2303-25-5

Basic information

• Product Name: 1-(3-Methylphenoxy)-4-nitrobenzene
• Synonyms: 1-Methyl-3-(4-nitrophenyl)oxybenzene;Attackweed;HE-314;RH-8378;TOPE;1-Methyl-3-(4-nitrophenoxy)benzene;1-(3-Methylphenoxy)-4-nitrobenzene
• CAS NO: 2303-25-5
• Molecular Formula: C₁₃H₁₁NO₃
• Molecular Weight: 229.2313
• Mol File: 2303-25-5.mol

Chemical Properties

• Boiling Point: 334.7°Cat760mmHg
• Flash Point: 142.2°C
• Appearance: /
• Density: 1.218g/cm³
• Vapor Pressure: 0.000245mmHg at 25°C
• Refractive Index: 1.596
• CAS DataBase Reference: 1-(3-Methylphenoxy)-4-nitrobenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(3-Methylphenoxy)-4-nitrobenzene(2303-25-5)
• EPA Substance Registry System: 1-(3-Methylphenoxy)-4-nitrobenzene(2303-25-5)

Safety Data

• Hazardous Substances Data: 2303-25-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1-(3-Methylphenoxy)-4-nitrobenzene is used as an intermediate in the synthesis of various pharmaceuticals due to its versatile chemical structure, which can be further modified to produce a range of medicinal compounds.
Used in Agrochemical Industry:
In the agrochemical sector, 1-(3-Methylphenoxy)-4-nitrobenzene is utilized as a starting material for the development of new agrochemicals, such as pesticides and herbicides, that can help improve agricultural productivity and crop protection.
Used in Dye and Pigment Production:
1-(3-Methylphenoxy)-4-nitrobenzene has been studied for its potential use as a precursor in the production of dyes and pigments, where its unique chemical properties can contribute to the creation of novel colorants for various applications.
Used in Research and Development:
1-(3-Methylphenoxy)-4-nitrobenzene is also important in the field of research and development, where it is investigated for its pharmacological properties. Studies have explored its potential as an anti-inflammatory and analgesic agent, which could lead to the development of new treatments for pain and inflammation.
Safety Precautions:
It is crucial to handle 1-(3-Methylphenoxy)-4-nitrobenzene with care, as it is considered hazardous and harmful if ingested or inhaled. Proper safety measures should be taken during its production, use, and disposal to minimize the risk of exposure and ensure the well-being of individuals and the environment.

InChI:InChI=1/C13H11NO3/c1-10-3-2-4-13(9-10)17-12-7-5-11(6-8-12)14(15)16/h2-9H,1H3

Upstream product

• 108-39-4 3-methyl-phenol 
• 100-00-5 4-chlorobenzonitrile 
• 586-78-7 para-nitrophenyl bromide 
• 350-46-9 4-Fluoronitrobenzene 
• 1077-02-7 3-methylphenyl methanesulfonate 
• 100-02-7 4-nitro-phenol 
• 17933-03-8 m-tolylboronic acid 
• 100-25-4 para-dinitrobenzene 
• 636-98-6 p-nitrobenzene iodide 

Downstream Products

• 59003-95-1 2-nitro-5-(4-nitro-phenoxy)-benzoic acid 
• 873977-84-5 acetic acid-[4-(4-bromo-3-methyl-phenoxy)-2-nitro-anilide] 
• 873977-67-4 acetic acid-[4-(4-chloro-3-methyl-phenoxy)-2-nitro-anilide] 
• 860597-21-3 2-bromo-5-(4-nitro-phenoxy)-benzoic acid 
• 873980-25-7 4-(4-bromo-3-methyl-phenoxy)-2-nitro-aniline 
• 873980-51-9 4-(4-chloro-3-methyl-phenoxy)-2-nitro-aniline 
• 873977-88-9 acetic acid-[4-(4-bromo-3-methyl-phenoxy)-anilide] 
• 873977-71-0 acetic acid-[4-(4-chloro-3-methyl-phenoxy)-anilide] 
• 192768-36-8 {(R)-1-[(4-m-Tolyloxy-phenylamino)-methyl]-2-tritylsulfanyl-ethyl}-carbamic acid tert-butyl ester 
• 22532-72-5 3-Methyl-4-chlor-4'-nitrodiphenylaether 
• 246511-70-6 1-bromo-2-methyl-4-(4-nitrophenoxy)benzene 
• 147837-21-6 3-(4-nitrophenoxy)benzyl bromide 
• 135210-04-7 (3-methyl-4-nitro-phenyl)-(4-nitro-phenyl)-ether 
• 27237-21-4 3-(4-nitrophenoxy)benzoic acid 

Relevant articles and documents

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.

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.

