367-27-1

Usage

Uses

Used in Pharmaceutical Synthesis:
2,4-Difluorophenol is used as an organic building block for the synthesis of various pharmaceutical compounds, including antivirulence agents. Its unique structure contributes to the development of new drugs targeting specific biological pathways.
Used in Antiviral Applications:
In the field of virology, 2,4-Difluorophenol is utilized in the synthesis of new α-Phenoxyacetamide derivatives, which act against the type III secretion system of Pseudomonas aeruginosa PAO1, a gram-negative bacteria. This application highlights its potential in developing novel treatments for bacterial infections.
Used in Fluorescent Dye Synthesis:
2,4-Difluorophenol serves as a starting reagent in the synthesis of 3-carboxy-6,8-difluoro-7-hydroxycoumarin (Pacific Blue), a fluorinated fluorescent dye. This dye is widely used in various applications, including cell staining, microscopy, and other fluorescence-based assays, due to its distinct spectral properties.
Used in Chemical Research:
As a chemical intermediate, 2,4-Difluorophenol is also used in the synthesis of other complex organic molecules for research purposes. Its reactivity and structural features make it a valuable compound in the development of new materials and chemical entities.

InChI:InChI=1/C6H4F2O/c7-4-1-2-6(9)5(8)3-4/h1-3,9H

Upstream product

• 452-10-8 2,4-difluoro-1-methoxybenzene 
• 367-25-9 2,4-difluorophenylamine 
• 108-95-2 phenol 
• 372-18-9 1,3-Difluorobenzene 
• 399-44-0 2-(2,4-difluorophenoxy)acetic acid 
• 10034-85-2 hydrogen iodide 
• 144025-03-6 2,4-difluorophenylboronic acid 
• 364-83-0 2',4'-difluoroacetophenone 
• 1550-35-2 2,4-difluorobenzaldehyde 
• 446-35-5 2,4-Difluoronitrobenzene 
• 132303-32-3 1-(tert-butyldimethylsilyloxy)-2,4-difluorobenzene 
• 540-36-3 para-difluorobenzene 
• 348-57-2 2,4-difluorobromobenzene 

Downstream Products

• 2267-99-4 2-chloro-4,6-difluoro-phenol 
• 98130-56-4 2-bromo-4,6-difluorophenol 
• 709-32-0 dichlorophosphoric acid-(2,4-difluoro-phenyl ester) 
• 399-44-0 2-(2,4-difluorophenoxy)acetic acid 
• 32861-99-7 C₁₃H₉F₂NO₄ 
• 32862-00-3 C₁₄H₁₁F₂NO₄ 
• 116687-14-0 1-[4-(2,4-Difluoro-phenoxy)-3-nitro-phenyl]-ethanone 
• 116686-91-0 3-(2,4-difluorophenoxy)-4-nitrobenzonitrile 
• 146139-80-2 3-(2,4-difluorophenoxy)-4-nitroacetanilide 
• 81614-72-4 5-(2,4-difluorophenoxy)-6-nitroindan 
• 146139-69-7 C₁₃H₆F₅NO₃ 
• 116686-85-2 3'-(2,4-difluorophenoxy)-4'-nitroacetophenone 
• 116686-89-6 1-[3-(2,4-Difluoro-phenoxy)-4-nitro-phenyl]-propan-1-one 
• 152434-86-1 1-(benzyloxy)-2,4-difluorobenzene 

Relevant academic research and scientific papers

Trinuclear Mn2+/Zn2+based microporous coordination polymers as efficient catalysts foripso-hydroxylation of boronic acids

