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Bromotrimethylsilane is used as a mild and selective reagent for cleavage of lactones, epoxides, acetals, phosphonate esters and certain ethers. Further, it is used as a brominating agent and an effective reagent for the formation of silyl enol ethers.
Silylating agent; see Appendix 4. About 104x more reactive than TMSCl in the conversion of ketones to their silyl enol ethers in the presence of Et3N: Liebigs Ann. Chem., 1718 (1980).
Converts alcohols to alkyl bromides: Tetrahedron Lett., 4483 (1978), and acyl chlorides to acyl bromides: Synthesis, 216 (1981).
Acetals, including MOM and THP ethers are readily cleaved, as are trityl and TBDMS ethers: Tetrahedron Lett., 25, 2515 (1984). Methyl glycosides are converted to the glycosyl bromides: Tetrahedron Lett., 22, 513 (1981).
Epoxides, oxetanes and THF are cleaved by the reagent: Synthesis, 383 (1981), as are small ring lactones: Angew. Chem. Int. Ed., 18, 689 (1979). The cleavage of acyclic ethers and esters is markedly catalyzed by IBr: J. Org. Chem., 48, 1678 (1983).
In combination with DMSO and Et3N, effects the bromolactonization of unsaturated acids: J. Chem. Soc., Perkin 1, 847 (1994).
Effective catalyst for Michaelis-Arbuzov rearrangement of trivalent organophosphorus P-O-R compounds to the corresponding P=O derivatives: Org. Lett., 5, 1661 (2003).
Compare also Iodotrimethylsilane, A12902.
Ferry, L.; Dorez, G.; Taguet, A.; Otazaghine, B.; Lopez-Cuesta, J. M. Chemical modification of lignin by phosphorus molecules to improve the fire behavior of polybutylene succinate. Polym. Degrad. Stab. 2015, 113, 135-143.
Willkomm, J.; Muresan, N. M.; Reisner, E. Enhancing H2 evolution performance of an immobilised cobalt catalyst by rational ligand design. Chem. Sci. 2015, 6, 2727-2736.
Hazard Statements: H225-H314-H318
Highly flammable liquid and vapour. Causes severe skin burns and eye damage. Causes serious eye damage.
Precautionary Statements: P210-P260u-P303+P361+P353-P305+P351+P338-P405-P501a
Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Do not breathe dusts or mists. 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. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.