Lithium tetramethylpiperidide

Lithium tetramethylpiperidide
	Structural formula of lithium tetramethylpiperidide
Names
	IUPAC name Lithium tetramethylpiperidide
	Systematic IUPAC name 1-Lithio-2,2,6,6-tetramethylpiperidine
Identifiers
CAS Number	38227-87-1
ChemSpider	21428984
Jmol 3D model	Interactive image; Interactive image
PubChem	11051814
	InChI InChI=1S/C9H18N.Li/c1-8(2)6-5-7-9(3,4)10-8;/h5-7H2,1-4H3;/q-1;+1 Key: ANYSGBYRTLOUPO-UHFFFAOYSA-N ;
	SMILES [Li]N1C(C)(C)CCCC1(C)C ; CC1(C)CCCC(C)(C)N1[Li] ;
Properties
Chemical formula	C9H18LiN
Molar mass	147.19 g·mol−1
Acidity (pKa)	37
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	verify (what is ?)
	Infobox references

Lithium tetramethylpiperidide (often abbreviated LiTMP or LTMP) is an chemical compound with the molecular formula C₉H₁₈LiN. It is used as a non-nucleophilic base, being comparable to LiHMDS in terms of pKa and 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.^[1] The compound is stable in a THF/ethylbenzene solvent mixture and commercially available as such.

Like many lithium reagents it has a tendency to aggregate, forming a tetramer in the solid state.^[2]

This article about an organic compound is a stub. You can help Wikipedia by expanding it.