4-Hydroxy-2,2,6,6-tetramethyl-piperidinooxy supplier

Name
4-Hydroxy-2,2,6,6-tetramethyl-piperidinooxy
EINECS 218-760-9
CAS No. 2226-96-2
Article Data66
CAS DataBase
Density 1.187 g/cm3
Solubility soluble in water
Melting Point 69-71 °C(lit.)
Formula C₉H₁₈NO₂
Boiling Point 269ºC
Molecular Weight 174.263
Flash Point 146°(295°F)
Transport Information
Appearance orange crystals
Safety 26-36-37/39-36/37/39-27
Risk Codes 22-36/37/38-36/38
Molecular Structure
Hazard Symbols Xn,Xi
Synonyms 4-Hydroxy-2,2,6,6-tetramethylpiperidino-1-oxyl;Piperidinooxy,4-hydroxy-2,2,6,6-tetramethyl- (7CI,8CI);1-Oxyl-2,2,6,6-tetramethyl-4-piperidinol;2,2,6,6-Tetramethyl-4-hydroxy-1-piperidinyloxy radical;2,2,6,6-Tetramethyl-4-hydroxypiperidin-1-oxyl;2,2,6,6-Tetramethyl-4-hydroxypiperidine N-oxide;2,2,6,6-Tetramethyl-4-hydroxypiperidine-1-oxyl;2,2,6,6-Tetramethyl-4-hydroxypiperidinooxy;2,2,6,6-Tetramethyl-4-hydroxypiperidinyl-1-oxyl;2,2,6,6-Tetramethyl-4-hydroxypiperidinyloxyl radical;2,2,6,6-Tetramethyl-4-oxypiperidine-1-oxyl;2,2,6,6-Tetramethyl-4-piperidinol 1-oxyl;2,2,6,6-Tetramethylpiperidine-4-hydroxy-1-oxyl;4-Hydroxy-2,2,6,6-tetramethyl-1-piperidinoxy;4-Hydroxy-2,2,6,6-tetramethyl-1-piperidinyloxy;4-Hydroxy-2,2,6,6-tetramethylpiperidine-N-oxy;
PSA 23.47000
LogP 1.28370

Synthetic route

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

: ethylenediaminetetraacetic acid disodium salt dihydrate

: 2226-96-2
tempol

Conditions

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

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

: 2226-96-2
tempol

Conditions

Conditions	Yield
With tert.-butylhydroperoxide; hexacarbonyl molybdenum In 1,2-dichloro-ethane	86%
With dihydrogen peroxide In water	76.5%
With sodium tungstate (VI) dihydrate; dihydrogen peroxide In methanol; acetonitrile at 20℃; for 48h;	70%
With dihydrogen peroxide for 8h;

: 7758-89-6
copper(I) chloride

: 2226-96-2
tempol

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

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

Conditions

Conditions	Yield
In N,N-dimethyl-formamide	99.5%

...Expand

: 108-30-5
succinic acid anhydride

: 2226-96-2
tempol

: 42585-26-2
C13H24NO5

Conditions

Conditions	Yield
With dmap In dichloromethane at 0 - 20℃; Inert atmosphere;	99%

: 2226-96-2
tempol

: 150-76-5
4-methoxy-phenol

: 80-62-6
methacrylic acid methyl ester

: 71424-71-0
iso-Bornyl acetate

: 16868-12-5
isobornyl methacrylate

Conditions

Conditions	Yield
With LiOH; calcium oxide In methanol	96.7%

...Expand

: 2226-96-2
tempol

: 814-68-6
acryloyl chloride

: 21270-85-9
4-acryloyloxy-2,2,6,6-tetramethylpiperidine-1-oxyl

Conditions

Conditions	Yield
With triethylamine In benzene at 20℃;	95%
With triethylamine In toluene at 20℃; for 16h;

: 2226-96-2
tempol

: 536-74-3
phenylacetylene

: (E)-2,2,6,6-tetramethyl-1-((2-nitro-1-phenylvinyl)oxy)piperidin-4-ol

Conditions

Conditions	Yield
With tert.-butylnitrite In tetrahydrofuran at 70℃; for 24h; stereoselective reaction;	95%

