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Bromoethane, also known as ethyl bromide, is a chemical compound of the haloalkanes group. It is abbreviated by chemists as EtBr (which is also used as an abbreviation for ethidium bromide ). This volatile compound has an ether-like odor.
Bromomethane, commonly known as methyl bromide, is an organobromine compound with formula C H 3 Br.This colorless, odorless, nonflammable gas is produced both industrially and biologically.
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.
The latter reaction is also viable laboratory synthesis. One laboratory technique for substitutive bromination treats propanol with a mixture of hydrobromic and sulfuric acids: CH 3 CH 2 CH 2 OH + HBr → CH 3 CH 2 CH 2 Br + H 2 O. Alternate synthetic routes include treating propanol with phosphorus tribromide [4] or via a Hunsdiecker reaction ...
On an industrial scale, base-promoted dehydrohalogenations as described above are disfavored. The disposal of the alkali halide salt is problematic. Instead thermally-induced dehydrohalogenations are preferred. One example is provided by the production of vinyl chloride by heating 1,2-dichloroethane: [3] CH 2 Cl-CH 2 Cl → CH 2 =CHCl + HCl
Short-chain alkyl halides are often carcinogenic.. The bromine atom is at the secondary position, which allows the molecule to undergo dehydrohalogenation easily to give propene, which escapes as a gas and can rupture closed reaction vessels.
Due to its toxicity, it is not used as a riot control agent anymore. Bromoacetone is a versatile reagent in organic synthesis. It is, for example, the precursor to hydroxyacetone by reaction with aqueous sodium hydroxide. [6]
For example, the synthesis of macrocidin A, a fungal metabolite, involves an intramolecular ring closing step via an S N 2 reaction with a phenoxide group as the nucleophile and a halide as the leaving group, forming an ether. [2] Reactions such as this, with an alkoxide as the nucleophile, are known as the Williamson ether synthesis.