Conditions | Yield |
---|---|
With ammonium hydroxide at -80 - 85℃; | 98% |
With ammonia; water | |
With ammonia | |
With ammonium hydroxide; sodium hydroxide 1.) 25 deg C, 3 days, 80 deg C, 60 min; 2.) 0-5 deg C; Yield given. Multistep reaction; | |
With ammonium hydroxide In water at 55 - 85℃; |
Conditions | Yield |
---|---|
With C44H66O8P4Pd2; methyl vinyl ketone In water; toluene at 105℃; for 16h; Inert atmosphere; chemoselective reaction; | 88% |
With 13,17-bis(2-methoxycarbonylethyl)-2,7,12,18-tetramethylporphinatocobalt(II); oxygen; isovaleraldehyde In acetonitrile at 60℃; for 1h; | 8 %Chromat. |
Conditions | Yield |
---|---|
With ammonia at 80℃; for 12h; Temperature; Autoclave; | 83.6% |
With ammonium chloride In water for 72h; | 33% |
With ammonia |
Conditions | Yield |
---|---|
With water In acetone Heating; UV irradiation; | 82% |
2,2,4,4,6-pentamethyl-2,3,4,5,tetrahydropyrimidine
cyclohexanone
A
2,2,6,6-Tetramethyl-4-piperidone
B
7-azadispiro[5.1.58.36]hexadecan-15-one
C
2,2-dimethyl-1-azaspiro[5.5]undecan-4-one
Conditions | Yield |
---|---|
With ammonium chloride at 60℃; for 10h; | A 16% B 30% C 52% |
With ammonium chloride at 60℃; for 10h; Product distribution; Mechanism; other ketones; | A 3% B 36% C 24% |
With ammonium chloride at 60℃; for 10h; | A 3% B 36% C 24% |
2,2,4,4,6-pentamethyl-2,3,4,5,tetrahydropyrimidine
octahydro-4,7-methano-inden-5-one
A
2,2,6,6-Tetramethyl-4-piperidone
Conditions | Yield |
---|---|
With ammonium chloride at 60℃; for 10h; | A n/a B 45% |
2,2,4,4,6-pentamethyl-2,3,4,5,tetrahydropyrimidine
Norbornan-2-on
A
2,2,6,6-Tetramethyl-4-piperidone
Conditions | Yield |
---|---|
With ammonium chloride at 60℃; for 10h; | A n/a B 42% |
4-oxo-2,2,6,6-tetramethylpiperidin-oxyl
A
2,2,6,6-Tetramethyl-4-piperidone
B
1-Ethanesulfonyl-2,2,6,6-tetramethyl-piperidin-4-one
Conditions | Yield |
---|---|
With ethanethiol In benzene Yields of byproduct given; | A 16% B n/a |
Conditions | Yield |
---|---|
With ethylenediamine In neat (no solvent) at 20℃; for 48h; Reagent/catalyst; | A 2% B n/a C n/a |
2,6-diamino-2,6-dimethyl-heptan-4-one
2,2,6,6-Tetramethyl-4-piperidone
Conditions | Yield |
---|---|
With water |
3-methyl-butan-2-one
2,2,4,4,6-pentamethyl-2,3,4,5,tetrahydropyrimidine
A
2,2,6,6-Tetramethyl-4-piperidone
B
2,2,6-trimethyl-6-isopropyl-4-oxopiperidine
Conditions | Yield |
---|---|
With ammonium chloride at 60℃; for 10h; Title compound not separated from byproducts; |
2,2,4,4,6-pentamethyl-2,3,4,5,tetrahydropyrimidine
2-Methylcyclopentanone
A
2,2,6,6-Tetramethyl-4-piperidone
Conditions | Yield |
---|---|
With ammonium chloride at 60℃; for 10h; Title compound not separated from byproducts; |
2,2,4,4,6-pentamethyl-2,3,4,5,tetrahydropyrimidine
4,4-dimethyl-pentan-2-one
A
2,2,6,6-Tetramethyl-4-piperidone
Conditions | Yield |
---|---|
With ammonium chloride at 60℃; for 10h; Title compound not separated from byproducts; |
