2,2,6,6-Tetramethylpiperidine

2,2,6,6-Tetramethylpiperidine
Names
	Preferred IUPAC name 2,2,6,6-Tetramethylpiperidine
	Other names Norpempidine; Tetramethylpiperidine
Identifiers
CAS Number	768-66-1 ;
3D model (JSmol)	Interactive image;
Abbreviations	TMP
ChEMBL	ChEMBL2448812;
ChemSpider	12493 ;
ECHA InfoCard	100.011.090
EC Number	212-199-3;
PubChem CID	13035;
UNII	44N9S1YCFM ;
CompTox Dashboard (EPA)	DTXSID0061113 ;
	InChI InChI=1S/C9H19N/c1-8(2)6-5-7-9(3,4)10-8/h10H,5-7H2,1-4H3 Key: RKMGAJGJIURJSJ-UHFFFAOYSA-N ; InChI=1/C9H19N/c1-8(2)6-5-7-9(3,4)10-8/h10H,5-7H2,1-4H3 Key: RKMGAJGJIURJSJ-UHFFFAOYAX;
	SMILES N1C(C)(CCCC1(C)C)C;
Properties
Chemical formula	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:
Pictograms
Signal word	Danger
Hazard statements	H226, H301, H302, H314, H315, H319, H332, H335
Precautionary statements	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). verify (what is ?) Infobox references

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 pK_aH (conjugate acid dissociation constant, a measure of basicity) is 11.07 at 25 °C,^[1] while its pK_a (acid dissociation constant, a measure of acidity) is approximately 37.^[2]

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.

2,6-Dimethylpiperidine
Pempidine
TEMPO ((2,2,6,6-Tetramethylpiperidin-1-yl)oxyl)

[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]
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.

[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.

[1]

[2]

[3]

2,2,6,6-Tetramethylpiperidine

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Preparation

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References

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