2,2,6,6-Tetramethylpiperidine

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.

2,2,6,6-Tetramethylpiperidine
Names
Preferred IUPAC name
2,2,6,6-Tetramethylpiperidine
Other names
Norpempidine
Tetramethylpiperidine
Identifiers
3D model (JSmol)
Abbreviations TMP
ChEMBL
ChemSpider
ECHA InfoCard 100.011.090
EC Number
  • 212-199-3
UNII
  • InChI=1S/C9H19N/c1-8(2)6-5-7-9(3,4)10-8/h10H,5-7H2,1-4H3 checkY
    Key: RKMGAJGJIURJSJ-UHFFFAOYSA-N checkY
  • InChI=1/C9H19N/c1-8(2)6-5-7-9(3,4)10-8/h10H,5-7H2,1-4H3
    Key: RKMGAJGJIURJSJ-UHFFFAOYAX
  • N1C(C)(CCCC1(C)C)C
Properties
C9H19N
Molar mass 141.254 g/mol
Appearance Clear liquid
Density 0.83 g/mL
Melting point −59 °C (−74 °F; 214 K)
Boiling point 152 °C (306 °F; 425 K)
Hazards
GHS labelling:
GHS02: FlammableGHS05: CorrosiveGHS06: ToxicGHS07: Exclamation mark
Danger
H226, H301, H302, H314, H315, H319, H332, H335
P210, P233, P240, P241, P242, P243, P260, P261, P264, P270, P271, P280, P301+P310, P301+P312, P301+P330+P331, P302+P352, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P310, P312, P321, P330, P332+P313, P337+P313, P362, P363, P370+P378, P403+P233, P403+P235, P405, P501
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

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
TMP synthesis

See also

References
  1. CRC handbook of chemistry and physics : a ready-reference book of chemical and physical data. William M. Haynes, David R. Lide, Thomas J. Bruno (96th ed.). Boca Raton, Florida. 2015. ISBN 978-1-4822-6096-0. OCLC 910908643.{{cite book}}: CS1 maint: location missing publisher (link) CS1 maint: others (link)
  2. Reich, Hans (2022). "Bordwell pKa table".
  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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