2,2,4,4,6-pentamethyl-2,3,4,5,tetrahydropyrimidine
thujone
A
2,2,6,6-Tetramethyl-4-piperidone
Conditions | Yield |
---|---|
With ammonium chloride at 60℃; for 10h; Title compound not separated from byproducts; |
2,2,4,4,6-pentamethyl-2,3,4,5,tetrahydropyrimidine
4-Phenyl-2-butanone
A
2,2,6,6-Tetramethyl-4-piperidone
Conditions | Yield |
---|---|
With ammonium chloride at 60℃; for 10h; Title compound not separated from byproducts; |
2,2,4,4,6-pentamethyl-2,3,4,5,tetrahydropyrimidine
(1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one
A
2,2,6,6-Tetramethyl-4-piperidone
Conditions | Yield |
---|---|
With ammonium chloride at 60℃; for 10h; Title compound not separated from byproducts; |
2,2,4,4,6-pentamethyl-2,3,4,5,tetrahydropyrimidine
2-Methylcyclohexanone
A
2,2,6,6-Tetramethyl-4-piperidone
Conditions | Yield |
---|---|
With ammonium chloride at 60℃; for 10h; Title compound not separated from byproducts; |
2,2,4,4,6-pentamethyl-2,3,4,5,tetrahydropyrimidine
cyclopentanone
A
2,2,6,6-Tetramethyl-4-piperidone
B
6-Aza-7,7-dimethyl-spiro<4.5>decan-9-on
Conditions | Yield |
---|---|
With ammonium chloride at 60℃; for 10h; Title compound not separated from byproducts; |
2,2,4,4,6-pentamethyl-2,3,4,5,tetrahydropyrimidine
(4-nitrophenyl)ethanone
A
2,2,6,6-Tetramethyl-4-piperidone
Conditions | Yield |
---|---|
With ammonium chloride at 60℃; for 10h; Title compound not separated from byproducts; |
2,2,4,4,6-pentamethyl-2,3,4,5,tetrahydropyrimidine
butanone
A
2,2,6,6-Tetramethyl-4-piperidone
B
2-ethyl-2,6,6-trimethylpiperidin-4-one
Conditions | Yield |
---|---|
With ammonium chloride at 60℃; for 10h; Title compound not separated from byproducts; |
2,2,4,4,6-pentamethyl-2,3,4,5,tetrahydropyrimidine
3-Methylcyclohexanone
A
2,2,6,6-Tetramethyl-4-piperidone
Conditions | Yield |
---|---|
With ammonium chloride at 60℃; for 10h; Title compound not separated from byproducts; |
4-oxo-2,2,6,6-tetramethylpiperidin-oxyl
A
Diethyl disulfide
B
2,2,6,6-Tetramethyl-4-piperidone
C
1-Ethanesulfonyl-2,2,6,6-tetramethyl-piperidin-4-one
Conditions | Yield |
---|---|
With ethanethiol In benzene | A 9.6 % Chromat. B 71.2 % Chromat. C 9.9 % Chromat. |
4-oxo-2,2,6,6-tetramethylpiperidin-oxyl
ethanethiol
A
Diethyl disulfide
B
2,2,6,6-Tetramethyl-4-piperidone
C
1-Ethanesulfonyl-2,2,6,6-tetramethyl-piperidin-4-one
Conditions | Yield |
---|---|
In benzene for 24h; Product distribution; other nitroxides; | A 9.6 % Chromat. B 71.2 % Chromat. C 9.9 % Chromat. |
hydrogenchloride
1-nitroso-2,2,6,6-tetramethyl-4-piperidone
2,2,6,6-Tetramethyl-4-piperidone
2,2,6,6-Tetramethyl-4-piperidone
Conditions | Yield |
---|---|
With water |
3,5-dibromo-2,2,6,6-tetramethylpiperidin-4-one
acetic acid
2,2,6,6-Tetramethyl-4-piperidone
Conditions | Yield |
---|---|
With hydrogenchloride; hydrogen; platinum(IV) oxide under 1.5 Torr; for 40h; | 100% |
With potassium hydroxide; hydrazine hydrate In diethylene glycol at 210℃; Wolff-Kishner-Huang reduction; | 83% |
