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Pyridine hydrobromide perbromide is used as a brominating reagent in alfa-bromination and alfa-thiocyanation of ketones, phenols, unsaturated and aromatic ethers. It is used as a raw material in the preparation of beta-adrenergic blocking agents. Furthermore, it is used as an analytical reagent.
Stable, crystalline, readily-handled source of bromine, useful for a wide range of brominations, including ɑ-bromination of ketones: J. Am. Chem. Soc., 70, 417 (1948), and conversion of alkenes to vic-dibromides. See, for example: Org. Synth. Coll., 5, 604 (1973), Note 2. The rate of addition to alkenes increases markedly on increased substitution, so that selective bromination of the more substituted of two double bonds can be achieved: Synthesis, 966 (1979).
In pyridine, cyclopentenones are converted directly to their ɑ-bromo derivatives (addition-elimination): Synth. Commun., 18, 1323 (1988).
Selective monobromination of anilines, predominantly at the para-position, can be effected in THF: Synth. Commun., 23, 855 (1993). In aqueous AcOH, alkyl aryl ethers are p-brominated in high yield: Synth. Commun., 28, 499 (1998), whereas aryl methyl ethers are demethylated on heating in xylene: Indian J. Chem., 33B, 288 (1994). Cleaves thioacetals in the presence of TBAB: J. Org. Chem., 46, 1745 (1981).
Hu, Y.; Ju, L.; Lu, L.; Ma, H.; Yu, X. Stereoselective alpha-indolylation of enals via an organocatalytic formal cross-coupling with indoles. Org. Biomol. Chem. 2015, 13 (33), 8869-8874.
Amaya, T.; Hirao, T. Chemistry of Sumanene. Chem Rec 2015, 15 (1), 310-321.
Hazard Statements: H314-H318
Causes severe skin burns and eye damage. Causes serious eye damage.
Precautionary Statements: P260u-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501a
IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.