(4-fluorophenyl)boronic acid

• ChemBase ID: 8345
• Molecular Formular: C6H6BFO2
• Molecular Mass: 139.9200432
• Monoisotopic Mass: 140.04448805
• SMILES: OB(O)c1ccc(cc1)F
• Canonical SMILES: OB(c1ccc(cc1)F)O
• InChI: InChI=1S/C6H6BFO2/c8-6-3-1-5(2-4-6)7(9)10/h1-4,9-10H
• InChIKey: LBUNNMJLXWQQBY-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4-fluorophenyl)boronic acid
• IUPAC Traditional name: 4-fluorophenylboronic acid; C6H6BFO2
• Synonyms: (4-Fluorophenyl)boric acid; (4-Fluorophenyl)dihydroxyborane; (4-Fluorophenyl)dihydroxyboron; (p-Fluorophenyl)boric acid; p-Fluorobenzylboronic acid; p-Fluorophenylboronic acid; NSC 142683; 4-Fluorobenzeneboronic acid; 4-Fluorophenylboronic acid; 4-Fluorophenylboronic acid; 4-Fluorobenzeneboronic acid; 4-Fluorophenylboric acid; 4-FLUOROBENZENEBORONIC ACID; 4-Fluorophenylboronic acid; 4-Fluorobenzeneboronic acid 97%; 对氟苯硼酸; 4-氟苯硼酸

Database IDs

• CAS Number: 1765-93-1
• MDL Number: MFCD00039136
• Beilstein Number: 2829653
• PubChem SID: 24866160; 160971652
• PubChem CID: 285645

CALCULATED PROPERTIES

• Acid pKa: 8.790703
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 1.7790788
• LogD (pH = 7.4): 1.7620788
• Log P: 1.7793
• Molar Refractivity: 30.8199 cm^3
• Polarizability: 13.2280445 Å^3
• Polar Surface Area: 40.46 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 260-265°C; 262-265 °C(lit.); 262-265°C; 267-268°C

Safety Information

• Storage Condition: 2-8°C
• Storage Warning: Harmful/Irritant/Keep Cold/Store under Argon; IRRITANT
• European Hazard Symbols: Irritant (Xi); Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-36/37/38; 36/37/38
• Safety Statements: 26-36; 26-37
• TSCA Listed: false; 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H315-H319-H335; 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: FC6H4B(OH)2

DETAILS

MP Biomedicals - 02159348

GLC reageant for diols.

Apollo Scientific Ltd - PC3482

Contains variable amounts of the anhydride GLC reagent for diols see: J. Chromatogr.,158,33,1978

Sigma Aldrich - 417556

Other Notes
Contains varying amounts of anhydride
Packaging
1, 5 g in glass bottle
25 g in poly bottle
Application
Reagent used for
• Suzuki coupling using microwave and triton B catalyst1
• Pd-catalyzed direct arylation of pyrazoles with phenylboronic acids2
• Mizoroki-Heck and Suzuki-Miyaura coupling reactions catalyzed by palladium nanoparticles3
• Cu-catalyzed Petasis reactions4
• Tandem-type Pd(II)-catalyzed oxidative Heck reaction and intramolecular C-H amidation sequence5
• Ruthenium catalyzed direct arylation6
• Rh-catalyzed asymmetric conjugate additions7
• Ligand-free copper-catalyzed coupling of nitro arenes with arylboronic acids8
• Regioselective arylation and alkynylation by Suzuki-Miyaura and Sonogashira cross-coupling reactions9

REFERENCES

• GC reagent for diols: J. Chromat., 158, 33 (1978); 186, 307 (1979).
• For reactions of boronic acids, see Appendix 5.