2,3-difluoro-4-pentylphenyl boronic acid

Description

2,3-difluoro-4-pentylphenyl boronic acid is an arylboronic acid built on a benzene core, carrying a pentyl chain and two lateral fluorines on adjacent ring positions. It serves as the nucleophilic partner in Suzuki-Miyaura cross-coupling, transferring its aryl group to a palladium centre under basic conditions.

Lateral fluorination changes what the coupled product does, not how the coupling runs. Fluorine is small enough to leave molecular shape essentially intact, yet electronegative enough to raise the dipole moment and depress the melting point – which is why fluorinated aryl fragments dominate display-grade liquid crystal formulations.

Key data

• Catalogue code: KC1040
• Category: Boronic Acids

What the substitution pattern does

The pentyl chain places this compound at n=5 in its homologous series. Chain length is not a cosmetic variable here: each added methylene lowers the melting point unevenly and shifts the balance between nematic and smectic order, because an odd-numbered chain sets its terminal bond at a different angle to the molecular long axis than an even one. Homologues therefore alternate in behaviour rather than trending smoothly, and an odd-numbered member frequently outperforms both of its neighbours for a given formulation.

Two fluorines on adjacent ring positions point their combined dipole across the molecular long axis, not along it. Lateral 2,3-difluorination is the standard route to negative dielectric anisotropy – the property required by vertically aligned display modes, where the field must reorient molecules that start out perpendicular to the substrate.

Typical applications

• formulation of negative-dielectric-anisotropy mixtures for VA display modes
• Suzuki-Miyaura cross-coupling with aryl halides and triflates
• construction of biphenyl and terphenyl cores for liquid crystal mixtures
• late-stage arylation in medicinal and agrochemical discovery routes
• Chan-Lam C-N and C-O couplings under copper catalysis

Ordering

This compound is supplied to order. Pricing depends on quantity and on the specification you need, so it is quoted rather than listed – send an enquiry stating the quantity and any purity or analytical requirement, and you will receive a written quotation.

Handling and documentation

Supplied for laboratory and industrial use by trained personnel only. Not for use as a medicine, food, cosmetic or biocide, and not for administration to humans or animals. Safety documentation is issued with the order; this page is not a source of hazard information.