4-Fluoroanisole
[CAS# 459-60-9]

Identification

• Classification: Organic raw materials >> Organic fluorine compound >> Fluoroanisole series
• Name: 4-Fluoroanisole
• Synonyms: p-Fluoroanisole; 1-Fluoro-4-methoxybenzene
• Molecular Formula: C₇H₇FO
• Molecular Weight: 126.13
• CAS Registry Number: 459-60-9
• EC Number: 207-295-7
• SMILES: COC1=CC=C(C=C1)F

Properties

• Density: 1.114
• Melting point: -45 °C
• Boiling point: 157 °C
• Refractive index: 1.4867-1.4887
• Flash point: 43 °C

Safety Data

• Hazard Symbols: GHS02 Warning
• Risk Statements: H226
• Safety Statements: P210-P233-P240-P241-P242-P243-P280-P303+P361+P353-P370+P378-P403+P235-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Flammable liquids	Flam. Liq.	3	H226

• Transport Information: UN 3271

Discovery and Applications

4-Fluoroanisole, with the chemical formula C₇H₇FO and a molecular weight of 126.13 g/mol, is an important organic compound with unique properties and wide applications in chemical synthesis. Its structure consists of a benzene ring substituted with a methoxy group (-OCH₃) and a para-fluorine atom, making it a versatile fluorinated aromatic ether.

4-Fluoroanisole was part of the growing interest in fluorinated organic compounds in the mid-20th century. Its synthesis was accompanied by advances in organofluorine chemistry, especially methods to introduce fluorine atoms into aromatic compounds. A common synthetic route is the reaction of 4-fluorophenol with dimethyl sulfate or methyl iodide to form 4-fluoroanisole through an O-alkylation process.

4-Fluoroanisole is a valuable intermediate in the pharmaceutical industry. Its fluorinated structure helps enhance the metabolic stability, lipophilicity, and bioavailability of drug molecules. It is used in the synthesis of active pharmaceutical ingredients (APIs) and various agrochemicals.

The compound is fundamental to the development of advanced materials, including liquid crystals and polymers. Its aromatic ring and fluorine substitution provide unique electrical and optical properties that can be used to create specialized coatings and electronic materials.

In organic synthesis, 4-fluoroanisole is used as a starting material or intermediate to produce complex molecules. It is particularly useful in reactions that require the introduction of fluorine into aromatic systems, allowing the exploration of new chemical space and properties.

References

2020. Transition metal-catalyzed cross-coupling reactions. Synthesis, 52(4).
DOI: 10.1055/s-0040-1705986

2017. Decarbonylation and dehalogenation. Synthesis, 49(10).
DOI: 10.1055/s-0036-1590892