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% |
TEMPOL
diazodiphenylmethane
A
4-hydroxy-2,2,6,6-tetramethylpiperidine
B
benzophenone
Conditions | Yield |
---|---|
In acetonitrile Product distribution; Rate constant; Mechanism; Ambient temperature; Irradiation; in chlorobenzene; | A n/a B 87% |
A
4-hydroxy-2,2,6,6-tetramethylpiperidine
B
2,2,2',2',6,6,6'6'-octamethyl-4,4'-dihydroxy-4,4'-bipiperidyl
Conditions | Yield |
---|---|
at 30 - 35℃; for 77.2h; electrochemical reduction at zinc cathode; | A 79% B 12% |
Conditions | Yield |
---|---|
Stage #1: acetone With ammonia In toluene at 50℃; for 3h; Green chemistry; Stage #2: With hydrogen In toluene at 50℃; for 3h; Catalytic behavior; Solvent; Reagent/catalyst; Temperature; Green chemistry; | 77% |
Conditions | Yield |
---|---|
With water In acetone Heating; UV irradiation; | 72% |
2,2,6,6-Tetramethyl-4-piperidone
A
2,2,6,6-tetramethyl-piperidine
B
4-hydroxy-2,2,6,6-tetramethylpiperidine
Conditions | Yield |
---|---|
With sulfuric acid at 25 - 30℃; for 4h; diapraghm electrolyzer, Cd cathode, concentration of II 0.65 mol/l; | A 66.1% B 20% |
With sulfuric acid at 25 - 30℃; for 4h; diapraghm electrolyzer, Cd cathode, concentration of II 1.3 mol/l; | A 27.7% B 54.6% |
With sulfuric acid at 24.85 - 29.85℃; Product distribution; Mechanism; electrochemical reduction (Cd or Pb cathodes, i=100 mA/cn2); var. reagents and temp.; |
1,2,2,6,6-pentamethyl-piperidin-4-ol
acetone
A
4-hydroxy-2,2,6,6-tetramethylpiperidine
B
1-(2-Hydroxy-2-methylpropyl)-2,2,6,6-tetramethyl-4-piperidol
C
4,4'-Dihydroxy-2,2,2',2',6,6,6',6'-octamethyl-1,1'-ethylenebispiperidine
Conditions | Yield |
---|---|
In benzene for 6h; Product distribution; Irradiation; irradiation with mercury quartz lamp; | A 1.4% B 9% C 52% |
In benzene for 7h; Product distribution; Heating; Irradiation; | A 2% B 21% C 51% |
In benzene for 7h; Heating; Irradiation; | A 2% B 21% C 51% |
2,2,6,6-tetramethylpiperidin-4-one hydrochloride
A
4-hydroxy-2,2,6,6-tetramethylpiperidine
B
2,2,6,6-tetramethyl-4-hydroxy-4-(1-hydroxy-1-methylethyl)piperidine
C
2,2,2',2',6,6,6'6'-octamethyl-4,4'-dihydroxy-4,4'-bipiperidyl
Conditions | Yield |
---|---|
With isopropyl alcohol for 22h; Heating; Irradiation; PRK-2 mercury-quartz lamp; | A 52% B 36% C 12% |
2,2,6,6-tetramethylpiperidin-4-one hydrochloride
isopropyl alcohol
A
4-hydroxy-2,2,6,6-tetramethylpiperidine
B
2,2,6,6-tetramethyl-4-hydroxy-4-(1-hydroxy-1-methylethyl)piperidine
C
2,2,2',2',6,6,6'6'-octamethyl-4,4'-dihydroxy-4,4'-bipiperidyl
Conditions | Yield |
---|---|
With isopropyl alcohol for 22h; Heating; Irradiation; PRK-2 mercury-quartz lamp; | A 52% B 36% C 12% |
1,2,2,6,6-pentamethyl-piperidin-4-ol
A
4-hydroxy-2,2,6,6-tetramethylpiperidine
B
1-(2-Hydroxy-2-methylpropyl)-2,2,6,6-tetramethyl-4-piperidol
C
