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

CAS Number
2857-97-8
Synonyms
TMS bromide
Trimethylbromosilane

Stock No. Size Price ($) Quantity Availability
A15334-09 10g 36.90
A15334-18 50g 125.00
A15334-30 250g 474.00
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Bromotrimethylsilane, 97%, stab. with copper powder or silver wire

MDL
MFCD00000048
EINECS
220-672-0

Chemical Properties

Formula
C3H9BrSi
Formula Weight
153.09
Melting point
-44°
Boiling Point
78-80°
Flash Point
-3°(26°F)
Density
1.183
Refractive Index
1.4250
Storage & Sensitivity
Keep Cold. Moisture Sensitive.
Solubility
Miscible with carbon tetrachloride, chloroform, dichloroethane, acetonitrile, toluene, dichloromethane and hexane.

Applications

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.

Notes

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: H226-H314-H335

Flammable liquid and vapour. Causes severe skin burns and eye damage. May cause respiratory irritation.

Precautionary Statements: P210-P233-P235-P240-P241-P242-P243-P260-P264b-P271-P280-P301+P330+P331-P303+P361+P353-P304+P340-P305+P351+P338-P310-P363-P370+P378q-P501c

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Keep container tightly closed. Keep cool. Ground/bond container and receiving equipment. Use explosion-proof electrical/ventilating/lighting/ equipment. Use only non-sparking tools. Take precautionary measures against static discharge. Do not breathe dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Immediately call a POISON CENTER or doctor/physician. Wash contaminated clothing before reuse. In case of fire: Use CO2, dry chemical, or foam Dispose of contents/ container to an approved waste disposal plant

Other References

Beilstein
1731135
Hazard Class
8
Packing Group
II
Harmonized Tariff Code
2931.90
TSCA
Yes

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