Global InformationThenoyltrifluoroacetone information
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| Names | |
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| Preferred IUPAC name
4,4,4-Trifluoro-1-(thiophen-2-yl)butane-1,3-dione | |
| Other names
2-thenoyltrifluoroacetone
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| Identifiers | |
CAS Number
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3D model (JSmol)
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| Abbreviations | TTFA |
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| ECHA InfoCard | 100.005.743 |
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PubChem CID
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CompTox Dashboard (EPA)
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InChI
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SMILES
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| Properties | |
Chemical formula
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C8H5F3O2S |
| Molar mass | 222.18 g mol−1 |
| Appearance | fine, slightly yellow crystals |
| Melting point | 40 to 44 °C (104 to 111 °F; 313 to 317 K) |
| Boiling point | 96 to 98 °C (205 to 208 °F; 369 to 371 K) 8 mmHg |
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Pictograms
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Signal word
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Warning |
Hazard statements
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H315, H319, H335 |
| Flash point | 12 °C (54 °F; 285 K) (closed cup) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references
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Thenoyltrifluoroacetone, C8H5F3O2S, is a chemical compound used pharmacologically as a chelating agent. It is an inhibitor of cellular respiration by blocking the respiratory chain at complex II.
Perhaps the first report of TTFA as an inhibitor of respiration was by A. L. Tappel in 1960.[2] Tappel had the (erroneous) idea that inhibitors like antimycin and alkyl hydroxyquinoline-N-oxide might work by chelating iron in the hydrophobic milieu of respiratory membrane proteins, so he tested a series of hydrophobic chelating agents. TTFA was a potent inhibitor, but not because of its chelating ability. TTFA binds at the quinone reduction site in Complex II, preventing ubiquinone from binding. The first x-ray structure of Complex II showing how TTFA binds, 1ZP0, was published in 2005 .[3]
Thenoyltrifluoroacetone can be made in a Claisen condensation of ethyl trifluoroacetate and 2-acetylthiophene.[4][5]
- ^ Sigma-Aldrich product page
- ^ Tappel (July 1960). "Inhibition of electron transport by antimycin A, alkyl hydroxy naphthoquinones and metal coordination compounds". Biochem. Pharmacol. 3 (4): 289–96. doi:10.1016/0006-2952(60)90094-0. PMID 13836892.
- ^ Sun, Fei; Huo, Xia; Zhai, Yujia; Wang, Aojin; Xu, Jianxing; Su, Dan; Bartlam, Mark; Rao, Zihe (2005). "Crystal Structure of Mitochondrial Respiratory Membrane Protein Complex II". Cell. 121 (7): 1043–1047. doi:10.1016/j.cell.2005.05.025. PMID 15989954. S2CID 16697879.
- ^ Gergel, Max G. (March 1977). Excuse me sir, would you like to buy a kilo of isopropyl bromide?. Pierce Chemical. p. 130.
- ^ Taydakov, Ilya V; Kreshchenova, Yuliya M; Dolotova, Ekaterina P (27 December 2018). "A convenient and practical synthesis of β-diketones bearing linear perfluorinated alkyl groups and a 2-thienyl moiety". Beilstein Journal of Organic Chemistry. 14: 3106–3111. doi:10.3762/bjoc.14.290. PMC 6317410. PMID 30643588.