2,2,6,6-Tetramethylpiperidinooxy supplier

Name
2,2,6,6-Tetramethylpiperidinooxy
EINECS 219-888-8
CAS No. 2564-83-2
Article Data103
CAS DataBase
Density 1 g/cm³
Solubility Soluble in all organic solvents. Insoluble in water.
Melting Point 36-38 °C(lit.)
Formula C₉H₁₈NO
Boiling Point 193 °C
Molecular Weight 158.264
Flash Point 154 °F
Transport Information UN 3263 8/PG 2
Appearance orange crystals or powder
Safety 26-36/37/39-45-24/25
Risk Codes 34-36/37/38
Molecular Structure
Hazard Symbols C,Xi
Synonyms Piperidinooxy,2,2,6,6-tetramethyl- (7CI,8CI);2,2,6,6-Tetramethyl-1-piperidinyloxy;2,2,6,6-Tetramethylpiperidin-1-oxylradical;2,2,6,6-TetramethylpiperidineN-oxide;2,2,6,6-Tetramethylpiperidine N-oxy;2,2,6,6-Tetramethylpiperidine N-oxyl radical;2,2,6,6-Tetramethylpiperidinenitroxide;2,2,6,6-Tetramethylpiperidine oxide;2,2,6,6-Tetramethylpiperidinyl-1-oxyl;2,2,6,6-Tetramethylpiperidinyloxy;HO 6;Tanan;Tanane;Tempo;
PSA 3.24000
LogP 2.31290

Synthetic route

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

: C18H41CuN7O2S(1+)*C24BF20(1-)

A: 2564-83-2
2,2,6,6-tetramethyl-piperidine-N-oxyl

B: C18H42CuN7O2S(2+)*C24BF20(1-)

Conditions

Conditions	Yield
In 2-methyltetrahydrofuran at -135℃; Kinetics;	A n/a B 94%

...Expand

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

: 2564-83-2
2,2,6,6-tetramethyl-piperidine-N-oxyl

Conditions

Conditions	Yield
With sodium sulfate In dichloromethane Electrolysis; aq. phosphate buffer;	82%

starch, native, potato: starch, native, potato

A: 2564-83-2
2,2,6,6-tetramethyl-piperidine-N-oxyl

B starch, native, potato, oxidised, 38% uronic acid content: starch, native, potato, oxidised, 38% uronic acid content

Conditions

Conditions	Yield
With 2,2,6,6-tetramethyl-1-oxo-piperidinium; sodium acetate; acetic acid In water at 20℃; pH=4.5; UF membrane;

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

: 2564-83-2
2,2,6,6-tetramethyl-piperidine-N-oxyl

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

: Ammonium paratungstate

: 2564-83-2
2,2,6,6-tetramethyl-piperidine-N-oxyl

Conditions

Conditions	Yield
With dihydrogen peroxide In acetonitrile
With dihydrogen peroxide In acetonitrile
With dihydrogen peroxide In methanol; acetonitrile

: 45842-10-2
2,2,6,6-tetramethyl-1-oxo-piperidinium

: 2564-83-2
2,2,6,6-tetramethyl-piperidine-N-oxyl

Conditions

Conditions	Yield
Alkaline conditions;

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

: [MnII(2-[bis(pyridin-2-ylmethyl)]amino-N-quinolin-8-yl-acetamidate)(OMe)](OTf)*0.3H2O

A: 2564-83-2
2,2,6,6-tetramethyl-piperidine-N-oxyl

B: [MnII(2-[bis(pyridin-2-ylmethyl)]amino-N-quinolin-8-yl-acetamidate)(HOMe)](1+)

Conditions

Conditions	Yield
In acetonitrile at 25℃; Mechanism; Activation energy; Inert atmosphere;

...Expand

: 109-99-9
tetrahydrofuran

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

: Co(BDPP)(O2)

