2,2,6,6-Tetramethylpiperidine supplier

Name
2,2,6,6-Tetramethylpiperidine
EINECS 212-199-3
CAS No. 768-66-1
Article Data78
CAS DataBase
Density 0.787 g/cm³
Solubility miscible with water
Melting Point -59 °C
Formula C₉H₁₉N
Boiling Point 157.6 °C at 760 mmHg
Molecular Weight 141.257
Flash Point 24.4 °C
Transport Information UN 1992 3/PG 3
Appearance clear colorless to light yellow-green liquid
Safety 26-37/39-16
Risk Codes 10-22-36/37/38
Molecular Structure
Hazard Symbols Xn, F, C
Synonyms Norpempidine;2,2,6,6-Tetramethylpiperidien;
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

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%

: 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

Conditions	Yield
In toluene at 100℃; for 8h; Rate constant; Thermodynamic data; ΔH(excit.), ΔS(excit.);	A 90% B 95% C 92%

...Expand

: 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

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%

...Expand

: triacetone-amine hydrate

: platinum (IV) oxide monohydrate

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

: 768-66-1
2,2,6,6-tetramethyl-piperidine

Conditions

Conditions	Yield
In sulfuric acid; water	89.6%

...Expand

: 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

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

...Expand

: 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

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%

: 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

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

: 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

Conditions	Yield
at 146℃; for 40h;	A 78 % Chromat. B 74%

...Expand

: 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

Conditions	Yield
In tetrahydrofuran for 0.0833333h; Inert atmosphere; Schlenk technique;	A n/a B n/a C 72%

...Expand

: 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

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

: 826-36-8
2,2,6,6-Tetramethyl-4-piperidone

A: 768-66-1
2,2,6,6-tetramethyl-piperidine

B: 2403-88-5
4-hydroxy-2,2,6,6-tetramethylpiperidine

Conditions

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.;

: 7031-93-8
2,2,6,6-tetramethylpiperidin-1-ol

A: 768-66-1
2,2,6,6-tetramethyl-piperidine

B: 2564-83-2, 45842-10-2
2,2,6,6-Tetramethyl-1-piperidinyloxy free radical

Conditions

Conditions	Yield
In diethyl ether; acetonitrile at 20℃; for 8h; Inert atmosphere; Schlenk technique; Sealed tube;	A n/a B 64%
at 70℃; for 2h; Schlenk technique; Inert atmosphere;	A 32 %Chromat. B 67 %Chromat.

: 104172-64-7
chloro(diphenylmethyl)(2,2,6,6-tetramethylpiperidino)borane

: 38227-87-1
2,2,6,6-tetramethylpiperidinyl-lithium

A: 768-66-1
2,2,6,6-tetramethyl-piperidine

B: 105309-74-8
benzyl(diphenylmethyl)(2,2,6,6-tetramethylpiperidino)borane

Conditions

Conditions	Yield
In toluene byproducts: LiCl; addn. of the lithiopiperidine in toluene to the borane in toluene and refluxing for 3 h; filtn. (LiCl), concn. (high vac.), distn. (vac.) and recrystn. from ether; elem. anal.;	A n/a B 63%

...Expand

: 696-62-8
para-iodoanisole

: [Li(μ-2,2,6,6-tetramethylpiperidide)(μ-bis[2-(N,N-dimethylamino)ethyl]ether)Al(isobutyl)2]

A: 768-66-1
2,2,6,6-tetramethyl-piperidine

B: C15H26N2O2

Conditions

Conditions	Yield
Stage #1: [Li(μ-2,2,6,6-tetramethylpiperidide)(μ-bis[2-(N,N-dimethylamino)ethyl]ether)Al(isobutyl)2] With zinc diacetate In tetrahydrofuran Inert atmosphere; Stage #2: para-iodoanisole With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate In tetrahydrofuran Inert atmosphere;	A n/a B 62%

...Expand

: 2564-83-2, 45842-10-2
2,2,6,6-Tetramethyl-1-piperidinyloxy free radical

A: 768-66-1
2,2,6,6-tetramethyl-piperidine

B: 7605-48-3
bis(4-tert-butylphenyl)disulfide

C: 2,2,6,6-tetramethylpiperidinium p-tert-butylbenzenesulphinate

D: 2,2,6,6-tetarmethylpiperidinium p-tert-butylbenzenesulphonate

Conditions

Conditions	Yield
With 4-t-butylbenzenethiol In benzene for 0.5h; Ambient temperature; Further byproducts given;	A 10% B 10% C 9% D 56%

