Structure via PubChem · Public domain (PubChem)
triacetonamine
Sign in to saveAlso known as triaceton amine, 2,2,6,6-Tetramethylpiperidinone
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: 3 (CH3)2CO + NH3 → OC(CH2CMe2)2NH + 2 H2O
Chemical data
- Formula
- C9H17NO
- Molecular weight
- 155.24 g/mol
- IUPAC name
- 2,2,6,6-tetramethylpiperidin-4-one
- SMILES
- CC1(CC(=O)CC(N1)(C)C)C
- InChIKey
- JWUXJYZVKZKLTJ-UHFFFAOYSA-N
- XLogP
- 0.5
- Polar surface area
- 29.1 Ų
- H-bond donors
- 1
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Mass
- 155.131
Show 4 more facts
- found in taxon
- Agelas oroides
- Commons category
- Triacetonamine
- chemical formula
- C₉H₁₇NO
- canonical SMILES
- CC1(CC(=O)CC(N1)(C)C)C
Sources (2)
via Wikidata · CC0
~1 min read
Encyclopedic overview
1 sectionsContents
- References
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: 3 (CH3)2CO + NH3 → OC(CH2CMe2)2NH + 2 H2O
Reductive amination of triacetonamine gives 4-amino-2,2,6,6-tetramethylpiperidine.
Excerpted from Wikipedia’s “triacetonamine” article, available under the CC BY-SA 4.0 licence.