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Bromotrimethylsilane

Catalog No. A15334 Name Alfa Aesar
CAS Number 2857-97-8 Website
M. F. C3H9BrSi Telephone
M. W. 153.09306 Fax
Purity 97%, stab. with copper powder or silver wire Email
Storage Chembase ID: 78793

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 Pictograms GHS02
GHS Pictograms GHS05
GHS Hazard statements H225-H314-H318
European Hazard Symbols Corrosive Corrosive (C)
European Hazard Symbols Flammable 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
Hazard Class 3
UN Number UN2924
Packing Group II

DETAILS

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).