828-27-3

Usage

Uses

Used in Pharmaceutical Industry:
p-Trifluoromethoxy phenol is used as a reactant in the preparation of 1-aryloxyethyl piperazine derivatives, which are Kv1.5 potassium channel inhibitors. These inhibitors play a crucial role in treating atrial fibrillation and other cardiovascular diseases by regulating the electrical activity of the heart.
Used in Chemical Synthesis:
p-Trifluoromethoxy phenol is employed in the catalytic enantioselective synthesis of esters. This process is vital for producing enantiomerically pure compounds, which are essential in various pharmaceutical and agrochemical applications due to their specific biological activities and reduced side effects.
Used in Liquid Crystal Industry:
p-Trifluoromethoxy phenol serves as an intermediate in the production of liquid crystals, which are widely used in display technologies such as LCD screens, computer monitors, and televisions. These liquid crystals offer superior properties, including improved temperature stability and faster response times, making them ideal for various electronic devices.

Synthesis Reference(s)

Journal of Medicinal Chemistry, 25, p. 1097, 1982 DOI: 10.1021/jm00351a018

InChI:InChI=1/C8H9FO2/c1-10-6-3-4-8(11-2)7(9)5-6/h3-5H,1-2H3

Upstream product

• 461-82-5 4-(trifluoromethoxy)aniline 
• 659-28-9 p-trifluoromethoxybenzaldehyde 
• 9005-25-8 starch 
• 474709-28-9 4,4,5,5-tetramethyl-2-(4-(trifluoromethyloxy)phenyl)-1,3,2-dioxaborolane 
• 456-55-3 1-trifluoromethoxybenzene 
• 34888-05-6 (trichloromethoxy)benzene 
• 100-66-3 methoxybenzene 
• 139301-27-2 4-trifluoromethoxyphenylboronic acid 
• 710-18-9 1-methoxy-4-(trifluoromethoxy)benzene 

Downstream Products

• 142739-07-9 Sulfuric acid mono-(4-trifluoromethoxy-phenyl) ester 
• 142739-09-1 2-Sulfooxy-5-trifluoromethoxy-benzenesulfonic acid 
• 142739-08-0 2-Hydroxy-5-trifluoromethoxy-benzenesulfonic acid 
• 142787-68-6 6-(trifluoromethoxy)benzo-1,3,2,4-dioxadithiin 2,2,4,4-tetraoxide 
• 23891-48-7 1-trifluoromethoxy-4-(2-nitro-phenoxy)-benzene 
• 150361-01-6 2-(4-trifluoromethoxy-phenoxy)-phenylamine 
• 129644-57-1 TFMSA 
• 213128-09-7 1-((1R,2R,3R)-2-Benzyloxymethyl-3-methoxy-4,4-dimethyl-cyclohexylmethoxy)-4-trifluoromethoxy-benzene 
• 185538-94-7 1-[(1R,2R,3S,6R)-2-Methoxy-3-methyl-6-(4-trifluoromethoxy-phenoxymethyl)-3-(2-trityloxy-ethyl)-cyclohexylmethyl]-1H-[1,2,4]triazole 
• 286844-91-5 1-(methylsulfonyl)-4-(4'-(trifluoromethoxy)phenoxy)benzene 
• 74030-44-7 1-nitro-4-(4-(trifluoromethoxy)phenoxy)benzene 
• 851341-46-3 triisopropyl[4-(trifluoromethoxy)phenoxy]silane 
• 851341-40-7 1-(methoxymethoxy)-4-(trifluoromethoxy)benzene 
• 70783-75-4 4-(trifluoromethoxy)-2-chlorophenol 

Relevant academic research and scientific papers

Catalytic C–O bond cleavage in a β-O-4 lignin model through intermolecular hydrogen transfer

A base-free and redox neutral approach for the selective breaking of aryl ether bond (C–O) contained by a lignin model compound mimicking a β-O-4 linkage is reported. A palladium loaded metal-organic framework (MOF) was used as a catalyst for this purpose. The reaction proceeds through dehydrogenation of benzylic alcohol moiety followed by the hydrogenolysis of the ether bonds. Therefore, no external hydrogen source is required for the reaction to take place.

A practical method for preparation of phenols from arylboronic acids catalyzed by iodopovidone in aqueous medium

A novel and efficient strategy for the ipso-hydroxylation of arylboronic acids to phenols has been developed using inexpensive, readily available, air-stable water-soluble povidone iodine as catalyst and aqueous hydrogen peroxide as oxidizing agent. The reactions were performed at room temperature under metal-, ligand- and base-free condition in a short reaction time. The corresponding substituted phenols were obtained in moderate to good yields by oxidative hydroxylation of arylboronic acids in aqueous medium.

