Benzoyl fluoride

Benzoyl fluoride

Identifiers
CAS Number	455-32-3
3D model (JSmol)	Interactive image
ChemSpider	61314
ECHA InfoCard	100.006.587
EC Number	207-244-9
PubChem CID	67999
UNII	LOR25I34HD
CompTox Dashboard (EPA)	DTXSID5060019
InChI InChI=1S/C7H5FO/c8-7(9)6-4-2-1-3-5-6/h1-5H Key: HPMLGNIUXVXALD-UHFFFAOYSA-N
SMILES C1=CC=C(C=C1)C(=O)F
Properties
Chemical formula	C7H5FO
Molar mass	124.114 g·mol−1
Appearance	colorless liquid
Density	1.14 g/cm3
Melting point	-28 °C
Boiling point	160 °C
Solubility in water	hydrolysis
Hazards
GHS labelling: [1]
Pictograms
Signal word	Danger
Hazard statements	H226, H314
Precautionary statements	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

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

• Benzoyl chloride

References

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.