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Triacetone amine

Triacetone amine

General
Systematic name	2,2,6,6-Tetramethylpiperidinone
Other names	Triacetone amine
Molecular formula	C₉H₁₇NO
SMILES	O=C1CC(C)(C)NC(C)(C)C1
Molar mass	155.23 g/mol
Appearance	Colorless low-melting solid
CAS number	[826-36-8]
Properties
Density and phase	? g/cm³
Solubility in water	Moderate
Other solvents	Most organic solvents
Melting point	43 °C
Boiling point	205 °C
Basicity (pK_b)	?
Viscosity	? cP at ? °C
Structure
Dipole moment	? D
Hazards
MSDS	External MSDS
Main hazards	flammable
NFPA 704
Flash point	164 °F
R/S statement	R: 22-36/37/38 S: 26-36/37
RTECS number	TO0127900
Supplementary data page
Structure and properties	n, ε_r, etc.
Thermodynamic data	Phase behaviour Solid, liquid, gas
Spectral data	UV, IR, NMR, MS
Related compounds
Related compounds	Piperidine
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and 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 used to prepare the hindered amine 2,2,6,6-tetramethylpiperidine, CH₂[CH₂C(CH₃)₂]₂NH.^[1]

References

^ 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.

Categories: Amines | Ketones