4,4'-Dihydroxy-2,2,2',2',6,6,6',6'-octamethyl-1,1'-ethylenebispiperidine
Conditions | Yield |
---|---|
With acetone In benzene for 7h; Heating; Irradiation; | A 2% B 21% C 51% |
benzophenone
1,2,2,6,6-pentamethyl-piperidin-4-ol
A
4-hydroxy-2,2,6,6-tetramethylpiperidine
B
tetraphenylethane-1,2-diol
C
4,4'-Dihydroxy-2,2,2',2',6,6,6',6'-octamethyl-1,1'-ethylenebispiperidine
D
1-(2-Hydroxy-2,2-diphenylethylethyl)-2,2,6,6-tetramethyl-4-piperidol
Conditions | Yield |
---|---|
In benzene for 6h; Product distribution; Irradiation; irradiation with mercury quartz lamp; | A 6% B 46% C 34% D 31% |
xanth-9-one
1,2,2,6,6-pentamethyl-piperidin-4-ol
A
4-hydroxy-2,2,6,6-tetramethylpiperidine
B
1-(9-Hydroxy-9-xanthenyl)methyl-2,2,6,6-tetramethyl-4-piperidol
C
4,4'-Dihydroxy-2,2,2',2',6,6,6',6'-octamethyl-1,1'-ethylenebispiperidine
Conditions | Yield |
---|---|
In benzene for 28h; Product distribution; Irradiation; | A 44% B 22% C 9% |
In benzene for 28h; Heating; Irradiation; | A 44% B 22% C 9% |
1,2,2,6,6-pentamethyl-piperidin-4-ol
A
4-hydroxy-2,2,6,6-tetramethylpiperidine
B
1-(9-Hydroxy-9-xanthenyl)methyl-2,2,6,6-tetramethyl-4-piperidol
C
4,4'-Dihydroxy-2,2,2',2',6,6,6',6'-octamethyl-1,1'-ethylenebispiperidine
Conditions | Yield |
---|---|
With xanth-9-one In benzene for 28h; Heating; Irradiation; | A 44% B 22% C 9% |
1,2,2,6,6-pentamethyl-piperidin-4-ol
acetophenone
A
4-hydroxy-2,2,6,6-tetramethylpiperidine
B
2,3-diphenyl-2,3-butanediol
C
4,4'-Dihydroxy-2,2,2',2',6,6,6',6'-octamethyl-1,1'-ethylenebispiperidine
D
1-(2-Hydroxy-2-phenylpropyl)-2,2,6,6-tetramethyl-4-piperidol
Conditions | Yield |
---|---|
In benzene for 6h; Product distribution; Irradiation; irradiation with mercury quartz lamp; | A 4% B 26% C 41% D 10% |
1,2,2,6,6-pentamethyl-piperidin-4-ol
acetophenone
A
4-hydroxy-2,2,6,6-tetramethylpiperidine
B
4,4'-Dihydroxy-2,2,2',2',6,6,6',6'-octamethyl-1,1'-ethylenebispiperidine
C
1-(2-Hydroxy-2-phenylpropyl)-2,2,6,6-tetramethyl-4-piperidol
Conditions | Yield |
---|---|
for 7h; Product distribution; Irradiation; | A 41% B 4% C 24% |
In benzene for 7h; Heating; Irradiation; | A 41% B 4% C 24% |
benzophenone
1,2,2,6,6-pentamethyl-piperidin-4-ol
A
4-hydroxy-2,2,6,6-tetramethylpiperidine
B
4,4'-Dihydroxy-2,2,2',2',6,6,6',6'-octamethyl-1,1'-ethylenebispiperidine
C
1-(2-Hydroxy-2,2-diphenylethylethyl)-2,2,6,6-tetramethyl-4-piperidol
Conditions | Yield |
---|---|
In benzene for 6h; Product distribution; Irradiation; | A 28% B 24% C 32% |
In benzene for 6h; Heating; Irradiation; | A 28% B 24% C 32% |
phenyl benzyl ketone
1,2,2,6,6-pentamethyl-piperidin-4-ol
A
4-hydroxy-2,2,6,6-tetramethylpiperidine
B
1-(2-Hydroxy-2,3-diphenylpropyl)2,2,6,6-tetramethyl-4-piperidol
C
4,4'-Dihydroxy-2,2,2',2',6,6,6',6'-octamethyl-1,1'-ethylenebispiperidine
Conditions | Yield |
---|---|
