Bromotrimethylsilane

• Catalog No.: A15334
• CAS Number: 2857-97-8
• M. F.: C3H9BrSi
• M. W.: 153.09306
• Purity: 97%, stab. with copper powder or silver wire

SYNONYMS

• Title: 三甲基溴硅烷
• IUPAC name: bromotrimethylsilane
• IUPAC Traditional name: bromotrimethylsilane
• Synonyms: Trimethylbromosilane; TMS bromide

DATABASE IDS

• CAS Number: 2857-97-8
• MDL Number: MFCD00000048
• EC Number: 220-672-0
• Beilstein Number: 1731135

PROPERTIES

• Purity: 97%, stab. with copper powder or silver wire
• Boiling Point: 78-80°C
• Density: 1.183
• Flash Point: -3°C(26°F)
• Melting Point: -44°C
• Refractive Index: 1.4250
• GHS Hazard statements: H225-H314-H318
• European Hazard Symbols: Corrosive (C)
• European Hazard Symbols: Flammable (F)
• GHS Precautionary statements: P210-P241-P303+P361+P353-P305+P351+P338-P405-P501A
• Risk Statements: 11-14-34
• Safety Statements: 16-26-36/37/39-45
• Storage Warning: Moisture Sensitive
• TSCA Listed: 是
• Hazard Class: 3
• UN Number: UN2924
• Packing Group: II

REFERENCES

• 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.
• Converts alcohols to alkyl bromides: Tetrahedron Lett., 4483 (1978), and acyl chlorides to acyl bromides: Synthesis, 216 (1981).
• 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).
• 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).