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Basic Information
CAS No.: 768-66-1
Name: 2,2,6,6-Tetramethylpiperidine
Article Data: 78
Molecular Structure:
Molecular Structure of 768-66-1 (2,2,6,6-Tetramethylpiperidine)
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: HarmfulXn, FlammableF, CorrosiveC
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
Synthetic route
826-36-8

2,2,6,6-Tetramethyl-4-piperidone

768-66-1

2,2,6,6-tetramethyl-piperidine

Conditions
ConditionsYield
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%
2564-83-2, 45842-10-2

2,2,6,6-Tetramethyl-1-piperidinyloxy free radical

[diphenyl-(2,2,6,6-tetramethyl-piperidin-1-yloxycarbonyl)-methylperoxy]-diphenyl-acetic acid 2,2,6,6-tetramethyl-piperidin-1-yl ester

A

768-66-1

2,2,6,6-tetramethyl-piperidine

B

119-61-9

benzophenone

C

102261-92-7

1-benzyloxy-2,2,6,6-tetramethylpiperidine

Conditions
ConditionsYield
In toluene at 100℃; for 8h; Rate constant; Thermodynamic data; ΔH(excit.), ΔS(excit.);A 90%
B 95%
C 92%
2564-83-2, 45842-10-2

2,2,6,6-Tetramethyl-1-piperidinyloxy free radical

622-47-9

4-tolylacetic acid

A

768-66-1

2,2,6,6-tetramethyl-piperidine

B

C18H27NO3

Conditions
ConditionsYield
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%

triacetone-amine hydrate

platinum (IV) oxide monohydrate

N-methyl-2,2,6,6-tetramethylpiperidone

768-66-1

2,2,6,6-tetramethyl-piperidine

Conditions
ConditionsYield
In sulfuric acid; water89.6%
145178-53-6

2,3-bis(trimethylsilyl)-1,3-butadiene-1,4-dione

A

768-66-1

2,2,6,6-tetramethyl-piperidine

B

102261-92-7

1-benzyloxy-2,2,6,6-tetramethylpiperidine

C

bis(trimethylsilyl) maleic anhydride

Conditions
ConditionsYield
With 2,2,6,6-tetramethyl-piperidine-N-oxyl In toluene at 90℃; for 3h;A 85%
B 76%
C 80%

2-iodo-2’-[(4-methoxyphenyl)ethynyl]-1,1’-biphenyl

A

768-66-1

2,2,6,6-tetramethyl-piperidine

B

9H,9′H-[9,9′-bifluorene]-9,9′-diylbis((4-methoxyphenyl)methanone)

Conditions
ConditionsYield
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%
2564-83-2, 45842-10-2

2,2,6,6-Tetramethyl-1-piperidinyloxy free radical

768-66-1

2,2,6,6-tetramethyl-piperidine

Conditions
ConditionsYield
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
108-88-3

toluene

618453-08-0

N-triphenylacetoxy-2,2,6,6-tetramethylpiperidine

A

768-66-1

2,2,6,6-tetramethyl-piperidine

B

2294-94-2

1,1,1,2-tetraphenylethane

Conditions
ConditionsYield
at 146℃; for 40h;A 78 % Chromat.
B 74%
2564-83-2

2,2,6,6-tetramethyl-piperidine-N-oxyl

(hydrotris-(3,5-dimethylpyrazolyl)borate)2U(benzophenone)

A

768-66-1

2,2,6,6-tetramethyl-piperidine

B

119-61-9

benzophenone

C

(hydrotris(3,5-dimethylpyrazolyl)borate)2(uranium(IV))(O)

Conditions
ConditionsYield
In tetrahydrofuran for 0.0833333h; Inert atmosphere; Schlenk technique;A n/a
B n/a
C 72%
366818-95-3

2-(2,2,6,6-tetramethyl-piperidin-1-yloxy)-hept-6-enoic acid 2,2,6,6-tetramethyl-piperidin-1-yl ester

A

768-66-1

2,2,6,6-tetramethyl-piperidine

B

2-(2,2,6,6-tetramethyl-piperidin-1-yloxymethyl)-cyclopentanecarboxylic acid 2,2,6,6-tetramethyl-piperidin-1-yl ester

Conditions
ConditionsYield
In tert-butyl alcohol at 130℃; for 24h;A 8%
B 70%
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Consensus Reports

Reported in EPA TSCA Inventory.

Specification

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.

Preparation of 2,2,6,6-Tetramethylpiperidine

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.