[3-(hydroxymethyl)phenyl]boronic acid

• ChemBase ID: 12411
• Molecular Formular: C7H9BO3
• Molecular Mass: 151.95556
• Monoisotopic Mass: 152.06447455
• SMILES: c1(cc(ccc1)CO)B(O)O
• Canonical SMILES: OCc1cccc(c1)B(O)O
• InChI: InChI=1S/C7H9BO3/c9-5-6-2-1-3-7(4-6)8(10)11/h1-4,9-11H,5H2
• InChIKey: HGTDLKXUWVKLQX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [3-(hydroxymethyl)phenyl]boronic acid
• IUPAC Traditional name: 3-(hydroxymethyl)phenylboronic acid
• Synonyms: 3-Boronobenzyl alcohol; 3-(Hydroxymethyl)benzeneboronic acid; 3-(Hydroxymethyl)phenylboronic acid; 3-Hydroxymethylbenzeneboronic acid; 3-(Hydroxymethyl)phenylboronic acid; 3-Hydroxymethylphenylboronic acid; (3-(hydroxymethyl)phenyl)boronic acid; 3-(Hydroxymethyl)phenylboronic acid; 3-(Hydroxymethyl)benzeneboronic acid; 3-羟甲基苯硼酸; 3-(羟基甲基)苯硼酸

Database IDs

• CAS Number: 87199-15-3
• MDL Number: MFCD01317846
• Beilstein Number: 8832019
• PubChem SID: 24873658; 160975718
• PubChem CID: 2734662

CALCULATED PROPERTIES

• Acid pKa: 8.723
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): 0.8042416
• LogD (pH = 7.4): 0.7844396
• Log P: 0.8045
• Molar Refractivity: 37.4194 cm^3
• Polarizability: 15.990165 Å^3
• Polar Surface Area: 60.69 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 93-98°C; 95-96°C; 95-99 °C(lit.)

Safety Information

• Storage Warning: IRRITANT; Irritant
• 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: 96%; 97%; 98%
• Linear Formula: HOCH2C6H4B(OH)2

DETAILS

Sigma Aldrich - 512834

Other Notes
Contains varying amounts of anhydride
Packaging
1, 10 g in glass bottle
Application
Reactant involved in:
• Copper-mediated trifluoromethylation1
• Copper-catalyzed transformations from arylboronic acids in water2
• Mitsunobu, Suzuki, and amidation reactions with hydroxyphenylamino bromopyrazinecarboxylate3Reactant involved in the synthesis of biologically active molecules including:
• Mycobacterium tuberculosis H37Rv chorismate mutase inhibitors via Suzuki coupling reactions4
• HIV protease inhibitors with antiviral activity against drug-resistant viruses5
• Pyrrole derivatives for use as PDE4B inhibitors6