Chemical Identity and Structure

5-Bromo-1-chloro-3-fluoro-2-iodobenzene (SKU B590271) is a tetrahalogenated benzene derivative in which bromine, chlorine, fluorine, and iodine substituents occupy four of the six ring positions. This unique arrangement places the iodo group ortho to chlorine and meta to fluorine, while bromine sits para to chlorine. The molecular formula is C₆H₂BrClFI with a molecular weight of approximately 371.34 g/mol.

The electronic properties of this compound are profoundly influenced by the combination of strongly electron-withdrawing fluorine and the larger, more polarizable halogen atoms. Fluorine exerts a dominant inductive withdrawal effect, while the heavier halogens provide sites for oxidative addition in metal-catalyzed reactions. The distinct reactivities of C–I, C–Br, C–Cl, and C–F bonds differ by several orders of magnitude, providing the chemist with orthogonal handles for sequential functionalization.

Reactivity and Synthetic Applications

The hallmark utility of 5-Bromo-1-chloro-3-fluoro-2-iodobenzene lies in the differential reactivity of its four C–halogen bonds. Under palladium or nickel catalysis, the C–I bond undergoes oxidative addition preferentially at low temperatures, enabling chemoselective Suzuki–Miyaura, Kumada, Negishi, Heck, and Sonogashira couplings at the iodo position without disturbing the remaining halogens. Subsequent transformations can then engage the C–Br bond under more forcing conditions, and finally the C–Cl bond, allowing stepwise construction of complex polyfunctionalized arenes.

The C–F bond, owing to the exceptional strength of the C(sp²)–F bond, typically remains intact under standard cross-coupling conditions, serving instead as a fluorine-retaining motif for pharmaceutical or agrochemical targets where aromatic fluorine improves metabolic stability and membrane permeability. Directed ortho-metalation strategies can also leverage the fluorine and the remaining halogens as directed metalation groups (DMGs), enabling introduction of additional functionality at defined ring positions.

Applications include the synthesis of multi-substituted biaryl frameworks, fluorinated heterocycles, and complex natural product analogs. The compound is particularly valuable in medicinal chemistry programs targeting kinases, GPCRs, and other biological targets where fluorine bioisosterism is exploited.

Handling, Storage, and Safety

As with all polyhalogenated aromatic compounds, 5-Bromo-1-chloro-3-fluoro-2-iodobenzene should be handled in a well-ventilated fume hood using appropriate personal protective equipment, including nitrile gloves, safety glasses, and a laboratory coat. Avoid inhalation of dust or vapors and contact with skin or eyes.

The compound should be stored in a tightly sealed container in a cool, dry location away from incompatible oxidizing agents and strong bases. Storage at room temperature under an inert atmosphere is generally recommended to maintain purity and prevent slow hydrolysis or decomposition. Refer to the Safety Data Sheet (SDS) supplied with SKU B590271 for detailed hazard classification, first-aid measures, and disposal guidance in accordance with local regulations.

Ordering and Specifications

5-Bromo-1-chloro-3-fluoro-2-iodobenzene is available from Aladdin Scientific under SKU B590271. The product is supplied at research-grade purity suitable for use as a synthetic building block in academic, pharmaceutical, and industrial research settings. For current pricing, available pack sizes, and lead times, please consult the Aladdin Scientific product page or contact our customer service team.

Bulk quantities and custom purity specifications may be available upon request. Certificate of Analysis (CoA) documents confirming purity by GC or HPLC, along with NMR spectral data where applicable, are available for each production lot.