(3-phenylphenyl)boronic acid

• ChemBase ID: 64070
• Molecular Formular: C12H11BO2
• Molecular Mass: 198.02554
• Monoisotopic Mass: 198.08520999
• SMILES: B(c1cc(c2ccccc2)ccc1)(O)O
• Canonical SMILES: OB(c1cccc(c1)c1ccccc1)O
• InChI: InChI=1S/C12H11BO2/c14-13(15)12-8-4-7-11(9-12)10-5-2-1-3-6-10/h1-9,14-15H
• InChIKey: GOXICVKOZJFRMB-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3-phenylphenyl)boronic acid
• IUPAC Traditional name: 3-phenylphenylboronic acid
• Synonyms: biphenyl-3-ylboronic acid; Biphenyl-3-boronic acid; Biphenyl-3-boronic acid; (3-Phenylphenyl)boronic acid; 3-(Dihydroxyboryl)-1,1′-biphenyl; 3-Phenylbenzeneboronic acid; 3-Biphenylboronic acid; [1,1'-Biphenyl]-3-ylboronic acid; 3-BIPHENYLBORONIC ACID; 3-苯基苯硼酸; 3-联苯硼酸

Database IDs

• CAS Number: 5122-95-2
• EC Number: 000-000-0
• MDL Number: MFCD01318102
• Beilstein Number: 2836311
• PubChem SID: 162029809; 24878588
• PubChem CID: 2734315

CALCULATED PROPERTIES

• Acid pKa: 8.713302
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 3.3239357
• LogD (pH = 7.4): 3.303697
• Log P: 3.3242
• Molar Refractivity: 55.7397 cm^3
• Polarizability: 24.57612 Å^3
• Polar Surface Area: 40.46 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 193-198 °C(lit.); 206-211°C

Safety Information

• Storage Warning: Corrosive; 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: 98%; 98+%
• Linear Formula: C6H5C6H4B(OH)2

DETAILS

Sigma Aldrich - 542199

Other Notes
Contains varying amounts of anhydride
Packaging
5 g in glass bottle
Application
Biological reagent used as a boronate-assisted fluorogenic chemosensor1Evaluated for pharmacological activity as fatty acid amide hydrolase inhibitors2Reactant involved in:
• Coupling with potassium cyanate3, quinones4, or fluorous tagged N-hydroxyphthalimide5
• Direct C-H arylation of electron-deficient heterocycles6

REFERENCES

• Fluorescent PET receptor useful in saccharide detection: Tetrahedron Lett., 36, 4825 (1995); Pure Appl. Chem., 68, 2179 (1996). For boronic acid chemistry, see Appendix 5.