Lithium tetramethylpiperidide

Lithium tetramethylpiperidide
IUPAC name Lithium tetramethylpiperidide
Systematic name 1-Lithio-2,2,6,6-tetramethylpiperidine
Identifiers
CAS number	38227-87-1 Y
PubChem	11051814
ChemSpider	21428984 Y
Jmol-3D images	Image 1 Image 2
SMILES [Li]N1C(C)(C)CCCC1(C)C CC1(C)CCCC(C)(C)N1[Li]
InChI InChI=1S/C9H18N.Li/c1-8(2)6-5-7-9(3,4)10-8;/h5-7H2,1-4H3;/q-1;+1 Y Key: ANYSGBYRTLOUPO-UHFFFAOYSA-N Y
Properties
Molecular formula	C9H18LiN
Molar mass	147.19 g mol−1
Exact mass	147.159928630 g mol-1
Acidity (pKa)	37
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Lithium tetramethylpiperidide or LiTMP is an organic base and a non-nucleophilic base. 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. The compound is stable in a THF/ethylbenzene solvent mixture and commercially available as such. LiTMP has a pKa of 37.