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2,2,6,6-Tetramethylpiperidine

2,2,6,6-Tetramethylpiperidine

Tetramethylpiperidine | NFPA-H = | NFPA-F = | NFPA-R = | NFPA-S =

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.

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, while its pKa (acid dissociation constant, a measure of acidity) is approximately 37.

Preparation

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

TMP synthesis

References

References

  1. (2015). "CRC handbook of chemistry and physics : a ready-reference book of chemical and physical data.". CRC Press.
  2. Reich, Hans. (2022). "Bordwell pKa table".
  3. (2005). "A Large-Scale Low-Cost Access to the Lithium 2,2,6,6-Tetramethylpiperidide Precursor". [[Synthesis (journal).
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piperidines reagents-for-organic-chemistry non-nucleophilic-bases
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