Triacetone amine

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Triacetone amine
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Names
IUPAC name
2,2,6,6-Tetramethylpiperidinone
Other names
Triacetone amine
Identifiers
826-36-8 N
ChEMBL ChEMBL117614 YesY
ChemSpider 12665 YesY
Jmol 3D model Interactive image
PubChem 13220
RTECS number TO0127900
  • InChI=1S/C9H17NO/c1-8(2)5-7(11)6-9(3,4)10-8/h10H,5-6H2,1-4H3 YesY
    Key: JWUXJYZVKZKLTJ-UHFFFAOYSA-N YesY
  • InChI=1/C9H17NO/c1-8(2)5-7(11)6-9(3,4)10-8/h10H,5-6H2,1-4H3
    Key: JWUXJYZVKZKLTJ-UHFFFAOYAQ
  • O=C1CC(NC(C)(C)C1)(C)C
Properties
C9H17NO
Molar mass 155.23 g/mol
Appearance Colorless low-melting solid
Density  ? g/cm3
Melting point 43 °C (109 °F; 316 K)
Boiling point 205 °C (401 °F; 478 K)
Moderate
Solubility in other solvents Most organic solvents
Vapor pressure {{{value}}}
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 YesYN ?)
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

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  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.
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