With potassium hydroxide; hydrazine In water; diethylene glycol at 127 - 200℃; Wolff-Kishner reduction; | 82% |
2,2,6,6-Tetramethyl-4-piperidone
3,5-dibromo-2,2,6,6-tetramethylpiperidin-4-one
Conditions | Yield |
---|---|
With bromine | 100% |
With bromine; acetic acid at 20℃; | 90% |
With bromine In acetic acid at 20℃; for 24h; | 84% |
2,2,6,6-Tetramethyl-4-piperidone
methylamine hydrochloride
4-N-methylamino-2,2,6,6-tetramethylpiperidine
Conditions | Yield |
---|---|
With C8H14BO4(1-)*Na(1+); triethylamine In tetrahydrofuran; dichloromethane at 20℃; for 6h; | 100% |
2,2,6,6-Tetramethyl-4-piperidone
N,N-phenylbistrifluoromethane-sulfonimide
Conditions | Yield |
---|---|
Stage #1: 2,2,6,6-Tetramethyl-4-piperidone With sodium hexamethyldisilazane In tetrahydrofuran at -78℃; for 0.25h; Stage #2: N,N-phenylbistrifluoromethane-sulfonimide In tetrahydrofuran at -78 - 20℃; | 100% |
2,2,6,6-Tetramethyl-4-piperidone
4-oxo-2,2,6,6-tetramethylpiperidin-oxyl
Conditions | Yield |
---|---|
With oxone; tetrabutylammomium bromide; potassium hydroxide In dichloromethane; water; acetone at 0℃; for 3h; pH=7.5 - 8; aq. phosphate buffer; | 99% |
With 3,3-dimethyldioxirane In acetone at 0℃; | 98% |
With sodium tungstate; ethylenediaminetetraacetic acid; dihydrogen peroxide In water at -5 - 20℃; for 240h; | 96% |
2,2,6,6-Tetramethyl-4-piperidone
dimethyl amine
4-dimethylamino-2,2,6,6-tetramethyl piperidine
Conditions | Yield |
---|---|
With formic acid In 5,5-dimethyl-1,3-cyclohexadiene at 130 - 135℃; for 5h; Inert atmosphere; | 98.3% |
With formic acid In 5,5-dimethyl-1,3-cyclohexadiene at 130 - 135℃; for 6h; Solvent; Temperature; Inert atmosphere; | 97.5% |
With palladium 10% on activated carbon; hydrogen In methanol at -10 - 60℃; under 2250.23 Torr; |
2,2,6,6-Tetramethyl-4-piperidone
N-butylamine
4-n-butylamino-2,2,6,6-tetramethylpiperidine
Conditions | Yield |
---|---|
Pt on carbon In water | 98% |
With hydrogen at 100℃; under 6750.68 Torr; for 5h; Pressure; Temperature; Autoclave; | 97.4% |
Stage #1: 2,2,6,6-Tetramethyl-4-piperidone; N-butylamine With acetic acid at 25℃; for 12h; Stage #2: With methanol; sodium tetrahydroborate for 8h; Temperature; Reagent/catalyst; | 95.2% |
Conditions | Yield |
---|---|
Pt on carbon In water | 98% |
2,2,6,6-Tetramethyl-4-piperidone
n-butyllithium
2,2,6,6-tetramethyl-4-n-butylpiperidin-4-ol
Conditions | Yield |
---|---|
In tetrahydrofuran at 20℃; | 97.3% |
2,2,6,6-Tetramethyl-4-piperidone
dimethyl sulfate
1,2,2,6,6-pentamethyl-4-piperidone
Conditions | Yield |
---|---|
With sodium hydroxide In N,N-dimethyl acetamide at 45℃; for 10h; Temperature; Solvent; | 97% |
2,2,6,6-Tetramethyl-4-piperidone
propynoic acid methyl ester
(E)-1-methoxycarbonyl-2-ethylene
Conditions | Yield |
---|---|
In dichloromethane for 2h; Ambient temperature; | 96% |
In methanol at 20℃; for 288h; | 81% |
In methanol at 20℃; for 288h; |
