371-41-5

Usage

Uses

Used in Pharmaceutical Industry:
4-Fluorophenol is used as an intermediate for the synthesis of pharmaceutical goods. It plays a crucial role in the industrial production of various pharmaceuticals, including cisapride and Sabeluzole from Janssen, Sorbinil from Pfizer, and Progabide from Synthelabo. Its unique chemical properties make it a valuable component in the development of these medications.
Used in Liquid Crystal Industry:
4-Fluorophenol is also utilized as an intermediate in the production of liquid crystals. Liquid crystals are widely used in various applications, such as displays for electronic devices, due to their unique properties. The fluorinated nature of 4-Fluorophenol contributes to the development of advanced liquid crystal materials with improved performance characteristics.

Preparation

Acetyl hypofluorite also will fluoro-demetallate benzene derivatives, for example mercury derivatives of phenol gave 4-fluorophenol.

Synthesis Reference(s)

Tetrahedron, 52, p. 23, 1996 DOI: 10.1016/0040-4020(95)00867-8

Hazard

Irritant.

InChI:InChI=1/C6H5FO/c7-5-1-3-6(8)4-2-5/h1-4,8H

Upstream product

• 693-03-8 n-butyl magnesium bromide 
• 75-44-5 phosgene 
• 60-29-7 diethyl ether 
• 1514-26-7 1-(4-fluorophenoxy)-3-methylbenzene 
• 459-60-9 1-fluoro-4-methoxybenzene 
• 540-36-3 para-difluorobenzene 
• 459-26-7 4-ethoxy-1-fluorobenzene 
• 123-30-8 4-amino-phenol 
• 371-40-4 4-fluoroaniline 
• 623-05-2 (4-hydroxyphenyl)methanol 
• 352-33-0 1-Chloro-4-fluorobenzene 
• 93453-79-3 1-(4-hydroxyphenyl)ethanol 
• 65109-75-3 N-(phenoxy)-4-methylbenzenesulfonamide 
• 623-07-4 4-hydroxyphenyl mercury(II) chloride 

Downstream Products

• 1579-78-8 3-(4-fluoro-phenoxy)propionic acid 
• 78550-50-2 5,5'-difluoro-2,2'-dihydroxy-diphenyl-methane 
• 659-36-9 (2-fluoro-ethyl)-(4-fluoro-phenyl)-ether 
• 347-54-6 5-fluoro-2-hydroxybenzaldehyde 
• 405-32-3 1,3-bis-(4-fluoro-phenoxy)-propan-2-ol 
• 370-15-0 fluoro-acetic acid-(4-fluoro-phenyl ester) 
• 378-65-4 2exo-(4-fluoro-phenoxy)-bornane 
• 405-51-6 4-fluorophenyl acetate 
• 344-20-7 2,6-dibromo-4-fluorophenol 
• 488-48-2 tetrabromobenzoquinone 
• 459-26-7 4-ethoxy-1-fluorobenzene 
• 392-72-3 4-fluoro-2,6-diiodophenol 
• 394-33-2 2-nitro-4-fluorophenol 
• 347-82-0 4-nitro-benzoic acid-(4-fluoro-phenyl ester) 

Relevant academic research and scientific papers

Unexpected phenol production from arylboronic acids under palladium-free conditions; Organocatalyzed air oxidation

An intriguing class of quinones that efficiently catalyze the air oxidation (overall hydroxylation) of arylboronic acids to the corresponding phenol is reported. Autocatalysis in the parent system is particularly efficient and leads to rapid, quantitative synthesis of quinones such as 4 from boronic acid 1 at room temperature using air as stoichiometric oxidant. The efficiency results from a balance between two-stage conjugate addition and migration with each step driven by aromatization of a naphthalene fragment.

Decarboxylative Hydroxylation of Benzoic Acids

Herein, we report the first decarboxylative hydroxylation to synthesize phenols from benzoic acids at 35 °C via photoinduced ligand-to-metal charge transfer (LMCT)-enabled radical decarboxylative carbometalation. The aromatic decarboxylative hydroxylation is synthetically promising due to its mild conditions, broad substrate scope, and late-stage applications.

Method for hydrolyzing diarylether compound to generate aryl phenol compound

The invention discloses a method for hydrolyzing a diarylether compound to generate an arylphenol compound. According to the method, visible light is utilized to excite a photosensitizer for catalysis. In a reaction solvent, the raw material in the formula (1) breaks a C (sp2)-O bond under the auxiliary action of acid, and hydrolysis is performed to obtain the bimolecular aryl phenol compounds in the formula (3) and the formula (4). The method can catalyze the reaction at room temperature, is green and environment-friendly, and is easy to operate; the universality is wide, the reaction yield is relatively high, and the tolerance of functional groups is strong; the synthesis method not only can realize small-scale hydrolysis conversion of various diarylether compounds, but also can realize hydrolysis of herbicidal ether, triclosan and a lignin template substrate, and even can realize large-scale hydrolysis of triclosan and the lignin template substrate to realize gram-level degradation. A new strategy is provided for recovering phenol derivatives through lignin hydrolysis, degrading pesticides and purifying wastewater containing a degerming agent or herbicide. The method has wide application prospect and use value.