Novel EDA transient electron donor-acceptor complex, and preparation method and applications thereof

The invention relates to a novel EDA transient electron donor-acceptor complex, and a preparation method and applications thereof. The structure of the complex is represented in the description, wherein R1 represents an electron-withdrawing group such as cyano, nitro, acetyl, trifluoromethyl, and the like; R2 represents any one substituent group such as hydrogen, an alkyl group (methyl, ethyl, etc.), chlorine, bromine, iodine, methoxyl, nitro, and the like; and the position of the substituent group can be an o-position, m-position, or p-position. According to the synthesis method, under the induction of visible light, phenol derivatives and electron deficient aryl halide carry out reactions under the action of basic cesium carbonate to generate the complex, and no transition metal catalyst, transition metal ligand, or photo oxidation-reduction agent is added. Through the reaction mechanism, a series of diaryl ether derivatives is prepared. The preparation method has the advantages of mild conditions, greenness, high efficiency, low cost, and simple operation.

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.

EDA (electronic design automation) transient electron donor-acceptor complex as well as preparation method and application thereof

The invention relates to an EDA (electronic design automation) transient electron donor-acceptor complex as well as a preparation method and application thereof. The compound has a structural formulashown in the specification, in the formula, R1 is an electron withdrawing group such as cyan, nitryl, acetyl and trifluoromethyl; R2 is any one of arbitrary substituent groups such as hydrogen, methyl, ethyl and other alkyl groups, chloro, bromo, iodo, methoxyl and nitryl; and the position relationship of the substituent groups is any one of an ortho-position, a meta-position and a para-position.According to a synthesis method, under induction of visible light, without addition of any transition metal catalyst, ligand or photoredox agent, the complex is prepared from a phenol derivative and an electron-deficient aryl halide under the action of alkali cesium carbonate through reactions. In addition, a series of diaryl ether derivatives are prepared through the reaction mechanism. The condition is gentle and green, the efficiency is high, the cost is low and operation is simple and convenient.

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.

Ullmann Coupling Reaction of Nitro-Substituted Aryl Halides with Phenols under Mild Conditions: Micro-/Mesoporous Hierarchical LaAlPO-5 Zeolite Catalyst

Heterogeneous catalytic reactions of aromatic organic molecules over zeolite catalysts present many challenges because of the shape selectivity of the micropores of conventional zeolites that limits the diffusion of aromatic molecules. Herein, Ullmann coupling reactions of phenols with nitro-substituted aryl halides were catalyzed by rare-earth-doped mesoporous AlPO-5 zeolites in the absence of ligands. The AlPO-5-MAlPO-5-M zeolites had a pure AFI structure and consisted of spherical particles assembled by nanofibers. The rare-earth elements were highly dispersed in the AlPO-5-MAlPO-5-M samples. The LaAlPO-5-MAlPO-5-M zeolite is an excellent catalyst for Ullmann coupling reactions of phenols and nitro-substituted aryl halides. Mesoporous LaAlPO-5 has an excellent stability and recyclability in the Ullmann coupling of p-X-nitrobenzene (X=Cl, Br, and I) with 2-naphthol. These results are important in the exploration of attractive Ullmann coupling reactions and in the development of mesoporous zeolite catalysts for other organic reactions.

Discovery of 1,2,4-triazole-1,3-disulfonamides as dual inhibitors of mitochondrial complex II and complex III

Respiratory chain succinate-ubiquinone oxidoreductase (SQR or complex II) and ubihydroquinone-cytochrome (cyt) c oxidoreductase (cyt bc1 or complex III) have been demonstrated as the promising targets of numerous antibiotics and fungicides. As a continuation of our research work on the development of new fungicides, a series of 1,2,4-triazole-1,3-disulfonamide derivatives with dual functions targeting both SQR and cyt bc1 were designed and synthesized by coupling diverse diphenyl ether moieties with triazolesulfonamide units. These newly synthesized compounds were characterized by elemental analyses, 1H NMR and ESI-MS spectrometry. The in vitro assay indicated that most of the synthesized compounds displayed good inhibition against porcine succinate-cytochrome reductase (SCR) with IC50 values ranging from 3.2 to 81.8 μM, revealing much higher activity than that of the commercial control amisulbrom whose IC50 value is 93.0 μM. Further evaluation against the respective SQR and cyt bc1 indicated that most compounds exhibited SQR-inhibiting activity as well as cyt bc1-inhibiting activity, but the inhibition potency against SQR is much higher than that against cyt bc1, showing that the SCR inhibition might be contributed greatly by the SQR inhibition. The further antibacterial evaluation against Xanthomonas oryzae pv. oryzae revealed that four compounds showed excellent potency at the concentration of 20 μg mL-1. In particular, compounds 6h and 6j exhibited much better antibacterial activity than the commercial control bismerthiazol in terms of their EC50. Impressively, 6j has an EC90 of 33.62 μg mL-1, more than 10-fold higher than that of bismerthiazol.

Betti base as an efficient ligand for copper-catalyzed ullmann coupling of phenol with aryl halides

GRAPHICAL ABSTRACT A simple, general, and highly efficient Betti base ligand has been developed for copper-catalyzed Ullmann coupling of phenol with aryl halides without the protection of an inert atmosphere. The reaction proceeds smoothly in the presence of K2CO3 as the base and dimethylsulfoxide as the solvent. The catalyst was reused several times with no evident loss of catalytic activity and is environmentally friendly.