Hexyllithium

n-Hexyllithium

Names
IUPAC name Hexyllithium
Other names HxLi, NHL
Identifiers
CAS Number	21369-64-2
ChemSpider	10626845
ECHA InfoCard	100.100.655
EC Number	404-950-0
InChI InChI=1S/C6H13.Li/c1-3-5-6-4-2;/h1,3-6H2,2H3; Key: RMKNFFPDYCVCDI-UHFFFAOYSA-N InChI=1/C6H13.Li/c1-3-5-6-4-2;/h1,3-6H2,2H3;/rC6H13Li/c1-2-3-4-5-6-7/h2-6H2,1H3 Key: RMKNFFPDYCVCDI-ZLJYRZARAB
Properties
Chemical formula	C6H13Li
Molar mass	92.11 g·mol−1
Solubility in water	Reacts violently
Solubility in other solvents	Soluble in hydrocarbons, ether, and THF
Acidity (pKa)	approx. 40
Hazards
GHS pictograms
GHS signal word	DANGER
GHS hazard statements	H260, H250, H314
Related compounds
Related organolithium compounds	Methyllithium n-Butyllithium tert-Butyllithium Phenyllithium Neopentyllithium Propyllithium
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

n-Hexyllithium, C₆H₁₃Li, sometimes abbreviated to HxLi or NHL, is an organolithium compound used in organic synthesis as a strong base or as a lithiation 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, 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 a clusters in solution and as a solid.