Bromotrimethylsilane, 97%, stab. with copper powder or silver wire, Thermo Scientific Chemicals

General References:

1. 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).
2. Converts alcohols to alkyl bromides: Tetrahedron Lett., 4483 (1978), and acyl chlorides to acyl bromides: Synthesis, 216 (1981).
3. 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).
4. 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).
5. In combination with DMSO and Et₃N, effects the bromolactonization of unsaturated acids: J. Chem. Soc., Perkin 1, 847 (1994).
6. Effective catalyst for Michaelis-Arbuzov rearrangement of trivalent organophosphorus P-O-R compounds to the corresponding P=O derivatives: Org. Lett., 5, 1661 (2003).
7. Compare also Iodotrimethyl silane, A12902.
8. 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.
9. 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.