...Expand

: 2564-83-2, 45842-10-2
2,2,6,6-Tetramethyl-1-piperidinyloxy free radical

: 2396-68-1
4-t-butylbenzenethiol

A: 768-66-1
2,2,6,6-tetramethyl-piperidine

B: 7605-48-3
bis(4-tert-butylphenyl)disulfide

C: 2,2,6,6-tetramethylpiperidinium p-tert-butylbenzenesulphinate

D: 2,2,6,6-tetarmethylpiperidinium p-tert-butylbenzenesulphonate

Conditions

Conditions	Yield
In benzene for 0.5h; Ambient temperature; Further byproducts given;	A 10% B 10% C 9% D 56%

...Expand

: 2396-68-1
4-t-butylbenzenethiol

A: 768-66-1
2,2,6,6-tetramethyl-piperidine

B: 7605-48-3
bis(4-tert-butylphenyl)disulfide

C: 2,2,6,6-tetramethylpiperidinium p-tert-butylbenzenesulphinate

D: 2,2,6,6-tetarmethylpiperidinium p-tert-butylbenzenesulphonate

Conditions

Conditions	Yield
With 2,2,6,6-tetramethyl-piperidine-N-oxyl In benzene for 0.5h; Ambient temperature; Further byproducts given;	A 10% B 10% C 9% D 56%

...Expand

: 2564-83-2, 45842-10-2
2,2,6,6-Tetramethyl-1-piperidinyloxy free radical

A: 768-66-1
2,2,6,6-tetramethyl-piperidine

B: 7031-93-8
2,2,6,6-tetramethylpiperidin-1-ol

Conditions

Conditions	Yield
With tris-(trimethylsilyl)silane In benzene at 80℃; for 3h; Product distribution; Mechanism; other reagents, reaction time, solvent, effect of irradiation and addition of initiators;	A 56% B 41%

: 79-55-0
1,2,2,6,6-pentamethylpiperidine

A: 768-66-1
2,2,6,6-tetramethyl-piperidine

B: 54262-97-4
2,2,6,6-tetramethylpiperidine-1-carboxaldehyde

Conditions

Conditions	Yield
With ruthenium tetroxide In tetrachloromethane for 2h;	A 4% B 53%
With 1,4-dimethylnaphtalene-1,4-endoperoxide In acetonitrile at 40℃; for 4h; Product distribution; Kinetics;	A 23 % Chromat. B 1.2 % Chromat.

: 2564-83-2, 45842-10-2
2,2,6,6-Tetramethyl-1-piperidinyloxy free radical

: 108-98-5
thiophenol

A: 768-66-1
2,2,6,6-tetramethyl-piperidine

B: 882-33-7
diphenyldisulfane

C: 2,2,6,6-tetramethylpiperidinium benzenesulphinate

D: 2,2,6,6-tetarmethylpiperidinium benzenesulphonate

Conditions

Conditions	Yield
In benzene for 0.5h; Ambient temperature; Further byproducts given;	A 9% B 8% C 14% D 49%

...Expand

: 2564-83-2, 45842-10-2
2,2,6,6-Tetramethyl-1-piperidinyloxy free radical

: 108-98-5
thiophenol

A: 768-66-1
2,2,6,6-tetramethyl-piperidine

B: N-benzenesulphinyl-2,2,6,6-tetramethylpiperidine

C: 2,2,6,6-tetramethylpiperidinium benzenesulphinate

D: 2,2,6,6-tetarmethylpiperidinium benzenesulphonate

Conditions

Conditions	Yield
In benzene for 0.5h; Ambient temperature; Further byproducts given;	A 9% B 5% C 14% D 49%

...Expand

: 2564-83-2, 45842-10-2
2,2,6,6-Tetramethyl-1-piperidinyloxy free radical

: 108-98-5
thiophenol

A: 768-66-1
2,2,6,6-tetramethyl-piperidine

B: N-benzenesulphonyl-2,2,6,6-tetramethylpiperidine

C: 2,2,6,6-tetramethylpiperidinium benzenesulphinate

D: 2,2,6,6-tetarmethylpiperidinium benzenesulphonate

Conditions

Conditions	Yield
In benzene for 0.5h; Ambient temperature; Further byproducts given;	A 9% B 7% C 14% D 49%