: 7732-18-5
water

A: 2564-83-2
2,2,6,6-tetramethyl-piperidine-N-oxyl

B: Co(BDPP)(OOH)*THF*2H2O

Conditions

Conditions	Yield
at -90℃; for 1h; Inert atmosphere; Schlenk technique;

...Expand

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

: C49H51FeNiP2

: 5259-72-3, 10060-40-9, 111-78-4
1,5-dicyclooctadiene

A: 2564-83-2
2,2,6,6-tetramethyl-piperidine-N-oxyl

B: 162476-91-7
[(1,1′-bis(diphenylphosphino)ferrocene)Ni(0)(1,5-cyclooctadiene)]

C: 717-74-8
1,3,5-triisopropyl benzene

Conditions

Conditions	Yield
In benzene-d6 at 20℃; for 24h;

...Expand

: 2564-83-2
2,2,6,6-tetramethyl-piperidine-N-oxyl

: 7787-70-4
copper(I) bromide

: 309752-65-6
6-(hydroxymethyl)-2-naphthol

: 78119-82-1
6-hydroxynaphthalene-2-carbaldehyde

Conditions

Conditions	Yield
In N,N-dimethyl-formamide	99.8%

...Expand

: 7758-89-6
copper(I) chloride

: 2564-83-2
2,2,6,6-tetramethyl-piperidine-N-oxyl

: 309752-65-6
6-(hydroxymethyl)-2-naphthol

: 78119-82-1
6-hydroxynaphthalene-2-carbaldehyde

Conditions

Conditions	Yield
In N,N-dimethyl-formamide	99.6%

...Expand

: 2564-83-2
2,2,6,6-tetramethyl-piperidine-N-oxyl

: 309752-65-6
6-(hydroxymethyl)-2-naphthol

: 78119-82-1
6-hydroxynaphthalene-2-carbaldehyde

Conditions

Conditions	Yield
In N,N-dimethyl-formamide; iron(II) chloride	99.2%
In chlorobenzene	92.6%

: 2564-83-2
2,2,6,6-tetramethyl-piperidine-N-oxyl

: 502-42-1
cycloheptanone

: 1394206-49-5
2-((2,2,6,6-tetramethylpiperidin-1-yl)oxy)cycloheptanone

Conditions

Conditions	Yield
With 2,6-di-tert-butyl-pyridine; 2-chloro-1,3,2-benzodioxaborole In dichloromethane at 0 - 20℃; for 3h;	99%

: 2564-83-2
2,2,6,6-tetramethyl-piperidine-N-oxyl

: 93-55-0
1-phenyl-propan-1-one

: 1189350-76-2
1-phenyl-2-((2,2,6,6-tetramethylpiperidin-1-yl)oxy)propan-1-one

Conditions

Conditions	Yield
With 2,6-di-tert-butyl-pyridine; 2-chloro-1,3,2-benzodioxaborole In dichloromethane at 0 - 20℃; for 3h;	99%

: 2564-83-2
2,2,6,6-tetramethyl-piperidine-N-oxyl

: 121-97-1
4-Methoxypropiophenone

: 1394206-50-8
1-(4-methoxyphenyl)-2-((2,2,6,6-tetramethylpiperidin-1-yl)oxy)propan-1-one

Conditions

Conditions	Yield
With 2,6-di-tert-butyl-pyridine; 2-chloro-1,3,2-benzodioxaborole In dichloromethane at 0 - 20℃; for 3h;	99%

: 6285-05-8
4'-chloropropiophenone

: 2564-83-2
2,2,6,6-tetramethyl-piperidine-N-oxyl

: 1394206-51-9
1-(4-chlorophenyl)-2-((2,2,6,6-tetramethylpiperidin-1-yl)oxy)propan-1-one

Conditions

Conditions	Yield
With 2,6-di-tert-butyl-pyridine; 2-chloro-1,3,2-benzodioxaborole In dichloromethane at 0 - 20℃; for 3h;	99%

