Hexyllithium

n-Hexyllithium

Names
IUPAC name Hexyllithium
Other names HxLi, NHL
Identifiers
CAS Number	21369-64-2
3D model (JSmol)	Interactive image
ChemSpider	10626845
ECHA InfoCard	100.100.655
EC Number	404-950-0
PubChem CID	2733163
CompTox Dashboard (EPA)	DTXSID0074899
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
SMILES [Li ].CCCCC[CH2-]
Properties
Chemical formula	C6H13Li
Molar mass	92.11 g·mol−1
Solubility in water	Reacts with water
Solubility in other solvents	Soluble in hydrocarbons, ether, and THF
Acidity (pKa)	approx. 40
Hazards
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H250, H260, H314
Precautionary statements	P210, P222, P223, P231 P232, P260, P264, P280, P301 P330 P331, P302 P334, P303 P361 P353, P304 P340, P305 P351 P338, P310, P321, P335 P334, P363, P370 P378, P402 P404, P405, P422, P501
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 clusters in solution and as a solid.