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 
• 617-86-7 triethylsilane 
• 130534-83-7 1,2:5,6-di-O-isopropylidene-3-O-(4-fluorophenoxy)thionocarbonyl-α-D-glucofuranose 
• 462-06-6 fluorobenzene 
• 20460-01-9 4-Fluoro-benzenediazonium 
• 623-05-2 (4-hydroxyphenyl)methanol 

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.

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.

Isotruxene-based porous polymers as efficient and recyclable photocatalysts for visible-light induced metal-free oxidative organic transformations

Two new isotruxene-based porous polymers were prepared and demonstrated to be highly efficient, metal-free heterogeneous photocatalysts for oxidative transformations using air as the mild oxidant under visible-light irradiation. Both catalysts show excellent recyclability. In addition, the reactions can be performed in water, further indicating the greenness of this method. This journal is

Cu2O/TiO2 as a sustainable and recyclable photocatalyst for gram-scale synthesis of phenols in water

A green and straightforward protocol was developed for the synthesis of phenols from aryl boronic acid using an inexpensive and available Cu2O/TiO2 photocatalyst under visible light and sunlight. This approach proceeded in mild reaction conditions in water and the presence of air as a green oxidant, resulting in the corresponding phenols in good to excellent yields. Sunlight was also a sustainable source for this photochemical reaction. Heterogeneous nano photocatalyst was successfully recovered in 8 consecutive runs. It is noteworthy that, the photocatalyst exhibited high activity for the large-scale synthesis of phenols.

Application of Electron-Rich Covalent Organic Frameworks COF-JLU25 for Photocatalytic Aerobic Oxidative Hydroxylation of Arylboronic Acids to Phenols

Visible-light-driven organic reactions are environmentally friendly green chemical transformations among which photosynthetic oxidative hydroxylation of arylboronic acids to phenols has attracted increasing research interest during the very recent years. Given the efficiency and reusability of heterogeneous catalysts, COF-JLU25, an electron-rich COF-based photocatalyst constructed by integrating electron-donating blocks 1,3,6,8-tetrakis(4-aminophenyl)pyrene (PyTA) and 4-[4-(4-formylmethyl)-2,5-dimethoxyphenyl] benzaldehyde (TpDA), was selected as a photocatalyst for the oxidative hydroxylation of arylboronic acids. In our studies, COF-JLU25 demonstrated excellent photocatalytic activity with high efficiency, robust reusability, and low catalyst loading, showcasing an application potential of previously underexplored COF-based photocatalyst composed solely of electron-rich units.

An efficient Ti0.95Cu0.05O1.95 catalyst for ipso – hydroxylation of arylboronic acid and reduction of 4-nitrophenol

A stable, active and selective Ti0.95Cu0.05O1.95 catalyst, crystallized in anatase TiO2 structure with 5% Cu2+ ions substituted for Ti4+ ions with 5% oxide ion vacancy has been synthesized by solution combustion method. The catalyst was coated over a cordierite monolith (Mg2Al4Si5O18) by solution combustion method. By the first principle density functional theory (DFT) calculations, 48 atoms bulk structure has been optimized and density of states (DOS) has been calculated. Ti – O bond distribution in Ti0.95Cu0.05O1.95 has been compared with pure TiO2. Bond distribution analysis has shown longer Cu – O and Ti – O bonds compared to those in CuO and TiO2 creating Cu2+ and oxide ion vacancy as electrophilic and nucleophilic active sites, respectively. This catalyst was found to be very active for ipso – hydroxylation of arylboronic acid and 4-nitrophenol reduction reactions at room temperature. Catalyst coated cordierite monolith was used in the recycling process of the reaction for 20 cycles and cumulative turnover frequency was found to be 184,840 h?1. Ti0.95Cu0.05O1.95 catalyst coated on cordierite monolith enhanced the rate of the reaction compared to powder catalyst and made the handling and recycling of the catalyst very easy. Graphic abstract: [Figure not available: see fulltext.]

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.

Alkylsulfenyl thiocarbonates: precursors to hydropersulfides potently attenuate oxidative stress

The recent discovery of the prevalence of hydropersulfides (RSSH) species in biological systems suggests their potential roles in cell regulatory processes. However, the reactive and transient nature of RSSH makes their study difficult, and dependent on the use of donor molecules. Herein, we report alkylsulfenyl thiocarbonates as a new class of RSSH precursors that efficiently release RSSH under physiologically relevant conditions. RSSH release kinetics from these precursors are tunable through electronic modification of the thiocarbonate carbonyl group's electrophilicity. In addition, these precursors also react with thiols to release RSSH with a minor amount of carbonyl sulfide (COS). Importantly, RSSH generation by these precursors protects against oxidative stress in H9c2 cardiac myoblasts. Furthermore, we demonstrate the ability of these precursors to increase intracellular RSSH levels.