: 2564-83-2
2,2,6,6-tetramethyl-piperidine-N-oxyl

: 495-40-9
butyrophenone

: 1394206-52-0
1-phenyl-2-((2,2,6,6-tetramethylpiperidin-1-yl)oxy)butan-1-one

Conditions

Conditions	Yield
With 2,6-di-tert-butyl-pyridine; 2-chloro-1,3,2-benzodioxaborole In dichloromethane at 0 - 20℃; for 3h;	99%

: 2564-83-2
2,2,6,6-tetramethyl-piperidine-N-oxyl

: 611-70-1
phenyl isopropyl ketone

: 1394206-54-2
2-methyl-1-phenyl-2-(2,2,6,6-tetramethylpiperidin-1-yloxy)propan-1-one

Conditions

Conditions	Yield
With 2,6-di-tert-butyl-pyridine; 2-chloro-1,3,2-benzodioxaborole In dichloromethane at 0 - 20℃; for 3h;	99%

: 2564-83-2
2,2,6,6-tetramethyl-piperidine-N-oxyl

: 529-34-0
3,4-dihydronaphthalene-1(2H)-one

: 1189350-77-3
2-((2,2,6,6-tetramethylpiperidin-1-yl)oxy)-3,4-dihydronaphthalen-1(2H)-one

Conditions

Conditions	Yield
With 2,6-di-tert-butyl-pyridine; 2-chloro-1,3,2-benzodioxaborole In dichloromethane at 0 - 20℃; for 3h;	98%

: 2564-83-2
2,2,6,6-tetramethyl-piperidine-N-oxyl

: 51315-69-6
N-tosyl-o-allylaniline

: 1094359-10-0
(S)-2-(2,2,6,6-tetramethyl-piperidin-1-yloxymethyl)-1-(toluene-4-sulfonyl)-2,3-dihydro-1H-indole

Conditions

Conditions	Yield
With copper(II) bis(trifluoromethanesulfonate); potassium carbonate; (4R,4'R,5S,5'S)-2,2'-(propane-2,2-diyl)bis(4,5-diphenyl-4,5-dihydrooxazole) In α,α,α-trifluorotoluene at 110℃; for 24h; Inert atmosphere; optical yield given as %ee;	97%
With α,α,α-trifluorotoluene; copper(II) bis(trifluoromethanesulfonate); potassium carbonate; (4R,4'R,5S,5'S)-2,2'-(propane-2,2-diyl)bis(4,5-diphenyl-4,5-dihydrooxazole) at 110℃; for 6h; enantioselective reaction;	97%

: 2564-83-2
2,2,6,6-tetramethyl-piperidine-N-oxyl

: 527737-44-6
N-(2,2-diphenyl-pent-4-enyl)-4-methylbenzenesulfonamide

: 1094359-32-6
1-[4,4-diphenyl-1-(toluene-4-sulfonyl)-pyrrolidin-2-ylmethoxy]-2,2,6,6-tetramethyl-piperidine

Conditions

Conditions	Yield
With oxygen; copper(II) bis(trifluoromethanesulfonate); potassium carbonate; (4R,4'R,5S,5'S)-2,2'-(propane-2,2-diyl)bis(4,5-diphenyl-4,5-dihydrooxazole) In α,α,α-trifluorotoluene at 120℃; under 760.051 Torr; for 24h; optical yield given as %ee;	97%

: 2564-83-2
2,2,6,6-tetramethyl-piperidine-N-oxyl

: 83-33-0
inden-1-one

: 1394206-53-1
2-(2,2,6,6-tetramethylpiperidin-1-yloxy)-1-indanone

Conditions

Conditions	Yield
With 2,6-di-tert-butyl-pyridine; 2-chloro-1,3,2-benzodioxaborole In dichloromethane at 0 - 20℃; for 3h;	97%

