I agree Our site saves small pieces of text information (cookies) on your device in order to deliver better content and for statistical purposes. You can disable the usage of cookies by changing the settings of your browser. By browsing our website without changing the browser settings you grant us permission to store that information on your device.
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. 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.