6377-63-5

Usage

Type of Compound

Organic chemical compound

Aromaticity

Aromatic

Functional Groups

Chlorine atom, p-tolyl group, benzene ring

Usage

Building block in the synthesis of various organic compounds and pharmaceuticals

Applications

Intermediate in the production of insecticides, dyes, and other industrial chemicals

Reactivity

Potential use as a reagent in organic chemistry reactions

Research and Development

Valuable for research and development in the field of organic synthesis

InChI:InChI=1/C13H11ClO/c1-10-2-6-12(7-3-10)15-13-8-4-11(14)5-9-13/h2-9H,1H3

Upstream product

• 106-38-7 para-bromotoluene 
• 1121-74-0 potassium 4-chlorophenoxide 
• 624-31-7 4-tolyl iodide 
• 106-48-9 4-chloro-phenol 
• 106-44-5 p-cresol 
• 637-87-6 1-Chloro-4-iodobenzene 
• 108-90-7 chlorobenzene 
• 73178-07-1 -p-chlorobenzene 
• 73177-96-5 <(hydroxy)(tosyloxy)iodo>-p-toluene 
• 59696-06-9 bis(4-chlorophenyl)iodonium tosylate 
• 1428064-54-3 4-chlorophenyl(2,4-dimethoxyphenyl)iodonium tosylate 
• 1428064-59-8 2,4-dimethoxyphenyl(4-methylphenyl)iodonium tosylate 
• 100-00-5 4-chlorobenzonitrile 
• 41295-20-9 4-(4-methylphenoxy)aniline 

Downstream Products

• 106-48-9 4-chloro-phenol 
• 21120-67-2 4-(4'-chlorophenoxy)-benzoic acid 
• 74448-92-3 4-(4'-chlorophenoxy)benzonitrile 
• 134312-17-7 2-<(p-chlorophenyl)oxy>-5-methylbenzophenone 
• 21153-22-0 2-chloro-8-methyl-10-phenyl-10H-phenoxaphosphine 10-oxide 
• 21153-29-7 (2-chloro-8-methyl-10-oxo-10H-10λ⁵-phenoxaphosphin-10-yl)-phenyl-amine 
• 21153-21-9 8-chloro-10-oxo-10-phenyl-10H-10λ⁵-phenoxaphosphine-2-carboxylic acid 
• 21071-78-3 8-chloro-10-oxo-10-phenyl-10H-10λ⁵-phenoxaphosphine-2-carboxylic acid (R)-1-phenyl-ethylamide 
• 21140-03-4 3-(2-chloro-8-methyl-10-oxo-10H-10λ⁵-phenoxaphosphin-10-yl)-propionic acid; (S)-1-phenyl-ethylamine salt 
• 21072-10-6 8-chloro-10-oxo-10-phenyl-10H-10λ⁵-phenoxaphosphine-2-carboxylic acid; (R)-1-phenyl-ethylamine salt 
• 134312-33-7 1-acetoxy-<2-<(p-chlorophenyl)oxy>-5-methylphenyl>-1,2-diphenylethene 
• 134312-30-4 2-<2-<(p-chlorophenyl)oxy>-5-methylphenyl>-1-methoxy-1,2-diphenylethene 
• 134312-19-9 1-<2-<(p-chlorophenyl)oxy>-5-methylphenyl>-1,2-diphenylethanol 
• 134333-40-7 1-bromo-2-<2-<(p-chlorophenyl)oxy>-5-methylphenyl>-1,2-diphenylethene 

Relevant academic research and scientific papers

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.].

Cu(I)-PNF, an organic-based nanocatalyst, catalyzed C-O and C-S cross-coupling reactions

Peptide nanofiber has been prepared via a self-assembly protocol and decorated with Cu(I) to prepare a nanostructural catalyst. The catalytic activity of this prepared nanomaterial (Cu(I)-PNF) was examined in C-O and C-S cross-coupling reactions. Compared with conventional copper-ligand catalytic systems, CuNP-PNF has unique advantages such as water solubility, high efficiency, and low cost, which makes it a highly efficient and beneficial catalyst to reuse in cross-coupling reactions.

