[4-(dihydroxyboranyl)phenyl]boronic acid

• ChemBase ID: 10559
• Molecular Formular: C6H8B2O4
• Molecular Mass: 165.74732
• Monoisotopic Mass: 166.06086954
• SMILES: c1c(ccc(c1)B(O)O)B(O)O
• Canonical SMILES: OB(c1ccc(cc1)B(O)O)O
• InChI: InChI=1S/C6H8B2O4/c9-7(10)5-1-2-6(4-3-5)8(11)12/h1-4,9-12H
• InChIKey: BODYVHJTUHHINQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [4-(dihydroxyboranyl)phenyl]boronic acid
• IUPAC Traditional name: 4-(dihydroxyboranyl)phenylboronic acid
• Synonyms: 1,4-Phenylenediboronic acid; p-Benzenediboronic acid; NSC 25410; 1,4-Phenylenebisboronic acid; p-Phenylenediboronic acid; Benzene-1,4-diboronic acid; Benzene-1,4-diboronic acid; Benzene-1,4-diboronic acid; 1,4-Benzenediboronic Acid; 1,4-Phenylenebis(boronic acid); 1,4-Benzenediboronic acid; 1,4-苯二硼酸; 对苯二硼酸; 苯基-1,4-二硼酸; 苯基-1,4-二硼酸; 1,4-苯二硼酸

Database IDs

• CAS Number: 4612-26-4
• MDL Number: MFCD00236018
• Beilstein Number: 2836921
• PubChem SID: 24866124; 160973866
• PubChem CID: 230478

CALCULATED PROPERTIES

• Acid pKa: 8.224804
• H Acceptors: 4
• H Donor: 4
• LogD (pH = 5.5): 1.2321866
• LogD (pH = 7.4): 1.1715219
• Log P: 1.233
• Molar Refractivity: 35.149 cm^3
• Polarizability: 16.752138 Å^3
• Polar Surface Area: 80.92 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: >300°C; >350 °C(lit.)

Safety Information

• Storage Warning: Harmful/Irritant; IRRITANT
• European Hazard Symbols: X; Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• Safety Statements: 26-36/37; 36
• TSCA Listed: false; 否
• GHS Pictograms: GHS06; GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H301; H302
• GHS Precautionary statements: P264-P270-P301+P310-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥95.0%; 96%; 98%; 99%
• Linear Formula: C6H4[B(OH)2]2

DETAILS

Sigma Aldrich - 417130

Other Notes
Contains varying amounts of anhydride
Packaging
5, 25 g in glass bottle
Application
Reagent used for
• Externally initiated Kumada catalyst-transfer polycondensation1
• Suzuki-Miyaura cross-coupling reactions2
• Energy transfer processes in optoelectronic devices3
• Palladium-catalyzed sequential alkenylation and conjugate addition reactions4
• Scholl cyclizations5 Reagent used in Preparation of
• Crosslinkers and cross-linked core-shell nanoparticles by RAFT polymerization and palladium-catalyzed Suzuki coupling reaction6
• Fluorescence and solution-processable coordination polymers7
• Cyclotricatechylene based porous crystalline material for gas storage8
• Indolizine derivatives as OLEDs2
• Helically p-stacked thiophene-based copolymers with circularly polarized fluorescence9
• Novel organic semiconductors and applications in organic thin-film transistors10
• Highly twisted polycyclic aromatic hydrocarbons with unexptected reactivity5