74448-92-3

Usage

Uses

Used in Pharmaceutical Industry:
4-(4-CHLOROPHENOXY)BENZONITRILE is used as a key intermediate for the synthesis of various pharmaceutical compounds, contributing to the development of new drugs and medications.
Used in Agrochemical Industry:
4-(4-CHLOROPHENOXY)BENZONITRILE is used as an active ingredient in weed control products, providing effective herbicidal properties for agricultural applications.
Used in Dye Industry:
4-(4-CHLOROPHENOXY)BENZONITRILE is used as a chemical intermediate in the production of various dyes, contributing to the creation of a wide range of colorants for different industries.
Used in Chemical Compound Synthesis:
4-(4-CHLOROPHENOXY)BENZONITRILE is used as a crucial component in the synthesis of other chemical compounds, playing a significant role in the development of new chemical products and materials.

InChI:InChI=1/C13H8ClNO/c14-11-3-7-13(8-4-11)16-12-5-1-10(9-15)2-6-12/h1-8H

Upstream product

• 101-79-1 4-amino-4'-chlorodiphenyl ether 
• 6377-63-5 4-chlorophenyl 4-methylphenyl ether 
• 1194-02-1 4-fluorobenzonitrile 
• 106-48-9 4-chloro-phenol 
• 623-00-7 4-bromobenzenecarbonitrile 
• 352-33-0 1-Chloro-4-fluorobenzene 
• 767-00-0 4-cyanophenol 
• 623-03-0 4-Cyanochlorobenzene 
• 619-72-7 4-nitrobenzonitrile 
• 459-57-4 4-fluorobenzaldehyde 
• 106-39-8 bromochlorobenzene 
• 1121-74-0 potassium 4-chlorophenoxide 
• 403-54-3 m-Fluorobenzonitrile 
• 3058-39-7 4-iodobenzonitrile 

Downstream Products

• 1443126-24-6 5-(4-(4-chlorophenoxy)phenyl)-1H-tetrazole 
• 2005-08-5 4-chlorophenyl benzoate 
• 104128-50-9 (4-cyanophenyl)(4-methylphenyl)sulfide 
• 83491-06-9 4-chlorophenyl dodecanoate 
• 774525-83-6 (4-(4-chlorophenoxy)phenyl)methanamine 
• 1613190-09-2 (Z)-2-(4-(4-chlorophenoxy)benzylidene)-6-hydroxybenzofuran-3(2H)-one 
• 1613189-92-6 (Z)-2-(4-(4-chlorophenoxy)benzylidene)benzofuran-3(2H)-one 

Relevant academic research and scientific papers

Solvent-free palladium-catalyzed C–O cross-coupling of aryl bromides with phenols

A new solvent-free procedure for C–O cross-coupling between phenols and aryl bromides comprising of Pd2(dba)3/ButBrettPhos catalytic system is efficient for substrates bearing donor or acceptor, as well as bulky substituents.

Oxalohydrazide Ligands for Copper-Catalyzed C?O Coupling Reactions with High Turnover Numbers

Here, we report a class of ligands based on oxalohydrazide cores and N-amino pyrrole and N-amino indole units that generates long-lived copper catalysts for couplings that form the C?O bonds in biaryl ethers. These Cu-catalyzed coupling of phenols with aryl bromides occurred with turnovers up to 8000, a value which is nearly two orders of magnitude higher than those of prior couplings to form biaryl ethers and nearly an order of magnitude higher than those of any prior copper-catalyzed coupling of aryl bromides and chlorides. This ligand also led to copper systems that catalyze the coupling of aryl chlorides with phenols and the coupling of aryl bromides and iodides with primary benzylic and aliphatic alcohols. A wide variety of functional groups including nitriles, halides, ethers, ketones, amines, esters, amides, vinylarenes, alcohols and boronic acid esters were tolerated, and reactions occurred with aryl bromides in pharmaceutically related structures.

