2-Bromophenylboronic Acid

Technical Specifications

Product Description & Scientific Applications

2-Bromophenylboronic acid (2-bromobenzeneboronic acid, o-bromophenylboronic acid) carries the boronic acid and the aryl bromide ortho to each other. This ortho relationship governs its Lewis acidity, substrate approach, chemoselectivity, and intramolecular/sequential coupling behaviour.

It may contain small amounts of the cyclic anhydride 2-bromophenylboroxine; the two forms re-equilibrate under aqueous or basic coupling conditions, with minor effect on yield.

Applications and Reactions

• Suzuki–Miyaura coupling at the boronic acid: Couples with aryl and heteroaryl electrophiles under matched Pd/phosphine/base conditions to install an ortho-bromoaryl group. Where the Ar–Br is reserved for a later intramolecular step, choose catalyst and electrophile to avoid premature oxidative addition at that bond.
• Tandem Suzuki / intramolecular arylation to fused frameworks: The retained ortho-Ar–Br serves intramolecular Pd-catalysed C–H or ring-closing arylation — giving fused-purine and phenanthridine systems (consecutive Suzuki then C–H arylation) and, by related tandem Suzuki/C–H arylation, fluoranthene-type polycyclic aromatics.
• Iterative cross-coupling with boron masking: Masking the boronic acid as its anthranilamide (AAM) boronate, which is inert under Suzuki conditions, allows coupling at the aryl bromide first; deprotection then reveals the boronic acid for the next step.
• Organocatalyst for direct amidation of carboxylic acids: A member of the Hall ortho-halogenoarylboronic acid catalyst family for direct amide formation from carboxylic acids and amines. Under room-temperature dichloromethane / 4 Å molecular sieve conditions it is active but less effective than the ortho-iodo and optimised MIBA catalysts.
• Organocatalyst for Diels–Alder reactions of α,β-unsaturated and 2-alkynoic carboxylic acids: Catalyses via reversible boronic-acid activation of the carboxyl group. Reported for acrylic-acid Diels–Alder chemistry and the most efficient catalyst screened for [4+2] cycloadditions of 2-alkynoic acids, where activation lowers the dienophile LUMO through a mixed acyl boronate intermediate.

For further reading: Boron reagent selection for Suzuki–Miyaura coupling

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