Two microporous coordination polymers based on hourglass trinuclear building units, [Mn3(bpdc)3(bpy)]·2DMF and [Zn3(bpdc)3(bpy)]·2DMF·4H2O (bpdc = 4,4′-biphenyl dicarboxylic acid, bpy = 4,4′-bipyridine), have been synthesized under solvothermal conditions employing DMF as the solvent. Each structure consists of two crystallographically distinct M2+(M1 and M2) centers that are connectedviacarboxylate bridges from six bpdc ligands, generating a trinuclear metal cluster, [M3(bpdc)3(bpy)]. Cluster representation of the structure resulted in an interpenetrated net of rarehextopological type. Catalytic activities of the CPs have been assessed for the oxidative hydroxylation of phenylboronic acids (PBAs) using aqueous hydrogen peroxide (H2O2). Various substituted aryl/hetero-arylboronic acids RB(OH)2[R = phenyl, 2,4-difluorophenyl, 4-aminophenyl, 2-thiopheneetc.] underwentipso-hydroxylation smoothly at room temperature to generate the corresponding phenols in excellent yields. The main advantages of this protocol are the aqueous medium reaction, heterogeneous catalytic system, and short reaction time with excellent yield.

Tetrahydroquinoline N-oxidation derivative as well as preparation method and application thereof

The invention relates to tetrahydroquinoline N-oxidation derivative as well as a preparation method and application thereof. The invention relates to a compound shown in a general formula (I) in the specification, a preparation method of the compound, a pharmaceutical composition containing the compound, and application of the compound as a BRD4 inhibitor in treating cancer, inflammation, chronicliver diseases, diabetes mellitus, cardiovascular diseases, AIDS and other related diseases.

Size-tunable ZnO nanotapes as an efficient catalyst for oxidative chemoselective C–B bond cleavage of arylboronic acids

Herein, we report a simple but effective chemical approach for the synthesis of size-tunable ZnO nanotapes by precipitation method in the presence of phytochemicals present in the flower extract of Lantana camara plant. The electron microscopic study confirmed that the size of ZnO nanotapes can be systematically controlled by varying the concentration of either flower extract or metal ions and the flower extract played the key role in controlling the growth of ZnO nanotapes. The phase and crystalline analysis was carried out by X-ray diffraction method which indicated that ZnO nanostructures are highly crystalline in nature and are free from any impurities. The synthesized ZnO nanostructures exhibited interesting optical properties as investigated by UV–vis absorption and photoluminescence spectroscopy. Further the surface functionalities affect the optical properties of ZnO nanostructures which possess relatively strong UV emissions; a blue emission and a green emission. The synthesized ZnO nanostructures showed excellent catalytic properties in the ipso-hydroxylation of different aryl/ hetero-arylboronic acid to phenol in a relatively greener reaction conditions. These catalysts are highly stable and are re-usable upto six cycles of ipso-hydroxylation without losing its catalytic properties.

Promotional effect of ionic liquids in the electrophilic fluorination of phenols

The influence of a stoichiometric amount of ionic liquids (IL) on the fluorination of phenols in various solvents has been studied. The fluorination of phenol, 1-naphthol and resorcinol was carried out using 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (F-TEDA-BF4, Selectfluor) with the formation of 2-fluoro-, 4-fluorophenol, 2-fluoro-, 4-fluoronaphthol and 4-fluoro-, 4,6-difluoro-benzene-1,3-diol as the main products. The use of a stoichiometric amount of ionic liquid as an additive results in acceleration of the reactions. The effect is most significant at low temperatures. It has been found that solvent polarity has an essential effect on the difference in yields of fluoroproducts obtained in the presence of IL and without it.

Process for preparing phenol fluoride by amine catalytic method

The invention relates to a process for preparing phenol fluoride by amine catalytic method and belongs to the technical field of chemical synthesis.The process comprises: adding phenol and a catalyst sequentially into a reactor for heating, introducing fluorine-nitrogen mixed gas into the reactor for reacting, purging with nitrogen after reacting to obtain crude phenol fluoride, charging purging gas and reaction tail gas sequentially into an activated carbon absorber and a solid sodium lime absorber for adsorption, discharging finally obtained non-condensable gas at a great height, rectifying and separating the crude phenol fluoride to obtain o-fluorophenol, p-fluorophenol, 2,4-difluorophenol and 2,6-difluorophenol.The problem that an existing preparation process has low product yield, high solvent consumption, high cost and environmental pollution is solved herein, the process has the advantages of material conversion completeness, little byproduct and low production cost, no additional solvent is added to maintain a certain temperature range, cost is saved, and solvent loss is reduced.

