2,2,6,6-Tetramethylpiperidine

2,2,6,6-Tetramethylpiperidine

2,2,6,6-Tetramethylpiperidine

Chemical compound

2,2,6,6-Tetramethylpiperidine, abbreviated TMP, HTMP, or TMPH, is an organic compound of the amine class. In appearance, it is a colorless liquid and has a "fishy", amine-like odor. This amine is used in chemistry as a hindered base (hindered amine). Although TMP finds limited use per se, its derivatives are a mainstay of hindered amine light stabilizers.

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TMP is the starting material for an even stronger base, lithium tetramethylpiperidide and the radical species TEMPO. Another non-nucleophilic base is N,N-diisopropylethylamine. Its aqueous pKaH (conjugate acid dissociation constant, a measure of basicity) is 11.07 at 25 °C,[1] while its pKa (acid dissociation constant, a measure of acidity) is approximately 37.[2]

Preparation

Many routes for the synthesis of TMP have been reported. One method[3] starts with a conjugate addition reaction of ammonia to phorone. The intermediate triacetone amine is then reduced in a Wolff-Kishner reaction.

TMP synthesis

See also

References

  1. [1]
    William M. Haynes, ed. (2015). CRC handbook of chemistry and physics : a ready-reference book of chemical and physical data (96th ed.). Boca Raton, Florida: CRC Press. ISBN 978-1-4822-6096-0. OCLC 910908643.
  2. [2]
    Reich, Hans (2022). "Bordwell pKa table".
  3. [3]
    Detlef Kampmann; Georg Stuhlmüller; Roger Simon; Fabrice Cottet; Frédéric Leroux; Manfred Schlosser (2005). "A Large-Scale Low-Cost Access to the Lithium 2,2,6,6-Tetramethylpiperidide Precursor". Synthesis. 2005 (6): 1028–1029. doi:10.1055/s-2004-834856. S2CID 93476763.
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