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Tert-Butyllithium



Tert-Butyllithium
IUPAC name 2-Lithio-2-methylpropane
Other names tert-Butyllithium
Identifiers
CAS number 594-19-4
Properties
Molecular formula C4H9Li
Molar mass 64.05 g/mol
Appearance colorless solid
Density 0.66 g·cm-3
Melting point

36-40 °C

Solubility in water decomp by water
Solubility alkanes
Hazards
Main hazards flammable
Related Compounds
Related compounds N-Butyllithium, sec-Butyllithium
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and references

tert-Butyllithium is the chemical compound with the formula (CH3)3CLi. This organolithium compound is used as an extremely strong base in certain applications of organic synthesis. The compound exists as a cluster, is capable of deprotonating many carbon acids, including benzene.

Additional recommended knowledge

tert-Butyllithium is extremely flammable and ignites spontaneously in air. It must be kept and handled under a dry nitrogen atmosphere. Even with standard dry nitrogen conditions (such as a Schlenk line), this presents a hazard - if the tBuLi is drawn into a syringe through a septum, when the needle is removed the tip of the needle will catch fire - while this is not always a problem, the combustion can block the tube, leaving the chemist holding a tube of very dangerous solution with no means of delivering it back to the nitrogen atmosphere. The solution is to keep the tip of the needle in an inert atmosphere. A short glass tube, with a septum in each end, flushed with inert gas, is pierced with the needle and then the tip is drawn into the tube after the liquid has been drawn.

 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Tert-Butyllithium". A list of authors is available in Wikipedia.
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