...Expand

: 108-98-5
thiophenol

A: 768-66-1
2,2,6,6-tetramethyl-piperidine

B: 882-33-7
diphenyldisulfane

C: 2,2,6,6-tetramethylpiperidinium benzenesulphinate

D: 2,2,6,6-tetarmethylpiperidinium benzenesulphonate

Conditions

Conditions	Yield
With 2,2,6,6-tetramethyl-piperidine-N-oxyl In benzene for 0.5h; Ambient temperature; Further byproducts given;	A 9% B 8% C 14% D 49%

...Expand

: 2564-83-2, 45842-10-2
2,2,6,6-Tetramethyl-1-piperidinyloxy free radical

: 106-45-6
para-thiocresol

A: 768-66-1
2,2,6,6-tetramethyl-piperidine

B: 103-19-5
di(p-tolyl) disulfide

C: 30680-88-7
2,2,6,6-tetarmethylpiperidinium p-toluenesulphonate

D: 2,2,6,6-tetarmethylpiperidinium p-toluenesulphinate

Conditions

Conditions	Yield
In benzene for 0.5h; Ambient temperature; Further byproducts given;	A 7% B 12% C 47% D 21%

...Expand

: 106-45-6
para-thiocresol

A: 768-66-1
2,2,6,6-tetramethyl-piperidine

B: 103-19-5
di(p-tolyl) disulfide

C: 30680-88-7
2,2,6,6-tetarmethylpiperidinium p-toluenesulphonate

D: 2,2,6,6-tetarmethylpiperidinium p-toluenesulphinate

Conditions

Conditions	Yield
With 2,2,6,6-tetramethyl-piperidine-N-oxyl In benzene for 0.5h; Ambient temperature; Further byproducts given;	A 7% B 12% C 47% D 21%

...Expand

: 2564-83-2, 45842-10-2
2,2,6,6-Tetramethyl-1-piperidinyloxy free radical

A: 768-66-1
2,2,6,6-tetramethyl-piperidine

B: 131309-38-1
1-Ethanesulfonyl-2,2,6,6-tetramethyl-piperidine

Conditions

Conditions	Yield
With ethanethiol In benzene Yields of byproduct given;	A 45% B n/a

: 79-55-0
1,2,2,6,6-pentamethylpiperidine

A: 768-66-1
2,2,6,6-tetramethyl-piperidine

B: 5132-07-0
TEMPO

C: 54262-97-4
2,2,6,6-tetramethylpiperidine-1-carboxaldehyde

Conditions

Conditions	Yield
With sodium periodate; ruthenium tetroxide In tetrachloromethane; water for 5h;	A 4% B 7% C 41%

...Expand

: 330938-05-1
phenylacetic acid 2,2,6,6-tetramethylpiperidin-1-yl ester

A: 768-66-1
2,2,6,6-tetramethyl-piperidine

B: 103-82-2
phenylacetic acid

Conditions

Conditions	Yield
In tert-butyl alcohol at 130℃; for 168h;	A 30% B 35%

: 2564-83-2, 45842-10-2
2,2,6,6-Tetramethyl-1-piperidinyloxy free radical

: 100-46-9
benzylamine

A: 768-66-1
2,2,6,6-tetramethyl-piperidine

B: 7031-93-8
2,2,6,6-tetramethylpiperidin-1-ol

C: 74601-40-4
phenyl(2,2,6,6-tetramethylpiperidin-1-yl)methanone

Conditions

Conditions	Yield
With tert.-butylhydroperoxide; zinc dibromide In pyridine; water at 80℃; for 16h;	A n/a B n/a C 35%

...Expand

: 79-55-0
1,2,2,6,6-pentamethylpiperidine

: 768-66-1
2,2,6,6-tetramethyl-piperidine

Conditions

Conditions	Yield
With Hg(II)-EDTA	28%
With Hg(II)-EDTA Product distribution; other reagent: Hg(OAc)2; also in HCOOH as solvent;	28%

: 768-66-1
2,2,6,6-tetramethyl-piperidine

: 14775-42-9
2,2,5,5-tetramethyl-4-(toluene-4-sulfonyloxy)-hexan-3-one

: 73333-60-5
2-(2,3-Di-tert-butyl-oxiranyl)-4-methyl-benzenesulfonic acid; compound with 2,2,6,6-tetramethyl-piperidine

Conditions

Conditions	Yield
With methyllithium Mechanism;	100%
With methyllithium Yield given. Multistep reaction;

