Lithium tetramethylpiperidide

Chemical compound From Wikipedia, the free encyclopedia

Lithium tetramethylpiperidide (often abbreviated LiTMP or LTMP) is a chemical compound with the molecular formula LiC9H18N. It is used as a non-nucleophilic base, being comparable to LiHMDS in terms of steric hindrance.

Quick facts Names, Identifiers ...
Lithium tetramethylpiperidide
Structural formula of lithium tetramethylpiperidide
Structural formula of lithium tetramethylpiperidide
Names
IUPAC name
Lithium tetramethylpiperidide
Systematic IUPAC name
1-Lithio-2,2,6,6-tetramethylpiperidine
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.209.926 Edit this at Wikidata
  • InChI=1S/C9H18N.Li/c1-8(2)6-5-7-9(3,4)10-8;/h5-7H2,1-4H3;/q-1;+1 checkY
    Key: ANYSGBYRTLOUPO-UHFFFAOYSA-N checkY
  • [Li]N1C(C)(C)CCCC1(C)C
  • CC1(C)CCCC(C)(C)N1[Li]
  • Cyclic tetramer: CC1(C)CCCC(C)(C)[N+]01[Li-][N+]1(C(C)(C)CCCC1(C)C)[Li-][N+]1(C(C)(C)CCCC1(C)C)[Li-][N+]1([Li-]0)C(C)(C)CCCC1(C)C
Properties
LiC9H18N
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).
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Synthesis

It is synthesised by the deprotonation of 2,2,6,6-tetramethylpiperidine with n-butyllithium, this is typically performed at −78 °C, although there are reports of it being performed at 0 °C.[1] The compound is stable in a THF/ethylbenzene solvent mixture and is commercially available as such.

Structure

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

See also

References

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