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4-Fluorobromobenzene is synthesized via bromination of fluorobenzene in the presence of a Lewis acid catalyst such as iron(III) bromide or aluminium tribromide. [2]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.
Bromoform was discovered in 1832 by Löwig who distilled a mixture of bromal and potassium hydroxide, as analogous to preparation of chloroform from chloral. [5]Bromoform can be prepared by the haloform reaction using acetone and sodium hypobromite, by the electrolysis of potassium bromide in ethanol, or by treating chloroform with aluminium bromide.
Monobromotoluene isomers [1] [2] [3] Common name Structure Systematic name: 1-bromo-2-methylbenzene 1-bromo-3-methylbenzene 1-bromo-4-methylbenzene Molecular formula: C 7 H 7 Br (C 6 H 4 BrCH 3) Molar mass: 171.03 g/mol Appearance colorless liquid colorless liquid white crystalline solid CAS number [95-46-5] [591-17-3]
This reagent can be used, e.g. in the reaction with carbon dioxide to prepare benzoic acid. [4] Other methods involve palladium-catalyzed coupling reactions , such as the Suzuki reaction . Bromobenzene is used as a precursor in the manufacture of phencyclidine .
In the European Union, 1-bromopropane has been classified as reproductive toxicant per Registration, Evaluation, Authorisation and Restriction of Chemicals, which makes it a "substance of very high concern". [12] As of January 5, 2022, 1-bromopropane has been added to the United States Clean Air Act list of Hazardous Air Pollutants (HAP). [13]
Benzyl bromide is used in organic synthesis for the introduction of the benzyl groups when the less expensive benzyl chloride is insufficiently reactive. [6] [7] Benzylations are often achieved in the presence of catalytic amounts of sodium iodide, which generates the more reactive benzyl iodide in situ. [3]
The London Amendment in 1990 added bromomethane to the list of ODS to be phased out. Phase-out began in the United States in 1993, manufactured amounts being capped at the 1991 level. All developed countries in the Montreal Protocol reduced both manufactured and imported amounts by 25% in 1999, 50% 2001, 75% 2003, 100% 2005. [ 11 ]
In contrast, the boiling points of PhF and benzene are very similar, differing by only 4 °C. It is considerably more polar than benzene, with a dielectric constant of 5.42 compared to 2.28 for benzene at 298 K. [4] Fluorobenzene is a relatively inert compound reflecting the strength of the C–F bond.