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| Names | |
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| IUPAC name
Hexyllithium
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| Other names
HxLi, NHL
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| Identifiers | |
3D model (JSmol)
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| Abbreviations | NHL HxLi n-HxLi nHxLi nHxLi |
| ChemSpider | |
| ECHA InfoCard | 100.100.655 |
| EC Number |
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PubChem CID
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CompTox Dashboard (EPA)
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| 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 |
| Hazards1 | |
| GHS labelling: | |
 
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| 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 | |
Related organolithium compounds
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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).
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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
Notes and references
Notes
- Within the European Union, the following additional hazard statement (EUH014) must also be displayed on labelling: Reacts violently with water.
References
- 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. Official Journal of the European Union L353, 31 December 2008, pp. 1–1355 at p 340.
- Terry L. Rathman "Hexyllithium" Encyclopedia of Reagents for Organic Synthesis, 2001. doi:10.1002/047084289X.rh024
- 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.