: 2564-83-2
2,2,6,6-tetramethyl-piperidine-N-oxyl

: 100-52-7
benzaldehyde

: 7031-95-0
1-benzoxy-2,2,6,6-tetramethylpiperidine

Conditions

Conditions	Yield
With styrene; tert.-butylhydroperoxide; iron(II) chloride In decane; acetonitrile at 85℃; for 1h; Inert atmosphere;	95%
With tert.-butylhydroperoxide; ethyl 1,5-diphenyl-4-methyl-1H-pyrazole-3-carboxylate; palladium(II) trifluoroacetate In 1,2-dichloro-ethane at 100℃; for 12h; Inert atmosphere;	63%
With tert.-butylhydroperoxide; iron(III) chloride hexahydrate In water; acetonitrile Mechanism; Inert atmosphere; Reflux;	59%

: 2564-83-2
2,2,6,6-tetramethyl-piperidine-N-oxyl

: 51315-69-6
N-tosyl-o-allylaniline

: 1094359-65-5
C25H34N2O3S

Conditions

Conditions	Yield
With (4S,4'S)-2,2'-(1-methylethylidene)bis[4,5-dihydro-4-(p-tert-butylphenyl)] oxazole; α,α,α-trifluorotoluene; oxygen; copper(II) bis(trifluoromethanesulfonate); potassium carbonate at 110℃; under 760.051 Torr; for 6h; enantioselective reaction;	95%

: 2564-83-2
2,2,6,6-tetramethyl-piperidine-N-oxyl

: 57181-82-5
4-bromo-isobutylbenzene

: 1333501-16-8
2,2,6,6-tetramethyl-1-(2-methyl-1-phenylpropoxy)piperidine

Conditions

Conditions	Yield
With copper(II) trifluoroacetate; copper; 4,4'-di-tert-butyl-2,2'-bipyridine In benzene at 75℃; for 22h; Inert atmosphere;	93%

: 2564-83-2
2,2,6,6-tetramethyl-piperidine-N-oxyl

: 1416916-77-2
3,5-di-tert-butyl-N-(2,2-dimethylpent-4-en-1-yl)benzenesulfonamide

: 1416916-81-8
(S)-1-((1-((3,5-di-tert-butylphenyl)sulfonyl)-4,4-dimethylpyrrolidin-2-yl)methoxy)-2,2,6,6-tetramethylpiperidine

Conditions

Conditions	Yield
With α,α,α-trifluorotoluene; oxygen; copper(II) bis(trifluoromethanesulfonate); potassium carbonate; (4R,4'R)-2,2'-(propane-2,2'diyl)bis(4-phenyl-4,5-dihydrooxazole) at 20 - 110℃; under 760.051 Torr; for 6h; enantioselective reaction;	92%

: 2564-83-2
2,2,6,6-tetramethyl-piperidine-N-oxyl

: 766-97-2
4-n-methylphenylacetylene

: (E)-2,2,6,6-tetramethyl-1-((2-nitro-1-(p-tolyl)vinyl)oxy)piperidine

Conditions

Conditions	Yield
With tert.-butylnitrite In tetrahydrofuran at 70℃; for 24h; stereoselective reaction;	92%

: 2564-83-2
2,2,6,6-tetramethyl-piperidine-N-oxyl

: 536-74-3
phenylacetylene

: (E)-2,2,6,6-tetramethyl-1-((2-nitro-1-phenylvinyl)oxy)piperidine

Conditions

Conditions	Yield
With tert.-butylnitrite In tetrahydrofuran at 70℃; for 24h; Catalytic behavior; Reagent/catalyst; Temperature; Solvent; Concentration; stereoselective reaction;	92%

: 75-91-2
tert.-butylhydroperoxide

: 2564-83-2
2,2,6,6-tetramethyl-piperidine-N-oxyl

: 68-12-2, 33513-42-7
N,N-dimethyl-formamide

: 100-46-9
benzylamine

A: 1-((tert-butyl)peroxy)-2,2,6,6-tetramethylpiperidine

B: 100-52-7
benzaldehyde

Conditions

Conditions	Yield
With hydrogenchloride; iodine In cyclohexane; water at 70 - 80℃; for 20h;	A n/a B 90%