In benzene for 7h; Product distribution; Irradiation; | A 30% B 27% C 15% |
In benzene for 7h; Heating; Irradiation; | A 30% B 27% C 15% |
1,2,2,6,6-pentamethyl-piperidin-4-ol
dihydrochalcone
A
4-hydroxy-2,2,6,6-tetramethylpiperidine
B
1-(2-Hydroxy-2,4-diphenylbutyl)-2,2,6,6-tetramethyl-4-piperidol
C
4,4'-Dihydroxy-2,2,2',2',6,6,6',6'-octamethyl-1,1'-ethylenebispiperidine
Conditions | Yield |
---|---|
In benzene for 38h; Product distribution; Irradiation; | A 9% B 8% C 23% |
In benzene for 38h; Heating; Irradiation; | A 9% B 8% C 23% |
TEMPOL
4-hydroxy-2,2,6,6-tetramethylpiperidine
Conditions | Yield |
---|---|
With ethanethiol In benzene | 19% |
4-AMINO-2,2,6,6-TETRAMETHYLPIPERIDINE
4-hydroxy-2,2,6,6-tetramethylpiperidine
Conditions | Yield |
---|---|
With hydrogenchloride; sodium nitrite |
2,2,6,6-Tetramethyl-4-piperidone
A
4-AMINO-2,2,6,6-TETRAMETHYLPIPERIDINE
B
4-hydroxy-2,2,6,6-tetramethylpiperidine
Conditions | Yield |
---|---|
With ammonium sulfate electrosynthesis, var. pH; | |
With ammonia; hydrogen; B113W In water at 55 - 100℃; under 30003 Torr; for 3h; Product distribution / selectivity; | A 92.10 %Chromat. B 5.49 %Chromat. |
1,2,2,6,6-pentamethyl-piperidin-4-ol
9,10-phenanthrenequinone
A
4-hydroxy-2,2,6,6-tetramethylpiperidine
B
0-hydroxy-9-(hydroxymethyl)anthrone
Conditions | Yield |
---|---|
In water; acetone Mechanism; Irradiation; var. amines and solvents; | |
In water; acetone Irradiation; |
C44H56O4*C9H19NO
A
4-hydroxy-2,2,6,6-tetramethylpiperidine
B
5,11,17,23-tetra-t-butyl-25,26,27,28-tetrahydroxycalix-4-arene
Conditions | Yield |
---|---|
In acetonitrile at 25℃; Equilibrium constant; |
4-hydroxy-2,2,6,6-tetramethylpiperidine
Conditions | Yield |
---|---|
With sodium amalgam; ethanol | |
With hydrogenchloride; sodium amalgam; ethanol |
hydrogenchloride
2,2,6,6-Tetramethyl-4-piperidone
4-hydroxy-2,2,6,6-tetramethylpiperidine
4-hydroxy-2,2,6,6-tetramethylpiperidine
TEMPOL
Conditions | Yield |
---|---|
With 3,3-dimethyldioxirane In acetone at 0℃; | 100% |
With decanesulfonic peracid In chloroform at 19.9℃; | 100% |
With sodium tungstate monohydrate; dihydrogen peroxide In methanol; water at 20℃; for 50h; Inert atmosphere; | 98% |
4-hydroxy-2,2,6,6-tetramethylpiperidine
2-[2-(vinyloxy)ethoxymethyl]oxirane
1-{2-hydroxy-3-[2-(vinyloxy)ethoxy]propyl}-2,2,6,6-tetra-methylpiperidin-4-ol
Conditions | Yield |
---|---|
at 135℃; for 4.5h; Sealed tube; regioselective reaction; | 100% |
4-hydroxy-2,2,6,6-tetramethylpiperidine
[2-(vinylthio)ethoxymethyl]oxirane
1-{2-hydroxy-3-[2-(vinylthio)ethoxy]propyl}-2,2,6,6-tetra-methylpiperidin-4-ol
Conditions | Yield |
---|---|
at 135℃; for 4.5h; Sealed tube; regioselective reaction; | 100% |
Conditions | Yield |
---|---|
With dihydrogen peroxide; sodium carbonate In water | 99.2% |
With dihydrogen peroxide; sodium hydrogencarbonate In water | |
