610-54-8

Basic information

• Product Name: 2,4-DINITROPHENETOLE
• Synonyms: 2,4-DINITROPHENETOLE;1-ETHOXY-2,4-DINITROBENZENE;2,4-Dinitro-1-ethoxy-benzene;2,4-Dinitrofenetol;2,4-dinitro-phenetol;2,4-Dinitrophenyl ethyl ether;2,4-dinitrophenylethylether;Phenetole, 2,4-dinitro-
• CAS NO: 610-54-8
• Molecular Formula: C₈H₈N₂O₅
• Molecular Weight: 212.16
• EINECS: 210-228-4
• Product Categories: Phenetole
• Mol File: 610-54-8.mol

Chemical Properties

• Melting Point: 86 °C
• Boiling Point: 211 °C / 15mmHg
• Flash Point: 176.5°C
• Appearance: /
• Density: 1.4945 (rough estimate)
• Vapor Pressure: 5.02E-05mmHg at 25°C
• Refractive Index: 1.6180 (estimate)
• CAS DataBase Reference: 2,4-DINITROPHENETOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-DINITROPHENETOLE(610-54-8)
• EPA Substance Registry System: 2,4-DINITROPHENETOLE(610-54-8)

Safety Data

• RTECS: SI7875000
• Hazardous Substances Data: 610-54-8(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
2,4-DINITROPHENETOLE is used as an intermediate in the synthesis of various organic compounds. Its aromatic ether structure and nitro-substituted positions make it a valuable building block for creating a wide range of chemical products, including pharmaceuticals, agrochemicals, and dyes.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2,4-DINITROPHENETOLE is used as a key component in the development of new drugs. Its unique chemical structure allows it to interact with specific biological targets, making it a promising candidate for the treatment of various diseases and medical conditions.
Used in Dye Manufacturing:
2,4-DINITROPHENETOLE is used as a starting material in the production of dyes. Its aromatic structure and nitro groups contribute to the color properties of the resulting dyes, making it an essential component in the dye manufacturing process.
Used in Agrochemicals:
In the agrochemical industry, 2,4-DINITROPHENETOLE is used as a precursor for the development of new pesticides and herbicides. Its chemical properties enable it to be modified and functionalized to create compounds with specific pesticidal or herbicidal activities, helping to improve crop protection and yield.
Used in Research and Development:
2,4-DINITROPHENETOLE is also used in research and development for its potential applications in various fields. Its unique chemical structure makes it an interesting subject for studying its properties, reactivity, and potential uses in different industries, including materials science, environmental science, and nanotechnology.

Purification Methods

Crystallise it from aqueous EtOH. The 1:1 naphthalene complex has m 41o and is obtained by fusing the compound with naphthalene in various ratios, then crystallizing the solidified mix with a little EtOH (Dermer & Smith J Am Chem Soc 61 748 1939). [Beilstein 6 H 254, 6 III 858, 6 IV 1373.]

InChI:InChI=1/C8H8N2O5/c1-2-15-8-4-3-6(9(11)12)5-7(8)10(13)14/h3-5H,2H2,1H3

Upstream product

• 584-48-5 2,4-dinitrobromobenzene 
• 64-17-5 ethanol 
• 53405-99-5 5-(2,4-dinitro-anilino)-penta-2,4-dienal 
• 119-27-7 2,4-dinitroanisole 
• 141-52-6 sodium ethanolate 
• 619-86-3 4-(ethoxy)benzoic acid 
• 860208-92-0 3-ethoxy-2,6-dinitro-aniline 
• 70-34-8 2,4-Dinitrofluorobenzene 
• 75-03-6 ethyl iodide 
• 97-00-7 1-chloro-2,4-dinitro-benzene 
• 51-28-5 2,4-Dinitrophenol 
• 122-51-0 orthoformic acid triethyl ester 
• 101-83-7 N-cyclohexyl-cyclohexanamine 
• 103-73-1 Phenetole 

Downstream Products

• 10242-17-8 1-propoxy-2,4-dinitrobenzene 
• 119-27-7 2,4-dinitroanisole 
• 4732-14-3 2,4,6-trinitro-phenetole 
• 5862-77-1 2,4-diamino-1-ethoxybenzene 
• 136-79-8 2-Amino-4-nitroethoxybenzen 
• 1777-87-3 4-ethoxy-3-nitroaniline 
• 97-02-9 2,4-Dinitroanilin 
• 51-28-5 2,4-Dinitrophenol 
• 119-26-6 (2,4-dinitro-phenyl)-hydrazine 
• 13417-44-2 n-Butyl 2,4-dinitrophenyl ether 
• 36400-76-7 (2,4-dinitro-phenyl)-isobutyl ether 
• 99842-11-2 (2,4-dinitro-phenyl)-isopentyl ether 
• 99-65-0 meta-dinitrobenzene 
• 615-71-4 benzene-1,2,4-triamine 

Relevant articles and documents

SNAr reactions of 1-halo-2,4-dinitrobenzenes with alkali-metal ethoxides: Differential stabilization of ground state and transition state determines alkali-metal ion catalysis or inhibition