...Expand

: 2564-83-2
2,2,6,6-tetramethyl-piperidine-N-oxyl

: 766-81-4
3-bromophenylacetylene

: (E)-1-((1-(3-bromophenyl)-2-nitrovinyl)oxy)-2,2,6,6-tetramethylpiperidine

Conditions

Conditions	Yield
With tert.-butylnitrite In tetrahydrofuran at 70℃; for 24h; stereoselective reaction;	90%

: 2564-83-2
2,2,6,6-tetramethyl-piperidine-N-oxyl

: 768-60-5
4-methoxyphenylacetylen

: (E)-1-((1-(4-methoxyphenyl)-2-nitrovinyl)oxy)-2,2,6,6-tetramethylpiperidine

Conditions

Conditions	Yield
With tert.-butylnitrite In tetrahydrofuran at 70℃; for 24h; stereoselective reaction;	90%

: 2564-83-2
2,2,6,6-tetramethyl-piperidine-N-oxyl

: 12126-50-0
bis(pentamethylcyclopentadienyl)iron(II)

: tris(pentafluorophenyl)alane toluene

: [Cp*2Fe][(C5H6)Me4NOAl(C6F5)3]

Conditions

Conditions	Yield
In toluene for 0.0166667h; Inert atmosphere; Schlenk technique; Glovebox;	90%

...Expand

: 2564-83-2
2,2,6,6-tetramethyl-piperidine-N-oxyl

: 12126-50-0
bis(pentamethylcyclopentadienyl)iron(II)

: 1109-15-5
tris(pentafluorophenyl)borate

: [Cp*2Fe][(C5H6)Me4NOB(C6F5)3]

Conditions

Conditions	Yield
In toluene for 0.0166667h; Inert atmosphere; Schlenk technique; Glovebox;	90%

...Expand

: 2564-83-2
2,2,6,6-tetramethyl-piperidine-N-oxyl

: 768-03-6
Phenyl vinyl ketone

: 1394206-65-5
3-chloro-1-phenyl-2-((2,2,6,6-tetramethylpiperidin-1-yl)oxy)propan-1-one

Conditions

Conditions	Yield
With 2-chloro-1,3,2-benzodioxaborole In dichloromethane at 0℃;	89%

: 2564-83-2
2,2,6,6-tetramethyl-piperidine-N-oxyl

: 1356133-16-8
N-(2-allyl-phenyl)-3,5-di-tert-butylbenzenesulfonamide

: 1416916-79-4
(S)-1-((3,5-di-tert-butylphenyl)sulfonyl)-2-(((2,2,6,6-tetramethylpiperidin-1-yl)oxy)methyl)indoline

Conditions

Conditions	Yield
With α,α,α-trifluorotoluene; copper(II) bis(trifluoromethanesulfonate); potassium carbonate; (4R,4'R)-2,2'-(propane-2,2'diyl)bis(4-phenyl-4,5-dihydrooxazole) at 20 - 110℃; for 6h; enantioselective reaction;	89%

: 2564-83-2
2,2,6,6-tetramethyl-piperidine-N-oxyl

: 1416916-78-3
3,5-di-tert-butyl-N-(2,2-dimethylpent-4-en-1-yl)-4-methoxybenzenesulfonamide

: 1416916-82-9
(S)-1-((1-((3,5-di-tert-butyl-4-methoxyphenyl)sulfonyl)-4,4-dimethylpyrrolidin-2-yl)methoxy)-2,2,6,6-tetramethylpiperidine

Conditions

Conditions	Yield
With α,α,α-trifluorotoluene; oxygen; copper(II) bis(trifluoromethanesulfonate); potassium carbonate; (4R,4'R)-2,2'-(propane-2,2'diyl)bis(4-phenyl-4,5-dihydrooxazole) at 20 - 110℃; under 760.051 Torr; for 6h; enantioselective reaction;	88%

