Chemical Properties
white to light yellow crystal powder
Uses
4-Fluoro-2-nitrobenzoic acid has been used to study the reactions of substituted pyridines with the salicyl phosphate dianion.
Biochem/physiol Actions
4-Fluoro-2-nitrobenzoic acid enhances the binding of insulin to adipocytes.
Synthesis
The general procedure for synthesizing 2-nitro-4-fluorobenzoic acid from 2-nitro-4-fluorotoluene is as follows: referring to the method of Examples 2-31, a mixture of 4-fluoro-2-nitrotoluene (25.0 g, 161 mmol), potassium permanganate (102 g, 645 mmol), and water (500 mL) was heated to 100 °C and stirred for 3 hours. Upon completion of the reaction, the mixture was cooled to room temperature and filtered through diatomaceous earth to remove insoluble manganese dioxide produced by the reduction of potassium permanganate. The filtrate was washed with diethyl ether and adjusted to acidity by adding concentrated hydrochloric acid. Subsequently, the organic material in the acidified aqueous phase was extracted with diethyl ether. The organic phases were combined, washed with saturated sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was removed by evaporation under reduced pressure to give 2-nitro-4-fluorobenzoic acid (10.1 g, 34% yield). The product was confirmed by NMR hydrogen spectroscopy (CDCl3): δ 7.40 (1H, ddd, J = 2.6 Hz, 7.4 Hz, 8.8 Hz), 7.53 (1H, dd, J = 2.6 Hz, 7.6 Hz), 8.00 (1H, dd, J = 5.6 Hz, 8.8 Hz), 8.52 (1H, br s).
References
[1] Patent: US2003/187014, 2003, A1
[2] Journal of Biological Chemistry, 1954, vol. 207, p. 411,412
[3] Journal of the American Chemical Society, 1963, vol. 85, p. 1792 - 1797
[4] Collection of Czechoslovak Chemical Communications, 1960, vol. 25, p. 784 - 796
[5] Patent: US6635657, 2003, B1
