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CAS No.: | 768-66-1 |
---|---|
Name: | 2,2,6,6-Tetramethylpiperidine |
Article Data: | 78 |
Molecular Structure: | |
Formula: | C9H19N |
Molecular Weight: | 141.257 |
Synonyms: | Norpempidine;2,2,6,6-Tetramethylpiperidien; |
EINECS: | 212-199-3 |
Density: | 0.787 g/cm3 |
Melting Point: | -59 °C |
Boiling Point: | 157.6 °C at 760 mmHg |
Flash Point: | 24.4 °C |
Solubility: | miscible with water |
Appearance: | clear colorless to light yellow-green liquid |
Hazard Symbols: | Xn, F, C |
Risk Codes: | 10-22-36/37/38 |
Safety: | 26-37/39-16 |
Transport Information: | UN 1992 3/PG 3 |
PSA: | 12.03000 |
LogP: | 2.64590 |
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-1-piperidinyloxy free radical
A
2,2,6,6-tetramethyl-piperidine
B
benzophenone
C
1-benzyloxy-2,2,6,6-tetramethylpiperidine
Conditions | Yield |
---|---|
In toluene at 100℃; for 8h; Rate constant; Thermodynamic data; ΔH(excit.), ΔS(excit.); | A 90% B 95% C 92% |
2,2,6,6-Tetramethyl-1-piperidinyloxy free radical
4-tolylacetic acid
A
2,2,6,6-tetramethyl-piperidine
Conditions | Yield |
---|---|
Stage #1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; 4-tolylacetic acid With N4,N4,N7,N7-tetramethyl-1,10-phenanthroline-4,7-diamine; iron(II) acetate In tetrahydrofuran at 60℃; for 96h; Molecular sieve; Inert atmosphere; Stage #2: With triethylamine In acetone Kinetics; Reagent/catalyst; Solvent; | A n/a B 90% |
2,2,6,6-tetramethyl-piperidine
Conditions | Yield |
---|---|
In sulfuric acid; water | 89.6% |
2,3-bis(trimethylsilyl)-1,3-butadiene-1,4-dione
A
2,2,6,6-tetramethyl-piperidine
B
1-benzyloxy-2,2,6,6-tetramethylpiperidine
Conditions | Yield |
---|---|
With 2,2,6,6-tetramethyl-piperidine-N-oxyl In toluene at 90℃; for 3h; | A 85% B 76% C 80% |
A
2,2,6,6-tetramethyl-piperidine
Conditions | Yield |
---|---|
With 4-methoxy-9H-thioxanthen-9-one; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical In dichloromethane; acetone at 20℃; for 48h; Reagent/catalyst; Solvent; Sealed tube; Irradiation; Inert atmosphere; | A n/a B 84% |
2,2,6,6-Tetramethyl-1-piperidinyloxy free radical
2,2,6,6-tetramethyl-piperidine
Conditions | Yield |
---|---|
With tert-Butyl peroxybenzoate; 1-cyano-1,2-benziodoxol-3-(1H)-one at 110℃; for 12h; Inert atmosphere; Glovebox; | 76% |
With thiophosgene at 20℃; for 24h; | 37% |
Multi-step reaction with 2 steps 1: 1) FClO3, BF3*(C2H5)2O / 1) hexane, 0 deg C 2: 1) FClO3, BF3*(C2H5)2O / 1) hexane, 0 deg C View Scheme |
toluene
N-triphenylacetoxy-2,2,6,6-tetramethylpiperidine
A
2,2,6,6-tetramethyl-piperidine
B
1,1,1,2-tetraphenylethane
Conditions | Yield |
---|---|
at 146℃; for 40h; | A 78 % Chromat. B 74% |
2,2,6,6-tetramethyl-piperidine-N-oxyl
A
2,2,6,6-tetramethyl-piperidine
B
benzophenone
Conditions | Yield |
---|---|
In tetrahydrofuran for 0.0833333h; Inert atmosphere; Schlenk technique; | A n/a B n/a C 72% |
2-(2,2,6,6-tetramethyl-piperidin-1-yloxy)-hept-6-enoic acid 2,2,6,6-tetramethyl-piperidin-1-yl ester
A
2,2,6,6-tetramethyl-piperidine
Conditions | Yield |
---|---|
In tert-butyl alcohol at 130℃; for 24h; | A 8% B 70% |
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Reported in EPA TSCA Inventory.
2,2,6,6-Tetramethylpiperidine, with CAS number of 768-66-1, can be called piperidine, 2,2,6,6-tetramethyl-; 2,2,6,6-Tetramethylpiperidin; TEMP. It is an organic compound of the amine class and a clear colorless to light yellow-green liquid. 2,2,6,6-Tetramethylpiperidine (CAS NO.768-66-1) is used in chemistry as a hindered base.
Physical properties about 2,2,6,6-Tetramethylpiperidine are: (1)ACD/LogP: 2.445; (2)ACD/LogD (pH 5.5): -0.65; (3)ACD/LogD (pH 7.4): -0.57; (4)ACD/BCF (pH 5.5): 1.00; (5)ACD/BCF (pH 7.4): 1.00; (6)ACD/KOC (pH 5.5): 1.00; (7)ACD/KOC (pH 7.4): 1.00; (8)#H bond acceptors: 1; (9)#H bond donors: 1; (10)Index of Refraction: 1.417; (11)Molar Refractivity: 45.05 cm3; (12)Molar Volume: 179.316 cm3; (13)Polarizability: 17.859 10-24cm3; (14)Surface Tension: 24.5450000762939 dyne/cm; (15)Density: 0.788 g/cm3; (16)Flash Point: 24.444 °C; (17)Enthalpy of Vaporization: 39.429 kJ/mol; (18)Boiling Point: 157.61 °C at 760 mmHg; (19)Vapour Pressure: 2.73200011253357 mmHg at 25°C
Preparation of 2,2,6,6-Tetramethylpiperidine: The recent production starts with a conjugate addition reaction of ammonia to phorone. The intermediate triacetone amine is then reduced in a Wolff-Kishner reaction.
When you are using this chemical, please be cautious about it as the following:
1. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice;
2. Wear suitable gloves and eye/face protection;
3. Keep away from sources of ignition - No smoking;
You can still convert the following datas into molecular structure:
(1)InChI=1S/C9H19N/c1-8(2)6-5-7-9(3,4)10-8/h10H,5-7H2,1-4H3;
(2)InChIKey=RKMGAJGJIURJSJ-UHFFFAOYSA-N;
(3)SmilesN1C(CCCC1(C)C)(C)C;
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | intravenous | 33mg/kg (33mg/kg) | Nature. Vol. 184, Pg. 1707, 1959. | |
mouse | LD50 | oral | 220mg/kg (220mg/kg) | Nature. Vol. 184, Pg. 1707, 1959. |