular aminocarbonylation and annulation
• Amprenavir-based P1-substituted bi-aryl derivatives as ultra-potent HIV-1 protease inhibitors
• Phenols via visible-light initiated aerobic oxidative hydroxylation of arylboronic acids using air as oxidant catalyzed by Ruthenium (Ru)-complex
• Glucose sensitive boronic acid-bearing block copolymers
• Trisulfonated calixarene upper-rim sulfonamido derivatives and their complexation with the trimethyllysine epigenetic mark

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 2
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves