(E)-3-(3-Fluorophenyl)acrylic acid – general description and preparation

Unfortunately, this article is currently only in English language. We are working on a translation. Thank you for understanding.

General description of (E)-3-(3-Fluorophenyl)acrylic acid:

(E)-3-(3-Fluorophenyl)acrylic acid [20595-30-6], 3-fluorocinnamic acid, or (2E)-3-(3-Fluorophenyl)-2-propenoic acid, is an organic acid belonging to acrylic acids group. In its pure form, it is a white crystalline solid with a melting point of 166,2-166,8 °C.^[1] It is soluble in water and polar organic solvents.

It is known that 3-fluorocinnamic acid can cause serious damage if swallowed and can be irritating in contact with skin or eyes (H301, H315, H319).^[2]

Preparation:

3-Fluorocinnamic acid can be prepared by Knowenagel-Doebner reaction of malonic acid or malonic ester with corresponding aldehyde. ^[3] It is also formed as side product in kinetic resolution of β-phenylalanine derivatives via selective conversion of a single enantiomer to the corresponding acrylic acid. ^[4] Recent research also showed that it can be prepared by Suzuki coupling of corresponding boronic acid with carbon dioxide. ^[5]

_______________________________________________________________________