With dihydrogen peroxide; sodium carbonate In water |
Conditions | Yield |
---|---|
With 3,3-dimethyldioxirane In acetone at 0℃; for 2h; | 99% |
With sodium tungstate; ethylenediaminetetraacetic acid; dihydrogen peroxide In water | |
With DMd In acetone | |
Multi-step reaction with 2 steps 1: sodium tungstate monohydrate; dihydrogen peroxide / methanol; water / 50 h / 20 °C / Inert atmosphere 2: phenylhydrazine / chloroform-d1 View Scheme |
Conditions | Yield |
---|---|
With di(n-butyl)tin oxide In toluene at 112 - 170℃; for 8h; Reagent/catalyst; Solvent; Temperature; Inert atmosphere; Industrial scale; | 98% |
4-hydroxy-2,2,6,6-tetramethylpiperidine
1-bromo-4-hydroxy-2,2,6,6-tetramethylpiperidine
Conditions | Yield |
---|---|
With hydrogen bromide; potassium bromide In benzene at 20 - 25℃; electrolysis; | 90% |
With sodium hypobromide In dichloromethane at 25℃; for 6h; Solvent; | 76% |
With bromine |
Conditions | Yield |
---|---|
In toluene at 230℃; for 0.333333h; Temperature; Microwave irradiation; chemoselective reaction; | 90% |
In toluene at 130℃; for 40h; Autoclave; Inert atmosphere; chemoselective reaction; | 80% |
4-hydroxy-2,2,6,6-tetramethylpiperidine
benzyl bromide
A
4-benzyloxy-2,2,6,6-tetramethylpiperidine
B
1-benzyl-4-hydroxy-2,2,6,6-tetramethylpiperidine
Conditions | Yield |
---|---|
In toluene at 230℃; for 0.333333h; Solvent; Temperature; Microwave irradiation; chemoselective reaction; | A 7 %Spectr. B 90% |
Conditions | Yield |
---|---|
In toluene at 130℃; for 40h; Temperature; Autoclave; chemoselective reaction; | 90% |
4-hydroxy-2,2,6,6-tetramethylpiperidine
methyl methacrylate
4-methacryloyloxy-2,2,6,6-tetramethylpiperidine
Conditions | Yield |
---|---|
With tetrabutoxytitanium; 2,4-dimethyl-6-tert-butylphenol In 5,5-dimethyl-1,3-cyclohexadiene at 90℃; for 7h; | 90% |
4-hydroxy-2,2,6,6-tetramethylpiperidine
tetramethyl 3,3',3'',3'''-(ethane-1,2-diylbis(azanetriyl))tetrapropanoate
tetrakis(2,2,6,6-tetramethylpiperidin-4-yl) 3,3',3'',3'''-(ethane-1,2-diylbis(azanetriyl))tetrapropanoate
Conditions | Yield |
---|---|
With titanium(IV) isopropylate In octane for 7h; Reflux; | 89.7% |
4-hydroxy-2,2,6,6-tetramethylpiperidine
tetramethyl 3,3',3'',3'''-(decane-1,10-diylbis(azanetriyl))tetrapropanoate
tetrakis(2,2,6,6-tetramethylpiperidin-4-yl) 3,3',3'',3'''-(decane-1,10-diylbis(azanetriyl))tetrapropanoate
Conditions | Yield |
---|---|
With titanium(IV) isopropylate In octane for 7h; Reflux; | 89.1% |
Conditions | Yield |
---|---|
Stage #1: 4-hydroxy-2,2,6,6-tetramethylpiperidine; 2,6-dichloropyridine With potassium tert-butylate In tetrahydrofuran at 20℃; for 1h; Stage #2: With hydrogenchloride In ethanol | 89% |
Conditions | Yield |
---|---|
