{4-[4-(dihydroxyboranyl)phenyl]phenyl}boronic acid

• ChemBase ID: 2355
• Molecular Formular: C12H12B2O4
• Molecular Mass: 241.84328
• Monoisotopic Mass: 242.09216966
• SMILES: B(O)(O)c1ccc(cc1)c1ccc(cc1)B(O)O
• Canonical SMILES: OB(c1ccc(cc1)c1ccc(cc1)B(O)O)O
• InChI: InChI=1S/C12H12B2O4/c15-13(16)11-5-1-9(2-6-11)10-3-7-12(8-4-10)14(17)18/h1-8,15-18H
• InChIKey: SLHKDOGTVUCXKX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {4-[4-(dihydroxyboranyl)phenyl]phenyl}boronic acid
• IUPAC Traditional name: @4,4'-biphenyldiboronic acid; 4,4'-biphenyldiboronic acid
• Synonyms: Biphenyl-4,4'-diylbisboronic acid; Biphenyl-4,4'-diboronic acid; 4,4'-Biphenyldiboronic Acid; 4,4′-(Dihydroxyboryl)-1,1′-biphenyl; 4,4′-Biphenylenediboronic acid; 4,4′-Biphenyldiboronic acid; 联苯基-4,4'-二硼酸; 4,4′-亚联苯基二硼酸; 4,4′-联苯基二硼酸

Database IDs

• CAS Number: 4151-80-8
• EC Number: 000-000-0
• MDL Number: MFCD00151795
• Beilstein Number: 2941876
• PubChem SID: 160965806; 46508163; 24869237
• PubChem CID: 2734608

CALCULATED PROPERTIES

JChem

• Acid pKa: 8.441313
• H Acceptors: 4
• H Donor: 4
• LogD (pH = 5.5): 2.9169056
• LogD (pH = 7.4): 2.879015
• Log P: 2.9174
• Molar Refractivity: 60.2852 cm^3
• Polarizability: 27.707808 Å^3
• Polar Surface Area: 80.92 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.6
• LOG S: -3.76
• Solubility (Water): 4.18e-02 g/l

PROPERTIES

Physical Property

• Melting Point: 300 °C (dec.)(lit.); 300(dec.)°C; ca 300°C dec.

Safety Information

• Storage Warning: Irritant/Store under Argon/Keep Cold
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-37
• TSCA Listed: 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%
• Linear Formula: (HO)2BC6H4C6H4B(OH)2

DETAILS

DrugBank - DB02627

Drug information: experimental

Sigma Aldrich - 456799

Packaging
500 mg in glass bottle
Application
Reactant involved in synthesis of:
• Organic field-effect transistors based on organic semiconductors containing diazaboroles1
• Cycloparaphenylenes via Suzuki coupling2
• 1,3,2-Diazaboroine derivatives for organic thin-film transistor applications3
• Back-to-back coupled 2,6-bis(triazol-1-yl)pyridine molecules4
• Rectangular host via electrochemical reactions with methylaquacobaloxime and diamine5
• Arylboronates from reactions with catechol, dihydroxynaphthalene and diaminobenzenedithiol for use as organic field-effect transistors and light emitting diodes6