| Identification | More | [Name]
2,2,6,6-Tetramethylpiperidinooxy | [CAS]
2564-83-2 | [Synonyms]
2,2,6,6-TETRAMETHYL-1-PIPERIDINOOXY
2,2,6,6-TETRAMETHYL-1-PIPERIDINYLOXY
2,2,6,6-TETRAMETHYL-1-PIPERIDINYLOXY,FREE RADICAL
2,2,6,6-TETRAMETHYL-1-PIPERIDINYLOXY, RADICAL
2,2,6,6-TETRAMETHYL-4-PIPERIDINYLOXY
2,2,6,6-TETRAMETHYLPIPERIDIN-1-OXYL FREE RADICAL
2,2,6,6-TETRAMETHYLPIPERIDINE-1-N-OXYL
2,2,6,6-TETRAMETHYLPIPERIDINE 1-OXYL
2,2,6,6-TETRAMETHYLPIPERIDINE 1-OXYL, RADICAL
2,2,6,6-TETRAMETHYLPIPERIDINE-N-OXYL
2,2,6,6-TETRAMETHYLPIPERIDINEOXIDE
2,2,6,6-TETRAMETHYLPIPERIDINOOXY
2,2,6,6-TETRAMETHYLPIPERIDINOOXY, FREE RADICAL
2,2,6,6-TETRAMETHYL PIPERIDINOXY
2,2,6,6-TETRAMETHYLPIPERIDINOXY FREE RADICAL
2,2,6,6-TETRAMETHYLPIPERIDINYLOXY
TEMPO
TEMPO, FREE RADICAL
1,1,5,5-Tetramethylpentamethylene nitroxide
1-Oxyl-2,2,6,6-tetramethylpiperidine | [EINECS(EC#)]
219-888-8 | [Molecular Formula]
C9H18NO * | [MDL Number]
MFCD00009599 | [Molecular Weight]
156.25 | [MOL File]
2564-83-2.mol |
| Chemical Properties | Back Directory | [Appearance]
orange crystals or powder | [Melting point ]
36-38 °C(lit.)
| [Boiling point ]
193°C | [density ]
1 g/cm3 | [vapor pressure ]
0.4 hPa (20 °C) | [refractive index ]
1.4350 (estimate) | [Fp ]
154 °F
| [storage temp. ]
2-8°C
| [solubility ]
9.7g/l | [form ]
Powder | [color ]
Yellow to green | [PH]
8.3 (9g/l, H2O, 20℃) | [Stability:]
Stable. Incompatible with strong acids, strong oxidizing agents. Refrigerate. | [Water Solubility ]
Soluble in all organic solvents. Insoluble in water. | [Detection Methods]
GC | [Merck ]
14,9140 | [BRN ]
1422418 | [InChI]
1S/C9H18NO/c1-8(2)6-5-7-9(3,4)10(8)11/h5-7H2,1-4H3 | [InChIKey]
RVWUHFFPEOKYLB-UHFFFAOYSA-N | [SMILES]
CC1(C)CCCC(C)(C)N1[O] | [CAS DataBase Reference]
2564-83-2(CAS DataBase Reference) | [NIST Chemistry Reference]
1-Piperidinyloxy, 2,2,6,6-tetramethyl-(2564-83-2) | [EPA Substance Registry System]
2564-83-2(EPA Substance) |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS05 | [Signal word ]
Danger | [Hazard statements ]
H314-H412 | [Precautionary statements ]
P260-P273-P280-P303+P361+P353-P304+P340+P310-P305+P351+P338 | [Hazard Codes ]
C,Xi | [Risk Statements ]
R34:Causes burns.
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
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 label where possible) .
