1. Uses

2. Production

3. Reactivity and synthesis

4. Safety

5. References

Uses

The electronegativity (withdrawal of electron density) of the halogens present (bromine and fluorine) on 4-bromofluorobenzene cause deactivation of the benzene ring and direct reactivity to ortho and para positions on the ring.^[2] This redirection of reactivity makes it useful as a precursor other compounds that serve a wide variety of needs.

The bromine on 4-bromofluorobenzene allows it to become a Grignard reagent when reacted with magnesium metal.^[3] Preparation of a Grignard reagent using it makes it useful as an intermediate in the synthesis of atypical antipsychotic agents (especially those with a 4-fluorophenyl moiety),^[1][4] and in pesticides such as Flusilazole.^[5]

This compound is also used as a tuning solution, internal standard, and/or surrogate (a compound that is similar in chemical composition to the analyte(s) of interest and is spiked into environmental and batch quality control samples prior to sample preparation and analysis) in several EPA gas chromatography methods, such as those for drinking water, wastewater pollutants, and organic pollutant monitoring in groundwater, wastewater, and solid waste.^[1]

Production

4-Bromofluorobenzene is regarded by the Toxic Substances Control Act as a high production volume chemical, that is, a chemical that 1 million pounds (about 500 tonnes) per year is either produced in or imported to the United States. As of 2002, companies producing or importing this compound reported 10 million (4,536,000 kilograms) used. This is up from 500,000 pounds (226,800 kilograms) used in 1986, as reported in the Inventory Update Rule of the Toxic Substances Control Act.^[1]

Reactivity and synthesis

Halogenated aromatic compounds are relatively unreactive, as reactivity is generally negatively related to degree of substitution of halogen atoms for hydrogen atoms.^[1]

4-Bromofluorobenzene is most commonly synthesized via electrophilic halogenation, a type of electrophilic aromatic substitution with fluorobenzene, bromine as the reagents and with a Lewis acid catalyst (i.e. iron(III) bromide or aluminium tribromide) .^[1] The fluorine on fluorobenzene is a para director,^[6] as it withdraws electron density from the ortho and meta ring positions.^[7] Below is the reaction mechanism:

Safety

This compound is a flammable liquid and vapor. It causes eye irritation, and may be harmful if swallowed, inhaled, or absorbed through the skin. It can cause depression of the central nervous system. It has a flash point of 53 °C.^[8]

References

• Liliana Delfino
• Liliana Diaz Mindurry
• Liliana Dobrescu
• Liliana DomAnguez
• Liliana Díaz Mindurry
• Liliana Fellner
• Liliana Flores
• Liliana Greenfield-Sanders
• Liliana Hernández
• Liliana Lozano
• Liliana Martinelli
• Liliana Mayo
• Liliana mayo
• Liliana Nastase
• Liliana Negre de Alonso
• Liliana Palihovici
• Liliana Popescu
• Liliana Porter
• Liliana Rojas-Suarez
• LiliAna Rose
• Liliana Rose
• Liliana Rose Andreano
• Lilian Astier
• Liliana Todorova
• Liliana Tomova