621-52-3

Usage

Uses

Used in Pharmaceutical Manufacturing:
3-Nitrophenetole is used as an intermediate in the synthesis of various pharmaceutical compounds, contributing to the development of new drugs and medications.
Used in Organic Synthesis:
As an intermediate in organic synthesis, 3-Nitrophenetole plays a crucial role in the production of a range of organic compounds, facilitating the creation of diverse chemical products.
Used in the Food Industry:
3-Nitrophenetole is utilized as a flavoring agent, enhancing the taste and aroma of certain food products, while ensuring that the quantity used complies with safety regulations to avoid its toxic effects.

InChI:InChI=1/C8H9NO3/c1-2-12-8-5-3-4-7(6-8)9(10)11/h3-6H,2H2,1H3

Upstream product

• 616-86-4 2-nitro-4-ethoxyaniline 
• 554-84-7 meta-nitrophenol 
• 80-40-0 ethyl ester of p-toluenesulfonic acid 
• 64-67-5 diethyl sulfate 
• 75-03-6 ethyl iodide 
• 64-17-5 ethanol 
• 369-57-3 benzenediazonium tetrafluoroborate 
• 586-36-7 3-nitrophenyldiazonium tetrafluoroborate 
• 74-96-4 ethyl bromide 
• 645-00-1 m-iodonitrobenzene 
• 108-01-0 2-(N,N-dimethylamino)ethanol 
• 105-58-8 Diethyl carbonate 
• 141-52-6 sodium ethanolate 
• 73377-26-1 p-Tolyl-m-nitrophenyliodonium Fluoroborate 

Downstream Products

• 32619-20-8 9-(4-amino-phenyl)-7-methyl-acridin-3-ylamine 
• 1034-18-0 3,3'-diethoxyhydrazobenzene 
• 557104-69-5 3,3'-diethoxyazoxybenzene 
• 621-33-0 m-phenetidine 
• 554-84-7 meta-nitrophenol 
• 90434-59-6 (3-ethoxy-phenyl)-hydrazine 
• 124769-44-4 2-(3-Ethoxy-phenylamino)-6-oxo-1,6-dihydro-pyrimidine-5-carboxylic acid ethyl ester 
• 124769-71-7 2-(3-Ethoxy-phenylamino)-6-oxo-1,6-dihydro-pyrimidine-5-carboxylic acid 
• 588-02-3 3,3'-diethoxyazobenzene 
• 99839-03-9 4-chloromethyl-3-nitro-phenetole 
• 91861-93-7 N-(m-Ethoxyphenyl)hydroxylamine 

Relevant academic research and scientific papers

Mustard Carbonate Analogues as Sustainable Reagents for the Aminoalkylation of Phenols

N,N-dialkyl ethylamine moiety can be found in numerous scaffolds of macromolecules, catalysts, and especially pharmaceuticals. Common synthetic procedures for its incorporation in a substrate relies on the use of a nitrogen mustard gas or on multistep syntheses featuring chlorine hazardous/toxic chemistry. Reported herein is a one-pot synthetic approach for the easy introduction of aminoalkyl chain into different phenolic substrates through dialkyl carbonate (β-aminocarbonate) chemistry. This new direct alcohol substitution avoids the use of chlorine chemistry, and it is efficient on numerous pharmacophore scaffolds with good to quantitative yield. The cytotoxicity via MTT of the β-aminocarbonate, key intermediate of this synthetic approach, was also evaluated and compared with its alcohol precursor.

[Cp?RhCl2]2-catalyzed alkyne hydroamination to 1,2-dihydroquinolines

[Cp?RhCl2]2 catalyzes the formation of 1,2-dihydroquinolines from the reaction of two terminal alkynes and an aniline. This reaction is believed to proceed via an alkyne hydroamination followed by an alkyne insertion.

General, mild, and intermolecular Ullmann-type synthesis of diaryl and alkyl aryl ethers catalyzed by diol-copper(I) complex

(Chemical Equation Presented) A wide range of diaryl ethers and alkyl aryl ethers are synthesized through intermolecular C(aryl)-O bond formation from the corresponding aryl iodides/aryl bromides and phenols/alcohols through Ullmann-type coupling reaction in the presence of a catalytic amount of easily available (±)-diol L3-CuI complex under very mild reaction conditions. Less reactive aryl bromides can also be used for O-arylation of phenols under the same reaction conditions without increasing the reaction temperature, catalyst loading, and time. The catalytic system not only is capable of coupling hindered substrate but also tolerates a broad range of a series of functional groups.

