828-27-3 | p-Trifluoromethoxy phenol

CAS:828-27-3 | p-Trifluoromethoxy phenol,Description

4-(Trifluoromethoxy)phenol is a chemical compound of interest in various fields such as pharmaceuticals, agrochemicals, and materials science due to its unique physical and electronic properties. The trifluoromethoxy group attached to the phenol ring influences the reactivity and stability of the molecule, making it a valuable moiety in chemical synthesis and applications.

Synthesis Analysis

The synthesis of 4-(trifluoromethyl)phenols, which are closely related to 4-(trifluoromethoxy)phenol, can be achieved through directed ortho-lithiation followed by reaction with electrophiles. The selectivity of this process is enhanced by the ortho-directing effect of a THP-protected hydroxy group. Additionally, a two-step O-trifluoromethylation of phenols has been developed, which involves the conversion of phenols to aryl xanthates and subsequent conversion to trifluoromethyl ethers under mild conditions.

Molecular Structure Analysis

The molecular structure of 4-(trifluoromethoxy)phenol is characterized by the presence of a trifluoromethoxy group (-OCF3) attached to a phenol ring. This group significantly affects the electronic distribution within the molecule, which can be exploited in various synthetic transformations. For instance, the trifluoromethanesulfonate (triflate) group derived from phenols is known for its reactivity in cross-coupling reactions.

Chemical Reactions Analysis

4-(Trifluoromethoxy)phenol can undergo various chemical reactions due to the reactivity of the phenol and trifluoromethoxy moieties. For example, electrophilic aromatic ring trifluoromethylthiolation of phenols has been achieved using specific reagents, leading to para-selective functionalization. The Fries rearrangement and direct acylation of phenol derivatives have also been catalyzed efficiently by hafnium trifluoromethanesulfonate.

Physical and Chemical Properties Analysis

The physical and chemical properties of 4-(trifluoromethoxy)phenol derivatives are influenced by the trifluoromethoxy group. For instance, novel polyimides derived from trifluoromethylphenol-related compounds exhibit good solubility in polar organic solvents, excellent thermal stability, and outstanding mechanical properties. Additionally, copper phthalocyanine derivatives containing a trifluoromethylthio group have been synthesized and characterized, showing interesting optical and surface properties.

Scientific Research Applications

Synthesis and Characterization in Copper(II) Phthalocyanines

A study focused on synthesizing and characterizing non-peripherally tetra-substituted copper(ii) phthalocyanines bearing 4-(trifluoromethoxy)phenol groups. These compounds were characterized using various spectroscopic techniques, and their optical and electrical properties were investigated, particularly for their application in fabricating photosensitive diodes (Günsel et al., 2019) .

Liquid-Crystalline Poly(Meth)acrylates Synthesis

Research involved the synthesis of side-group liquid-crystalline polymers with fluorine-containing mesogens, specifically using 4-trifluoromethoxy-aniline. These polymers demonstrated potential applications in various fields, including materials science (Prescher et al., 1995).

Ring-Opening Polymerisation with Group 4 Metal Complexes

A study explored the use of 4-(trifluoromethoxy)phenol in the preparation of group 4 metal complexes, which were then applied in the ring-opening polymerisation of cyclic esters. This research highlights its role in advancing polymer chemistry (Whitelaw et al., 2009).

Electrochemistry in Ionic Liquids

Research examined the electrochemistry of phenol and its derivatives, including 4-trifluoromethoxy-phenol, in specific ionic liquids. The study provided insights into the oxidation mechanisms of these compounds, which can be relevant in environmental and analytical chemistry (Villagrán et al., 2006) .

Synthetic Transformations Involving Triflates

A study discussed the increasing use of vinyl and aryl trifluoromethanesulfonates (triflates) derived from compounds like 4-(trifluoromethoxy)phenol. These triflates were shown to be useful in various synthetic transformations, including cross-coupling reactions, which are crucial in organic synthesis (Ritter, 1993).

Adsorption Studies on Activated Carbon Fibers

A study focused on the adsorption capacities of various phenols, including derivatives of 4-(trifluoromethoxy)phenol, on activated carbon fibers. These findings have implications in environmental remediation and waste treatment (Liu et al., 2010).

Photoconductive Diode Fabrication

Another study delved into the molecular structure and supra-molecular dynamics of 4-(trifluoromethoxy)phenol derivatives, assessing their optical and optoelectronic parameters for the fabrication of photoconductive diodes (Günsel et al., 2020) .

Gas-phase Thermochemical Properties

Research utilized density functional theory to investigate the gas-phase thermochemical properties of tri-substituted phenols, including 4-(trifluoromethoxy)phenol derivatives. Such studies are important in understanding the energetics and stability of these compounds (Miranda et al., 2015).

Safety And Hazards

4-(Trifluoromethoxy)phenol is considered hazardous according to the 2012 OSHA Hazard Communication Standard. It is combustible and toxic if swallowed. It can cause skin irritation, serious eye damage, and may cause respiratory irritation.

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