Chlorine (triisopropyl) silane
Structural formula | ||||||||||||||||
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General | ||||||||||||||||
Surname | Chlorine (triisopropyl) silane | |||||||||||||||
other names |
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Molecular formula | C 9 H 21 ClSi | |||||||||||||||
Brief description |
colorless to yellow liquid |
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properties | ||||||||||||||||
Molar mass | 192.81 g mol −1 | |||||||||||||||
Physical state |
liquid |
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density |
0.908 g cm −3 (20 ° C) |
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boiling point |
197-200 ° C (983 hPa) |
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Vapor pressure |
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solubility |
Decomposes with water |
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safety instructions | ||||||||||||||||
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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 .