An efficient intermolecular BINAM-copper(I) catalyzed Ullmann-type coupling of aryl iodides/bromides with aliphatic alcohols

A wide range of alkyl aryl ethers are synthesized from the corresponding aryl iodides and aliphatic alcohols through Ullmann-type intermolecular coupling reactions in the presence of a catalytic amount of easily available BINAM-CuI complex. Less reactive aryl bromides have also been shown to react with aliphatic alcohols under identical reaction conditions to give good yields of the alkyl aryl ethers without increasing the reaction temperature and time.

Solvent-free Williamson synthesis: An efficient, simple, and convenient method for chemoselective etherification of phenols and bisphenols

Etherification of phenols with dimethyl- and diethylsulfates and benzyl chloride was performed efficiently in the presence of a suitable solid base, NaHCO3 or K2CO3, under solvent-free conditions. The reaction proceeded rapidly at low temperature, and the corresponding ethers were obtained with high purity and excellent yield. Selective etherification of electron-poor phenols in the presence of electron-rich ones and also selective mono-etherification of bisphenols are the noteworthy advantages of this method. This method is environmentally friendly. Copyright Taylor & Francis Group, LLC.

A product analytical study of the thermal and photolytic decomposition of some arenediazonium salts in solution

Products of thermal and photochemical reactions of eleven arenediazonium tetrafluoroborates in various solvents have been analyzed. All compounds in most solvents undergo unimolecular heterolysis to give singlet aryl cations which are captured by solvent. This mechanism is dominant for arenediazonium ions without electron-withdrawing substituents in all solvents, and the only reaction observed in water. Additionally, appreciable yields of fluoroarenes are obtained by fluoride abstraction by the aryl cation from fluorinated solvents and from tetrafluoroborate in fluorinated solvents. Yields from photochemical processes are very similar to those from thermal reactions indicating that the main reactions proceed through common or very similar intermediates. Aryl cations formed from ion-paired diazonium ions may react with the counterion, but fragmentation of dissociated diazonium ions leads only to solvent-derived product. Some arenediazonium ions in some solvents undergo an alternative radical reaction leading principally to hydrodediazoniation. It is proposed that this reaction involves initial rate-limiting electron transfer from ethanol to the arenediazonium ion followed rapidly by homolysis of the resultant aryldiazenyl radical. Within the same solvent cage, the aryl radical then either abstracts an α-hydrogen from the ethanol radical cation generated in the first step to give the reduction product and protonated acetaldehyde, or combines with it at the oxygen to give a protonated aryl ethyl ether.

Dediazoniation reactions of arenediazonium ions under solvolytic conditions: Fluoride anion abstraction from trifluoroethanol and α-hydrogen atom abstraction from ethanol

Arenediazonium salts decompose thermally and photochemically in trifluoroethanol to yield trifluoroethyl ethers and (in part by fluoride abstraction from the solvent) fluoroarenes; the less reactive compounds in trifluoroethanol decompose readily in ethanol to give arenes in a radical reaction involving abstraction of the α-hydrogen from the ethanol.

Chemoselective O-methylation of phenols under non-aqueous condition

Chemoselective O-methylation of substituted phenols takes place in dry. tetrahydrofuran (THF) in the presence of LiOH.H2O and dimethylsulfate (DMS). Quantitative methyl transfer from DMS preserves the atom economy.

Process for the preparation of nitrophenyl alkyl ethers

Nitrophenyl alkyl ethers can be advantageously prepared by reacting a nitrophenol with an alkyl halide in water as the reaction medium in such a manner that the nitrophenol is laid before with the water and the alkyl halide and a hydrogen halide-binding compound are then added simultaneously.

Further Evidence for the Triplet Mechanism in the Photosubstitution of Nitroaryl Ethers in Alkaline Medium.

Mechanistic studies show that nitroaryl ethers (3-nitroanisole, 3-nitrophenetole, n-butyl 3-nitrophenyl ether, 2-chloro-5-nitroanisole, 2-bromo-5-nitroanisole and 3,5-dinitroanisole) undergo nucleophilic aromatic photosubstitution with hydroxide ions through an SN23Ar* mechanism.An investigation of the quenching of excited states of nitroaryl ethers by bromide and thiosulfate ions in aqueous solutions is reported and lends support to the proposed SN23Ar* mechanism.Key Words: Photosubstitution; Nitroaryl Ethers; Triplet Lifetime; Quencher.