3-Fluorophenylboronic acid
Chemical Intermediates 2025-03-19
3-Fluorophenylboronic acid is an organoboron compound with a fluorine substituent on the phenyl ring and a boronic acid group. This compound is widely used in organic synthesis and material science due to its unique reactivity and structural properties.
Key Properties
| Property | Details |
|---|---|
| IUPAC Name | 3-Fluorophenylboronic acid |
| CAS Number | 768-35-4 |
| Molecular Formula | C₆H₆BFO₂ |
| Molecular Weight | 139.92 g/mol |
| Appearance | White to light yellow crystalline powder |
| Boiling Point | ~271.4°C |
| Melting Point | 214-218°C |
| Density | ~1.24 g/cm³ |
| Acidity (pKa) | 7.50±0.10 (predicted) |
| Solubility | Soluble in methanol |
| Synthesis Method | Grignard reagent reaction with trimethyl borate |
| Applications | Organic synthesis, medicinal chemistry, development of novel pharmaceuticals |
Synthesis
3-Fluorophenylboronic acid can be synthesized via a Grignard reagent reaction. The process involves reacting 3-fluorobromobenzene with magnesium turnings in 2-methyltetrahydrofuran under nitrogen atmosphere to generate the Grignard reagent, which is then reacted with trimethyl borate. After hydrolysis and recrystallization, 3-Fluorophenylboronic acid is obtained.
Applications
In organic synthesis, 3-Fluorophenylboronic acid serves as a valuable building block for the preparation of complex molecules, particularly those requiring defined stereochemistry and functionality. The fluorophenylboronic acid moiety makes it a promising candidate for the development of novel pharmaceuticals, agrochemicals, and functional materials. The boronic acid group can be further transformed into other functional groups, expanding the scope of its applications.
