Hexyllithium

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.

n-Hexyllithium
Names
IUPAC name
Hexyllithium
Other names
HxLi, NHL
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.100.655
EC Number
  • 404-950-0
  • 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
  • [Li+].CCCCC[CH2-]
Properties
C6H13Li
Molar mass 92.11 g·mol−1
Reacts with water
Solubility in other solvents Soluble in hydrocarbons, ether, and THF
Acidity (pKa) approx. 40
Hazards[1]
GHS labelling:
Water-react. 1, Pyr. Sol. 1Skin Corr. 1A
Danger
H250, H260, H314 [note 1]
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
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

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]

Notes and references

Notes
  1. Within the European Union, the following additional hazard statement (EUH014) must also be displayed on labelling: Reacts violently with water.

References
  1. Index no. 003-002-00-X of Annex VI, Part 3, to Regulation (EC) No 1272/2008 of the European Parliament and of the Council of 16 December 2008 on classification, labelling and packaging of substances and mixtures, amending and repealing Directives 67/548/EEC and 1999/45/EC, and amending Regulation (EC) No 1907/2006. OJEU L353, 31.12.2008, pp 1–1355 at p 340.
  2. Terry L. Rathman "Hexyllithium" Encyclopedia of Reagents for Organic Synthesis, 2001. doi:10.1002/047084289X.rh024
  3. Abel, Edward W.; Stone, F. Gordon A.; Wilkinson, Geoffrey, eds. (1995), Main-Group Metal Organometallics in Organic Synthesis, Comprehensive Organometallic Chemistry II, vol. 11, Elsevier, p. 3, ISBN 0-08-042318-3.
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