What Is 2-Bromo-3,4,5-trifluoro-1-nitrobenzene?

2-Bromo-3,4,5-trifluoro-1-nitrobenzene (SKU B189361) is a polyhalogenated aromatic compound featuring a benzene ring substituted with a bromine atom at position 2, fluorine atoms at positions 3, 4, and 5, and a nitro group at position 1. The combination of strongly electron-withdrawing groups (nitro and fluorines) renders the ring highly electron-deficient, which dramatically activates specific ring positions toward nucleophilic aromatic substitution (SNAr). The bromine substituent simultaneously provides a handle for palladium-catalyzed cross-coupling reactions such as Suzuki-Miyaura, Buchwald-Hartwig, and Negishi couplings. This dual reactivity profile makes the compound an exceptionally useful building block in modern synthetic chemistry.

Chemical Properties and Structure

The molecular formula of 2-Bromo-3,4,5-trifluoro-1-nitrobenzene is C6HBrF3NO2 with a molecular weight of approximately 261.98 g/mol. The compound contains a single aromatic hydrogen, consistent with penta-substitution of the benzene ring. The electron-withdrawing nitro group at the 1-position acts synergistically with the adjacent fluorine atoms to substantially lower the electron density of the ring, particularly at the ipso and ortho/para positions relative to the nitro group. This electronic character is critical for SNAr reactivity. The C–F bonds in the ring are strong yet polar, and fluorine atoms ortho and para to the nitro group are the most susceptible to displacement by suitable nucleophiles under mild conditions. The C–Br bond, being weaker and more polarizable, is the preferred site for oxidative addition in transition-metal catalysis.

Handling, Storage, and Safety

As with most polyhalogenated nitroaromatic compounds, 2-Bromo-3,4,5-trifluoro-1-nitrobenzene should be handled with appropriate personal protective equipment including chemical-resistant gloves, safety goggles, and a lab coat. Operations should be performed in a well-ventilated fume hood to minimize inhalation exposure. The compound should be stored in a tightly sealed container in a cool, dry, and well-ventilated location, away from incompatible materials such as strong reducing agents and strong bases. Users are advised to consult the current Safety Data Sheet (SDS) provided by Aladdin Scientific for complete hazard information, first-aid measures, and disposal guidelines before use. Regulatory classifications and transport requirements should be verified with the SDS prior to shipping or procurement.

Note: Specific GHS hazard classifications, flash point, and exact LD50 values are not listed in the available source material. Please refer to the official Aladdin SDS for authoritative safety data.

Synthetic Applications and Reactivity

2-Bromo-3,4,5-trifluoro-1-nitrobenzene is valued primarily as a difunctionalized electrophilic scaffold in multistep synthesis. Its key applications include:

• Nucleophilic Aromatic Substitution (SNAr): The fluorine atoms activated by the ortho/para nitro group can be selectively displaced by amines, thiols, alkoxides, and other nucleophiles, enabling rapid diversification of the aromatic core. Selectivity between the fluorine positions can often be controlled by choice of nucleophile and reaction conditions.
• Palladium-Catalyzed Cross-Coupling: The aryl bromide undergoes efficient Suzuki-Miyaura coupling with boronic acids and esters, Buchwald-Hartwig amination with amines, and Negishi coupling with organozinc reagents, providing access to a wide variety of biaryl and heteroaryl frameworks.
• Pharmaceutical and Agrochemical Intermediates: Fluorinated nitroaromatics are important precursors in the synthesis of active pharmaceutical ingredients (APIs) and crop-protection compounds, where fluorine substitution is widely used to modulate metabolic stability, lipophilicity, and bioavailability.
• Reduction to Aniline Derivatives: The nitro group can be reduced to a primary amine under standard conditions (e.g., catalytic hydrogenation or iron/acetic acid), yielding a fluorinated bromoaniline for further functionalization.

Ordering and Quality Information

2-Bromo-3,4,5-trifluoro-1-nitrobenzene is available from Aladdin Scientific under SKU B189361. Researchers are encouraged to contact Aladdin Scientific's technical support team for information regarding available pack sizes, purity specifications, certificate of analysis (CoA), and current pricing. Bulk and custom quantities may be available upon request. For procurement and shipping queries, please visit the Aladdin Scientific website or contact customer service directly.

Note: Specific purity grades, available pack sizes, and pricing are not included in the current source material and should be confirmed directly with Aladdin Scientific prior to ordering.