| Identification | More | [Name]
Triacetonediamine | [CAS]
36768-62-4 | [Synonyms]
2,2,6,6-TETRAMETHYL-4-AMINOPIPERIDINE
2,2,6,6-TETRAMETHYL-4-PIPERIDYLAMINE
2,2,6,6-TETRAMETHYL-PIPERIDIN-4-YLAMINE
4-AMINO-2,2,6,6-TETRAMETHYLPIPERIDINE
TAD
TEMP
TIMTEC-BB SBB001789
TRIACETONEDIAMINE
2,2,6,6-tetramethyl-4-piperidinamin
2,2,6,6-Tetramethyl-4-piperidinamine
4-amino-2,2,6,6-tetramethyl-piperidin
Piperidine, 4-amino-2,2,6,6-tetramethyl-
4-AMINO-2,2,6,6-TETRAMETHYLPIPERIDINE, 9 8%
Amino-2,2,6,6-tetramethylpiperidine
4-Amion-2,2,6,6-Tetramentylniperidine
4-Amino-2,2,6,6-tetramethylpiperidine, pure, 98%
4-Amino-2,2,6,6-tetra-methyl
4-Piperidinamine, 2,2,6,6-tetramethyl-
4-amino-2,2,6,6-tetramethylpiperidine (TAD
2,2,6,6-Tetramethyl-4-piperidylamin | [EINECS(EC#)]
253-197-2 | [Molecular Formula]
C9H20N2O3 | [MDL Number]
MFCD00005984 | [Molecular Weight]
204.27 | [MOL File]
36768-62-4.mol |
| Chemical Properties | Back Directory | [Appearance]
CLEAR SLIGHTLY YELLOW LIQUID | [Melting point ]
16-18 °C(lit.)
| [Boiling point ]
188-189 °C(lit.)
| [density ]
0.912 g/mL at 25 °C(lit.)
| [vapor pressure ]
<=20 hPa (20 °C) | [refractive index ]
n20/D 1.470(lit.)
| [Fp ]
162 °F
| [storage temp. ]
Store below +30°C. | [form ]
clear liquid | [pka]
10.83±0.10(Predicted) | [color ]
Colorless to Light orange to Yellow | [Specific Gravity]
0.912 | [PH]
12.3 (99g/l, H2O, 20℃) | [Water Solubility ]
soluble | [Detection Methods]
GC,T | [BRN ]
105038 | [InChIKey]
FTVFPPFZRRKJIH-UHFFFAOYSA-N | [LogP]
0.94 at 20℃ | [Surface tension]
67.11-68.09mN/m at 1g/L and 20℃ | [CAS DataBase Reference]
36768-62-4(CAS DataBase Reference) | [NIST Chemistry Reference]
4-Piperidinamine, 2,2,6,6-tetramethyl-(36768-62-4) | [Storage Precautions]
Heat sensitive;Store under nitrogen | [EPA Substance Registry System]
36768-62-4(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn,Xi,C | [Risk Statements ]
R22:Harmful if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin .
R34:Causes burns. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37:Wear suitable protective clothing and gloves .
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 . | [RIDADR ]
UN 2735 8/PG 3
| [WGK Germany ]
2
| [RTECS ]
TM4290100
| [Autoignition Temperature]
300 °C | [Hazard Note ]
Irritant | [TSCA ]
Yes | [HazardClass ]
8 | [PackingGroup ]
III | [HS Code ]
29333999 | [Toxicity]
LD50 orally in Rabbit: 1000 mg/kg |
| Hazard Information | Back Directory | [Chemical Properties]
CLEAR SLIGHTLY YELLOW LIQUID | [Uses]
Triacetonediamine have been investigated as new anticancer drugs with high activity and low toxicity. | [Preparation]
Triacetonediamine 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
| [Reactions]
Triacetonediamine is an intermediate in the preparation of 2,2,6,6-tetramethylpiperidine, a sterically hindered base and precursor to the reagent called TEMPO. Reductive amination of triacetonamine gives 4-amino-2,2,6,6-tetramethylpiperidine. | [Safety Profile]
Moderately toxic by ingestion.When heated to decomposition it emits toxic vapors ofNOx. | [Synthesis]
The general procedure for the synthesis of 2,2,6,6-tetramethylpiperidinamine from 2,2,6,6-tetramethylpiperidin-4-one is as follows:
Examples 1-12: 300 g of 2,2,6,6-tetramethylpiperidin-4-one, deionized water and 11 g of catalyst (sequentially using B113W nickel-based catalyst and B2112Z cobalt-based catalyst from Evonik Degussa GmbH) were added to a 1-liter stirred autoclave under argon protection. The autoclave was equipped with a paddle stirrer, an electric heating system, an air cooling unit and a hydrogen mass flow regulator. The autoclave was then flushed three times with nitrogen. The stirrer speed was set to 300 rpm and then 83 g of liquid ammonia was slowly added. The system was adjusted to the pressure and temperature conditions required for the main reaction under hydrogen atmosphere. The reaction was carried out at 150 °C and 50 bar pressure for about 3 hours. Deviations from other reaction conditions are recorded in Table 1, which shows both the process parameters and the results for each embodiment. | [References]
[1] Anales de Quimica, 1998, vol. 94, # 1, p. 36 - 45
[2] Collection of Czechoslovak Chemical Communications, 1987, vol. 52, # 1, p. 182 - 191
[3] Collection of Czechoslovak Chemical Communications, 1987, vol. 52, # 1, p. 182 - 191
[4] Collection of Czechoslovak Chemical Communications, 1987, vol. 52, # 1, p. 182 - 191
[5] Collection of Czechoslovak Chemical Communications, 1987, vol. 52, # 1, p. 182 - 191 |
| Well-known Reagent Company Product Information | Back Directory | [Acros Organics]
4-Amino-2,2,6,6-tetramethylpiperidine, pure, 98%(36768-62-4) | [Alfa Aesar]
4-Amino-2,2,6,6-tetramethylpiperidine, 98%(36768-62-4) | [Sigma Aldrich]
36768-62-4(sigmaaldrich) | [TCI AMERICA]
4-Amino-2,2,6,6-tetramethylpiperidine,>97.0%(GC)(36768-62-4) |
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