(pentafluorophenyl)boronic acid

• ChemBase ID: 59374
• Molecular Formular: C6H2BF5O2
• Molecular Mass: 211.881896
• Monoisotopic Mass: 212.0068008
• SMILES: c1(c(c(c(c(c1F)B(O)O)F)F)F)F
• Canonical SMILES: Fc1c(F)c(B(O)O)c(c(c1F)F)F
• InChI: InChI=1S/C6H2BF5O2/c8-2-1(7(13)14)3(9)5(11)6(12)4(2)10/h13-14H
• InChIKey: VASOMTXTRMYSKD-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (pentafluorophenyl)boronic acid
• IUPAC Traditional name: pentafluorophenylboronic acid
• Synonyms: Pentafluorophenylboronic acid; Pentafluorobenzeneboronic acid 97%; Pentafluorophenylboronic acid; (Pentafluorophenyl)boronic acid; 2,3,4,5,6-Pentafluorophenylboronic acid; 2,3,4,5,6-Pentafluorobenzeneboronic acid; 2,3,4,5,6-PENTAFLUOROBENZENEBORONIC ACID; 五氟苯硼酸; 2,3,4,5,6-五氟苯硼酸

Database IDs

• CAS Number: 1582-24-7
• EC Number: 000-000-0
• MDL Number: MFCD01074663
• Beilstein Number: 3033960
• PubChem SID: 24870245; 162064137
• PubChem CID: 2775922

CALCULATED PROPERTIES

• Acid pKa: 7.469553
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 2.3326912
• LogD (pH = 7.4): 2.0698154
• Log P: 2.3373
• Molar Refractivity: 31.6855 cm^3
• Polarizability: 12.869896 Å^3
• Polar Surface Area: 40.46 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 176-179°C; 250-255°C

Safety Information

• Storage Warning: IRRITANT; Irritant; Moisture Sensitive
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36; 26-37
• TSCA Listed: false; 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: 97%; 98%
• Linear Formula: C6F5B(OH)2

DETAILS

Sigma Aldrich - 465097

Other Notes
Contains varying amounts of anhydride
Packaging
5 g in glass bottle
Application
Reactant for:
• Preparation of phenylboronic catechol esters as promising anion receptors for polymer electrolytes1
• Preparation of biaryls via palladium-catalyzed homocoupling reaction2
• Prepartion of quaternary a,a-heterodiaryl carboxylic esters via rhodium-catalyzed cross-coupling3
• C-C cross-coupling reactions4

REFERENCES

• Conditions have been reported for successfully accomplishing the normally difficult Suzuki cross-coupling reactions of this boronic acid with aryl halides: Org. Lett., 7, 4915 (2005).