Hexyllithium
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| Names | |
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| IUPAC name Hexyllithium | |
| Other names HxLi, NHL | |
| Identifiers | |
3D model (JSmol) |
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| 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 |
| Hazards[1] | |
| 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 |
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). | |
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. OJEU L353, 31.12.2008, 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.