: 768-66-1
2,2,6,6-tetramethyl-piperidine

: 7031-93-8
2,2,6,6-tetramethylpiperidin-1-ol

Conditions

Conditions	Yield
With Oxone; silica gel In water at 80℃; for 24h; Oxidation;	100%

: 768-66-1
2,2,6,6-tetramethyl-piperidine

: isopentenyl trifluoroacetate

: C13H25N

Conditions

Conditions	Yield
With C36H47Cl2N2P2PdTi(2+) In chloroform-d1 at 20℃; for 0.0833333h; Glovebox;	100%

: 768-66-1
2,2,6,6-tetramethyl-piperidine

: zinc trimethylacetate

: 6921-34-2
benzylmagnesium chloride

: TMPZnCl*Mg(OPiv)2, TMP - 2,2,6,6-tetramethylpiperidyl, OPiv -pivalate

Conditions

Conditions	Yield
Stage #1: 2,2,6,6-tetramethyl-piperidine; benzylmagnesium chloride In tetrahydrofuran at 40℃; Inert atmosphere; Schlenk technique; Stage #2: zinc trimethylacetate In tetrahydrofuran at 20℃; for 0.333333h; Inert atmosphere; Schlenk technique;	100%
Stage #1: 2,2,6,6-tetramethyl-piperidine; benzylmagnesium chloride In tetrahydrofuran at 20 - 40℃; for 12h; Inert atmosphere; Schlenk technique; Stage #2: zinc trimethylacetate In tetrahydrofuran at 20℃; for 1h; Inert atmosphere; Schlenk technique;

...Expand

: 768-66-1
2,2,6,6-tetramethyl-piperidine

: 32579-76-3
1-chloro-2,2,6,6-tetramethylpiperidine

Conditions

Conditions	Yield
With chlorine; sodium hydroxide In water at 5 - 20℃; for 1.5h; Reagent/catalyst; Time; Inert atmosphere;	99%
With sodium hypochlorite pentahydrate; sodium acetate trihydrate; acetic acid In water at 20℃; for 2h;	91%
With hydrogenchloride; sodium chloride In tetrachloromethane at 20℃; electrolysis;	72%

: 768-66-1
2,2,6,6-tetramethyl-piperidine

: 1623-99-0
phenyl sodium

: 770-09-2
benzyltrimethylsilane

Conditions

Conditions	Yield
With sodium In chlorobenzene; toluene	99%

: 768-66-1
2,2,6,6-tetramethyl-piperidine

: 124-38-9
carbon dioxide

: 79-55-0
1,2,2,6,6-pentamethylpiperidine

Conditions

Conditions	Yield
With phenylsilane In N,N-dimethyl acetamide at 60℃; for 2h; Sealed tube;	99%
With phenylsilane In N,N-dimethyl-formamide at 90℃; under 760.051 Torr; for 24h; Schlenk technique;	95%
With diphenylsilane; C21H41N3NiP2 In acetonitrile at 120℃; under 2052.14 Torr; for 24h; Autoclave;	84%

: 768-66-1
2,2,6,6-tetramethyl-piperidine

: 76-05-1
trifluoroacetic acid

: 563-47-3
3-Chloro-2-methylpropene

: 2,2,6,6-tetramethyl-1-(2-methallyl)piperidine trifluoroacetate

Conditions

Conditions	Yield
Stage #1: 2,2,6,6-tetramethyl-piperidine; 3-Chloro-2-methylpropene With C36H45Cl2N2P2PdTi(1+) In dichloromethane at 20℃; for 0.166667h; Stage #2: trifluoroacetic acid In methanol; dichloromethane Reagent/catalyst;	99%

...Expand

: 768-66-1
2,2,6,6-tetramethyl-piperidine

: 6130-93-4
2,2,6,6-tetramethyl-1-nitrosopiperidine

Conditions

Conditions	Yield
With hydrogenchloride; sodium nitrite at 75 - 100℃; Nitrosation;	98%
With hydrogenchloride; sodium nitrite at 75 - 100℃; Nitrosation;	98%
With hydrogenchloride; sodium nitrite for 96h; Heating;	89%

: 768-66-1
2,2,6,6-tetramethyl-piperidine

: 104-15-4
toluene-4-sulfonic acid

: 30680-88-7
2,2,6,6-tetarmethylpiperidinium p-toluenesulphonate

Conditions

Conditions	Yield
In acetone at 15 - 20℃; for 0.5h;	98%
In acetonitrile Yield given;

