2, 2, 6, 6 Tetramethylpiperidine

2,2,6,6 Tetramethylpiperidine

Synonym(s): 2,2,6,6 tetramethylpiperidide, 2,2,6,6-tetramethylpiperidine, Norpempidine, TEMP, TMPH

2,2,6,6 Tetramethylpiperidine, often known as TMP, HTMP, or TMPH, is a chemical molecule in the amine class. It appears to be a white liquid with a “fishy” amine-like odor. This amine is known in chemistry as a hindered base. Although TMP is not widely used, its derivatives are a key component of hindered amine light stabilizers.

TMP is the precursor of lithium tetramethylpiperidide, an even stronger base, as well as the radical species TEMPO. Another non-nucleophilic base is N,N-diisopropylethylamine. At 25 °C, its aqueous pKaH (conjugate acid dissociation constant, a measure of basicity) is 11.07, while its pKa (acid dissociation constant, a measure of acidity) is around 37.

There have been several reports on various TMP synthesis methods. One approach begins with a conjugate addition reaction of ammonia and phorone. The intermediate triacetone amine is subsequently reduced by a Wolff-Kishner reaction.