Chlorine (triisopropyl) silane

Structural formula
General
Surname	Chlorine (triisopropyl) silane
other names	Chlorotriisopropylsilane; Triisopropylchlorosilane; Triisopropylsilyl chloride; TIPSCl;
Molecular formula	C 9 H 21 ClSi
Brief description	colorless to yellow liquid
External identifiers / databases
EC number	603-492-0
ECHA InfoCard	100.132.307
PubChem	139400
Wikidata	Q2453270
properties
Molar mass	192.81 g mol −1
Physical state	liquid
density	0.908 g cm −3 (20 ° C)
boiling point	197-200 ° C (983 hPa)
Vapor pressure	4.08 hPa (20 ° C); 10 hPa (80 ° C);
solubility	Decomposes with water
safety instructions
GHS labeling of hazardous substances danger
H and P phrases	H: 314
	P: 280-301 + 330 + 331-305 + 351 + 338
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Chlor (triisopropyl) silane (also triisopropylsilyl chloride, TIPSCl) is an organosilicon compound that is used to introduce the triisopropylsilyl protective group for alcohols in synthetic organic chemistry .

properties

Chlor (triisopropyl) silane is a colorless to yellow compound that is liquid at room temperature and boils at 198 ° C under a pressure of 983 hPa . It decomposes with water to form hydrogen chloride .

use

TIPSCl is used to introduce a triisopropylsilyl protecting group for alcohols. For this purpose, the alcohol is first deprotonated using a base . The alcoholate formed then attacks the silicon with a nucleophile , splitting off the chloride .

The relatively base- and acid-stable silyl ether can be deprotected with fluoride sources such as TBAF ( tetrabutylammonium fluoride ).

Individual evidence

↑ ^a ^b ^c ^d ^e data sheet chlorotriisopropylsilane (PDF) from Merck , accessed on April 24, 2011.
↑ ^a ^b ^c ^d ^e data sheet triisopropylsilyl chloride from AlfaAesar, accessed on March 30, 2010 ( PDF )(JavaScript required) .
^ RF Cunico and L. Bedell: The Triisopropylsilyl Group as a Hydroxyl-Protecting Function in Journal of Organic Chemistry . 1980: 45: 4797-4798. doi : 10.1021 / jo01311a058 .

[merck-1] ↑ ^a ^b ^c ^d ^e data sheet chlorotriisopropylsilane (PDF) from Merck , accessed on April 24, 2011.

[alfa-2] ↑ ^a ^b ^c ^d ^e data sheet triisopropylsilyl chloride from AlfaAesar, accessed on March 30, 2010 ( PDF )(JavaScript required) .

[3] RF Cunico and L. Bedell: The Triisopropylsilyl Group as a Hydroxyl-Protecting Function in Journal of Organic Chemistry . 1980: 45: 4797-4798. doi : 10.1021 / jo01311a058 .