2,2,6,6-Tetramethyl-4-piperidone
ethynyl p-tolyl sulfone
Conditions | Yield |
---|---|
In dichloromethane for 2h; Ambient temperature; | 96% |
Conditions | Yield |
---|---|
In methanol | 96% |
Conditions | Yield |
---|---|
With sodium tetrahydroborate In ethanol at 20℃; for 4h; | 95% |
With sodium tetrahydroborate In ethanol at 0 - 20℃; for 2h; Inert atmosphere; | 93% |
With sodium tetrahydroborate In ethanol at 0 - 20℃; for 2h; | 93% |
2,2,6,6-Tetramethyl-4-piperidone
3,5-Dibromo-4-oxo-2,2,6,6-tetramethylpiperidine Hydrobromide
Conditions | Yield |
---|---|
Stage #1: 2,2,6,6-Tetramethyl-4-piperidone With acetic acid at 20℃; Stage #2: With bromine at 20℃; for 16h; | 95% |
With bromine In acetic acid | 93% |
With bromine; acetic acid at 10 - 20℃; for 2h; Inert atmosphere; | 91% |
Conditions | Yield |
---|---|
With hydroxylamine In sulfuric acid for 1h; | 95% |
With hydroxylamine hydrochloride; sodium methylate In ethanol; water at 20℃; for 16h; | 89.6% |
With hydroxylamine hydrochloride; sodium acetate In water | 18% |
2,2,6,6-Tetramethyl-4-piperidone
2,2,6,6-Tetramethyl-4,4-bis(hydroperoxy)piperidinium-sulfat
Conditions | Yield |
---|---|
With sulfuric acid; dihydrogen peroxide | 95% |
2,2,6,6-Tetramethyl-4-piperidone
ethanolamine
4-[(2-hydroxyethyl)amino]-2,2,6,6-tetramethylpiperidine
Conditions | Yield |
---|---|
With methanol; sodium tetrahydroborate at 20℃; for 24h; | 95% |
With hydrogenchloride; sodium cyanoborohydride In methanol for 72h; Ambient temperature; | 61% |
2,2,6,6-Tetramethyl-4-piperidone
n-Dodecylamine
N-(2,2,6,6-tetramethyl-4-piperidyl)-n-dodecylamine
Conditions | Yield |
---|---|
With methanol; sodium tetrahydroborate at 20℃; for 24h; | 95% |
In methanol | |
With sodium tetrahydroborate In methanol at 20℃; |
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In acetone; toluene at 110℃; for 8h; | 95% |
Conditions | Yield |
---|---|
With n-butyllithium In diethyl ether at -70℃; for 3.5h; | 94% |
2,2,6,6-Tetramethyl-4-piperidone
Pentaerythritol
2,2,4,4,14,14,16,16-octamethyl-7,11,18,21-tetraoxa-3,15-diaza-trispiro[5.2.2.5.2.2]heneicosane
Conditions | Yield |
---|---|
Stage #1: 2,2,6,6-Tetramethyl-4-piperidone; Pentaerythritol With toluene-4-sulfonic acid In toluene at 110℃; Dean-Stark; Stage #2: With N,N-dimethyl-formamide In toluene at 110℃; for 12h; Dean-Stark; | 94% |
Stage #1: 2,2,6,6-Tetramethyl-4-piperidone; Pentaerythritol With toluene-4-sulfonic acid In toluene for 12h; Reflux; Dean-Stark trap; Stage #2: With sodium hydroxide In water; toluene | 72% |
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In ethanol; 1,3,5-trimethyl-benzene at 160℃; for 2h; | 94% |
Conditions | Yield |
---|---|
With acetic acid In 5,5-dimethyl-1,3-cyclohexadiene; acetone at 140℃; for 6h; | 93% |
Conditions | Yield |
---|---|
In methanol | 92% |
In methanol |
2,2,6,6-Tetramethyl-4-piperidone
potassium cyanide
ammonium carbonate
1,3,8-triaza-7,7,9,9-tetramethyl-spiro[4.5]decane-2,4-dione
