Triacetone amine

Triacetone amine

Names
IUPAC name 2,2,6,6-Tetramethylpiperidinone
Other names Triacetone amine
Identifiers
CAS Number	826-36-8
ChEMBL	ChEMBL117614
ChemSpider	12665
Jmol interactive 3D	Image
PubChem	13220
RTECS number	TO0127900
InChI InChI=1S/C9H17NO/c1-8(2)5-7(11)6-9(3,4)10-8/h10H,5-6H2,1-4H3 Key: JWUXJYZVKZKLTJ-UHFFFAOYSA-N 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	155.23 g/mol
Appearance	Colorless low-melting solid
Density	? g/cm^3
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
Main hazards	flammable
R-phrases	22-36/37/38
S-phrases	26-36/37
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).
verify (what is  ?)
Infobox references

Triacetone amine is the heterocycle that arises via the condensation of acetone and ammonia according to the following equation:

3 CH₃C(O)CH₃ + NH₃ → OC(CH₂C(CH₃)₂)₂NH + 2 H₂O

It is primarily used as a light stabilizer for plastics 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,^[1] as well as the radical oxidizer 4-Hydroxy-TEMPO.^[2]

References

1. 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:10.1002/047084289.
2. 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.