CoII Immobilized on Aminated Magnetic-Based Metal–Organic Framework: An Efficient Heterogeneous Nanostructured Catalyst for the C–O Cross-Coupling Reaction in Solvent-Free Conditions

Abstract: In this paper, we report the synthesis of Fe3O4?AMCA-MIL53(Al)-NH2-CoII NPs based on the metal–organic framework structures as a magnetically separable and environmentally friendly heterogeneous nanocatalyst. The prepared nanostructured catalyst efficiently promotes the C–O cross-coupling reaction in solvent-free conditions without the need for using toxic solvents and/or expensive palladium catalyst. Graphic Abstract: [Figure not available: see fulltext.].

Optimization of N-benzyl-5-nitrofuran-2-carboxamide as an antitubercular agent

The optimization campaign for a nitrofuran antitubercular hit (N-benzyl-5-nitrofuran-2-carboxamide; JSF-3449) led to the design, synthesis, and biological profiling of a family of analogs. These compounds exhibited potent in vitro antitubercular activity (MIC = 0.019–0.20 μM) against the Mycobacterium tuberculosis H37Rv strain and low in vitro cytotoxicity (CC50 = 40–>120 μM) towards Vero cells. Significant improvements in mouse liver microsomal stability and mouse pharmacokinetic profile were realized by introduction of an α α-dimethylbenzyl moiety. Among these compounds, JSF-4088 is highlighted due to its in vitro antitubercular potency (MIC = 0.019 μM) and Vero cell cytotoxicity (CC50 > 120 μM). The findings suggest a rationale for the continued evolution of this promising series of antitubercular small molecules.

Design, synthesis, insecticidal, and acaricidal activities of novel pyrimidinamine derivatives containing a biphenyl ether

A series of original pyrimidinamine derivatives containing a biphenyl ether moiety were designed and synthesized. Their structures were confirmed by 1H NMR, MS, and elemental analyses. Their insecticidal activities against lepidopteran and hemiptera insects and acaricidal activities were tested. The results of bioassay demonstrated that 9k showed the best activity (LC50 = 2.08 mg/L) against Tetranychus urticae, which is comparable with the positive control, spirotetramat (LC50 = 2.27 mg/L), and 9g showed better activity (LC50 = 0.52 mg/L) against Aphis fabae than the positive control, imidacloprid (LC50 = 1.02 mg/L), and relatively good activity (LC50 = 2.49 mg/L) against T urticae. Their structure-activity relationships indicated that both an ethyl group on the 4-position of the pyrimidine ring and alkyl chain as a para-substituent group of the benzene ring showed good biological activity.

A diaryl ether compounds of the novel preparation method and application thereof

The invention relates to a diaryl ether compounds of the novel preparation method, in particular compound is added to the reactor in sequence 1, dimethyl sulfoxide, cesium carbonate, compound 2, stirring at room temperature 10 - 60 minutes; then placing the reaction temperature is set to 70 - 120 °C the pot of the oil bath, and incandescent lamp for irradiation, the course of the reaction by TLC detection, to be after the reaction, the reaction solution by filtration, extraction and column chromatography, to obtain the target compound, the completion of the diaryl ether compound preparation. The technical scheme of the present invention visible under light induction, does not add any transition metal catalyst and ligand firmly oxidation reducing agent, aryl halide with phenol derivatives in photocatalytic C - O cross-coupling reaction. Preparation of mild conditions, green, high efficiency, low cost, simple and convenient operation. The preparation of this compound is a biological, medical, in the field of organic synthesis in particular pharmaceutical synthesis of important synthetic intermediate.

