Fluorobenzene
[CAS# 462-06-6]

Identification

• Classification: Organic raw materials >> Hydrocarbon compounds and their derivatives >> Hydrocarbon halide
• Name: Fluorobenzene
• Molecular Formula: C₆H₅F
• Molecular Weight: 96.10
• CAS Registry Number: 462-06-6
• EC Number: 207-321-7
• SMILES: C1=CC=C(C=C1)F

Properties

• Density: 1.024
• Melting point: -42 °C
• Boiling point: 85 °C
• Refractive index: 1.4643-1.4663
• Flash point: -15 °C
• Water solubility: INSOLUBLE

Safety Data

• Hazard Symbols: GHS02;GHS05;GHS07;GHS09 Danger
• Risk Statements: H225-H318-H319-H411-H412
• Safety Statements: P210-P233-P240-P241-P242-P243-P264+P265-P273-P280-P303+P361+P353-P305+P351+P338-P305+P354+P338-P317-P337+P317-P370+P378-P391-P403+P235-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Flammable liquids	Flam. Liq.	2	H225
Serious eye damage	Eye Dam.	1	H318
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411
Eye irritation	Eye Irrit.	2	H319
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Specific target organ toxicity - repeated exposure	STOT RE	2	H373
Skin irritation	Skin Irrit.	2	H315
Acute hazardous to the aquatic environment	Aquatic Acute	3	H402
Eye irritation	Eye Irrit.	2A	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Flammable liquids	Flam. Liq.	3	H226

• Transport Information: UN 2387

Discovery and Applications

Fluorobenzene is a simple aromatic compound characterized by a benzene ring with a single fluorine atom substituent. Its chemical formula is C₆H₅F, and it serves as a fundamental building block in organic chemistry. The discovery of fluorobenzene dates back to the early 20th century when chemists began systematically exploring halogenated aromatic compounds. Its synthesis typically involves the direct fluorination of benzene using fluorine gas, a reaction that was first successfully conducted in the 1930s.

Fluorobenzene is notable for its role in various chemical syntheses due to the influence of the fluorine atom on the chemical properties of the benzene ring. The presence of fluorine, an electronegative element, significantly affects the reactivity and stability of the compound. This characteristic makes fluorobenzene a valuable intermediate in the production of more complex fluorinated organic molecules.

One of the primary applications of fluorobenzene is in the synthesis of pharmaceuticals and agrochemicals. The introduction of fluorine into organic molecules often enhances their biological activity and metabolic stability. For example, fluorobenzene is used as a precursor in the synthesis of various drugs, including those used in the treatment of cancer and neurological disorders. The ability of fluorine to modify the electronic properties of aromatic compounds enables the design of molecules with specific biological activities.

In addition to pharmaceuticals, fluorobenzene plays a crucial role in the development of advanced materials. It is used in the synthesis of fluorinated polymers and resins, which possess unique properties such as chemical resistance and thermal stability. These materials find applications in industries ranging from electronics to coatings, where their performance characteristics are highly valued.

Fluorobenzene is also employed in organic synthesis as a reagent for introducing fluorine atoms into other organic compounds. This is particularly important in the field of medicinal chemistry, where the incorporation of fluorine can significantly impact the pharmacological properties of drug candidates. Fluorobenzene's role as a fluorinating agent extends to various synthetic transformations, including the preparation of fluorinated derivatives of other aromatic compounds.

Overall, fluorobenzene is an essential compound in both research and industrial applications. Its unique chemical properties, influenced by the presence of the fluorine atom, make it a versatile building block in the synthesis of a wide range of fluorinated organic compounds. Its applications span pharmaceuticals, advanced materials, and organic synthesis, highlighting its significance in modern chemical science.

References

2024. Fluorine-benzene reaction. Russian Journal of Physical Chemistry B, 18(4).
DOI: 10.1134/s1990793124700192

2024. Suzuki-Miyaura coupling under acidic conditions. Nature Synthesis.
DOI: 10.1038/s44160-024-00631-4