34113-69-4

Usage

Uses

Used in Pharmaceutical Industry:
4-Chloro-3-hydroxybenzoic acid is used as an active pharmaceutical ingredient for the treatment of influenza. It acts as a potential inhibitor of influenza endonuclease, a key enzyme involved in the replication of the influenza virus, thereby helping to combat the infection.
Used in Oncology:
In the field of oncology, 4-Chloro-3-hydroxybenzoic acid is utilized in the synthesis of highly selective Tie-2 kinase inhibitors. These inhibitors play a crucial role in the treatment of various types of tumors by targeting the Tie-2 receptor, which is often overexpressed in cancer cells, leading to uncontrolled cell growth and angiogenesis.
Additionally, 4-Chloro-3-hydroxybenzoic acid may also find applications in other industries, such as the chemical industry, where it can be used as an intermediate for the synthesis of various compounds with potential applications in different fields.

InChI:InChI=1/C7H5ClO3/c8-5-2-1-4(7(10)11)3-6(5)9/h1-3,9H,(H,10,11)

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Relevant academic research and scientific papers

CARBOXAMIDE DERIVATIVES AS MUSCARINIC RECEPTOR ANTAGONISTS

The invention relates to compounds of Formula (I) processes and intermediates for their preparation, their use as muscarinic antagonists and pharmaceutical composition containing them.

Kinetics of chlorination of phenol and monosubstituted phenols by t-butyl hypochlorite in aqueous alkaline medium

The kinetics of chlorination of the parent and sixteen monosubstituted phenols (2-chloro, 2-methyl, 2-carboxy, 2-nitro, 3-chloro, 3-methyl, 3-carboxy, 4-fluoro, 4-chloro, 4-bromo, 4-methyl, 4-ethyl, 4-methoxy, 4-carboxy, 4-acetyl and 4-nitro) by t-BuOCl have been studied in aqueous alkaline medium. The rates of reactions show first order kinetics each in |t-BuOCl| and |XC 6H4OH| and inverse first order in |OH-|. Variation in either ionic strength or addition of reaction product has no significant effect on the rates of reactions, while lowering of the dielectric constant of the medium increases the rate. The rates are measured at different temperatures and the activation parameters for all the phenols computed. A mechanism involving the electrophilic attack of phenoxide ions by HOCl in the rate determining step is suggested. The rates decrease in the order: 3-CH 3 > 2-CH3 > 4-OCH3 > 4-CH3 > 4-C2H5 > H > 3-Cl > 3-COO- > 4-F > 2-COO- > 4-Br > 2-Cl > 4-Cl > 4-COO- > 4-COCH3 > 2-NO2 > 4-NO2. Hammett equation of the type, log k = -3.44 - 2.35 ρ is found to be valid for substituent effects. The enthalpy and entropy of activation are correlated.

Kinetics and mechanism of chlorination of phenol and substituted phenols by sodium hypochlorite in aqueous alkaline medium

The kinetics of chlorination of the parent and thirteen substituted phenols (2-methyl, 2-chloro, 2-carboxy, 3-methyl, 3-chloro, 3-carboxy, 4-methyl, 4-ethyl, 4-chloro, 4-bromo, 4-carboxy, 4-acetyl and 4-nitro phenols) by NaOCl have been studied in aqueous alkaline medium under varying conditions. The rates show first order kinetics each in [NaOCl] and [(X)C6H4(OH)] and inverse first order in [OH-]. Variation in ionic strength of the medium and addition of Cl have no significant effect on the rates of reactions. The rates of the reactions are measured at different temperatures and the activation parameters for all the phenols computed. A mechanism involving the electrophilic attack of the phenoxide ions by NaOCl in the rate determining step has been considered. The values of the pre-equilibrium and the rate determining steps have been calculated for all the phenols. The rates decrease in the order: 3-CH3 >2-CH3 >4-C2H5 = 4-CH3 >phenol >3-COO = 3-Cl > 2-COO >4-COO >2-Cl ? 4-Cl ? 4-Br > 4-COCH3 >4-NO2. Hammett plot of the type, log kobs = -2.88 -3.2980σ is found to be valid. The correlation between the enthalpies and the free energies of activations is reasonably linear with an isokinetic temperature of 300 K. Further, the energies of activation of all the phenols are optimised corresponding to the log A of the parent phenol through the equation, Ea = 2.303 RT (log A - log kobs). Similarly log A values of all the phenols are optimised corresponding to the Ea of PhOH through the equation, log A = log kobs + Ea/2.303RT. Ea increases with the introduction of electron-withdrawing groups into the benzene ring, while the introduction of the electron-releasing groups lowers Ea for the reaction. Similarly log A decreases with the substitution of electron-withdrawing groups, while log A increases on substitution with the electron-releasing groups.

PHOTOREACTION OF BENZOIC ACID WITH SODIUM HYPOCHLORITE IN AQUEOUS ALKALI

The photoreaction of benzoic acid with sodium hypochlorite in aqueous alkali (pH > 12) has been studied.At a low initial ratio of , e.g, 0.1, hydroxylation and chlorination at the aromatic ring occur simultaneously with ipso-substitution of the carboxylate group to give hydroxy- and chlorobenzoic acids together with phenol.The product distribution depends on the wavelength of the light, which implies the dependence on the concentration of avtive species generated from ClO(1-) and on the light stability of products.At comparable concentrations of ClO(1-) and PhCOO(1-), the products initially formed from the photoreaction react further with ClO(1-) in the dark to give polychlorinated derivatives.The initial steps for the photoreaction are discussed on the basis of the reactivity of the active species, O(3P), O(1D), O(1-)(.), and Cl(.), generated by photolysis of ClO(1-).