Preparation method of diaryl ether compound

The invention relates to a preparation method of a diaryl ether compound. Particularly, under catalysis of chitosan supported cuprous oxide, an arylation reaction used for phenols is achieved, the corresponding diaryl ether compound is obtained, the technological condition is simple, the yield is good, operability is high, and wide functional group durability is achieved.

Palladium-on-Carbon-Catalyzed Coupling of Nitroarenes with Phenol: Biaryl Ether Synthesis and Evidence of an Oxidative-Addition-Promoted Mechanism

Nucleophilic substitution in nitroarenes to form biaryl ethers is of fundamental importance in organic synthesis. Under non-catalytic conditions, this can occur if highly activated nitroarenes are used or if the nucleophile is activated by a strong stoichiometric base. We established a new method involving the use of a ligand-free palladium-on-carbon (Pd/C) catalyst for the cross-coupling of activated nitroarenes with relatively non-nucleophilic phenol derivatives, including naphthol, in the absence of harsh bases. Control experiments, hot filtration, the three-phase test, and inductively coupled plasma atomic emission spectroscopy analysis revealed that the catalysis proceeded through an usual oxidative addition step of the nitroarene to Pd/C, which resulted in the release of active palladium particles having extremely high catalytic activity. DFT calculations revealed the origin of the selectivity of the activated nitroarenes.

Copper-catalyzed Ullmann-type synthesis of diaryl ethers assisted by salicylaldimine ligands

A series of salicylaldimine ligands were designed to promote the copper-catalyzed Ullmann cross-coupling reaction. After a screening process, 2-((2-isopropylphenylimino)methyl)phenol was found to serve as a good supporting ligand for this reaction. Employing this Schiff-base ligand as a new supporting ligand, the copper-catalyzed coupling reactions of aryl bromides and aryl iodides with various phenols successfully proceeded in good yields under mild conditions. Various diaryl ethers were obtained with excellent yields in dioxane in the presence of K3PO4 and a catalytic amount of copper(I) salt.

Facile preparation of unsymmetrical diaryl ethers from unsymmetrical diaryliodonium tosylates and phenols with high regioselectivity

Unsymmetrical diaryl ethers were efficiently obtained in good yields by the reactions of aryl(4-methoxyphenyl)iodonium tosylates with phenols, and aryl(2,4-dimethoxyphenyl)iodonium tosylates with phenols, in the presence of potassium carbonate in acetonitrile, respectively. The latter iodonium tosylates provided the corresponding unsymmetrical diaryl ethers in good yields with high regioselectivities, together with the quantitative formation of 1-iodo-2,4-dimethoxybenzene. Georg Thieme Verlag Stuttgart New York.

Methenamine as an efficient ligand for copper-catalyzed coupling of phenols with aryl halides

Employing methenamine as a new supporting ligand, the copper-catalyzed coupling reactions of aryl bromides or aryl iodides with various phenols successfully proceeded in good yields under mild conditions. A series of diaryl ethers were obtained with excellent yields in the presence of K 3PO4 and copper(I) salt. Copyright

Cross-coupling reactions of aryl halides with amines, phenols, and thiols catalyzed by an N,N′-dioxide-copper(I) catalytic system

The coupling reactions of various N, O, and S nucleophilic reagents with aryl halides have been successfully carried out under mild conditions by using a novel chiral N,N′-dioxide-copper(I) catalytic system as the catalyst. This versatile and efficient catalyst system has been demonstrated to facilitate the cross-coupling reactions of aryl halides with amines, phenols, and thiols to afford the corresponding desired products in good to excellent yields.

A recyclable heterogeneous copper(II) Schiff base catalyst for the O-arylation reaction of phenols with aryl halides

Immobilisation of copper acetate onto a modified polystyrene provided a polymer-supported copper(II) Schiff base catalyst, which is effective in the O-arylation reaction of phenols with aryl halides to give diaryl ethers in high yields. This catalyst is air-stable and was recycled for five times with minimal loss of activity.