Lithium tetramethylpiperidide
- Lithium tetramethylpiperidide
Chembox new
ImageFile = Lithium 2,2,6,6-tetramethylpiperidide.png ImageSize =
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Section1 = Chembox Identifiers
CASNo = 38227-87-1
PubChem =
SMILES = CC1(C)CCCC(C)(C)N1 [Li]
Section2 = Chembox Properties
Formula = C9H18LiN
MolarMass = 147.187 g/mol
Appearance =
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Section3 = Chembox Hazards
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Lithium tetramethylpiperidide or LiTMP is an organic base and a non-nucleophilic base. [ [http://www.fmclithium.com/products/pds/LiTMP.pdf datasheet] data sheet ] 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. [ [http://www.chem.wisc.edu/areas/reich/Handouts/lireagents/amidebases.pdf amide primer] H. J. Reich 2002 ] The compound is stable in a THF/ethylbenzene solvent mixture and commercially available as such. LiTMP has a pKa of 37. [ [http://www.chem.wisc.edu/areas/reich/Handouts/lireagents/amidebases.pdf amide primer] H. J. Reich 2002 ]
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