34113-69-4

Basic information

• Product Name: 4-Chloro-3-hydroxybenzoic acid
• Synonyms: 4-CHLORO-3-HYDROXYBENZOIC ACID;TIMTEC-BB SBB008503;4-CHLORO-3-HYDROXYBENZOIC ACID ---PURITY 98%---;5-Carboxy-2-chlorophenol;4-Chloro-3-hydroxybenzoic Acid, 97+%
• CAS NO: 34113-69-4
• Molecular Formula: C₇H₅ClO₃
• Molecular Weight: 172.5658
• Product Categories: Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Carboxylic Acids;Phenyls & Phenyl-Het;Carboxylic Acids;Phenyls & Phenyl-Het
• Mol File: 34113-69-4.mol
• Article Data: 4

Chemical Properties

• Melting Point: 219.5-220.5 °C
• Boiling Point: 345.4 °C at 760 mmHg
• Flash Point: 162.7 °C
• Appearance: /
• Density: 1.536 g/cm³
• Vapor Pressure: 2.34E-05mmHg at 25°C
• Refractive Index: 1.629
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: DMSO, Methanol
• PKA: 3.85±0.10(Predicted)
• CAS DataBase Reference: 4-Chloro-3-hydroxybenzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Chloro-3-hydroxybenzoic acid(34113-69-4)
• EPA Substance Registry System: 4-Chloro-3-hydroxybenzoic acid(34113-69-4)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 34113-69-4(Hazardous Substances Data)

Usage

Description

4-Chloro-3-hydroxybenzoic acid is an organic compound characterized by the presence of a hydroxyl group and a chlorine atom attached to a benzene ring. It is a white crystalline solid with a molecular formula of C7H5ClO3 and is known for its potential applications in the pharmaceutical and chemical industries.

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)

Upstream product

• 99-06-9 3-Carboxyphenol 
• 2374-03-0 4-aminosalicylic acid 
• 7664-93-9 sulfuric acid 
• 7782-50-5 chlorine 
• 64-19-7 acetic acid 
• 931409-94-8 3-methoxy-4-chlorobenzoic acid allyl ester 

Downstream Products

• 166272-81-7 4-Chloro-3-hydroxy-benzoic acid methyl ester 

Relevant articles and documents

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 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.