Conditions | Yield |
---|---|
In ethanol; water at 85℃; for 12h; | 91% |
2,2,6,6-Tetramethyl-4-piperidone
carbonic acid dimethyl ester
1,2,2,6,6-pentamethyl-4-piperidone
Conditions | Yield |
---|---|
With 1,4-diaza-bicyclo[2.2.2]octane In N,N-dimethyl-formamide at 110℃; for 3h; Reagent/catalyst; Temperature; Solvent; | 91% |
methanol
2,2,6,6-Tetramethyl-4-piperidone
methyl 2,2,5,5-tetramethyl-3-pyrrolidinecarboxylate
Conditions | Yield |
---|---|
Stage #1: methanol; 2,2,6,6-Tetramethyl-4-piperidone With sodium; potassium iodide Electrochemical reaction; Stage #2: With sodium amalgam Electrochemical reaction; | 90% |
Product Name: Triacetonamine (CAS NO.826-36-8)
Molecular Formula: C9H17NO
Molar mass: 155.23738 g/mol
Density: 0.882 g/cm3
Flash Point: 73.2 °C
Boiling Point: 205.6 °C at 760 mmHg
Index of Refraction: 1.427
Stability: Stable under normal temperatures and pressures
Vapour Pressure: 0.248 mmHg at 25°C
Melting point: 58-62°C
Appearance: White or light yellow powder
Solubility: soluble in acetone, alcohol, ether and water
Storage temp: Refrigerator (+4°C)
Surface Tension: 23.4 dyne/cm
Enthalpy of Vaporization: 44.18 kJ/mol
Index of Refraction: 1.427
Molar Refractivity: 45.18 cm3
Molar Volume: 175.8 cm3
XLogP3-AA: 0.5
H-Bond Donor: 1
H-Bond Acceptor: 2
Structure Descriptors of Triacetonamine (CAS NO.826-36-8):
IUPAC Name: 2,2,6,6-tetramethylpiperidin-4-one
Canonical SMILES: CC1(CC(=O)CC(N1)(C)C)C
InChI: InChI=1S/C9H17NO/c1-8(2)5-7(11)6-9(3,4)10-8/h10H,5-6H2,1-4H3
InChIKey: JWUXJYZVKZKLTJ-UHFFFAOYSA-N
Product Categories: Industrial/Fine Chemicals; Nitrogen cyclic compounds; API intermediates
Triacetonamine (CAS NO.826-36-8) can be used as the intermediates of hindered amine light stabilizer and pharmaceutical.
1. | orl-rat LD50:1539 mg/kg | GTPZAB Gigiena Truda i Professionalnye Zabolevaniia. Labor Hygiene and Occupational Diseases. 28 (5)(1984),53. | ||
2. | ipr-rat LD50:385 mg/kg | APPHAX Acta Poloniae Pharmaceutica. 24 (1967),652. |
Reported in EPA TSCA Inventory.
Poison by intraperitoneal route. Moderately toxic by ingestion. When heated to decomposition it emits toxic vapors of NOx.
Safety Information of Triacetonamine (CAS NO.826-36-8):
Hazard Codes:C,Xn
Risk Statements:
22: Harmful if swallowed
34: Causes burns
36: Irritating to the eyes
37: Irritating to the respiratory system
38: Irritating to the skin
Safety Statements:
22: Do not breathe dust
26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36: Wear suitable protective clothing
37: Wear suitable gloves
39: Wear eye/face protection
45: In case of accident or if you feel unwell, seek medical advice immediately (show label where possible)
Triacetonamine , its CAS NO. is 826-36-8, the synonyms are Tetramethylpiperidinone ; 2,2,6,6-Tetramethyl-4-piperidone ; IKh 196 ; NSC 16579 ; Odoratine ; TEMP ; Vincubina ; Vincubine .
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