Hexyllithium

n-Hexyllithium
IUPAC name

Hexyllithium
Other names

HxLi, NHL
Identifiers
CAS number 21369-64-2
ChemSpider 10626845
EC-number 404-950-0
Properties
Molecular formula C6H13Li
Molar mass 92.11 g mol−1
Solubility in water reacts violently
Acidity (pKa) approx. 40
Hazards[1]
GHS pictograms
GHS signal word DANGER
GHS hazard statements H260, H250, H314 [note 1]
EU Index 003-002-00-X
Related compounds
Related organolithium compounds Methyllithium
n-Butyllithium
tert-Butyllithium
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 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.

n-Hexyllithium has similar chemical properties to n-butyllithium (BuLi). Its main advantage over BuLi, particularly in industrial use, is the production of liquid n-hexane as a byproduct rather than gaseous (and highly flammable) butane.[2] 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.

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. ^ Abel, Edward W.; Stone, F. Gordon A.; Wilkinson, Geoffrey, eds. (1995), Main-Group Metal Organometallics in Organic Synthesis, Comprehensive Organometallic Chemistry II, 11, Elsevier, p. 3, ISBN 0080423183 .