(4-hydroxyphenyl)boronic acid

• ChemBase ID: 32872
• Molecular Formular: C6H7BO3
• Molecular Mass: 137.92898
• Monoisotopic Mass: 138.04882448
• SMILES: c1(ccc(cc1)O)B(O)O
• Canonical SMILES: Oc1ccc(cc1)B(O)O
• InChI: InChI=1S/C6H7BO3/c8-6-3-1-5(2-4-6)7(9)10/h1-4,8-10H
• InChIKey: COIQUVGFTILYGA-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4-hydroxyphenyl)boronic acid
• IUPAC Traditional name: 4-hydroxyphenylboronic acid
• Synonyms: 4-Boronophenol; 4-Hydroxybenzeneboronic acid; 4-Hydroxyphenylboronic acid; 4-Hydroxybenzeneboronic acid; (4-hydroxyphenyl)boronic acid; 4-Hydroxyphenylboronic acid; (p-Hydroxyphenyl)boronic acid; 4-Hydroxybenzeneboronic acid; p-hydroxy-benzeneboronic acid; 4-Hydroxyphenylboronic acid; 4-羟基苯硼酸

Database IDs

• CAS Number: 71597-85-8
• EC Number: 000-000-0
• MDL Number: MFCD01074628
• Beilstein Number: 2963491
• PubChem SID: 160996179; 24874383
• PubChem CID: 2734360

CALCULATED PROPERTIES

• Acid pKa: 8.451059
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): 1.3549159
• LogD (pH = 7.4): 1.3181796
• Log P: 1.3554
• Molar Refractivity: 32.5844 cm^3
• Polarizability: 14.143737 Å^3
• Polar Surface Area: 60.69 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: >230 °C(lit.); 232 - 234°C; 285(dec.)°C; ca 285°C dec.
• Hydrophobicity(logP): 0.928

Safety Information

• Storage Warning: Harmful/Irritant/Store under Argon/Keep Cold; IRRITANT
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36; 26-37
• TSCA Listed: false; 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥95.0%; 95%; 97%; 98%
• Linear Formula: HOC6H4B(OH)2

DETAILS

Sigma Aldrich - 523976

Other Notes
Contains varying amounts of anhydride
Packaging
1, 5 g in glass bottle
Application
Reagent used for
• Suzuki-Miyaura coupling and Stille coupling and potential for introducing different alkyl groups1
• Palladium-catalyzed aminocarbonylation and cross-coupling reactions2
• Bio-supported palladium nanoparticles as phosphine-free catalyst for Suzuki reaction in water3
• Cu2O-catalyzed aerobic oxidative cross-coupling of tetrazoles4 Reagent used in Preparation of
• PDK1 inhibitory activity (cancer cell growth, survival, and tumorigenesis inhibitor)5
• Rod-like dendronized polymers contg. G4 and G5 ester dendrons via macromonomer approach by living ROMP6
• Estrone-derived cyclopamine analogs as Sonic Hedgehog signaling inhibitors for anti-cancer chemotherapeutics7
• Enzymatic inhibitors for the treatment of gram-negative bacterial infections8