Lithium tetramethylpiperidide

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.

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
  • 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
  • [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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Infobox references
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