Benzoyl fluoride
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3D model (JSmol)
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| ChemSpider | |
| ECHA InfoCard | 100.006.587 |
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CompTox Dashboard (EPA)
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| Properties | |
| C7H5FO | |
| Molar mass | 124.114 g·mol−1 |
| Appearance | colorless liquid |
| Density | 1.14 g/cm3 |
| Melting point | −28 °C |
| Boiling point | 160 °C |
| hydrolysis | |
| Hazards | |
| GHS labelling:[1] | |
| Danger | |
| H226, H314 | |
| P210, P233, P240, P241, P242, P243, P260, P264, P280, P301+P330+P331, P302+P361+P354, P303+P361+P353, P304+P340, P305+P354+P338, P316, P321, P363, P370+P378, P403+P235, P405, P501 | |
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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Benzoyl fluoride is an organic, aromatic compound of carbon, hydrogen, fluorine, and oxygen. It is the acyl fluoride of benzoic acid; its chemical formula is C7H5FO. It was initially isolated by Alexander Borodin in 1863.[2][3][4]
Synthesis
Benzoyl fluoride can be prepared by the reaction of benzoyl chloride or benzoic anhydride with potassium fluoride,[5] or by using trifluorotoluene as a precoursor in presence of niobium pentoxide as a catalyst.[6]
Chemical properties
Benzoyl fluoride hydrolyzes in water to benzoic acid and reacts with alkalis to form salts:[7]
- C6H5COF + H2O → C6H5COOH + HF
- C6H5COF + 2NaOH → C6H5COONa + NaF + H2O
Physical properties
Benzoyl fluoride is a colorless liquid that is soluble in ethanol, diethyl ether, and acetone.
Uses
The compound can be used as an ionic liquid[8] and as a silicone depolymerization agent.
See also
References
- ^ "Benzoyl fluoride". pubchem.ncbi.nlm.nih.gov.
- ^ Borodine, A. (January 1863). "Zur Geschichte der Fluorverbindungen und über das Fluorbenzoyl". Justus Liebigs Annalen der Chemie. 126 (1): 58–62. doi:10.1002/jlac.18631260105. Retrieved 22 August 2025.
- ^ Olah, G. A.; Ohannesian, L.; Arvanaghi, M. (1987). "Formylating Agents". Chemical Reviews. 87 (4): 671–686. doi:10.1021/cr00080a001.
- ^ Roscoe, Henry Enfield; Schorlemmer, Karl (1892). A Treatise on Chemistry. D. Appleton and Company. p. 170. Retrieved 23 August 2025.
- ^ Döhlert, Peter; Pfrommer, Johannes; Enthaler, Stephan (5 January 2015). "Recycling Concept for End-of-Life Silicones: Boron Trifluoride Diethyl Etherate as Depolymerization Reagent to Produce Difluorodimethylsilane as Useful Commodity". ACS Sustainable Chemistry & Engineering. 3 (1): 163–169. Bibcode:2015ASCE....3..163D. doi:10.1021/sc500666d. Retrieved 22 August 2025.
- ^ Zakzeski, Joseph; Fan, Irene S.; Bell, Alexis T. (May 2009). "Preparation of benzoyl fluoride from benzotrifluoride catalyzed by niobium oxide" (PDF). Applied Catalysis A: General. 360 (1): 33–37. Bibcode:2009AppCA.360...33Z. doi:10.1016/j.apcata.2009.02.042.
- ^ Nature: The International Journal of Science. Macmillan Publishers Limited, part of Springer Nature. 1891. p. 64. Retrieved 23 August 2025.
- ^ Jander, Gerhart; Schwiegk, Lothar (May 1961). "Benzoylfluorid als ionisierendes Lösungsmittel. I". Zeitschrift für anorganische und allgemeine Chemie (in German). 310 (1–2): 1–11. Bibcode:1961ZAACh.310....1J. doi:10.1002/zaac.19613100102. ISSN 0044-2313. Retrieved 22 August 2025.