Electrochemical-induced hydroxylation of aryl halides in the presence of Et3N in water

A thorough study of mild and environmentally friendly electrochemical-induced hydroxylation of aryl halides without a catalyst is presented. The best protocol consists of hydroxylation of different aryl iodides and aryl bromides by water solution in the presence of Et3N under air, affording the target phenols in good isolated yields. Moreover, aryl chlorides were successfully employed as substrates. This methodology also provides a direct pathway for the formation of deoxyphomalone, which displayed a significant anti-proliferation effect.

Selective hydroxylation of aryl iodides to produce phenols under mild conditions using a supported copper catalyst

Owing to the high activity and low-cost, copper-based catalysts are promising candidates for transforming aromatic halides to yield phenols. In this work, we report the selective hydroxylation of aromatic iodides to produce phenols using an atomically dispersed copper catalyst (Cu-ZnO-ZrO2) under mild reaction conditions. The reactions were conducted without the use of additional organic ligands, and the protection of an inert atmosphere environment is not required. The catalyst can be easily prepared, scalable, and is very efficient for a wide range of substrates. The catalytic reactions can be carried out with only 1.24 mol% Cu loading, which shows great potential in mass production.

A copper nitride catalyst for the efficient hydroxylation of aryl halides under ligand-free conditions

Copper nitride (Cu3N) was used as a heterogeneous catalyst for the hydroxylation of aryl halides under ligand-free conditions. The cubic Cu3N nanoparticles showed high catalytic activity, comparable to those of conventional Cu catalysts with nitrogen ligands, demonstrating that the nitrogen atoms in Cu3N act as functional ligands that promote hydroxylation.

Photocatalytic synthesis of phenols mediated by visible light using KI as catalyst

A transition-metal-free hydroxylation of iodoarenes to afford substituted phenols is described. The reaction is promoted by KI under white LED light irradiation and uses atmospheric oxygen as oxidant. By the use of triethylamine as base and solvent, the corresponding phenols are obtained in moderate to good yields. Mechanistic studies suggest that KI and catalysis synergistically promote the cleavage of C-I bond to form free aryl radicals.

Highly recyclable Ti0.97Ni0.03O1.97catalyst coated on cordierite monolith for efficient transformation of arylboronic acids to phenols and reduction of 4-nitrophenol

A stable Ni2+substituted TiO2catalyst (Ti0.97Ni0.03O1.97) has been synthesized by a solution combustion method with an average crystallite size of 7.5 nm. Ti1?xNixO2?x(x= 0.01-0.06) crystallizes in the TiO2anatase structure with Ni2+substituted in Ti4+ion sites and Ni taking a nearly square planar geometry. This catalyst is found to be highly active in the transformation of diverse arylboronic acids to the corresponding phenols. The catalyst coated cordierite monolith can even be recycled for up to 20 cycles with a cumulative TOF of 1.8 × 105h?1. In scale-up reactions, various phenols are synthesized by employing a single cordierite monolith. It also shows high performance in the reduction of 4-nitrophenol.

Catalyst-free rapid conversion of arylboronic acids to phenols under green condition

A catalyst-free and solvent-free method for the oxidative hydroxylation of aryl boronic acids to corresponding phenols with hydrogen peroxide as the oxidizing agent was developed. The reactions could be performed under green condition at room temperature within very short reaction time. 99% yield of phenol could be achieved in only 1 min. A series of different arenes substituted aryl boronic acids were further carried out in the hydroxylation reaction with excellent yield. It was worth nothing that the reaction could completed within 1 min in all cases in the presence of ethanol as co-solvent.

Highly efficient heterogeneous V2O5@TiO2 catalyzed the rapid transformation of boronic acids to phenols

A V2O5@TiO2 catalyzed green and efficient protocol for the hydroxylation of boronic acid into phenol has been developed utilizing environmentally benign oxidant hydrogen peroxide. A wide range of electron-donating and the electron-withdrawing group-containing (hetero)aryl boronic acids were transformed into their corresponding phenol. The methodology was also applied successfully to transform various natural and bioactive molecules like tocopherol, amino acids, cinchonidine, vasicinone, menthol, and pharmaceuticals such as ciprofloxacin, ibuprofen, and paracetamol. The other feature of the methodology includes gram-scale synthetic applicability, recyclability, and short reaction time.