Triacetonamine

Triacetonamine is an organic compound with the formula OC(CH₂CMe₂)₂NH (where Me = CH₃). It is a colorless or white solid that melts near room temperature. The compound is an intermediate in the preparation of 2,2,6,6-tetramethylpiperidine, a sterically hindered base and precursor to the reagent called TEMPO. Triacetonamine is formed by the poly-aldol condensation of acetone in the presence of ammonia and calcium chloride:^[1]

3 (CH₃)₂CO + NH₃ → OC(CH₂CMe₂)₂NH + 2 H₂O

Triacetone amine

Names
Preferred IUPAC name 2,2,6,6-Tetramethylpiperidin-4-one
Other names Triacetone amine
Identifiers
CAS Number	826-36-8 N
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL117614 Y
ChemSpider	12665 Y
ECHA InfoCard	100.011.413
EC Number	212-554-2
PubChem CID	13220
RTECS number	TO0127900
UNII	2K4430S3XP
CompTox Dashboard (EPA)	DTXSID4041527
InChI InChI=1S/C9H17NO/c1-8(2)5-7(11)6-9(3,4)10-8/h10H,5-6H2,1-4H3 Y Key: JWUXJYZVKZKLTJ-UHFFFAOYSA-N Y InChI=1/C9H17NO/c1-8(2)5-7(11)6-9(3,4)10-8/h10H,5-6H2,1-4H3 Key: JWUXJYZVKZKLTJ-UHFFFAOYAQ
SMILES O=C1CC(NC(C)(C)C1)(C)C
Properties
Chemical formula	C9H17NO
Molar mass	155.241 g·mol−1
Appearance	Colorless low-melting solid
Density	0.882 g/cm3
Melting point	43 °C (109 °F; 316 K)
Boiling point	205 °C (401 °F; 478 K)
Solubility in water	Moderate
Solubility in other solvents	Most organic solvents
Hazards
Occupational safety and health (OHS/OSH):
Main hazards	flammable
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H290, H302, H314, H315, H317, H319, H335, H412
Precautionary statements	P234, P260, P261, P264, P270, P271, P272, P273, P280, P301+P312, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P312, P321, P330, P332+P313, P333+P313, P337+P313, P362, P363, P390, P403+P233, P404, P405, P501
Flash point	73 °C; 164 °F; 346 K
Related compounds
Related compounds	Piperidine
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

Reductive amination of triacetonamine gives 4-amino-2,2,6,6-tetramethylpiperidine.

It is primarily used as a stabilizer for plastics, typically via its conversion to number of hindered amine light stabilizers, but also finds use as a chemical feedstock. It is used to prepare the hindered amine 2,2,6,6-tetramethylpiperidine, CH₂[CH₂C(CH₃)₂]₂NH,^[2] as well as the radical oxidizer 4-Hydroxy-TEMPO.^[3]

References

1. Nabyl Merbouh; James M. Bobbitt; Christian Brückner (2004). "Preparation of Tetramethylpiperdine-1-oxoammonlum Salts and Their Use as Oxidants in Organic Chemistry. A Review". Organic Preparations and Procedures International. 36: 1–31. doi:10.1080/00304940409355369. S2CID 98117103.
2. Sorgi, K. L. "2,2,6,6-Tetramethylpiperidine" in Encyclopedia of Reagents for Organic Synthesis (Ed: L. Paquette) 2004, J. Wiley & Sons, New York. doi:10.1002/047084289X.
3. Ciriminna, Rosaria; Pagliaro, Mario (15 January 2010). "Industrial Oxidations with Organocatalyst TEMPO and Its Derivatives". Organic Process Research & Development. 14 (1): 245–251. doi:10.1021/op900059x.