Trifluoroacetyl fluoride
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| Preferred IUPAC name
2,2,2-trifluoroacetyl fluoride | |
| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
| ECHA InfoCard | 100.005.963 |
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PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |
| C2F4O | |
| Molar mass | 116.015 g·mol−1 |
| Appearance | colorless gas |
| Boiling point | −59 °C |
| reacts with water | |
| Hazards | |
| GHS labelling: | |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
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Trifluoroacetyl fluoride is an organic compound of fluorine, oxygen, and carbon with the chemical formula C2F4O.[1] The compound belongs to the group of carboxylic acid fluorides, specifically the fluoride of trifluoroacetic acid.
Synthesis
Trifluoroacetyl fluoride can be prepared by the reaction of trifluoroacetic anhydride and anhydrous hydrogen fluoride:[2]
- (CF3CO)2O + HF → CF3COF + CF3COOH
or by the reaction of trifluoroacetic acid and vanadium pentafluoride:[3]
- CF3COOH + VF5 → VOF3 + HF + CF3COF↑
Chemical properties
Trifluoroacetyl fluoride can react with rubidium fluoride or cesium fluoride in acetonitrile to form the corresponding pentafluoroethanolate:[4]
- CF3COF + MF → CF3CF2OM (M = Rb, Cs)
The compound reacts with sulfur trioxide to form trifluoroacetyl fluorosulfonate:[5]
- CF3COF + SO3 → CF3C(O)OSO2F
The compound hydrolyses in water.[6]
Uses
Trifluoroacetyl fluoride is an important industrial intermediate for trifluoroacetic acid, which is produced by its hydrolysis.[7]
References
- ^ "Trifluoroacetyl fluoride". NIST. Retrieved 22 August 2025.
- ^ Olah, G; Kuhn, S (1 January 1961). "Notes. Organic Fluorine Compounds. XXVII. Preparation of Acyl Fluorides with Anhydrous Hydrogen Fluoride. The General Use of the Method of Colson and Fredenhagen". The Journal of Organic Chemistry. 26 (1): 237–238. doi:10.1021/jo01060a600. ISSN 0022-3263. Retrieved 22 August 2025.
- ^ Fowler, Brian R.; Moss, Kenneth C. (1 January 1980). "The reaction of vanadium pentafluoride with phosphorus oxytrifluoride and with trifluoroacetic acid". Journal of Fluorine Chemistry. 15 (1): 67–73. Bibcode:1980JFluC..15...67F. doi:10.1016/S0022-1139(00)85159-3. ISSN 0022-1139. Retrieved 22 August 2025.
- ^ Seel, F.; Budenz, R.; Gombler, W. (1967). "Cesium and Rubidium Pentafluoroethoxide". Angewandte Chemie International Edition in English. 6 (3): 256. doi:10.1002/anie.196702561. ISSN 1521-3773. Retrieved 22 August 2025.
- ^ Krespan, Carl G.; England, David C. (1 October 1975). "Addition of sulfur trioxide to acid halides and esters". The Journal of Organic Chemistry. 40 (20): 2937–2940. doi:10.1021/jo00908a018. ISSN 0022-3263. Retrieved 22 August 2025.
- ^ Song, Xinli (1 December 2018). "Catalytic hydrolyses of trifluoroacetyl fluoride by water". Chemical Physics Letters. 713: 137–144. Bibcode:2018CPL...713..137S. doi:10.1016/j.cplett.2018.10.038. ISSN 0009-2614. Retrieved 22 August 2025.
- ^ López, Simón E.; Salazar, José (1 December 2013). "Trifluoroacetic acid: Uses and recent applications in organic synthesis". Journal of Fluorine Chemistry. 156: 73–100. Bibcode:2013JFluC.156...73L. doi:10.1016/j.jfluchem.2013.09.004. ISSN 0022-1139. Retrieved 22 August 2025.