Tert-Butyllithium

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.

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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.