2-Fluorophenol

1 mmol of phenol was added to 4 ml of 10% acetic acid aqueous solution, followed by the addition of 1.5 mmol of Selectfluor and 0.05 mmol of Eosin Y. The reaction was carried out under 12W blue light at room temperature for 6 hours. After the reaction was completed, saturated NaCl aqueous solution was added to the reaction solution, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulfate, filtered, and evaporated under reduced pressure to obtain the crude compound. The crude compound was subjected to silica gel column chromatography using a mobile phase of ethyl acetate and petroleum ether in a volume ratio of 1:9. The eluent with an Rf value of 0.3-0.5 was collected by TLC. The collected eluent was subjected to solvent removal under reduced pressure and dried to obtain 90 mg of 2-fluorophenol (yield 77%).

Clear colourless to yellow liquid

2-Fluorophenol is a competitive inhibitor in the oxidation of 3,4-dihydroxyphenylalanine (L-DOPA), a catecholamine precursor that is used as a therapeutic agent for patients with ParkinsonтАЩs disease. 2-Fluorophenol is also used as a sole carbon energy source for bacteria.

Tetrahedron, 52, p. 23, 1996 DOI: 10.1016/0040-4020(95)00867-8
Journal of the American Chemical Society, 103, p. 1964, 1981 DOI: 10.1021/ja00398a015

Liquid or crystalline solid melting at 14-16°C. Corrosive. Density 1.246 g / cm3.

Highly flammable.

2-Fluorophenol reacts as a weak organic acid. May be incompatible with strong reducing substances such as hydrides, nitrides, alkali metals, and sulfides. Flammable gas (H2) is often generated, and the heat of the reaction may ignite the gas. Heat is also generated by the acid-base reaction with bases. Such heating may initiate polymerization of the organic compound. Sulfonated very readily (for example, by concentrated sulfuric acid at room temperature). The reactions generate heat. Nitrated very rapidly, even by dilute nitric acid.

ACUTE/CHRONIC HAZARDS: Toxic and irritant.

Pass o-fluorophenol at least twice through a gas chromatographic column for small quantities; otherwise fractionally distil it under reduced pressure. [Beilstein 6 I 97, 6 IV 770.]