Method for preparing diaryl ether compound

The invention relates to a novel preparation method of a diaryl ether compound. The novel preparation method specifically comprises the following steps: sequentially putting a derivative of benzene, dimethyl sulfoxide, cesium carbonate and a phenol derivative into a reactor, and carrying out stirring for 30-60 minutes at room temperature; putting the mixture into an oil bath pot of which the reaction temperature is set as 70-120 DEG C, lighting the mixture with an incandescent light bulb, detecting the reaction process with TLC (thin layer chromatography), after the reaction is completed, carrying out filtering on a reaction liquid, and carrying out extraction and column chromatography, so as to obtain a target compound and complete preparation of the diaryl ether compound. By adopting thetechnical scheme of the invention, under induction of visible light, without addition of any transition metal catalyst, ligand or photoredox agent, an aryl halide and a phenol derivative are subjected to a photocatalytic C-O cross coupling reaction. The preparation method is mild in condition, green, efficient, low in cost and simple and convenient in operation. The prepared compound is a significant synthesis intermediate in fields such as biologics, medicines and organic synthesis, particularly in medicine synthesis.

Novel cobalt-valine catalyzed O-arylation of phenols with electron deficient aryl iodides

Abstract: A Novel cobalt-catalyzed O-arylation of phenols with electron deficient aryl iodides is described. The reaction employs cheap and easy-to-handle cobalt acetate tetrahydrate as the catalyst precursor and naturally occurring l-valine as the ligand without the use of any transmetallating or reducing agents. The new protocol offers a wide scope for a variety of phenols towards O-arylation with moderate to excellent yields with electron deficient aryl iodides.

Probing the Azaaurone Scaffold against the Hepatic and Erythrocytic Stages of Malaria Parasites

The potential of azaaurones as dual-stage antimalarial agents was investigated by assessing the effect of a small library of azaaurones on the inhibition of liver and intraerythrocytic lifecycle stages of the malaria parasite. The whole series was screened against the blood stage of a chloroquine-resistant Plasmodium falciparum strain and the liver stage of P. berghei, yielding compounds with dual-stage activity and sub-micromolar potency against erythrocytic parasites. Studies with genetically modified parasites, using a phenotypic assay based on the P. falciparum Dd2-ScDHODH line, which expresses yeast dihydroorotate dehydrogenase (DHODH), showed that one of the azaaurone derivatives has the potential to inhibit the parasite mitochondrial electron-transport chain. The global urgency in finding new therapies for malaria, especially against the underexplored liver stage, associated with chemical tractability of azaaurones, warrants further development of this chemotype. Overall, these results emphasize the azaaurone chemotype as a promising scaffold for dual-stage antimalarials.