: 768-66-1
2,2,6,6-tetramethyl-piperidine

: 372-09-8
cyanoacetic acid

: 1360789-22-5
3-oxo-3-(2,2,6,6-tetramethylpiperidin-1-yl)propanenitrile

Conditions

Conditions	Yield
Stage #1: cyanoacetic acid With 2-chloro-1-methyl-pyridinium iodide In dichloromethane for 0.25h; Inert atmosphere; Stage #2: 2,2,6,6-tetramethyl-piperidine In dichloromethane at 18℃; Inert atmosphere;	98%

: 768-66-1
2,2,6,6-tetramethyl-piperidine

: 7646-85-7
zinc(II) chloride

: bis(2,2,6,6-tetramethyl-1-piperidyl)zinc

Conditions

Conditions	Yield
Stage #1: 2,2,6,6-tetramethyl-piperidine With n-butyllithium In pentane at -78℃; for 1h; Inert atmosphere; Stage #2: zinc(II) chloride In diethyl ether; pentane at -78 - 23℃; Inert atmosphere;	98%
Stage #1: 2,2,6,6-tetramethyl-piperidine With n-butyllithium In hexane at 0℃; for 1h; Inert atmosphere; Schlenk technique; Stage #2: zinc(II) chloride In diethyl ether; hexane at 0℃; for 48h; Inert atmosphere; Schlenk technique;	58%
Stage #1: 2,2,6,6-tetramethyl-piperidine With n-butyllithium In hexane at 0℃; for 1h; Inert atmosphere; Schlenk technique; Stage #2: zinc(II) chloride In diethyl ether for 48h; Inert atmosphere; Schlenk technique;	58%

: 768-66-1
2,2,6,6-tetramethyl-piperidine

: 1493-13-6
trifluorormethanesulfonic acid

: 1252594-28-7
2,2,6,6-tetramethylpiperidinium triflate

Conditions

Conditions	Yield
In ethyl acetate at 15 - 20℃; for 0.5h;	98%

: 768-66-1
2,2,6,6-tetramethyl-piperidine

: 13450-90-3
Gallium trichloride

: bis(2,2,6,6-tetramethylpiperidino)gallium chloride

Conditions

Conditions	Yield
With n-butyllithium In diethyl ether; hexane byproducts: LiCl; under inert atmosphere, piperidine in hexane reacted with n-BuLi in hexane, dropwise addn. of GaCl3 in diethyl ether at room temp. with stirring, refluxed for 2 h; filtered, cooled to -78°C; elem. anal.;	97%

: 768-66-1
2,2,6,6-tetramethyl-piperidine

: 2,2,6,6-tetramethylpiperidinylmagnesium chloride lithium chloride complex

Conditions

Conditions	Yield
With isopropyl chloride; magnesium; lithium chloride In tetrahydrofuran; toluene at 40 - 80℃; under 5171.62 Torr; Inert atmosphere; Flow reactor;	97%
With TurboGrignard In tetrahydrofuran at 20℃; for 48h; Inert atmosphere;
With TurboGrignard In tetrahydrofuran for 48h; Inert atmosphere;

: 768-66-1
2,2,6,6-tetramethyl-piperidine

: 13894-21-8
ethynyl p-tolyl sulfone

: 2,2,6,6-Tetramethyl-1-[(E)-2-(toluene-4-sulfonyl)-vinyl]-piperidine

Conditions

Conditions	Yield
In dichloromethane for 1h; Ambient temperature;	96%

: 768-66-1
2,2,6,6-tetramethyl-piperidine

: 922-67-8
propynoic acid methyl ester

: 118061-26-0
(E)-1-methoxycarbonyl-2-ethylene

Conditions

Conditions	Yield
In dichloromethane for 1h; Ambient temperature;	96%

: 768-66-1
2,2,6,6-tetramethyl-piperidine

: 64-18-6
formic acid

: 96927-50-3
[2,2,,6,6-Me4C5H6NH2][O2CH]

Conditions

Conditions	Yield
In diethyl ether	96%
In diethyl ether

: 768-66-1
2,2,6,6-tetramethyl-piperidine

: 75-75-2
methanesulfonic acid

: 2,2,6,6-tetramethylpiperidinium mesylate

Conditions

Conditions	Yield
In acetone at 15 - 20℃; for 0.5h;	96%

: 768-66-1
2,2,6,6-tetramethyl-piperidine

: 81428-20-8
(1-Brom-2,2-dimethyl-1-phenylpropyl)isocyanat

: 81428-34-4
3-(2,2-Dimethyl-1-phenylpropyliden)-1,1-(1,1,5,5-tetramethyl-1,5-pentandiyl)harnstoff

