4-Fluoroaniline

Chemical properties

4-Fluoroaniline is a light yellow to gold-coloured liquid.It is easy to oxidize and turn red in air.

The Uses of 4-Fluoroaniline

4-Fluoroaniline is a degradation product of Ezetimibe (E975000). 4-Fluoroaniline is used as an analytical reagent in the enzymic detection of glucose.

The Uses of 4-Fluoroaniline

Intermediate in the manufacture of herbicides and plant growth regulators.

The Uses of 4-Fluoroaniline

4-Fluoroaniline may be employed as one of the target pollutant during the investigation of biodegradability of fluorinated compounds under aerobic conditions. It may be used for the synthesis of luminescent and cationic monocyclometalated gold(III) monoaryl complexes.

Definition

ChEBI: 4-fluoroaniline is a primary arylamine that is the derivative of aniline in which the hydrogen at position 4 has been substituted by fluorine. It is used as an intermediate in the manufacture of pharmaceuticals, herbicides and plant growth regulators. It is a primary arylamine and a fluoroaniline.

Preparation

The better process in the one-step process is the nitrobenzene method, which is obtained by deoxygenation, hydrogenation and fluorination. With PdCl2-V2O5 as the catalyst and carbon monoxide as the reducing agent, the reaction was carried out at 160°C for 3h, and the yield of 4-fluoroaniline could reach 90%, with another 10% of aniline as a by-product. With PtO2 as the catalyst, BF3-HF as the fluorinating agent and hydrogen as the reducing agent, the reaction was carried out at 42℃ for 12.5h, with 100% conversion and 95% yield.

Synthesis Reference(s)

Journal of the American Chemical Society, 70, p. 654, 1948 DOI: 10.1021/ja01182a065
The Journal of Organic Chemistry, 26, p. 4014, 1961 DOI: 10.1021/jo01068a089

General Description

4-fluoroaniline is a light-colored oily liquid. Mixture of three isomers. Insoluble in water and denser than water. Contact may cause irritation to skin, eyes, and mucous membranes. May be toxic by ingestion. Used to make other chemicals. The barriers to inversion and internal rotation of the NH2 group in 4-fluoroaniline has been investigated by far infrared gas spectra.

Hazard

Toxic material.

Flammability and Explosibility

Not classified

Safety Profile

Poison by ingestion. Mutation data reported. A severe skin and eye irritant. When heated to decomposition it emits very toxic fumes of NOx and F-.