Hexyllithium
| n-Hexyllithium | |
|---|---|
| IUPAC name | Hexyllithium |
| Other names | HxLi, NHL |
| Identifiers | |
| InChI | 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 |
| InChIKey | RMKNFFPDYCVCDI-ZLJYRZARAB |
| Standard InChI | InChI=1S/C6H13.Li/c1-3-5-6-4-2;/h1,3-6H2,2H3; |
| Standard InChIKey | RMKNFFPDYCVCDI-UHFFFAOYSA-N |
| CAS number | [] |
| EC number | |
| ChemSpider | |
| Properties | |
| Chemical formula | C6H13Li |
| Molar mass | 92.11 g mol−1 |
| Solubility in water | reacts violently |
| Acidity (pKa) | approx. 40 |
| Hazards[1] | |
| EU index number | 003-002-00-X |
| GHS pictograms |  
|
| GHS signal word | DANGER |
| GHS hazard statements | H260, H250, H314 [note 1] |
| Related compounds | |
| Other 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) | |
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.
- ↑ Main-Group Metal Organometallics in Organic Synthesis; Abel, Edward W.; Stone, F. Gordon A.; Wilkinson, Geoffrey, Eds.; Comprehensive Organometallic Chemistry II; Elsevier, 1995; Vol. 11, p 3. ISBN 0080423183.
External links
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See also the corresponding article on Wikipedia. |
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