EFFLUX-PUMP INHIBITORS AND THERAPEUTIC USES THEREOF

The present invention relates to compounds of formula I or pharmaceutically acceptable salt, solvate or hydrate thereof, wherein ASC is -N(R8)(R9)ASC-1 ASC-1 is Ring A represents a 4- to 6-membered saturated ring containing carbon atoms as ring members in addition to the nitrogen atom and wherein one CH2 moiety in ring A is optionally replaced by CH(R21) and wherein one carbon atom in ring A that is not adjacent to the nitrogen atom is optionally replaced by O, and wherein ring A is connected to X via a carbon atom; X represents a bond, -CH2- or -C(=O)-; ARl, AR2 represent independently phenyl or a 5- to 6- membered heteroaryl ring containing one to three heteroatoms selected from O, S and N, wherein AR1 is connected to LI via a carbon atom, and wherein AR2 is connected to L1 and L2 via a carbon atom; R1, R2, R3 represent independently hydrogen, halogen, cyano, hydroxyl, C1-C6alkyl, C1-C6haloalkyl, C3- C8cycloalkyl, C1-C6alkoxy, C1-C6haloalkoxy, -C1-C6alkylene-N(R12)R13, -N(R12)R13, -C(O)OR11l, - C(O)N(R12)R13, -S(O)OR11 or phenyl; R4 represents hydroxyl, hydrogen, halogen, nitro, cyano, amino, C1-C6alkyl optionally substituted by 1 to 5 R14, C2-C6alkenyl optionally substituted by 1 to 5 R14, C2-C6alkynyl optionally substituted by 1 to 5 R14, C1-C6alkoxy optionally substituted by 1 to 5 R14, C2-C6alkenyloxy optionally substituted by 1 to 5 R14, C2-C6alkynyloxy optionally substituted by 1 to 5 R14, -C(O)OR15, -CHO, -C(O)N(R16)R17, -C1- C6alkylene-N(R9)(R16)R17, -O-Cycle-P or -O-Cycle-Q; R5, R6, R7 represent independently hydrogen, halogen, cyano, Cl-C6alkyl, C1-C6haloalkyl, Cl-C6alkoxy or C1-C6haloalkoxy; R8 represents hydrogen, methyl or ASC-1; R9 is methyl or absent, and wherein when R9 is present the respective nitrogen atom carries a positive charge; R10 represents hydrogen or methyl; Rl11 represents independently at each occurrence hydrogen or C1-C6alkyl; R12, R13 represent independently at each occurrence hydrogen or C1-C6alkyl; R14 represents independently at each occurrence halogen, cyano, hydroxyl, C1-C6alkoxy, C1-C6haloalkoxy, C3-C8cycloalkyl, -C(O)OR11, -CHO, -C(O)N(R12)R13, -C1-C6alkylene-N(R12)R13, Cycle-P, O-Cycle-P, Cycle-Q or O-Cycle-Q; Cycle-P represents independently at each occurrence a saturated or partially unsaturated C3-C8 carbocyclic ring optionally substituted by 1 to 3 R18, or a saturated or partially unsaturated C3-C8 heterocyclic ring optionally substituted by 1 to 3 Rl 8 containing carbon atoms as ring members and one or two ring members independently selected from N(R9)(R12), N(R9) and O; Cycle-Q represents independently at each occurrence phenyl optionally substituted by 1 to 3 R19 or a 5- to 6-membered heteroaryl ring containing one to four heteroatoms selected from O, S and N, optionally substituted by 1 to 3 R19; R15 represents independently at each occurrence hydrogen or C1-C6alkyl optionally substituted by 1 to 5 R14; R16 and R17 represent independently at each occurrence hydrogen or C1-C6alkyl optionally substituted by 1 to 5 R14; R18 and R19 represent independently at each occurrence halogen, cyano, hydroxyl, oxo, amino, C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, Cl-C4haloalkoxy or -CO(O)R11; R20 represents independently at each occurrence hydrogen or methyl; R21 represents N(R20)2 or CH2-N(R20)2; LI represents -CH=CH-, -CH2-O-, -O-CH2-, -CH2-O-CH2-,-CH2-S-, -S-CH2-, -CH2-S(O)-, -CH2-S(O2)-, -S(O)-CH2-; -S(O2)-CH2-, -C(CH3)(CH3)-, -C(=O)-NH-, -NH-C(=O)-, -CH2-CH2-, -CH=CH-CH2-, - CH2-NH-C(=O)-, -C(=O)-NH-CH2, -C≡C-, -S(O2)-NH-CH2-, -S(02)-NH, -O-CH2-CH2-O-, -O-, -NH- CH2-, -CH2-NH-, -CH2-CH2-O-, or -NH-C(=O)-CH2-O-, or a bond; L2 represents Cl-C7alkylene, wherein one or more CH2 moieties in the alkylene are optionally replaced independently by -N(R9)(R20)-, -CH(N(R9)(R20)(R20))-, or -C(=0)-, wherein within L2 there are no adjacent C(=O) moieties or adjacent -N(R9)(R20)- moieties, and wherein the terminal moiety of L2 is not - N(R9)(R20)-, or L2 represents -O-C1-C6alkylene-, or L2 represents a bond, providing that X represents - CH2- when L2 is a bond; as well as methods of using the compounds of formula I for treating or preventing bacterial infections.