Fluorobenzene

Fluorobenzene, also known as phenyl fluoride, is an aryl fluoride with the chemical formula C6H5F[1]. It is a colorless liquid and the simplest of the fluorobenzenes, often abbreviated as PhF[1]. Fluorobenzene is a precursor to many fluorophenyl compounds and is used as an insecticide and as a reagent for plastic and resin polymers[3].

Preparation

Fluorobenzene was first reported in 1886 by O. Wallach at the University of Bonn[1]. On the laboratory scale, it is prepared by the thermal decomposition of the benzenediazonium tetrafluoroborate[1]. The technical synthesis involves the reaction of cyclopentadiene with difluorocarbene, which undergoes a ring expansion and subsequent elimination of hydrogen fluoride[1].

Properties

Fluorobenzene has a melting point of -93.9 °C and a boiling point of 65 °C[2]. It is a highly flammable liquid, with a flash point of 52 °F (11 °C)[2]. The compound is also toxic if absorbed through skin, swallowed, or inhaled, and may cause dizziness, nausea, muscle weakness, narcosis, and respiratory failure[2][3]. It is classified as a hazardous substance due to its flammability and potential health risks[2][3].

Solvent Properties

Fluorobenzene is a useful solvent for highly reactive species due to its low melting point and high dielectric constant[1]. It is more polar than benzene, with a dielectric constant of 5.42 compared to 2.28 for benzene at 298 K[1]. Although it is usually considered a non-coordinating solvent, a metal complex of PhF has been crystallized[1].

Safety and Handling

Fluorobenzene requires special handling and storage due to its hazardous properties[2][3]. It should be stored in a tightly closed container, away from heat and open flames, and handled by persons trained in the safe handling of hazardous chemicals[2][3]. Protective equipment, including gloves and respirators, should be worn when handling the compound, and it should not be ingested or allowed to come into contact with skin or eyes[2][3].

References

[1] Wikipedia. (n.d.). Fluorobenzene. Retrieved from <https://en.wikipedia.org/wiki/Fluorobenzene>

[2] AccuStandard. (n.d.). CAS No. 462-06-6 - Fluorobenzene. Retrieved from <https://www.accustandard.com/prod0004759.html>

[3] New Jersey Department of Health. (n.d.). Common Name: FLUOROBENZENE CAS Number: 462-06-6. Retrieved from <https://nj.gov/health/eoh/rtkweb/documents/fs/0939.pdf>

[4] NIST. (n.d.). Benzene, fluoro-. Retrieved from <https://webbook.nist.gov/cgi/cbook.cgi?Name=Fluorobenzene&Units=SI>

[5] Sigma-Aldrich. (n.d.). Fluorobenzene analytical standard 462-06-6. Retrieved from <https://www.sigmaaldrich.com/US/en/product/sial/51411>

Citations:

[1] https://en.wikipedia.org/wiki/Fluorobenzene

[2] https://www.accustandard.com/prod0004759.html

[3] https://nj.gov/health/eoh/rtkweb/documents/fs/0939.pdf

[4] https://webbook.nist.gov/cgi/cbook.cgi?Name=Fluorobenzene&Units=SI

[5] https://www.sigmaaldrich.com/US/en/product/sial/51411