CAS No.2226-96-2,4-Hydroxy-2,2,6,6-tetramethyl-piperidinooxy Suppliers

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Basic Information

Molecular Structure:
CAS No.:	2226-96-2
Name:	4-Hydroxy-2,2,6,6-tetramethyl-piperidinooxy
Article Data:	66
Cas Database

Formula:	C₉H₁₈NO₂
Molecular Weight:	174.263
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;
EINECS:	218-760-9
Density:	1.187 g/cm3
Melting Point:	69-71 °C(lit.)
Boiling Point:	269ºC
Flash Point:	146°(295°F)
Solubility:	soluble in water
Appearance:	orange crystals
Hazard Symbols:	Xn,Xi
Risk Codes:	22-36/37/38-36/38
Safety:	26-36-37/39-36/37/39-27
Transport Information:	N/A
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

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Consensus Reports

Reported in EPA TSCA Inventory.

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,