| Identification | More | [Name]
Triacetonamine | [CAS]
826-36-8 | [Synonyms]
2,2,6,6-TETRAMETHYL-4-PIPERIDINONE
2,2,6,6-TETRAMETHYL-4-PIPERIDONE
2,2,6,6-TETRAMETHYL-PIPERIDIN-4-ONE
2,2,6,6-TETRAMETHYLTETRAHYDRO-4(1H)-PYRIDINONE
LABOTEST-BB LT00159409
TAA
TETRAMETHYLPIPERIDINONE
TRIACETONAMINE
TRIACETONEAMINE
2,2,6,6-Tetramethyl-4-oxopiperidine
2,2,6,6-tetramethyl-4-piperidinon
2,2,6,6-tetramethyl-4-piperidon
2,2,6,6-Tetramethylpiperidinone
2,2,6,6-Tetramethylpiperidone
4-Oxo-2,2,6,6-tetramethylpiperidine
4-Piperidinone,2,2,6,6-tetramethyl-
4-Piperidone, 2,2,6,6-tetramethyl-
4-Piperidone,2,2,6,6-tetramethyl-
Ikh 196
IKh196 | [EINECS(EC#)]
212-554-2 | [Molecular Formula]
C9H15NO3 | [MDL Number]
MFCD00005975 | [Molecular Weight]
185.22 | [MOL File]
826-36-8.mol |
| Chemical Properties | Back Directory | [Appearance]
white crystalline powder | [Melting point ]
59-61 °C | [Boiling point ]
105-105°C/18mm | [density ]
0.9796 (rough estimate) | [refractive index ]
1.4680 (estimate) | [Fp ]
73°C | [storage temp. ]
Refrigerator (+4°C) | [solubility ]
DMSO, Methanol | [form ]
Solid | [pka]
9.20±0.60(Predicted) | [color ]
Pale Orange to Light Brown Low Melting | [Water Solubility ]
249g/L at 20℃ | [InChI]
1S/C9H17NO/c1-8(2)5-7(11)6-9(3,4)10-8/h10H,5-6H2,1-4H3 | [InChIKey]
JWUXJYZVKZKLTJ-UHFFFAOYSA-N | [SMILES]
CC1(C)CC(=O)CC(C)(C)N1 | [LogP]
1.32 at 25℃ | [CAS DataBase Reference]
826-36-8(CAS DataBase Reference) | [NIST Chemistry Reference]
4-Piperidinone, 2,2,6,6-tetramethyl-(826-36-8) | [EPA Substance Registry System]
826-36-8(EPA Substance) |
| Safety Data | Back Directory | [Symbol(GHS) ]
 
GHS05,GHS07 | [Signal word ]
Danger | [Hazard statements ]
H290-H302-H314-H317-H412 | [Precautionary statements ]
P260-P273-P280-P301+P330+P331-P303+P361+P353-P305+P351+P338 | [Hazard Codes ]
C,Xn | [Risk Statements ]
R34:Causes burns.
R22:Harmful if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S22:Do not breathe dust .
S36/37:Wear suitable protective clothing and gloves . | [WGK Germany ]
2 | [RTECS ]
TO0127900 | [TSCA ]
TSCA listed | [REACH Registrations]
Active | [HS Code ]
29333990 | [Storage Class]
8B - Non-combustible corrosive hazardous materials | [Hazard Classifications]
Acute Tox. 4 Oral
Aquatic Chronic 3
Eye Dam. 1
Met. Corr. 1
Skin Corr. 1B
Skin Sens. 1A |
| Questions And Answer | Back Directory | [Triacetone amine]
Triacetonamine has anti-arrhythmic and anti-myocardial ischemia effect.
Take Triacetonamine as raw materials, ethanol as the solvent, perform hydrogenation reaction in the presence of catalyst (normal pressure or 3~4MPa) and obtain raw material of histamine-type light stabilizer 2,2,6,6-tetramethyl-4-piperidinol.
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| [Chemical Properties]
It appears as white or light yellow powder with the melting point being 43 ℃ and boiling point being 205 ℃. It is soluble in acetone, alcohol, ether and water.
The above information is edited by the chemicalbook of Dai Xiongfeng.
| [Uses]
The product is the intermediate and pharmaceutical intermediate of histamine light stabilizer. Itself also has light-stabilizing effect. It has important application in pharmaceuticals.
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| Hazard Information | Back Directory | [Definition]
ChEBI: Triacetonamine is a member of piperidones. | [Synthesis Reference(s)]
Synthesis, p. 735, 1976 DOI: 10.1055/s-1976-24178 | [Synthesis]
The routes of triacetonamine synthesis includes[1]:
a. From acetone and ammonia. Triacetonamine was initially prepared by the method of Francisfrom acetone and ammonia in the presence of an acidic catalyst like calcium chloride in a 20% yield. Co-catalysts bromine or iodine combined with acid halides of the type XCH2COX acted as synergists.
b. From phorone and ammonia. Phorone reacted with ammonia to give triacetonamine via the nucleophilic addition of nitrogen to the olefi nic bond.
c. From N-oxides. Triacetonamine was formed via reduction of cation in the presence of NaOH in acetone media.
d. From alcohols. Photogenerated singlet oxygen was used in oxidation of alcohol with formation of triacetonamine under mild and facile conditions using the catalyst CoIIDPDME.
e. From dimethylamine derivatives. Dimethylamine was alkylated by methyl iodide. The following hydrolysis gave triacetonamine. | [in vivo]
Triacetonamine (Purchased from MCE; 200 mg, 300 mg, 400 mg/Kg/day; gavage; 2 days) shows typical hepatoenteropathology of ALF with 300 mg/Kg/day and 400 mg/Kg/day, while the group of 400 mg/Kg/day had higher mortality[2]. | Animal Model: | Rats (half male and female, 6-8 weeks old, 200?±?10 g)[2] | | Dosage: | 200 mg, 300 mg, 400 mg/Kg | | Administration: | Gavage; daily; 2 days | | Result: | Showed typical hepatoenteropathology of ALF with 300 mg/Kg/day and 400 mg/Kg/day, while the group of 400 mg/Kg/day had higher mortality.
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| [References]
[1] Yousif, M. N. M., Soliman, H. A., Said, M. M., Hassan, N. A., & Abdel-Megeid, F. M. E. (2020). Synthesis and Biological Activity of Triacetonamine. Russian Journal of General Chemistry, 90 3, 460–469. https://doi.org/10.1134/S1070363220030202
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