https://wikimd.org/index.php?action=history&feed=atom&title=Tert-ButyllithiumTert-Butyllithium - Revision history2026-05-11T19:20:29ZRevision history for this page on the wikiMediaWiki 1.44.2https://wikimd.org/index.php?title=Tert-Butyllithium&diff=5800365&oldid=prevPrab: CSV import2024-05-19T20:22:16Z<p>CSV import</p>
<p><b>New page</b></p><div>[[file:tert-Butyllithium,_Mesomerie.svg|thumb|left]] [[file:Zersetzung_THF_tert-Butyllithium1.svg|thumb|left]] [[file:Zersetzung_THF_tert-Butyllithium2.svg|thumb|right]] '''Tert-Butyllithium''' ('''t-BuLi''') is a highly reactive [[organolithium reagent]] with the chemical formula (CH₃)₃CLi. It is commonly used in [[organic synthesis]] for the deprotonation of weak acids and as a strong base in various chemical reactions.<br />
<br />
==Properties==<br />
Tert-Butyllithium is a colorless liquid that is highly flammable and pyrophoric, meaning it can ignite spontaneously upon exposure to air. It is typically handled in a [[hydrocarbon]] solvent such as [[hexane]] or [[pentane]] to mitigate its reactivity. The compound is known for its strong basicity and nucleophilicity, making it a valuable reagent in [[synthetic chemistry]].<br />
<br />
==Synthesis==<br />
Tert-Butyllithium is synthesized by the reaction of [[tert-butyl chloride]] with [[lithium metal]] in the presence of a hydrocarbon solvent. The reaction proceeds as follows:<br />
<br />
(CH₃)₃CCl + 2Li → (CH₃)₃CLi + LiCl<br />
<br />
This process requires careful control of temperature and exclusion of moisture and air to prevent unwanted side reactions.<br />
<br />
==Applications==<br />
Tert-Butyllithium is widely used in [[organic chemistry]] for various applications, including:<br />
<br />
* **Deprotonation Reactions**: It is used to deprotonate weak acids, such as [[alcohols]], [[amines]], and [[alkynes]], to generate the corresponding [[carbanions]].<br />
* **Metalation Reactions**: t-BuLi is employed to introduce lithium into organic molecules, a process known as [[metalation]].<br />
* **Polymerization**: It is used as an initiator in the [[anionic polymerization]] of certain monomers, such as [[styrene]] and [[butadiene]].<br />
<br />
==Safety and Handling==<br />
Due to its extreme reactivity, tert-butyllithium must be handled with great care. It is typically stored under an inert atmosphere, such as [[nitrogen]] or [[argon]], to prevent contact with air and moisture. Proper personal protective equipment (PPE), including gloves and eye protection, is essential when working with this reagent.<br />
<br />
==See Also==<br />
* [[Organolithium reagent]]<br />
* [[Deprotonation]]<br />
* [[Nucleophilicity]]<br />
* [[Anionic polymerization]]<br />
<br />
==References==<br />
{{Reflist}}<br />
<br />
==External Links==<br />
{{Commons category|Tert-Butyllithium}}<br />
<br />
[[Category:Organolithium compounds]]<br />
[[Category:Reagents for organic chemistry]]<br />
[[Category:Pyrophoric chemicals]]<br />
[[Category:Chemical synthesis]]<br />
<br />
{{chemistry-stub}}</div>Prab