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2226-96-2

Basic Information
CAS No.: 2226-96-2
Name: 4-Hydroxy-2,2,6,6-tetramethyl-piperidinooxy
Article Data: 66
Molecular Structure:
Molecular Structure of 2226-96-2 (4-Hydroxy-2,2,6,6-tetramethyl-piperidinooxy)
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: HarmfulXn,IrritantXi
Risk Codes: 22-36/37/38-36/38
Safety: 26-36-37/39-36/37/39-27
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
ConditionsYield
With dihydrogen peroxide; sodium carbonate In water99.2%
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
ConditionsYield
With tert.-butylhydroperoxide; hexacarbonyl molybdenum In 1,2-dichloro-ethane86%
With dihydrogen peroxide In water76.5%
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
ConditionsYield
In N,N-dimethyl-formamide99.5%
108-30-5

succinic acid anhydride

2226-96-2

tempol

42585-26-2

C13H24NO5

Conditions
ConditionsYield
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
ConditionsYield
With LiOH; calcium oxide In methanol96.7%
2226-96-2

tempol

814-68-6

acryloyl chloride

21270-85-9

4-acryloyloxy-2,2,6,6-tetramethylpiperidine-1-oxyl

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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%
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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,