Benzoyl fluoride

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Benzoyl fluoride
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.006.587 Edit this at Wikidata
EC Number
  • 207-244-9
UNII
  • InChI=1S/C7H5FO/c8-7(9)6-4-2-1-3-5-6/h1-5H
    Key: HPMLGNIUXVXALD-UHFFFAOYSA-N
  • C1=CC=C(C=C1)C(=O)F
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]
GHS02: FlammableGHS05: Corrosive
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).

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

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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

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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

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Benzoyl fluoride is a colorless liquid that is soluble in ethanol, diethyl ether, and acetone.

Uses

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The compound can be used as an ionic liquid[8] and as a silicone depolymerization agent.

See also

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References

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  1. ^ "Benzoyl fluoride". pubchem.ncbi.nlm.nih.gov.
  2. ^ 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.
  3. ^ Olah, G. A.; Ohannesian, L.; Arvanaghi, M. (1987). "Formylating Agents". Chemical Reviews. 87 (4): 671–686. doi:10.1021/cr00080a001.
  4. ^ Roscoe, Henry Enfield; Schorlemmer, Karl (1892). A Treatise on Chemistry. D. Appleton and Company. p. 170. Retrieved 23 August 2025.
  5. ^ 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.
  6. ^ 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.
  7. ^ Nature: The International Journal of Science. Macmillan Publishers Limited, part of Springer Nature. 1891. p. 64. Retrieved 23 August 2025.
  8. ^ 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.