Bromotrimethylsilane

Structural formula
General
Surname	Bromotrimethylsilane
other names	TMBS; Trimethylbromosilane; Trimethylsilyl bromide;
Molecular formula	C 3 H 9 BrSi
Brief description	colorless liquid
External identifiers / databases
ECHA InfoCard	100,018,793
PubChem	76113
ChemSpider	68599
Wikidata	Q62455523
properties
Molar mass	153.09 g mol −1
Physical state	liquid
density	1.16 g cm −3 (25 ° C)
Melting point	−44 ° C
boiling point	79 ° C
solubility	miscible with carbon tetrachloride , chloroform , dichloroethane , acetonitrile , toluene , dichloromethane and hexane
Refractive index	1.424 (20 ° C)
safety instructions
H and P phrases	H: 226-314
	P: 280-305 + 351 + 338-310
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

Bromotrimethylsilane is a chemical compound from the group of silanes .

Extraction and presentation

Bromotrimethylsilane is produced on a laboratory scale from trimethylsilyl-4-bromo-2-alkenoates in almost quantitative yield. The compound can also be prepared by reacting trimethylsilyl chloride with magnesium bromide or other methods.

properties

Bromotrimethylsilane is a colorless to light yellow liquid.

use

Bromotrimethylsilane is used as a mild and selective reagent for the cleavage of lactones, epoxides, acetals, phosphonate esters and certain ethers. It is also used as a brominating agent and an effective reagent for the formation of silyl enol ethers.

Individual evidence

^ ^A ^b ^c Philip L. Fuchs: Reagents for Silicon-Mediated Organic Synthesis . John Wiley & Sons, 2013, ISBN 978-1-118-63613-8 ( limited preview in Google Book Search).
↑ ^a ^b ^c ^d ^e ^f ^g Data sheet trimethylsilyl bromide, 97% from Sigma-Aldrich , accessed on March 25, 2019 ( PDF ).
↑ ^a ^b ^c data sheet bromotrimethylsilane, 97%, stab. with copper powder or silver wire at AlfaAesar, accessed on March 25, 2019 ( PDF )(JavaScript required) .
↑ M. Bellassoued, A. El Borgi, M. Gaudemar: A New Convenient Laboratory Synthesis of Trimethylsilyl Bromide. In: Synthetic Communications . 15, 2006, p. 973, doi : 10.1080 / 00397918508076828 .
^ John W Gillard, Mervyn Israel: Trimethylsilyl bromide as a mild, stereoselective anomeric brominating agent. In: Tetrahedron Letters . 22, 1981, p. 513, doi : 10.1016 / S0040-4039 (01) 90142-X .

[Philip_L._Fuchs-1] A ^b ^c Philip L. Fuchs: Reagents for Silicon-Mediated Organic Synthesis . John Wiley & Sons, 2013, ISBN 978-1-118-63613-8 ( limited preview in Google Book Search).

[Sigma-2] ↑ ^a ^b ^c ^d ^e ^f ^g Data sheet trimethylsilyl bromide, 97% from Sigma-Aldrich , accessed on March 25, 2019 ( PDF ).

[Alfa-3] ta sheet bromotrimethylsilane, 97%, stab. with copper powder or silver wire at AlfaAesar, accessed on March 25, 2019 ( PDF )(JavaScript required) .

[DOI10.1080/00397918508076828-4] M. Bellassoued, A. El Borgi, M. Gaudemar: A New Convenient Laboratory Synthesis of Trimethylsilyl Bromide. In: Synthetic Communications . 15, 2006, p. 973, doi : 10.1080 / 00397918508076828 .

[DOI10.1016/S0040-4039(01)90142-X-5] John W Gillard, Mervyn Israel: Trimethylsilyl bromide as a mild, stereoselective anomeric brominating agent. In: Tetrahedron Letters . 22, 1981, p. 513, doi : 10.1016 / S0040-4039 (01) 90142-X .