523976

4-Hydroxyphenylboronic acid

≥95.0%

• Synonym(s): (p-Hydroxyphenyl)boronic acid, 4-Hydroxybenzeneboronic acid, p-hydroxy-benzeneboronic acid
• Linear Formula: HOC₆H₄B(OH)₂
• CAS Number: 71597-85-8
• Molecular Weight: 137.93
• MDL number: MFCD01074628
• UNSPSC Code: 12352103
• PubChem Substance ID: 24874383
• NACRES: NA.22

Properties

• Quality Level: 100
• assay: ≥95.0%
• form: solid
• mp: >230 °C (lit.)
• SMILES string: OB(O)c1ccc(O)cc1
• InChI: 1S/C6H7BO3/c8-6-3-1-5(2-4-6)7(9)10/h1-4,8-10H
• InChI key: COIQUVGFTILYGA-UHFFFAOYSA-N

Description

Application

4-Hydroxyphenylboronic acid can be used as a reactant in:

• Suzuki-Miyaura coupling and Stille coupling reactions.[1]
• Palladium-catalyzed aminocarbonylation and cross-coupling reactions.[2]
• Suzuki reaction for preparation of bio-supported palladium nanoparticles as phosphine-free catalysts.[3]
• Cu₂O-catalyzed aerobic oxidative cross-coupling of tetrazoles.[4]

It can also be used to prepare/promote:

• PDK1 inhibitory activity (cancer cell growth, survival, and tumorigenesis inhibitor).[5]
• Rod-like dendronized polymers containing G4 and G5 ester dendrons via macromonomer approach by living ROMP.[6]
• Estrone-derived cyclopamine analogs as Sonic Hedgehog signaling inhibitors for anti-cancer chemotherapeutics.[7]
• Enzymatic inhibitors for the treatment of Gram-negative bacterial infections.[8]
• Oligoarenes by Suzuki-Miyaura palladium-catalyzed cross-coupling.[9]

Other Notes

Contains varying amounts of anhydride

Safety Information

• pictograms: GHS07
• signalword: Warning
• hcodes: H315,H319
• pcodes: P264 - P280 - P302 + P352 - P305 + P351 + P338 - P332 + P313 - P337 + P313
• Hazard Classifications: Eye Irrit. 2 - Skin Irrit. 2
• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: dust mask type N95 (US), Eyeshields, Gloves