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| CAS No.: | 2226-96-2 |
|---|---|
| Name: | 4-Hydroxy-2,2,6,6-tetramethyl-piperidinooxy |
| Molecular Structure: | |
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| 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 |
| PSA: | 23.47000 |
| LogP: | 1.28370 |
| 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 |
| 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; |
copper(I) chloride
tempol
6-(hydroxymethyl)-2-naphthol
6-hydroxynaphthalene-2-carbaldehyde
| Conditions | Yield |
|---|---|
| In N,N-dimethyl-formamide | 99.5% |
| Conditions | Yield |
|---|---|
| With dmap In dichloromethane at 0 - 20℃; Inert atmosphere; | 99% |
tempol
4-methoxy-phenol
methacrylic acid methyl ester
iso-Bornyl acetate
isobornyl methacrylate
| Conditions | Yield |
|---|---|
| With LiOH; calcium oxide In methanol | 96.7% |
tempol
acryloyl chloride
4-acryloyloxy-2,2,6,6-tetramethylpiperidine-1-oxyl
| Conditions | Yield |
|---|---|
| With triethylamine In benzene at 20℃; | 95% |
| With triethylamine In toluene at 20℃; for 16h; |
| Conditions | Yield |
|---|---|
| With tert.-butylnitrite In tetrahydrofuran at 70℃; for 24h; stereoselective reaction; | 95% |
tempol
isobutyraldehyde
i-propyl-4-hydroxy-2,2,6,6-tetramethylpiperidinyl-1-oxyl
| Conditions | Yield |
|---|---|
| With dihydrogen peroxide; copper(l) chloride In water; isopropyl alcohol at 20℃; for 12h; | 91% |
tempol
| Conditions | Yield |
|---|---|
| In hexane; dichloromethane at 60℃; for 0.333333h; | 91% |
| 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% |
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Reported in EPA TSCA Inventory.
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.
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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%.
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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, |
