(2,4,6-trifluorophenyl)boronic acid

• ChemBase ID: 32592
• Molecular Formular: C6H4BF3O2
• Molecular Mass: 175.9009696
• Monoisotopic Mass: 176.02564443
• SMILES: c1c(cc(c(c1F)B(O)O)F)F
• Canonical SMILES: OB(c1c(F)cc(cc1F)F)O
• InChI: InChI=1S/C6H4BF3O2/c8-3-1-4(9)6(7(11)12)5(10)2-3/h1-2,11-12H
• InChIKey: IPEIGKHHSZFAEW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2,4,6-trifluorophenyl)boronic acid
• IUPAC Traditional name: 2,4,6-trifluorophenylboronic acid
• Synonyms: 2,4,6-Trifluorophenylboronic acid; 2,4,6-Trifluorophenylboronic acid; 2,4,6-Trifluorobenzeneboronic acid; 2,4,6-Trifluorophenylboronic acid; 2,4,6-Trifluorobenzeneboronic acid; 2,4,6-三氟苯硼酸

Database IDs

• CAS Number: 182482-25-3
• EC Number: 000-000-0
• MDL Number: MFCD01863169
• Beilstein Number: 8549766
• PubChem SID: 160995899; 24874390
• PubChem CID: 2779329

CALCULATED PROPERTIES

• Acid pKa: 7.7191854
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 2.0557003
• LogD (pH = 7.4): 1.8886501
• Log P: 2.0583
• Molar Refractivity: 31.2527 cm^3
• Polarizability: 12.928747 Å^3
• Polar Surface Area: 40.46 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 228-235 °C(lit.); ca 235°C; ca 235°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%
• Linear Formula: F3C6H2B(OH)2

DETAILS

Sigma Aldrich - 524107

Other Notes
Contains varying amounts of anhydride
Packaging
1, 5 g in glass bottle
Application
Reactant involved in:
• Synthesis of phenylboronic catechol esters1
• Suzuki-Miyaura coupling reactions with aryl chlorides2 and unstable polyfluorophenyl3
• Enantioselective borane reduction of trifluoroacetophenone4
• Transmetalation5,6