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2857-97-8 - Bromotrimethylsilane, 97%, stab. with copper powder or silver wire - TMS bromide - Trimethylbromosilane - A15334 - Alfa Aesar

A15334 Bromotrimethylsilane, 97%, stab. with copper powder or silver wire

CAS Number
TMS bromide

Size Price ($) Quantity Availability
10g 35.80
50g 119.00
250g 451.00
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Bromotrimethylsilane, 97%, stab. with copper powder or silver wire


Chemical Properties

Formula Weight
Melting point
Boiling Point
Flash Point
Refractive Index
Moisture Sensitive
Miscible with carbon tetrachloride, chloroform, dichloroethane, acetonitrile, toluene, dichloromethane and hexane.


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.


Moisture sensitive. Store in a cool place. Incompatible with strong acids, water and strong oxidizing agents.

Literature References

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.

GHS Hazard and Precautionary Statements

Hazard Statements: H225-H314-H318

Highly flammable liquid and vapour. Causes severe skin burns and eye damage. Causes serious eye damage.

Precautionary Statements: P210-P260-P280-P303+P361+P353-P305+P351+P338-P301+P330+P331-P304+P340-P310-P405-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Do not breathe dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/face protection. 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. IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Immediately call a POISON CENTER or doctor/physician. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

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