''n''-Hexyllithium, C₆H₁₃Li, sometimes abbreviated to HxLi or NHL, is an

organolithium compound In organometallic chemistry, organolithium reagents are chemical compounds that contain carbon–lithium (C–Li) bonds. These reagents are important in organic synthesis, and are frequently used to transfer the organic group or the lithium atom ...

used in

organic synthesis Organic synthesis is a special branch of chemical synthesis and is concerned with the intentional construction of organic compounds. Organic molecules are often more complex than inorganic compounds, and their synthesis has developed into one o ...

as a

strong base In chemistry, there are three definitions in common use of the word base, known as Arrhenius bases, Brønsted bases, and Lewis bases. All definitions agree that bases are substances that react with acids, as originally proposed by G.-F. ...

or as a

lithiation In organometallic chemistry, organolithium reagents are chemical compounds that contain carbon–lithium (C–Li) bonds. These reagents are important in organic synthesis, and are frequently used to transfer the organic group or the lithium atom ...

reagent. It is usually encountered as a colorless or pale yellow solution in hexanes. Such solutions are highly sensitive to air and can ignite when treated with water. In terms of chemical properties, hexyllithium and ''n''-butyllithium (BuLi) are very similar. As a base, hexyllithium generates ''n''-hexane as a byproduct rather than gaseous

butane Butane () or ''n''-butane is an alkane with the formula C4H10. Butane is a gas at room temperature and atmospheric pressure. Butane is a highly flammable, colorless, easily liquefied gas that quickly vaporizes at room temperature. The name bu ...

, which results from the use of BuLi. Another advantage for HxLi is that it is slightly less reactive. Both of these aspects encourage industrial applications. It is commercially available as a solution in mixed hexanes, usually at a concentration of about 2 M for laboratory use or 33% for industrial use. As for BuLi, the structure and formula for HxLi are often depicted as a monomer. Like all organolithium compounds, it exists as clusters in solution and as a solid..

Notes and references

Notes

References

{{Lithium compounds Organolithium compounds Reagents for organic chemistry