Triacetonamine
[CAS# 826-36-8]

Identification

• Classification: Natural product >> Alkaloid
• Name: Triacetonamine
• Synonyms: Triacetoneamine; Tetramethylpiperidinone; 2,2,6,6-Tetramethyl-4-piperidone; IKh 196; NSC 16579; Odoratine; TEMP; Vincubina; Vincubine
• Molecular Formula: C₉H₁₇NO
• Molecular Weight: 155.24
• CAS Registry Number: 826-36-8
• EC Number: 212-554-2
• SMILES: CC1(CC(=O)CC(N1)(C)C)C

Properties

• Melting point: 58-62 °C

Safety Data

• Hazard Symbols: GHS05;GHS07 Danger
• Risk Statements: H290-H302-H314-H315-H317-H318-H319-H335-H412
• Safety Statements: P234-P260-P261-P264-P264+P265-P270-P271-P272-P273-P280-P301+P317-P301+P330+P331-P302+P352-P302+P361+P354-P304+P340-P305+P351+P338-P305+P354+P338-P316-P317-P319-P321-P330-P332+P317-P333+P317-P337+P317-P362+P364-P363-P390-P403+P233-P405-P406-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Skin corrosion	Skin Corr.	1B	H314
Serious eye damage	Eye Dam.	1	H318
Skin sensitization	Skin Sens.	1A	H317
Substances or mixtures corrosive to metals	Met. Corr.	1	H290
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin sensitization	Skin Sens.	1	H317

Discovery and Applications

Triacetonamine, also known as diacetoneamine, is an organic compound that was first discovered in the early 20th century. It is derived from acetone and ammonia and is structurally related to acetone and acetone oxime. Triacetonamine was initially synthesized through the condensation reaction of acetone and ammonia under specific conditions. Its discovery opened up new avenues for research in organic chemistry, particularly in the field of amine derivatives.

Triacetonamine and its derivatives are utilized in pharmaceutical formulations as intermediates for the synthesis of various drugs. They serve as precursors for the production of pharmaceutical compounds with diverse biological activities. Triacetonamine derivatives are often used in the synthesis of heterocyclic compounds, which are key structural motifs found in many pharmaceutical agents.

Triacetonamine is employed in the agrochemical industry for the production of herbicides, insecticides, and fungicides. Its derivatives can act as active ingredients or intermediates in the synthesis of agrochemical formulations.

Triacetonamine is used in the coatings industry as a curing agent for epoxy resins. Its reactivity with epoxy groups allows it to crosslink polymer chains, forming durable and chemically resistant coatings. Triacetonamine-based epoxy coatings are applied in various applications, including automotive finishes, industrial flooring, and marine coatings, where high-performance coatings are required.

Triacetonamine acts as a versatile solvent in various chemical processes and formulations. It is particularly useful for dissolving polar and nonpolar compounds. Triacetonamine is employed as a solvent in paint and ink formulations, as well as in cleaning products and industrial processes.

Triacetonamine is a valuable tool in chemical research for studying organic reactions and developing new synthetic methodologies. Triacetonamine derivatives serve as versatile building blocks for the synthesis of complex organic molecules, contributing to advancements in medicinal chemistry, materials science, and other fields.

References

2024. Synthesis of spin-labeled bispidines. Russian Chemical Bulletin, 73(5).
DOI: 10.1007/s11172-024-4241-7

2024. The first example of the use of 4-amino-2,2,6,6-tetramethylpiperidine-1-oxyl in the Mannich reaction to obtain radical-labeled bispidines. Russian Chemical Bulletin, 73(5).
DOI: 10.1007/s11172-024-4266-y

2023. Tetramethylphosphinane as a new secondary phosphine synthon. Communications Chemistry, 6(1).
DOI: 10.1038/s42004-023-00876-8