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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
In the Vinony graph
Within Vinony's link graph, triacetonamine is referenced by 10 other articles, and connects out to mass density, digital object identifier and chemical formula.
Vinony files it under Chembox having GHS data, Cyclic ketones and ECHA InfoCard ID from Wikidata.
Its subject is documented across 9 Wikipedia language editions.
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.