2,5-Dibromophenylboronic Acid | CAS 1008106-93-1 | ≥97%

Suzuki–Miyaura Cross-Coupling

2,5-Dibromophenylboronic acid participates in palladium-catalysed Suzuki–Miyaura cross-coupling via its boronic acid group, enabling carbon–carbon bond formation with aryl halides, vinyl halides, and triflates under standard conditions. Both aryl bromide handles remain intact and available for further synthetic elaboration after the boronic acid has been consumed in coupling, providing a route to dibromo-functionalised biaryl products that serve as advanced intermediates for subsequent transformations.

• Compatible with Pd(PPh₃)₄, Pd(dppf)Cl₂, and Pd₂(dba)₃/phosphine catalyst systems across THF, DMF, toluene, and aqueous-organic solvent mixtures
• Applied in the construction of dibromo-biaryl intermediates used as further coupling substrates in multi-step synthetic sequences

Trifluoroborate Salt Preparation

Documented in the primary literature (Eur. J. Org. Chem., 2013, p. 3023–3032) as a direct precursor to potassium (2,5-dibromophenyl)trifluoroborate — a bench-stable, crystalline boron reagent used as an alternative to the free boronic acid in Suzuki–Miyaura coupling and iterative cross-coupling workflows. Trifluoroborate salts offer improved stability toward protodeboronation and allow orthogonal coupling strategies under anhydrous conditions.

• Conversion to the trifluoroborate salt is performed using KHF₂ and proceeds in good yield without isolation of intermediates
• The resulting trifluoroborate is compatible with coupling conditions where the free boronic acid is prone to hydrolytic decomposition

Conjugated Polymer Synthesis & OLED Materials

Dibromoarenes are well-established monomers in Suzuki polycondensation (SPC) — the polymer-forming extension of the Suzuki–Miyaura reaction — in which alternating dibromo and diboronic acid monomers undergo step-growth coupling to produce conjugated polyarylene backbones. This compound is classified under OLED Materials and Small Molecule Semiconductor Building Blocks by established chemical suppliers, consistent with its role as a phenylene-based building block for conjugated polymer and oligomer architectures used in organic light-emitting diodes (OLEDs), organic field-effect transistors (OFETs), and related organic electronic devices.

• Dibromobenzene derivatives including 1,4-dibromobenzene and substituted analogues are reported monomers in SPC for the synthesis of poly(p-phenylene)s and amphiphilic polyphenylenes
• Applied in AA/BB-type SPC with diboronic acid esters under Pd catalysis to produce conjugated polyarylene chains with controlled backbone geometry and optoelectronic properties

Pharmaceutical & Fine Chemical Intermediate

Classified by multiple chemical suppliers as a pharmaceutical intermediate and fine chemical building block. The combination of a boronic acid group and two aryl bromide handles on a single phenylene unit provides three orthogonal sites for elaboration, making this compound a compact trifunctional scaffold for the construction of multi-substituted arene cores in drug discovery and agrochemical research programmes.

• Used as a starting material or intermediate in the preparation of asymmetrically substituted phenylene-based frameworks
• Applied in fragment-based synthesis and building block assembly strategies where sequential functionalisation of the arene core is required