S24/25:Avoid contact with skin and eyes . | [RIDADR ]
UN 3263 8/PG 2
| [WGK Germany ]
3
| [RTECS ]
TN8991900
| [Autoignition Temperature]
275 °C | [TSCA ]
Yes | [HazardClass ]
8 | [PackingGroup ]
III | [HS Code ]
29333999 | [Storage Class]
8A - Combustible corrosive hazardous materials | [Hazard Classifications]
Aquatic Chronic 3
Eye Dam. 1
Skin Corr. 1C |
| Hazard Information | Back Directory | [Description]
2,2,6,6-Tetramethylpiperidine is a product that is used for the most diverse purposes because of its strong basicity, for example, as a light stabilizer for polyolefins, as a cocatalyst in olefin polymerizations (Ziegler catalysts), as a building block for the synthesis of pharmaceuticals and crop protection products, as a cocatalyst in the synthesis of dichloroacetyl chloride. The 4-unsubstituted 2.2.6,6-tetramethylpiperidine is generally prepared from the corresponding 4-oxo compound. It is known that triacetonamine can be converted by hydrazine to the hydrazone, which is then cleaved in the presence of alkali into 2,26,6-tetramethylpiperidine and nitrogen.
| [Chemical Properties]
orange crystals or powder | [Characteristics]
2,2,6,6-Tetramethylpiperidinooxy(TEMPO) has the characteristics of high yield, good selectivity, good stability, and recyclable use. | [Uses]
In organic chemistry as a radical trap, 2,2,6,6-Tetramethylpiperidinooxy can be used as a catalyst and in polymerization mediation.
| [Uses]
TEMPO(2,2,6,6-Tetramethylpiperidinooxy) is a stable radical prepared through the oxidation of 2,2,6,6-tetramethylpiperidine. TEMPO has a wide range of applications including use as a free radical scavenger, a reagent in organic synthe sis and as a structural probe in electron spin resonance spectroscopy. TEMPO can also be used as a mediator in free radical polymerization.
| [Reactions]
TEMPO derivatives are widely used as two-electron redox mediators for selective oxidation of various organic substrates. The oxoammonium form of TEMPO contains an electrophilic nitrogen atom, to which different nucleophiles such as alcohols or amines can attach. While the substrate contains an alpha-hydrogen atom, the subsequent proton shift and oxidative elimination of the TEMPO in hydroxylamine form may occur, which results in a formal 1,2-dehydrogenation of the substrate. The catalytic cycle can then be closed by two-electron oxidation of the hydroxylamine form to oxoammonium form using chemical oxidants[1].
 | [General Description]
For a synthetic protocol using NMP initiators, contributed by Prof. Karen Wooley, please visit our technology spotlight. | [reaction suitability]
reagent type: oxidant | [Synthesis]
(1) Take an appropriate amount of 2.2.6.6-tetramethylpiperidine, add catalyst and methanol and mix well, and the mass:mass:volume ratio of 2.2.6.6-tetramethylpiperidine to catalyst and methanol is (8 to 10):2:3;
(2) heat the mixture to 50 to 70°C (p | [Purification Methods]
Purify TEMPO by sublimation (33o, water aspirator) [Hay & Fincke J Am Chem Soc 109 8012 1987, Keana Chem Rev 78 37 1978]. | [References]
[1] Vereshchagin, A., Kalnin, A. Y., Volkov, A., Lukyanov, D., Levin, O. (2022). Key Features of TEMPO-Containing Polymers for Energy Storage and Catalytic Systems. Energies. https://doi.org/10.3390/en15072699
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| Spectrum Detail | Back Directory | [Spectrum Detail]
2,2,6,6-Tetramethylpiperidinooxy(2564-83-2)MS
2,2,6,6-Tetramethylpiperidinooxy(2564-83-2)1HNMR
2,2,6,6-Tetramethylpiperidinooxy(2564-83-2)IR1
2,2,6,6-Tetramethylpiperidinooxy(2564-83-2)IR2
2,2,6,6-Tetramethylpiperidinooxy(2564-83-2)Raman
2,2,6,6-Tetramethylpiperidinooxy(2564-83-2)ESR
|
| Well-known Reagent Company Product Information | Back Directory | [Acros Organics]
2,2,6,6-Tetramethylpiperidinooxy, 98%(2564-83-2) | [Alfa Aesar]
TEMPO, free radical, 98+%(2564-83-2) | [Sigma Aldrich]
2564-83-2(sigmaaldrich) | [TCI AMERICA]
2,2,6,6-Tetramethylpiperidine 1-Oxyl Free Radical,>98.0%(GC)(T)(2564-83-2) |
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