: 2564-83-2
2,2,6,6-tetramethyl-piperidine-N-oxyl

: 108-67-8
1,3,5-trimethyl-benzene

: 1-((3,5-dimethylbenzyl)oxy)-2,2,6,6-tetramethylpiperidine

Conditions

Conditions	Yield
With iridium(III) chloride; di-tert-butyl peroxide; N-methyl-N-phenylmethacrylamide at 120℃; for 24h; Mechanism; Inert atmosphere; Schlenk technique;	88%

: 2564-83-2
2,2,6,6-tetramethyl-piperidine-N-oxyl

: 766-49-4
(2-fluorophenyl)acetylene

: (E)-1-((1-(2-fluorophenyl)-2-nitrovinyl)oxy)-2,2,6,6-tetramethylpiperidine

Conditions

Conditions	Yield
With tert.-butylnitrite In tetrahydrofuran at 70℃; for 24h; stereoselective reaction;	88%

2,2,6,6-Tetramethylpiperidinooxy Chemical Properties

Molecular structure of 2,2,6,6-Tetramethylpiperidinooxy (CAS NO.2564-83-2) is:

Product Name: 2,2,6,6-Tetramethylpiperidinooxy
CAS Registry Number: 2564-83-2
IUPAC Name: 1-λ¹-oxidanyl-2,2,6,6-tetramethylpiperidine
Molecular Weight: 156.24532 [g/mol]
Molecular Formula: C₉H₁₈NO
XLogP3: 1.4
H-Bond Donor: 0
H-Bond Acceptor: 1
EINECS: 219-888-8
Melting Point: 36-38 °C(lit.)
Density: 1 g/cm³
Flash Point: 154 °F
Boiling Point: 193 °C
Storage temp.: 2-8°C
Other Registry Number: 125012-91-1 ;126517-51-9 ;25657-03-8 ;26933-82-4 ;54637-06-8 ;64104-42-3
Stability: Stable. Incompatible with strong acids, strong oxidizing agents. Refrigerate.
Product Categories: Analytical Chemistry;Environmentally-friendly Oxidation;ESR Spectrometry;Oxidation;Redox Catalysts (Environmentally-friendly Oxidation);Spin Labels;Synthetic Organic Chemistry

2,2,6,6-Tetramethylpiperidinooxy Toxicity Data With Reference

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
rabbit	LDLo	skin	2gm/kg (2000mg/kg)	BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)	United States Environmental Protection Agency, Office of Pesticides and Toxic Substances. Vol. 8EHQ-0786-0607S,
rat	LCLo	inhalation	4500mg/m³/2H (4500mg/m³)		United States Environmental Protection Agency, Office of Pesticides and Toxic Substances. Vol. 8EHQ-0786-0607S,

2,2,6,6-Tetramethylpiperidinooxy Safety Profile

Hazard Codes: Corrosive C; Irritant Xi
Risk Statements: 34-36/37/38
R34:Causes burns.
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36/37/39-45-24/25
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
S24/25:Avoid contact with skin and eyes.
RIDADR: UN 3263 8/PG 2
WGK Germany: 3
RTECS: TN8991900
HazardClass: 8
PackingGroup: III
HS Code: 29333999

2,2,6,6-Tetramethylpiperidinooxy Specification

2,2,6,6-Tetramethylpiperidinooxy , its cas register number is 2564-83-2. It also can be called 2,2,6,6-Tetramethyl-1-piperidinyloxy ; 2,2,6,6-Tetramethylpiperidine-1-oxyl ; 2,2,6,6-Tetramethylpiperidinooxyl ; Tanan ; Tetramethylpiperidine nitroxide ; Tetramethylpiperidinooxy .It is a orange crystals or powder.

Product Name

2,2,6,6-Tetramethylpiperidinooxy

Synthetic route

2,2,6,6-Tetramethylpiperidinooxy Chemical Properties

2,2,6,6-Tetramethylpiperidinooxy Toxicity Data With Reference

2,2,6,6-Tetramethylpiperidinooxy Safety Profile

2,2,6,6-Tetramethylpiperidinooxy Specification

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