129644-69-5

Basic information

• Product Name: 2,6-Dimethyl-4-(trifluoromethylthio)phenol
• CAS NO: 129644-69-5
• Molecular Formula: C9H9F3OS
• Molecular Weight: 0
• Mol File: 129644-69-5.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2,6-Dimethyl-4-(trifluoromethylthio)phenol(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-Dimethyl-4-(trifluoromethylthio)phenol(129644-69-5)
• EPA Substance Registry System: 2,6-Dimethyl-4-(trifluoromethylthio)phenol(129644-69-5)

Safety Data

• Hazardous Substances Data: 129644-69-5(Hazardous Substances Data)

Usage

General Description

2,6-Dimethyl-4-(trifluoromethylthio)phenol is a chemical compound with the molecular formula C9H9F3OS. It is a phenolic compound with a trifluoromethylthio group attached to the phenol ring, and two methyl groups in the 2 and 6 positions. This chemical is commonly used as an intermediate in the synthesis of pharmaceuticals and agrochemicals. It is also used as a building block for the production of specialty chemicals and in organic synthesis. It has been identified as a potential environmental contaminant and may pose risks to aquatic organisms. Additionally, it has been studied for its potential antimicrobial and antioxidant properties.

Upstream product

• 576-26-1 2.6-dimethylphenol 
• 1045821-71-3 N-[(trifluoromethyl)sulfanyl]aniline 

Relevant articles and documents

Acid-promoted direct electrophilic trifluoromethylthiolation of phenols

The electrophilic aromatic ring trifluoromethylthiolation of various substituted phenols was accomplished using PhNHSCF3 (N-trifluoromethylsulfanyl)aniline, (1) in the presence of BF3·Et2O (2) or triflic acid as the promoter. The functionalization was exclusively para-selective; phenols unsubstituted in both the ortho- and para positions solely gave the para-substituted SCF3-products in all cases, while para-substituted phenols gave the ortho-substituted SCF3-products. 3,4-Dialkyl substituted phenols yielded the corresponding products according to the Mills-Nixon effect, and estrone and estradiol furnished biologically interesting SCF3-analogues. The highly reactive catechol and pyrogallol substrates gave the expected products smoothly in the presence of BF3·Et2O, whereas less reactive phenols required triflic acid. 2-Allylphenol gave the expected p-SCF3 analogue, which underwent an addition/cyclization sequence and furnished a new di-trifluoromethylthio substituted 2,3-dihydrobenzofuran derivative. Some additional transformations of 4-(trifluoromethylthio)phenol with NBS, NIS, HNO3, HNO3/H2SO4 and 4-bromobenzyl bromide were performed giving bromo-, iodo-, nitro- and benzyl substituted products. The latter derivative underwent Suzuki-Miyaura coupling with phenylboronic acid.