Chemical Identity and Physical Properties

3-Bromo-5-iodobenzonitrile is a meta-disubstituted aryl halide in which bromine and iodine substituents occupy the 3- and 5-positions of a benzonitrile scaffold. The presence of the electron-withdrawing nitrile group at C-1 renders the ring electron-deficient, moderately activating both carbon–halogen bonds toward oxidative addition with low-valent transition-metal catalysts.

The compound is typically a white to off-white crystalline solid at room temperature. Its molecular weight is approximately 307.91 g/mol (C₇H₃BrIN). The nitrile group is IR-active and provides a characteristic strong absorption near 2230 cm⁻¹, useful for confirming compound identity by FT-IR spectroscopy. The two distinct halogens are readily distinguishable by ¹³C NMR and mass spectrometry.

Review flag: Exact melting point, logP, and solubility data were not available in the source material and have been omitted to avoid unverified claims.

Synthetic Applications and Reactivity

The principal synthetic value of 3-Bromo-5-iodobenzonitrile lies in its two chemically distinct C–halogen bonds. Because carbon–iodine bonds undergo oxidative addition to Pd(0) and Ni(0) species faster than carbon–bromine bonds under mild conditions, researchers can exploit the chemoselectivity of the C–I bond to install one coupling partner first, then activate the remaining C–Br bond in a subsequent step under modified conditions.

Common reaction manifolds include:

• Suzuki–Miyaura coupling – selective mono-arylation or sequential diarylation using arylboronic acids or esters.
• Sonogashira coupling – introduction of terminal alkynes at the iodo position under Pd/Cu catalysis.
• Negishi coupling – reaction with organozinc reagents for C–C bond formation.
• Buchwald–Hartwig amination – formation of C–N bonds with primary or secondary amines, valuable for medicinal chemistry programmes.
• Cyanation and other nucleophilic substitutions – the electron-poor ring can facilitate ipso-substitution reactions under forcing conditions.

The nitrile group itself may be transformed downstream into carboxylic acids (hydrolysis), primary amines (reduction), tetrazoles (1,3-dipolar cycloaddition), or heterocyclic motifs, further broadening the utility of this building block.

Safe Handling, Storage and Disposal

As with all organohalide reagents, appropriate precautions must be observed when working with 3-Bromo-5-iodobenzonitrile. Users should consult the current Safety Data Sheet (SDS) before use.

Personal Protective Equipment (PPE): Wear appropriate chemical-resistant gloves (e.g., nitrile gloves), a laboratory coat, and safety goggles. Where dust generation is possible, use a NIOSH-approved particulate respirator or work inside a fume hood.

Storage: Store in a tightly sealed container in a cool, dry, well-ventilated location away from direct light and incompatible materials (strong oxidisers, strong bases). Recommended storage temperature is typically ambient or slightly below; confirm with the SDS supplied with your shipment.

Disposal: Dispose of waste material and its container in accordance with local, regional, and national regulations. Do not discharge to drains or waterways. Halogenated organic waste should be segregated and handed to a licensed waste-disposal contractor.

Review flag: Specific GHS hazard classifications (H-statements, P-statements) and exact storage temperature range were not confirmed from supplier SDS in the source material. These must be verified against the current Aladdin Scientific SDS before publication.

Quality, Purity and Ordering Information

Aladdin Scientific supplies 3-Bromo-5-iodobenzonitrile under SKU B732353. For optimal experimental outcomes, researchers should confirm purity specifications at the time of ordering, as reagent-grade purity is critical for reproducible cross-coupling reactions where catalyst poisoning by trace impurities can significantly reduce yields.

Typical analytical characterisation for this class of compound includes:

• HPLC or GC purity determination
• ¹H and ¹³C NMR spectral confirmation
• Elemental analysis or high-resolution mass spectrometry (HRMS)

Lot-specific certificates of analysis (CoA) are available on request. Contact Aladdin Scientific technical support or your local sales representative for bulk-quantity pricing, custom pack sizes, or additional analytical data.

Review flag: Specific purity percentage (e.g., ≥97%) was not confirmed in the source material and must be retrieved from the product listing or CoA before publication.