: 2226-96-2
tempol

: 78-84-2
isobutyraldehyde

: 1001080-97-2
i-propyl-4-hydroxy-2,2,6,6-tetramethylpiperidinyl-1-oxyl

Conditions

Conditions	Yield
With dihydrogen peroxide; copper(l) chloride In water; isopropyl alcohol at 20℃; for 12h;	91%

: 2226-96-2
tempol

: cis-CoII(hexafluoroacetylacetonato)2(H2O)2

: [CoII(hexafluoroacetylacetonato)2(4-hydroxy-2,2,6,6-tetramethylpiperidine-1-oxyl)]n

Conditions

Conditions	Yield
In hexane; dichloromethane at 60℃; for 0.333333h;	91%

: 2226-96-2
tempol

: 18107-18-1
diazomethyl-trimethyl-silane

: 581-96-4
2-naphthylacetic acid

: methyl 2-((4-hydroxy-2,2,6,6-tetramethylpiperidin-1-yl)oxy)-2-(naphthalen-2-yl)acetate

Conditions

Conditions	Yield
Stage #1: tempol; 2-naphthylacetic acid With N4,N4,N7,N7-tetramethyl-1,10-phenanthroline-4,7-diamine; iron(II) acetate In tetrahydrofuran at 60℃; for 24h; Molecular sieve; Inert atmosphere; Schlenk technique; Stage #2: diazomethyl-trimethyl-silane With methanol In tetrahydrofuran; hexane for 1h; Inert atmosphere; Stage #3: With acetic acid In tetrahydrofuran; hexane; ethyl acetate chemoselective reaction;	89%

Yield

Stage #1: tempol; 2-naphthylacetic acid With N4,N4,N7,N7-tetramethyl-1,10-phenanthroline-4,7-diamine; iron(II) acetate In tetrahydrofuran at 60℃; for 24h; Molecular sieve; Inert atmosphere; Schlenk technique;
Stage #2: diazomethyl-trimethyl-silane With methanol In tetrahydrofuran; hexane for 1h; Inert atmosphere;
Stage #3: With acetic acid In tetrahydrofuran; hexane; ethyl acetate chemoselective reaction;

89%

...Expand

: 2226-96-2
tempol

: 3637-10-3
tempol

Conditions

Conditions	Yield
With formaldehyd; dihydrogen peroxide; copper(l) chloride at 30℃; for 16h;	87%
With ethylenediaminetetraacetic acid; β-nicotinamide adenine dinucleotide reduced; hypoxanthine; catalase; xanthine oxidase pH=7.4; Kinetics; aq. phosphate buffer;

: 2226-96-2
tempol

: 630-19-3
pivalaldehyde

: 1-t-butoxy-4-hydroxy-2,2,6,6-tetramethylpiperidine

Conditions

Conditions	Yield
With dihydrogen peroxide; copper(l) chloride In ethanol; water at 20℃; for 17h;	85%

: 2226-96-2
tempol

: 5497-67-6
2,2-dimethyl-4-pentenal

: 1110726-99-2
1-(1,1-dimethyl-but-3-enyloxy)-2,2,6,6-tetramethylpiperidin-4-ol

Conditions

Conditions	Yield
With dihydrogen peroxide; copper(l) chloride In water; tert-butyl alcohol at 20℃; for 28h;	84%

: 2226-96-2
tempol

: 123-72-8
butyraldehyde

: 239792-70-2
1-n-propoxy-4-hydroxy-2,2,6,6-tetramethylpiperidine

Conditions

Conditions	Yield
With dihydrogen peroxide; copper(l) chloride In water; butan-1-ol at 35℃; for 15h;	84%

: 563-80-4
3-methyl-butan-2-one

: 2226-96-2
tempol

A: 122586-72-5
1-methoxy-2,2,6,6-tetramethylpiperidin-4-ol

B: 1001080-97-2
i-propyl-4-hydroxy-2,2,6,6-tetramethylpiperidinyl-1-oxyl

Conditions

Conditions	Yield
With dihydrogen peroxide; copper(l) chloride In water; butanone at 20℃; for 12h; Acidic conditions;	A 7% B 82%

...Expand

: 2226-96-2
tempol

: 5878-19-3
Methoxyacetone

A: 122586-72-5
1-methoxy-2,2,6,6-tetramethylpiperidin-4-ol

B: 1001080-99-4
C11H23NO3

Conditions

Conditions	Yield
With dihydrogen peroxide; copper(l) chloride In water; toluene at 20℃;	A 6% B 82%

