3-(dihydroxyboranyl)benzoic acid

• ChemBase ID: 9447
• Molecular Formular: C7H7BO4
• Molecular Mass: 165.93908
• Monoisotopic Mass: 166.0437391
• SMILES: c1cc(cc(c1)B(O)O)C(=O)O
• Canonical SMILES: OB(c1cccc(c1)C(=O)O)O
• InChI: InChI=1S/C7H7BO4/c9-7(10)5-2-1-3-6(4-5)8(11)12/h1-4,11-12H,(H,9,10)
• InChIKey: DBVFWZMQJQMJCB-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-(dihydroxyboranyl)benzoic acid
• IUPAC Traditional name: 3-(dihydroxyboranyl)benzoic acid
• Synonyms: 3-Boronobenzoic acid; 3-Carboxybenzeneboronic acid; 3-Carboxyphenylboronic acid; μ-Carboxyphenylboronic acid; 3-(Dihydroxyborane)benzoic acid; 3-(Dihydroxyboryl)benzoic acid; 3-Carboxybenzeneboronic acid; 3-Carboxyphenylboronic acid; 3-Carboxyphenylboronic acid; 3-Carboxybenzeneboronic acid; 3-(dihydroxyboryl)benzoic acid; 3-(dihydroxyboranyl)benzoic acid; 3-Carboxyphenylboronic acid; 3-羧基苯硼酸

Database IDs

• CAS Number: 25487-66-5
• EC Number: 000-000-0
• MDL Number: MFCD00036833
• Beilstein Number: 2967400
• PubChem SID: 160972754; 24869232
• PubChem CID: 2733957

CALCULATED PROPERTIES

• Acid pKa: 3.966159
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -0.38780957
• LogD (pH = 7.4): -2.1019704
• Log P: 1.1557
• Molar Refractivity: 37.8597 cm^3
• Polarizability: 15.905134 Å^3
• Polar Surface Area: 77.76 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 228 - 230°C; 243-247 °C(lit.); 243-247°C; ca 240°C dec.
• Hydrophobicity(logP): 1.338

Safety Information

• Storage Warning: IRRITANT; Irritant
• RTECS: CY8750000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 2
• Risk Statements: 36/37/38
• Safety Statements: 26-37
• TSCA Listed: false; 否
• GHS Pictograms: GHS07
• GHS Hazard statements: H315-H319-H335-H303
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A

Product Information

• Purity: 95%; 97%; 98%
• Linear Formula: HO2CC6H4B(OH)2

DETAILS

Sigma Aldrich - 456764

Application
Widely used in Suzuki coupling chemistry.1,2,3
Other Notes
Contains varying amounts of anhydride
Packaging
1, 10 g in glass bottle