3586-14-9

Usage

Uses

Used in Pesticide Industry:
3-Phenoxytoluene is used as a key intermediate in the synthesis of insecticides such as pyrethroids. It plays a vital role in the production of these insecticides due to its ability to form stable and effective compounds that target and control pests.
Used in Fungicide Synthesis:
In addition to its application in insecticides, 3-Phenoxytoluene is also utilized in the production of fungicides, specifically Difenoconazole (D445370). Its chemical properties allow it to be incorporated into the structure of these fungicides, which are designed to protect crops and plants from fungal infections and diseases.

InChI:InChI=1/C13H12O/c1-11-6-5-9-13(10-11)14-12-7-3-2-4-8-12/h2-10H,1H3

Upstream product

• 108-86-1 bromobenzene 
• 108-39-4 3-methyl-phenol 
• 6415-38-9 benzenediazonium sulphate 
• 108-95-2 phenol 
• 624-31-7 4-tolyl iodide 
• 139-02-6 sodium phenoxide 
• 81447-67-8 m-methyldiphenyliodonium chloride 
• 106-38-7 para-bromotoluene 
• 108-98-5 thiophenol 
• 62-53-3 aniline 
• 591-17-3 meta-bromotoluene 
• 591-50-4 iodobenzene 
• 108-90-7 chlorobenzene 
• 690274-99-8 3-phenoxybenzaldehyde N-tert-butyldimethylsilylhydrazone 

Downstream Products

• 108-39-4 3-methyl-phenol 
• 46412-20-8 3-methylphenoxathiine 
• 591-23-1 m-methylcyclohexanol 
• 3739-38-6 3-phenoxybenzoic acid 
• 58775-88-5 2'-methyl-4'-phenoxyacetophenone 
• 53874-67-2 3-phenoxybenzal bromide 
• 50789-44-1 3-phenoxybenzyl acetate 
• 51632-29-2 3-phenoxyphenylacetonitrile 
• 51632-16-7 3-phenoxybenzyl bromide 
• 52322-81-3 3-phenoxy-6-chlorotoluene 
• 50789-43-0 methyl 3-phenoxybenzoate 
• 13826-35-2 3-Phenoxybenzyl alcohol 
• 39515-51-0 3-Phenoxybenzaldehyde 
• 77317-53-4 1-bromo-2-methyl-4-phenoxybenzene 

Relevant academic research and scientific papers

Synthesis of m-phenoxybenzaldehyde starting from chlorobenzene and m-cresol: Some aspects of process development

m-Phenoxybenzaldehyde (MPB) is an important intermediate for synthetic pyrethroids. In the present paper, an economic process scheme was developed to synthesize MPB starting from cheaper reactants. The process scheme was started with the synthesis of m-phenoxytoluene (MPT). Oxidation of MPT by air gave MPB, but the selectivity was found to be high at low conversions of about 10%, and if the conversion level was increased, then large amounts of the undesired m-phenoxybenzoic acid (MPBA) was formed. To obtain the desired aldehyde, Rosenmund reduction of MPBA was carried out to give high yields of the MPB. The effects of different parameters such as catalyst, substrate concentration, temperature, etc., were studied for all three of the reactions, viz., Ullmann ether synthesis, oxidation, and Rosenmund reduction. MPT was prepared from chlorobenzene, a relatively cheaper starting material, in the presence of polyethylene glycol) as cosolvent and cuprous chloride as the catalyst. A selectivity of 97% was obtained with 86% conversion to the product. Oxidation of MPT was carried out by air in the presence of cobalt acetate as catalyst and sodium bromide as catalyst promoter. The selectivity with respect to the aldehyde and the ester was 37.4 and 30.6%, respectively, at a restricted overall conversion of 24%. The process parameters were controlled to achieve high selectivity towards the aldehyde. The acid, formed as the side product, was reduced to the aldehyde by Rosenmund reduction via the acyl chloride. At a conversion level of 85%, a selectivity of 87% to MPB was obtained using Pd/C.