...Expand

: 2226-96-2
tempol

: 556-56-9
allyl iodid

: 217496-13-4
4-allyloxy-2,2,6,6-tetramethylpiperidine-1-oxyl radical

Conditions

Conditions	Yield
Stage #1: tempol With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 1h; Inert atmosphere; Reflux; Stage #2: allyl iodid In N,N-dimethyl-formamide; mineral oil at 0 - 60℃; for 3.5h; Inert atmosphere; Reflux; Stage #3: In mineral	82%

: 2226-96-2
tempol

: 106-89-8
epichlorohydrin

: 122413-85-8
4-glycidyloxy-2,2,6,6-tetramethylpiperidine-1-oxyl,

Conditions

Conditions	Yield
With tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide In water at 30℃; for 4h;	80%
With tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide In water at 20℃;

: 2226-96-2
tempol

: 78-93-3
butanone

A: 1-ethoxy-4-hydroxy-2,2,6,6-tetramethylpiperidine

B: 122586-72-5
1-methoxy-2,2,6,6-tetramethylpiperidin-4-ol

Conditions

Conditions	Yield
With dihydrogen peroxide; copper(l) chloride In water; butanone for 12h; pH=3.5 - 4;	A 78% B 9%

...Expand

: 2226-96-2
tempol

: 144701-48-4
telmisatran

: 1276682-49-5
temposartan

Conditions

Conditions	Yield
With dmap; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 48h; Cooling with ice;	78%
With dmap; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 48h; Cooling with ice;	78%

: 2226-96-2
tempol

: 922-68-9
Methyl glyoxylate

: 1001081-00-0
4-hydroxy-2,2,6,6-tetramethylpiperidin-1-yl carbonic acid methyl ester

Conditions

Conditions	Yield
With dihydrogen peroxide; copper(l) chloride at 20℃; for 13h;	76%

: 2226-96-2
tempol

: 123-05-7
d,l-2-ethylhexanal

: 1001081-26-0
1-(1-ethyl-pentyloxy)-2,2,6,6-tetramethylpiperidin-4-ol

Conditions

Conditions	Yield
With dihydrogen peroxide; copper(l) chloride In water; isopropyl alcohol at 30℃; for 16h;	75%

: 2226-96-2
tempol

: 460-40-2
3,3,3-trifluoropropanal

: 1110727-10-0
2,2,6,6-tetramethyl-1-(2,2,2-trifluoro-ethoxy)-piperidin-4-ol

Conditions

Conditions	Yield
With dihydrogen peroxide; copper(l) chloride In water; tert-butyl alcohol at 20℃; for 72h;	74%

: 2226-96-2
tempol

: 112-13-0
n-decanoyl chloride

: C19H38NO3

Conditions

Conditions	Yield
With pyridine In diethyl ether at 0 - 20℃; for 3.08333h;	73%

: 2226-96-2
tempol

: 75-07-0
acetaldehyde

: 122586-72-5
1-methoxy-2,2,6,6-tetramethylpiperidin-4-ol

Conditions

Conditions	Yield
With dihydrogen peroxide; copper(l) chloride In water at 65 - 70℃; for 5h;	72%
With dihydrogen peroxide; copper(l) chloride In water for 4h; Reflux;

: 2226-96-2
tempol

: 100-50-5
3-Cyclohexene-1-carboxaldehyde

: 1001073-58-0
1-(cyclohex-3-enyloxy)-2,2,6,6-tetramethylpiperidin-4-ol

Conditions

Conditions	Yield
With dihydrogen peroxide; copper(l) chloride In water; tert-butyl alcohol at 30℃; for 13h;	72%

: 2226-96-2
tempol

: 67-64-1
acetone

A: 122586-98-5
1-methoxy-2,2,6,6-tetramethylpiperidin-4-one

B: 122586-72-5
1-methoxy-2,2,6,6-tetramethylpiperidin-4-ol

Conditions

Conditions	Yield
With dihydrogen peroxide; copper(l) chloride In water at 10 - 20℃;	A n/a B 71%

