63981-76-0

Basic information

• Product Name: (2-hydroxyphenyl)-N,N,N-trimethylmethanaminium bromide
• CAS NO: 63981-76-0
• Molecular Formula: C₁₀H₁₆BrNO
• Molecular Weight: 246.1441
• Mol File: 63981-76-0.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (2-hydroxyphenyl)-N,N,N-trimethylmethanaminium bromide(CAS DataBase Reference)
• NIST Chemistry Reference: (2-hydroxyphenyl)-N,N,N-trimethylmethanaminium bromide(63981-76-0)
• EPA Substance Registry System: (2-hydroxyphenyl)-N,N,N-trimethylmethanaminium bromide(63981-76-0)

Safety Data

• Hazardous Substances Data: 63981-76-0(Hazardous Substances Data)

Usage

General Description

The chemical compound (2-hydroxyphenyl)-N,N,N-trimethylmethanaminium bromide, also known as cetylpyridinium bromide, is a quaternary ammonium compound commonly used as an antiseptic and preservative in various pharmaceutical and personal care products. It is known for its broad spectrum antibacterial and antifungal properties, making it effective in preventing the growth and spread of various microorganisms. Cetylpyridinium bromide is also used in dental products such as mouthwashes and toothpastes due to its ability to inhibit the formation of dental plaque and reduce gingivitis. Additionally, it is used in some industrial applications as a surfactant and emulsifying agent. However, it is important to use this compound with caution and according to recommended guidelines, as it can be toxic if ingested or inhaled in large amounts.

Upstream product

• 195062-59-0 2-methylphenylboronic acid pinacol ester 
• 16419-60-6 2-Methylphenylboronic acid 
• 1447933-45-0 trimethyl-[2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzyl]-quaternaryammonium bromide 
• 377780-72-8 2-(2-(bromomethyl)phenyl)-4,4,5,5,-tetramethyl-1,3,2-dioxaborolane 

Relevant articles and documents

Substituent effects on oxidation-induced formation of quinone methides from arylboronic ester precursors

A series of arylboronic esters containing different aromatic substituents and various benzylic leaving groups (Br or N+Me3Br -) have been synthesized. The substituent effects on their reactivity with H2O2 and formation of quinone methide (QM) have been investigated. NMR spectroscopy and ethyl vinyl ether (EVE) trapping experiments were used to determine the reaction mechanism and QM formation, respectively. QMs were not generated during oxidative cleavage of the boronic esters but by subsequent transformation of the phenol products under physiological conditions. The oxidative deboronation is facilitated by electron-withdrawing substituents, such as aromatic F, NO2, or benzylic N+Me 3Br-, whereas electron-donating substituents or a better leaving group favor QM generation. Compounds containing an aromatic CH 3 or OMe group, or a good leaving group (Br), efficiently generate QMs under physiological conditions. Finally, a quantitative relationship between the structure and activity has been established for the arylboronic esters by using a Hammett plot. The reactivity of the arylboronic acids/esters and the inhibition or facilitation of QM formation can now be predictably adjusted. This adjustment is important as some applications may benefit and others may be limited by QM generation. Tunable quinone methide formation: Aromatic substituents and the benzylic leaving group strongly affect the H 2O2-induced formation of quinone methides (QMs) from arylboronic esters (see scheme). The reactivity of arylboronic esters can be predictably adjusted by varying substituents. Copyright