Stage #1: 4-hydroxy-2,2,6,6-tetramethylpiperidine; phenylmalonic acid With dmap In dichloromethane for 0.5h; Inert atmosphere; Stage #2: With dicyclohexyl-carbodiimide In dichloromethane at -10 - 20℃; for 6h; Inert atmosphere; | 88.5% |
4-hydroxy-2,2,6,6-tetramethylpiperidine
2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl bromide
2,2,6,6-tetramethylpiperidin-4-yl tetra-O-benzyl-α-D-glucopyranoside hydrobromide
Conditions | Yield |
---|---|
With molecular sieve; N-ethyl-N,N-diisopropylamine; tetraethylammonium bromide In dichloromethane for 72h; Ambient temperature; dark; | 88.4% |
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 |
---|---|
In toluene at 130℃; for 40h; Autoclave; Inert atmosphere; chemoselective reaction; | 88% |
4-hydroxy-2,2,6,6-tetramethylpiperidine
tetrakis(2,2,6,6-tetramethylpiperidin-4-yl) 3,3',3'',3'''-(hexane-1,6-diylbis(azanetriyl))tetrapropanoate
Conditions | Yield |
---|---|
With titanium(IV) isopropylate In octane for 7h; Reflux; | 87.2% |
Conditions | Yield |
---|---|
Stage #1: 4-hydroxy-2,2,6,6-tetramethylpiperidine; 3-phenylglutaric acid With dmap In dichloromethane for 0.5h; Inert atmosphere; Stage #2: With dicyclohexyl-carbodiimide In dichloromethane at -5 - 20℃; for 8h; Inert atmosphere; | 86.2% |
Product Name: 2,2,6,6-Tetramethyl-4-piperidinol (CAS NO.2403-88-5)
Molecular Formula: C9H19NO
Molecular Weight: 157.25g/mol
Mol File: 2403-88-5.mol
EINECS: 219-291-2
Appearance: white to slightly beige crystalline powder
Melting Point: 129-131 °C(lit.)
Boiling point: 214.1 °C at 760 mmHg
Flash Point: 53 °C
Density: 0.891 g/cm3
Water Solubility: 130 g/L (23 °C)
Index of Refraction: 1.441
Molar Refractivity: 46.64 cm3
Molar Volume: 176.3 cm3
Surface Tension: 28 dyne/cm
Enthalpy of Vaporization: 52.38 kJ/mol
Vapour Pressure: 0.035 mmHg at 25°C
XLogP3-AA: 0.9
H-Bond Donor: 2
H-Bond Acceptor: 2
Structure Descriptors of 2,2,6,6-Tetramethyl-4-piperidinol (CAS NO.2403-88-5):
IUPAC Name: 2,2,6,6-tetramethylpiperidin-4-ol
Canonical SMILES: CC1(CC(CC(N1)(C)C)O)C
InChI: InChI=1S/C9H19NO/c1-8(2)5-7(11)6-9(3,4)10-8/h7,10-11H,5-6H2,1-4H3
InChIKey: VDVUCLWJZJHFAV-UHFFFAOYSA-N
Product Categories: Industrial/Fine Chemicals; Nitrogen cyclic compounds; Miscellaneous; API intermediates
Used as key intermediates for synthesis of hindered amine light stabilizers and hindered amine-type light stabilizer.
Safety Information of 2,2,6,6-Tetramethyl-4-piperidinol (CAS NO.2403-88-5):
Hazard Codes: Xi
Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36:Wear suitable protective clothing.
RIDADR: UN3259 8/PG 2
WGK Germany: 1
Hazard Note: Irritant
HS Code: 29333999
2,2,6,6-Tetramethyl-4-piperidinol , its CAS NO. is 2403-88-5, the synonyms are ,2,6,6-Tetramethyl-4-hydroxypiperidine ; 2,2,6,6-Tetramethylpiperidin-4-ol ; 4-Piperidinol, 2,2,6,6-tetramethyl- .
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