Trichloroacetonitrile as an efficient activating agent for the: Ipso -hydroxylation of arylboronic acids to phenolic compounds

A metal-free and base-free Cl3CCN mediated method was developed for the ipso-hydroxylation of aryl boronic acids to their corresponding phenols, which was promoted by a key unstable Lewis adduct intermediate. This transformation has broad functional group tolerance, and late-stage functionalization was successful as well. After simple investigation, two pathways (radical/ionic mechanism) were suggested, and the beneficial action of blue light needs to be further studied.

Solar-driven conversion of arylboronic acids to phenols using metal-free heterogeneous photocatalysts

Solar-driven conversion of arylboronic acids to phenols was achieved by employing graphitic carbon nitride (g-C3N4) as heterogeneous photocatalyst, where [rad]O2? was the main active species. By loading g-C3N4 onto the easy weaving low melting point sheath-core composite polyester fibers (LMPET), g-C3N4-based artificial photosynthetic catalytic fabric (g-C3N4/LMPET) with a large light receiving area was prepared. It displayed the efficient conversion of arylboronic acid and excellent recycling performance. This system offers more possibilities to construct an artificial photosynthetic system with excellent solar-to-chemicals conversion efficiency.

A catalytic oxidation fragrant boron class compound preparing phenol method (by machine translation)

The invention discloses a method for catalytic oxidation of phenolic compounds fragrant boron class compound synthesis method, the flux in the solvent in the aqueous solution, under the action of alkali, adding hydrazine hydrate or acid hydrazides catalyst, catalytic oxidation fragrant boron class compound directly for the preparation of phenolic compound. The invention of the method of preparation of the phenol compound, the catalyst is a cheap hydrazine hydrate or hydrazine compound, the oxidizing agent is atmospheric pressure of air or oxygen, the reaction does not need good and activeness metal catalyst, is extensive and stable substrate, substrate-sensitive functional group compatibility good and wide range of application. In the optimized under the reaction conditions, the yield of the target product separation up to 99%. (by machine translation)

PROCESS FOR THE PREPARATION OF 4-SUBSTITUTED-1-(TRIFLUOROMETHOXY)BENZENE COMPOUNDS

The present invention provides the process for the preparation of 4-substituted-1- (trifluoromethoxy) benzene compounds..

An efficient and chemoselective deprotection of aryl tert-butyldimethylsilyl (TBDMS) ethers by NaCN

Phenolic tert-butyldimethylsilyl (TBDMS) ethers can be deprotected to yield phenols in excellent yield using sodium cyanide (NaCN) as catalyst in ethanol. The deprotectation of various phenolic TBDMS ethers were found to be very convenient, fast, high yielding and chemoselective.

Modification of an Enzyme Biocatalyst for the Efficient and Selective Oxidative Demethylation of para-Substituted Benzene Derivatives

The bacterial CYP199A4 enzyme is able to oxidise a narrow range of aromatic acids, which includes 4-methoxybenzoic acid, efficiently. A serine 244 to aspartate variant was identified with enhanced activity for a wide range of para-methoxy-substituted benzenes. Substrates in which the acidic benzoic acid moiety is replaced with a phenol and the amide, aldehyde and bromide analogues were all oxidised with high activity by the S244D mutant (product formation rate >600 nmol nmolCYP ?1 min?1) with turnover numbers of up to 20 000. If the carboxylate moiety was modified to a nitro, ketone, boronic acid, hydroxymethyl or nitrile group, these substrates were also oxidised at a significantly higher activity by S244D than the wild-type enzyme. 3,4-Dimethoxybenzaldehyde was demethylated selectively and oxidatively to 3-methoxy-4-hydroxybenzaldehyde by the S244D mutant 84-fold more rapidly than with the wild-type enzyme. CYP199A4 would have applications in the catalytic regioselective oxidative demethylation of suitably substituted benzene substrates under mild conditions and in the presence of more oxidatively sensitive functional groups, such as an aldehyde.

Ligand- and base-free synthesis of phenols by rapid oxidation of arylboronic acids using iron(III) oxide

Fe2O3 catalyzed rapid oxidation of arylboronic acids to obtain phenols in excellent yields (90-95%) in the presence of atmospheric oxygen under solar VIS-light irradiation using α-Fe2O3 as a catalyst in ligand- and base-free conditions is presented.

Ligand- and base-free synthesis of phenols by rapid oxidation of arylboronic acids using iron(III) oxide

Fe2O3 catalyzed rapid oxidation of arylboronic acids to obtain phenols in excellent yields (90-95%) in the presence of atmospheric oxygen under solar VIS-light irradiation using α-Fe2O 3 as a catalyst in ligand- and base-free conditions is presented.