Conditions

Conditions	Yield
With triethylamine In diethyl ether at -78℃; for 0.25h;	95%

: 768-66-1
2,2,6,6-tetramethyl-piperidine

: bis[2,2,6,6-tetramethylpiperidinium] hexafluorosilicate

Conditions

Conditions	Yield
With hydrogen fluoride; silica gel	95%

: 768-66-1
2,2,6,6-tetramethyl-piperidine

: 107819-90-9
1,3-bis(tert-butoxycarbonyl)-2-methyl-2-thiopseudourea

: [N,N'-bis(tert-butoxycarbonyl)carboxamidino]-2,2,6,6-tetramethylpiperidine

Conditions

Conditions	Yield
With potassium carbonate; copper(l) chloride In tetrahydrofuran at 40℃; for 12h;	95%

: 768-66-1
2,2,6,6-tetramethyl-piperidine

: 13450-90-3
Gallium trichloride

tetramethylpiperidine gallium trichloride: 154626-03-6
tetramethylpiperidine gallium trichloride

Conditions

Conditions	Yield
In benzene addn. of tetramethylpiperidine to a stirred soln. of GaCl3 at -78°C, warmed up to 25°C over 2 h, stirring for 6 h; removal of the solvent in vac., extn. in toluene, filtn., concg. of the filtrate, cooling at -30°C for 2 wk, elem. anal.;	95%

: 768-66-1
2,2,6,6-tetramethyl-piperidine

: 1109-15-5
tris(pentafluorophenyl)borate

: C9H19N*C18HBF15(1-)*H(1+)

Conditions

Conditions	Yield
With hydrogen In toluene at 20℃; under 760.051 Torr; for 1h;	95%
With hydrogen at -80℃;
With hydrogen under 5168.02 Torr; Thermodynamic data; Inert atmosphere;

: 768-66-1
2,2,6,6-tetramethyl-piperidine

: TMPMgCl*LiCl

Conditions

Conditions	Yield
With TurboGrignard In tetrahydrofuran at 25℃; for 48h; Inert atmosphere;	95%

: 768-66-1
2,2,6,6-tetramethyl-piperidine

: 7646-85-7
zinc(II) chloride

: zinc chloride-2,2,6,6-tetramethylpiperidin-1-ide lithium chloride complex

Conditions

Conditions	Yield
Stage #1: 2,2,6,6-tetramethyl-piperidine With n-butyllithium In hexane at -40 - -10℃; for 1h; Stage #2: zinc(II) chloride In tetrahydrofuran; hexane at -10 - 25℃; for 1h;	95%
Stage #1: 2,2,6,6-tetramethyl-piperidine With n-butyllithium In tetrahydrofuran; hexane at -40 - 25℃; for 2h; Inert atmosphere; Stage #2: zinc(II) chloride In tetrahydrofuran; hexane Inert atmosphere;

: 768-66-1
2,2,6,6-tetramethyl-piperidine

: 27286-84-6
((4,5-dimethyl-1,2-phenylene)bis(ethyne-2,1-diyl))dibenzene

: 1109-15-5
tris(pentafluorophenyl)borate

: C42H17BF15(1-)*C9H19N*H(1+)

Conditions

Conditions	Yield
In pentane at 20℃;	95%

...Expand

: 768-66-1
2,2,6,6-tetramethyl-piperidine

: 124-38-9
carbon dioxide

: 844504-52-5
tris(pentafluorophenyl)silyl triflate

A: 1252594-28-7
2,2,6,6-tetramethylpiperidinium triflate

B: C28H18F15NO2Si

Conditions

Conditions	Yield
In dichloromethane-d2 Glovebox; Schlenk technique;	A n/a B 95%

...Expand

2,2,6,6-Tetramethylpiperidine Consensus Reports

Reported in EPA TSCA Inventory.

2,2,6,6-Tetramethylpiperidine 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.

Product Name

2,2,6,6-Tetramethylpiperidine

Synthetic route

2,2,6,6-Tetramethylpiperidine Consensus Reports

2,2,6,6-Tetramethylpiperidine Specification

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