Supported CuO/γ-Al2O3 as heterogeneous catalyst for synthesis of diaryl ether under ligand-free conditions

CuO/γ-Al2O3 was employed as catalyst in the coupling reaction of iodobenzene with m-cresol to give 3-methyldiphenyl ether under ligand-free conditions. It performed more efficiently than other supported CuO catalysts (CuO/SBA-15, CuO/ZrO2, CuO/CeO2, CuO/La2O3). Reaction conditions were investigated and the yield reached 76% under the optimized terms. As a heterogeneous catalyst, CuO/γ-Al2O3 could be reused for three cycles with moderate to good yields. According to the results of XRD, TPR and XPS, the catalytic activities of supported CuO catalysts were due to the highly dispersed Cu(II) species and independent of the electronic state of these copper species.

L-Proline N-oxide dihydrazides as an efficient ligand for cross-coupling reactions of aryl iodides and bromides with amines and phenols

A novel catalytic system based on L-proline N-oxide/CuI was developed and applied to the cross-coupling reactions of various N- and O- nucleophilic reagents with aryl iodides and bromides. This strategy featured in the employment of an-proline derived dihydrazides N-oxide compound as the superior supporting ligand. By using this protocol, a variety of products, including N-arylimidazoles, N-arylpyrazoles, N-arylpyrroles, N-arylamines, and aryl ethers, were synthesized with up to 99% yield.

Preparation method of m-phenoxy benzaldehyde

The invention provides a preparation method of m-phenoxy benzaldehyde, and belongs to the technical field of synthesis of medical intermediates. The preparation method comprises the following steps: mixing m-cresol, halogenated benzene, inorganic base and a catalyst for condensation reaction to obtain m-phenoxy toluene; mixing the m-phenoxy toluene with an oxidant, and carrying out an oxidation reaction under acidic conditions to obtain m-phenoxy benzaldehyde. According to the preparation method, m-cresol and halogenated benzene are taken as raw materials, the cost of the raw materials is low, m-phenoxy toluene is firstly prepared through a condensation reaction, then m-phenoxy toluene is oxidized into m-phenoxy benzaldehyde, the yield of the product is high, and the preparation is simple. The result of the embodiment shows that the yield of the m-phenoxybenzaldehyde prepared by the method is 56.8% or above.

Preparation method of m-phenoxy benzaldehyde

The invention provides a preparation method of m-phenoxy benzaldehyde, and belongs to the technical field of organic synthesis. The preparation method provided by the invention comprises the following steps: condensing m-cresol serving as a raw material with halogenated benzene to obtain m-phenoxytoluene, reacting the m-phenoxytoluene with chlorine to chloridize methyl to obtain a m-phenoxytoluene chloro product, oxidizing the m-phenoxytoluene chloro product through Komblum to obtain an oxide of the m-phenoxytoluene chloro product, and directly hydrolyzing the m-phenoxytoluene chloro product without separation to obtain the product m-phenoxy benzaldehyde. The preparation method provided by the invention has the advantages that the raw materials are cheap and easily available, the yield is high, the product quality meets the market demand, the problems of high raw material price, many side reactions, many impurities, low yield, large wastewater amount and serious environmental pollution in the traditional process are solved, and the production cost of m-phenoxybenzaldehyde is greatly reduced. Data of the embodiment shows that the total yield of m-phenoxybenzaldehyde obtained by the preparation method provided by the invention is 83.5%, and the gas phase content is 99.3%.

Preparation and characterization of Cu based on 5,5'-bistetrazole as a recyclable metal-organic framework and application in synthesis of diaryl ether by the Ullmann coupling reaction

Cu based on 5,5′-bistetrazole ([Cu2BT · 2H2O] n) as a recyclable metal-organic framework (MOF) heterogeneous catalyst was characterized by FT-IR, 13C NMR, XRD, SEM, EDX, BET, BJH, and ICP-AES analysis. The catalytic activity of the catalyst was probed through the Ullmann reaction for synthesis of diaryl ether derivatives from two component reactions of aromatic arylhalides and phenol derivatives in DMSO. Simple procedure, high yields, short reaction time, and environmentally benign methods are advantages of this protocol. The catalyst was readily separated by simple filtration and reusable without significant loss of its catalytic efficiency.

