Uses
3,5-Dichloro-4-hydroxybenzoic Acid can be used as cyclin dependent kinase inhibitors to treat cell proliferative disorders, such as, cancer.
Definition
ChEBI: 3,5-dichloro-4-hydroxybenzoic acid is a derivative of p-salicylic acid with chloro- substituents at C-3 and C-5 of the benzene ring. It is a monohydroxybenzoic acid and a dichlorobenzene. It is functionally related to a benzoic acid and a 4-hydroxybenzoic acid. It is a conjugate acid of a 3,5-dichloro-4-hydroxybenzoate.
Synthesis
The general procedure for the synthesis of 3,5-dichloro-4-hydroxybenzoic acid from 4-hydroxybenzoic acid was as follows: 10 mL of 33% hydrogen peroxide solution was slowly added to a suspension of 10 mL hydrochloric acid and 20 mL water containing 3.5 g (0.025 mol) of 4-hydroxybenzoic acid. Upon completion of the reaction, the resulting white precipitate was collected by filtration, washed well with hot water and purified by recrystallization from ethanol. Finally, 3.19 g of white crystalline product was obtained in 63.5% yield with a melting point of 265 °C. The 1H NMR spectral data of the product was as follows (ppm): 7.84 (s, 2H, H2,6). Elemental analysis results: measured values (%) C 40.64, H 1.87, Cl 34.34; calculated values (%) C 40.58, H 1.93, Cl 34.30 (molecular formula: C7H4Cl2O2).
References
[1] Organic Process Research and Development, 1999, vol. 3, # 1, p. 10 - 16
[2] Russian Journal of General Chemistry, 2015, vol. 85, # 3, p. 577 - 583
[3] Zh. Obshch. Khim., 2015, vol. 85, # 3, p. 413 - 419,7
[4] Zhurnal Obshchei Khimii, 1949, vol. 19, p. 1167,1168
[5] Chem. Zentralbl., 1950, vol. 121, p. 1063