...Expand

: 2226-96-2
tempol

: 124-19-6
nonan-1-al

: 131807-04-0
1-octyloxy-2,2,6,6-tetramethyl-4-hydroxy-piperidine

Conditions

Conditions	Yield
With dihydrogen peroxide; copper(l) chloride In water; tert-butyl alcohol at 40℃; for 17h;	71%

: 2226-96-2
tempol

: 571167-64-1
toluene-4-sulfonic acid 2-(2-{2-[2-(tert-butyldimethylsilanyloxy)ethoxy]ethoxy}ethoxy)ethyl ester

: 1333501-32-8
4-[2-(2-{2-[2-(tert-butyldimethylsilyloxy)ethoxy]ethoxy}ethoxy)ethoxy]-2,2,6,6-tetramethylpiperidine-1-oxyl radical

Conditions

Conditions	Yield
Stage #1: tempol With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 1h; Inert atmosphere; Stage #2: toluene-4-sulfonic acid 2-(2-{2-[2-(tert-butyldimethylsilanyloxy)ethoxy]ethoxy}ethoxy)ethyl ester In N,N-dimethyl-formamide; mineral oil at 0 - 60℃; Inert atmosphere;	71%

4-Hydroxy-2,2,6,6-tetramethyl-piperidinooxy Consensus Reports

Reported in EPA TSCA Inventory.

4-Hydroxy-2,2,6,6-tetramethyl-piperidinooxy Specification

The IUPAC name of 4-Hydroxy-2,2,6,6-tetramethyl-piperidinooxy is 1-λ1-oxidanyl-2,2,6,6-tetramethylpiperidin-4-ol. With CAS registry number 2226-96-2, it is also named as 2,2,6,6-Tetramethyl-4-piperidinol-N-oxyl. The product's categories are analytical chemistry; ESR spectrometry; spin labels. It is orange crystals which is soluble in ethanol, benzene and other organic solvents, soluble in water. In addition, this chemical is stable and incompatible with strong oxidizing agents. Moreover, it should be sealed in the container and stored in the cool and dry place.

The other characteristics of this product can be summarized as: (1)XLogP3-AA: 0.9; (2)H-Bond Donor: 1; (3)H-Bond Acceptor: 2; (4)Rotatable Bond Count: 0; (5)Exact Mass: 172.133754; (6)MonoIsotopic Mass: 172.133754; (7)Topological Polar Surface Area: 24.5; (8)Heavy Atom Count: 12; (9)Formal Charge: 0; (10)Complexity: 159; (11)Covalently-Bonded Unit Count: 1.

Preparation of 4-Hydroxy-2,2,6,6-tetramethyl-piperidinooxy: It can be obtained by 2,2,6,6-tetramethyl-piperidine-1,4-diol. This reaction needs reagent H₂O₂, Trilon B, catalytic agent K₂WO₄ and solvent H₂O at temperature of 25 °C.

Uses of 4-Hydroxy-2,2,6,6-tetramethyl-piperidinooxy: It has good inhibition effect to acrylic acid esters, methyl acrylate, acrylic acid, acrylonitrile, styrene and butadiene. And it can react with benzene-1,2,4-tricarbonyl trichloride to get tris(2,2,6,6-tetramethyl-1-oxyl-4-piperidyloxy)trimellitate. This reaction needs reagent pyridine. The yield is 68%.

When you are using this chemical, please be cautious about it as the following:
It is not only harmful if swallowed, but also irritating to eyes, respiratory system and skin. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing, gloves and eye/face protection.

People can use the following data to convert to the molecule structure.
1. SMILES:CC1(CC(CC(N1[O])(C)C)O)C
2. InChI:InChI=1/C9H18NO2/c1-8(2)5-7(11)6-9(3,4)10(8)12/h7,11H,5-6H2,1-4H3
3. InChIKey:UZFMOKQJFYMBGY-UHFFFAOYAG

The following are the toxicity data which has been tested.

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
rat	LD50	oral	1053mg/kg (1053mg/kg)	SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD LUNGS, THORAX, OR RESPIRATION: DYSPNEA	National Technical Information Service. Vol. OTS0536225,

Product Name

4-Hydroxy-2,2,6,6-tetramethyl-piperidinooxy

Synthetic route

4-Hydroxy-2,2,6,6-tetramethyl-piperidinooxy Consensus Reports

4-Hydroxy-2,2,6,6-tetramethyl-piperidinooxy Specification

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