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 |
| Solubility in other solvents | Soluble in hydrocarbons, ether, and THF |
| 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 Phenyllithium Neopentyllithium Propyllithium |
| Except where noted otherwise, 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.
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
- ↑ 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.
- ↑ 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 0-08-042318-3.