Lithium tetramethylpiperidide
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| Identifiers | |
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3D model (JSmol)
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| ECHA InfoCard | 100.209.926 |
CompTox Dashboard (EPA)
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| Properties | |
| C9H18LiN | |
| Molar mass | 147.187 g/mol |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Lithium tetramethylpiperidide or LiTMP is an organic base and a non-nucleophilic base.[1] It is traditionally synthesised from 2,2,6,6-tetramethylpiperidine and n-butyllithium at -78 °C, but recent reports show this reaction is sluggish and is better formed at 0 °C.[2] The compound is stable in a THF/ethylbenzene solvent mixture and commercially available as such. LiTMP has a pKa of 37.[2]
References
- ^ datasheet data sheet
- ^ a b amide primer H. J. Reich 2002
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