Benzoyl fluoride Identifiers ChemSpider ECHA InfoCard 100.006.587 EC Number UNII InChI=1S/C7H5FO/c8-7(9)6-4-2-1-3-5-6/h1-5H
Key: HPMLGNIUXVXALD-UHFFFAOYSA-N
Properties C 7 H 5 F O Molar mass −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).
Chemical compound
Benzoyl fluoride is an organic, aromatic compound of carbon, hydrogen, fluorine, and oxygen. It is theacyl fluoride ofbenzoic acid ; its chemical formula isC7 H5 FO . It was initially isolated byAlexander Borodin in 1863.[ 2] [ 3] [ 4]
Benzoyl fluoride can be prepared by the reaction ofbenzoyl chloride orbenzoic anhydride withpotassium fluoride ,[ 5] trifluorotoluene as a precoursor in presence ofniobium pentoxide as a catalyst.[ 6]
Chemical properties [ edit ] Benzoyl fluoride hydrolyzes in water tobenzoic acid and reacts with alkalis to form salts:[ 7]
C6 H5 COF + H2 O → C6 H5 COOH + HF C6 H5 COF + 2NaOH → C6 H5 COONa + NaF + H2 O Physical properties [ edit ] Benzoyl fluoride is a colorless liquid that is soluble inethanol ,diethyl ether , andacetone .
The compound can be used as anionic liquid [ 8]
^ "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 . Retrieved22 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 . Retrieved23 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 . Retrieved22 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 . Retrieved23 August 2025 .^ Jander, Gerhart; Schwiegk, Lothar (May 1961)."Benzoylfluorid als ionisierendes Lösungsmittel. I" Zeitschrift für anorganische und allgemeine Chemie 310 (1– 2):1– 11.Bibcode :1961ZAACh.310....1J .doi :10.1002/zaac.19613100102 .ISSN 0044-2313 . Retrieved22 August 2025 .
Salts and covalent derivatives of the
fluoride ion
PF− 6 ,AsF− 6 ,SbF− 6 compoundsAlF2− 5 ,AlF3− 6 compoundschlorides, bromides, iodides SiF2− 6 ,GeF2− 6 compoundsOxyfluorides Organofluorides with transition metal, nitric acids bifluorides thionyl, phosphoryl,
