4-Oxo-TEMPO
Comment: All the sources appear to be either primary (research papers, database entries) or unreliable (YouTube). We need significant coverage in secondary sources to clear WP:GNG. WeirdNAnnoyed (talk) 22:12, 20 August 2026 (UTC)
- Comment: Can you find more academia sources on this substance? PubChem and ChemSpider are databases, and an entry does not show any kind of notability. Chemical Euphoria would not be counted as a reliable source, as not peer reviewed or made by a know expert. (Though is a good supplement). Konaka is good, but not enough in itself to show this is notable. There are companies selling this, so almost certainly it is notable. Chemspider gets info from these companies. Graeme Bartlett (talk) 22:49, 19 June 2026 (UTC)
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3D model (JSmol)
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| ECHA InfoCard | Lua error in Module:Wikidata at line 879: attempt to index field 'wikibase' (a nil value). Lua error in Module:Wikidata at line 879: attempt to index field 'wikibase' (a nil value). |
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PubChem CID
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CompTox Dashboard (EPA)
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| Properties[2] | |
| C9H16NO2 | |
| Molar mass | 170.232 g·mol−1 |
| Appearance | Yellowish-orange powder (needle-like crystals) |
| Odor | Weak, camphor-like |
| Melting point | 36–40 °C (97–104 °F; 309–313 K)[3] |
| Solubility | soluble in hexane |
| 1.36 D[1] | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
4-Oxo-TEMPO or TEMPONE is a remarkably stable free radical,[2]:{{{1}}} related to the more well known compounds 4-hydroxy-TEMPO and TEMPO.[4]
Synthesis
4-Oxo-TEMPO was first prepared by Lebedev and co-workers in 1961, via the condensation of phorone with ammonia in alkaline aqueous solution at 100 °C, producing a triacetonamine-containing mixture, followed immediately by oxidation with hydrogen peroxide and sodium tungstate in the presence of tetrasodium EDTA at 50 °C.[2]:{{{1}}} It is also possible to use the same reagents to directly oxidize triacetonamine at room temperature, which yields a much easier-to-purify product.[2]:{{{1}}}
Properties
It is a yellowish-orange solid,[5] storable for several months in solid form.[2]:{{{1}}} It dissolves in water and other polar solvents to form yellow solutions, and in ether, ethanol, and benzene to form ruby-red solutions.[2]:{{{1}}}
It forms a series of adducts with n-alkanes from heptane onwards, each of which has a well-defined melting point, unlike the corresponding adducts formed by urea with n-alkanes.[2]:{{{1}}} Their formation is perhaps attributable[2]:{{{1}}} to the twist-boat conformation adopted by 4-oxo-TEMPO, which differs from related aminoxyls, for example, 4-hydroxy-TEMPO, which adopts a boat confirmation.[1]:{{{1}}}
Applications
4-Oxo-TEMPO has been used to investigate the generation of singlet oxygen by photoexcited titanium dioxide in ethanol by ESR spectroscopy.[6] It can also be used as a catalyst in various reactions.[7]
References
- ↑ 1.0 1.1 Rozantsev, E. G.; Gur'yanova, E. N. (June 1966). "Some structural peculiarities of nitroxides of the piperidine series". Bulletin of the Academy of Sciences, USSR Division of Chemical Science. 15 (6): 936–939. doi:10.1007/BF00846043.
- ↑ 2.0 2.1 2.2 2.3 2.4 2.5 2.6 2.7 Rozantsev, Eduard Grigori'evich (1970). "§II.2 2,2,6,6-Tetramethyl-4-oxopiperidine-1-oxyl, An Individual Free Radical". Free Nitroxyl Radicals. Translated by Hazzard, B. J. Plenum Press. pp. 55–66. doi:10.1007/978-1-4757-0710-6. ISBN 978-1-4757-0710-6. Search this book on
- ↑ "TEMPONE". www.chemspider.com. Retrieved 2026-06-15.
- ↑ PubChem. "Tempone". pubchem.ncbi.nlm.nih.gov. Retrieved 2026-06-15.
- ↑ Chemical Euphoria - Leek Labs. (2025-11-18). Synthesis of 4-oxo-TEMPO - Organic Synthesis ENG. Retrieved 2026-06-15 – via YouTube.
- ↑ Konaka, Ryusei; Kasahara, Emiko; Dunlap, Walter C; Yamamoto, Yorihiro; Chien, Kuang Chang; Inoue, Masayasu (1999-08-01). "Irradiation of titanium dioxide generates both singlet oxygen and superoxide anion". Free Radical Biology and Medicine. 27 (3): 294–300. doi:10.1016/S0891-5849(99)00050-7. ISSN 0891-5849.
- ↑ "4-Oxo-TEMPO". Nordmann. Retrieved 2026-06-21.
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