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 ;
3D model (JSmol)	Interactive image; Interactive image;
ChemSpider	21428984 ;
ECHA InfoCard	100.209.926
PubChem CID	11051814;
CompTox Dashboard (EPA)	DTXSID00453330 ;
	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 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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[1] tasheet data sheet

[amide_primer-2] rimer H. J. Reich 2002

[1]

[2]