The bromination kinetics of phenolic compounds in aqueous solution
Related Experiment Video
Updated: Jun 22, 2026

Elucidating the Metabolism of 2,4-Dibromophenol in Plants
Published on: February 10, 2023
1School of Resource and Environmental Engineering, East China University of Science and Technology, Shanghai 200237, China. gmguo@126.com
Abstract:
The purpose of this study was to investigate the bromination kinetics of selected phenolic compounds in aqueous solutions over the pH range of 5-11. The experiment results indicated that the reaction of hypobromous acid with the phenoxide ions controlled the overall reaction rate, whereas the reaction between hypobromite ion and the phenoxide ions and the reaction between hypobromous acid and the undissociated phenolic species were considered to be negligible respectively in the pH range of 7-9. The apparent second-order rate constants of the reaction of hypobromous acid with the phenoxide ions ranged from 7.9 x 10(6) M(-1) s(-1) for 3-chlorophenol to 6.5 x 10(8) M(-1) s(-1) for 3-methoxyphenol, respectively. The Hammett correlation could be successfully used to estimate the reactivity of bromine with substituted phenols and the linear regression was log(k(2))=-2.85 sigma+8.00. The rate constants of the reaction of bromine with phenol-like organic compounds were about three orders of magnitude higher than with chlorine and two to three orders of magnitude lower than with ozone.
More Related Videos
07:50Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
Published on: May 26, 2019
05:34Efficient Synthesis of Polyfunctionalized Benzenes in Water via Persulfate-promoted Benzannulation of α,β-Unsaturated Compounds and Alkynes
Published on: December 16, 2019
Related Concept Videos
Acidity and Basicity of Alcohols and Phenols
Oxidation of Phenols to Quinones
o-hydroxy phenols are oxidized to o-quinones and p-hydroxy phenols to p-quinones. Such redox reactions involve the transfer of two electrons and two protons. The reversible redox property is crucial in...
Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene
Hydrolysis of Chlorobenzene to Phenol: Dow Process
Formation of Halohydrin from Alkenes
Radical Substitution: Allylic Bromination