Trimethoxyphenyl (TMP) as a Useful Auxiliary for in situ Formation and Reaction of Aryl(TMP)iodonium Salts: Synthesis of Diaryl Ethers

Herein, we describe a synthetic approach for arylation that exploits the in situ formation and reaction of an unsymmetrical diaryliodonium salt. In this way, aryl iodides are used as reagents in a metal-free reaction with phenols, and a trimethoxyphenyl (TMP) group is used as a “dummy” group to facilitate transfer of a wide range of aryl moieties. The scope of aryl electrophiles and phenol nucleophiles is broad (>30 examples) and the yields are high (52–95%, 80% avg.). One-pot coupling reactions avoid the synthesis of diaryliodonium salts and provide opportunities for sequential reactions and novel chemoselectivity. (Figure presented.).

Pd based on 2-Aminopyrimidine and 1H-benzo[d]imidazol-2-amine functionalizedFe3O4 nanoparticles as novel recyclable magnetic nanocatalysts for Ullmann coupling reaction

In this study, Pd based on 2-Aminopyrimidine and 1H-benzo[d]imidazol-2-amine functionalized Fe3O4 magnetic nanoparticles [(Pd-APM-PSi-Fe3O4) and (Pd-BIA-PSi-Fe3O4)] was designed and used for the synthesis of di aryl ether by Ulmann cross-coupling reactions. Ulmann reaction performed with mixing of the arylhalides and phenol derivatives in DMF solvent. The prepared catalysts were characterized with various analytical techniques such as FT-IR, XRD, TGA, SEM, TEM, EDX, ICP and VSM. Pd-APM-PSi-Fe3O4 and Pd-BIA-PSi-Fe3O4 catalysts demonstrated good to excellent yields catalytic efficiency for Ulmann reactions in comparison with to commercial palladium catalysts. The catalyst is easily recycled and reused without loss of the catalytic activity. The combined merits of reusable catalyst conditions make the condensation with safe operation, no leaching of pd into environment, low pollution, rapid access to products and simple workup. Also, these novel magnetic nanocatalysts are superior to the industry standard Pd in every relevant aspect. They feature a way higher initial activity, a much more convenient separation, better recycling, and less contamination of the products. Last but not least, they can be very easily prepared from commercially available Fe3O4 nanoparticles using standard laboratory equipment.

Preparation and characterization of isatin complexed with Cu supported on 4-(aminomethyl) benzoic acid-functionalized Fe3O4 nanoparticles as a novel magnetic catalyst for the Ullmann coupling reaction

Isatin complexed with Cu supported on 4-(aminomethyl) benzoic acid-functionalized Fe3O4 nanoparticles (Cu-IS-AMBA-MNPs) as a new catalyst was designed, prepared and characterized by appropriate analyses. The heterogeneous reusable catalyst was successfully used for the efficient and widespread syntheses of diaryl ethers and diarylamines via the Ullmann coupling reaction. This green catalyst was easily removed, reused several times with no significant loss of its activity, and provided a clean synthesis with excellent yield and reduced time.

Magnetically recyclable nano copper/chitosan in O-arylation of phenols with aryl halides

Interaction of chitosan (CS) with Fe3O4, followed by embedding Cu nanoparticles (NPs) on the magnetic surface through adsorption of Cu2+, and its reduction to Cuo via NaBH4, offers a reusable efficient catalyst (Fe3O4/CS-Cu NPs) that is employed in cross-coupling reactions of aryl halides with phenols, which affords the corresponding diaryl ethers, with good to excellent yields. The catalyst is completely recoverable from the reaction mixture by using an external magnet. It can be reused four times, without significant loss in its catalytic activity.