Lithium tetramethylpiperidide

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Lithium tetramethylpiperidide
Identifiers
CAS number	[38227-87-1]
SMILES	CC1(C)CCCC(C)(C)N1[Li]
Properties
Molecular formula	C9H18LiN
Molar mass	147.187 g/mol
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

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.^[3]

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