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[1]
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H250, H260, H314 [note 1]
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.^[2] 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.^[3]