[3-(benzyloxy)phenyl]boronic acid

• ChemBase ID: 10569
• Molecular Formular: C13H13BO3
• Molecular Mass: 228.05152
• Monoisotopic Mass: 228.09577468
• SMILES: c1(cccc(c1)B(O)O)OCc1ccccc1
• Canonical SMILES: OB(c1cccc(c1)OCc1ccccc1)O
• InChI: InChI=1S/C13H13BO3/c15-14(16)12-7-4-8-13(9-12)17-10-11-5-2-1-3-6-11/h1-9,15-16H,10H2
• InChIKey: WIJNYNBSPQMJGO-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [3-(benzyloxy)phenyl]boronic acid
• IUPAC Traditional name: 3-(benzyloxy)phenylboronic acid
• Synonyms: 3-Benzyloxybenzeneboronic acid; 3-Phenylmethyloxyphenylboronic acid; 3-(Benzyloxy)phenylboronic acid; [(3-Boronophenoxy)methyl]benzene; 3-(Benzyloxy)benzeneboronic acid; 3-Benzyloxyphenylboronic acid; 3-Benzyloxyphenylboronic acid; 3-Benzyloxybenzeneboronic acid; 3-苄氧基苯硼酸; 3-苯甲氧基苯硼酸

Database IDs

• CAS Number: 156682-54-1
• EC Number: 000-000-0
• MDL Number: MFCD02093063
• Beilstein Number: 6808244
• PubChem SID: 24874547; 160973876
• PubChem CID: 2734313

CALCULATED PROPERTIES

• Acid pKa: 8.654109
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 3.1633973
• LogD (pH = 7.4): 3.1402824
• Log P: 3.1637
• Molar Refractivity: 61.6793 cm^3
• Polarizability: 25.64578 Å^3
• Polar Surface Area: 49.69 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 122-124°C; 125-130 °C(lit.); 125-130°C

Safety Information

• Storage Warning: IRRITANT; Irritant/Keep Cold/Store under Argon
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-37
• TSCA Listed: false; 否
• GHS Pictograms: GHS07
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥95%; 98%; 98+%
• Linear Formula: C6H5CH2OC6H4B(OH)2

DETAILS

Sigma Aldrich - 526339

General description
Contains varying amounts of anhydride.
Packaging
5, 25 g in glass bottle
Application
Reactant for:
• Microwave Suzuki-Miyaura coupling1
• Preparation of palladium-based fluoride-derived electrophilic fluorination reagent for PET imaging agents2
• Synthesis of substituted isoindolines via palladium-catalyzed cascade reaction3
• Ruthenium-catalyzed hydrogenation4
• Suzuki coupling reactions5