Biosilica as an efficient heterogeneous catalyst for ipso-hydroxylation of arylboronic acids

A mild and efficient protocol for the conversion of arylboronic acids to phenol via ipso-hydroxylation has been developed using aqueous hydrogen peroxide as oxidant and biosilica as heterogeneous catalyst. The recyclability of the catalyst is also evaluated and could be reused up to six consecutive cycles without a significant loss in catalytic activity.

Catalytic defluorination of perfluorinated aromatics under oxidative conditions using N-bridged diiron phthalocyanine

Carbon-fluorine bonds are the strongest single bonds in organic chemistry, making activation and cleavage usually associated with organometallic and reductive approaches particularly difficult. We describe here an efficient defluorination of poly- and perfluorinated aromatics under oxidative conditions catalyzed by the μ-nitrido diiron phthalocyanine complex [(Pc)Fe III(μ-N)FeIV(Pc)] under mild conditions (hydrogen peroxide as the oxidant, near-ambient temperatures). The reaction proceeds via the formation of a high-valent diiron phthalocyanine radical cation complex with fluoride axial ligands, [(Pc)(F)FeIV(μ-N)FeIV(F) (Pc+?)], which was isolated and characterized by UV-vis, EPR, 19F NMR, Fe K-edge EXAFS, XANES, and Kβ X-ray emission spectroscopy, ESI-MS, and electrochemical techniques. A wide range of per- and polyfluorinated aromatics (21 examples), including C6F6, C6F5CF3, C6F5CN, and C6F5NO2, were defluorinated with high conversions and high turnover numbers. [(Pc)FeIII(μ-N)Fe IV(Pc)] immobilized on a carbon support showed increased catalytic activity in heterogeneous defluorination in water, providing up to 4825 C-F cleavages per catalyst molecule. The μ-nitrido diiron structure is essential for the oxidative defluorination. Intramolecular competitive reactions using C6F3Cl3 and C6F3H 3 probes indicated preferential transformation of C-F bonds with respect to C-Cl and C-H bonds. On the basis of the available data, mechanistic issues of this unusual reactivity are discussed and a tentative mechanism of defluorination under oxidative conditions is proposed.

Oxidation of organotrifluoroborates via oxone

A method for the oxidation of organotrifluoroborates using Oxone was developed. A variety of aryl-, heteroaryl-, alkenyl-, and alkyltrifluoroborates were converted into the corresponding oxidized products in excellent yields. This method proved to be tolerant of a broad range of functional groups, and in secondary alkyl substrates it was demonstrated to be completely stereospecific.

Fluorination of aromatic compounds with N-fluorobenzenesulfonimide under solvent-free conditions

Reactions of N-fluorobenzenesulfonimide with methylbenzenes, phenols, and phenol ethers were studied under solvent-free conditions. The rate constant ratio for the reactions with mesitylene and durene indicates polar mechanism of the process. Solvent-free fluorination of aromatic compounds with N-fluorobenzenesulfonimide in some cases is more selective than reactions with other N-F reagents in a solvent.

ALPHA ARYL OR HETEROARYL METHYL BETA PIPERIDINO PROPANAMIDE COMPOUNDS AS ORL1-RECEPTOR ANTAGONIST

This invention provides the compounds of formula (I): or a pharmaceutically acceptable ester of such compound, or a pharmaceutically acceptable salt thereof, wherein Ri and R2 independently represent a hydrogen atom or the like; R3 represents a hydrogen atom, or the like; R4 represents a hydrogen atom or the like; (formula II) represents one of the following or the like; R5 represents an aryl group having from 6 to 10 ring atoms or the like; X represents an oxygen atom, or the like; Y represents an oxgen atom or the like and n represents an integer 0, 1 or 2. These compounds have ORL1-receptor antagonist activity; and therefore, are useful to treat diseases or conditions such as pain, various CNS diseases etc.