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| Names | |
|---|---|
| IUPAC name Lithium tetramethylpiperidide | |
| Systematic IUPAC name 1-Lithio-2,2,6,6-tetramethylpiperidine | |
| Identifiers | |
| CAS Number | |
| 3D model (JSmol) |
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| ChemSpider | |
| ECHA InfoCard | 100.209.926 
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| PubChem CID | |
| CompTox Dashboard (EPA) | |
InChI
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SMILES
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| Properties | |
| Chemical formula | LiC9H18N |
| Molar mass | 147.19 g·mol |
| Acidity (pKa) | 37 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa).
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Infobox references
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Lithium tetramethylpiperidide (often abbreviated LiTMP or LTMP) is a chemical compound with the molecular formula LiC9H18N. It is used as a non-nucleophilic base, being comparable to LiHMDS in terms of steric hindrance.
Synthesis
It is synthesised by the deprotonation of 2,2,6,6-tetramethylpiperidine with n-butyllithium at −78 °C. Recent reports show that this reaction can also be performed 0 °C. The compound is stable in a THF/ethylbenzene solvent mixture and is commercially available as such.
Structure
Like many lithium reagents it has a tendency to aggregate, forming a tetramer in the solid state.
See also
References
- amide primer H. J. Reich 2002
- M.F. Lappert; M.J. Slade; A. Singh; J.L. Atwood; R.D. Rogers; R. Shakir (1983). "Structure and reactivity of sterically hindered lithium amides and their diethyl etherates: crystal and molecular structures of 2 and tetrakis(2,2,6,6-tetramethylpiperidinatolithium)". Journal of the American Chemical Society. 105 (2): 302–304. doi:10.1021/ja00340a031.