(3-bromophenyl)boronic acid

• ChemBase ID: 10571
• Molecular Formular: C6H6BBrO2
• Molecular Mass: 200.82564
• Monoisotopic Mass: 199.96442183
• SMILES: c1(cccc(c1)B(O)O)Br
• Canonical SMILES: Brc1cccc(c1)B(O)O
• InChI: InChI=1S/C6H6BBrO2/c8-6-3-1-2-5(4-6)7(9)10/h1-4,9-10H
• InChIKey: AFSSVCNPDKKSRR-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3-bromophenyl)boronic acid
• IUPAC Traditional name: 3-bromophenylboronic acid
• Synonyms: 3-Bromobenzeneboronic acid; 3-Bromobenzeneboronic acid; 3-Bromophenylboronic acid; 3-Bromophenylboronic acid; 3-Bromophenylboronic acid; 3-Bromobenzeneboronic acid; 3-溴苯硼酸

Database IDs

• CAS Number: 89598-96-9
• EC Number: 000-000-0
• MDL Number: MFCD00239386
• Beilstein Number: 3127104
• PubChem SID: 160973878; 24867690
• PubChem CID: 2734318

CALCULATED PROPERTIES

• Acid pKa: 8.67537
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 2.4313116
• LogD (pH = 7.4): 2.4092731
• Log P: 2.4316
• Molar Refractivity: 38.2263 cm^3
• Polarizability: 16.38122 Å^3
• Polar Surface Area: 40.46 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 164-168 °C(lit.); 164-168°C; 164-168°C

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: 97%; 98%; 98+%
• Linear Formula: BrC6H4B(OH)2

DETAILS

Sigma Aldrich - 441627

Other Notes
Contains varying amounts of anhydride
Packaging
5 g in glass bottle
Application
Reactant involved in a variety of organic reactions including:
• Oxidative cross coupling1,2
• Gold salt catalyzed homocoupling3
• 1,4-Addition reactions with α,β-unsaturated ketones4
• Enantioselective addition reactions5
• Suzuki-Miyaura coupling for synthesis of anthranilamide-protected arylboronic acids6
• C-H Functionalization of quinones7