A kinetic study on SNAr reactions of 1-halo-2,4-dinitrobenzenes (6a-6d) with alkali-metal ethoxides (EtOM; M = Li, Na, K and 18-crown-6-ether-complexed K) is reported. The plots of pseudo-first-order rate constant (kobsd) vs. [EtOM]

The effect of varying the anion of an ionic liquid on the solvent effects on a nucleophilic aromatic substitution reaction

A variety of ionic liquids, each containing the same cation but a different anion, were examined as solvents for a nucleophilic aromatic substitution reaction. Varying the proportion of ionic liquid was found to increase the rate constant as the mole fraction of ionic liquid increased demonstrating that the reaction outcome could be controlled through varying the ionic liquid. The solvent effects were correlated with the hydrogen bond accepting ability (β) of the ionic liquid anion allowing for qualitative prediction of the effect of changing this component of the solute. To determine the microscopic origins of the solvent effects, activation parameters were determined through temperature-dependent kinetic analyses and shown to be consistent with previous studies. With the knowledge of the microscopic interactions in solution, an ionic liquid was rationally chosen to maximise rate enhancement demonstrating that an ionic solvent can be selected to control reaction outcome for this reaction type.

Rationalising the effects of ionic liquids on a nucleophilic aromatic substitution reaction

The nucleophilic aromatic substitution reaction between 1-fluoro-2,4-dinitrobenzene and ethanol was examined in a series of ionic liquids across a range of mole fractions. Temperature-dependent kinetic analyses were undertaken to determine the activation parameters for this reaction at the highest mole fraction. As the mole fraction of ionic liquid was increased, the rate constant of the reaction also increased, however the microscopic origin of the rate enhancement was shown to be different between different ionic liquids and also between different solvent compositions. These results indicate a balance between microscopic interactions that result in the observed solvent effects and a qualitative method for analysing such interactions is introduced.

NITRATION OF AROMATIC COMPOUNDS

The present invention provides a process for nitrating aromatic compounds without the need for a solid catalyst and/or any organic solvents and/or any other additives. A typical process includes combining or admixing a nitric acid and an anhydride compound under conditions sufficient to produce a reactive intermediate. The aromatic compound to be nitrated is then added to this reactive intermediate to produce a nitroaromatic compound. The nitroaromatic compound can be substituted with one or more, typically, one to three, and often one or two nitrate (-NO2) groups.

Novel Chloroimidazolium-Based Ionic Liquids: Synthesis, Characterisation and Behaviour as Solvents to Control Reaction Outcome

Novel ionic liquids containing chlorine atoms on the imidazolium cation were synthesised. The physicochemical properties of these ionic liquids were investigated extensively, including glass transition, melting and decomposition temperatures, density, vis

Regioselective dinitration of simple aromatics over zeolite Hβ/nitric acid/acid anhydride systems

Various nitration systems comprising nitric acid, acid anhydride and zeolite H￡] in the absence of solvent are described. Direct double nitration of toluene with a nitric acid, propanoic anhydride and zeolite Hβ system has been developed to give 2,4-dinitrotoluene in 98% yield, with a 2,4-:2,6-dinitrotoluene ratio of 123:1. This system also nitrates activated mono-substituted benzenes (anisole and phenetole) and moderately activated mono-substituted benzenes (ethylbenzene and propylbenzene) to give mainly 2,4-dinitro derivatives. The zeolite can be recovered, regenerated and reused to give almost the same yield as that given when fresh zeolite is used. ARKAT-USA, Inc.

Alkali-metal ion catalysis and inhibition in snar reaction of 1-halo-2,4-dinitrobenzenes with alkali-metal ethoxides in anhydrous ethanol

A kinetic study is reported for SNAr reaction of 1-fluoro-2,4- dinitrobenzene (5a) and 1-chloro-2,4-dinitrobenzene (5b) with alkali-metal ethoxides (EtOM, M = Li, Na, K and 18-crown-6-ether complexed K) in anhydrous ethanol. The second-order rate constant

Alkali-Metal Ion Catalysis and Inhibition in SNAr Displacement: Relative Stabilization of Ground State and Transition State Determines Catalysis and Inhibition in SNAr Reactivity

We report here the first observation of alkali-metal ion catalysis and inhibition in SNAr reactions. The plot of kobsd versus [alkali-metal ethoxide] exhibits downward curvature for the reactions of 1-(4-nitrophenoxy)-2,4-dinitrobenzene with EtOLi, EtONa, and EtOK, but upward curvature for the corresponding reaction with EtOK in the presence of 18-crown-6-ether (18C6). Dissection of kobsd into the second-order rate constants for the reactions with the dissociated EtO- and the ion-paired EtOM (i.e., k EtO - and kEtOM, respectively) has revealed that the reactivity increases in the order EtOLi-+, Na+, and K+ ions but is catalyzed by 18C6 K+ ion. The reactions of 1-(Y-substituted-phenoxy)-2,4-dinitrobenzenes have been proposed to proceed through a stepwise mechanism, in which expulsion of the leaving group occurs after the rate-determining step based on the kinetic result that σo constants exhibit a much better Hammett correlation than σ- constants. Alkali-metal ion catalysis or inhibition has been discussed in terms of differential stabilization of ground-state and transition-state complexes through a qualitative energy profile. A π-complexed transition-state structure is proposed to account for the kinetic results.

Highly regioselective dinitration of toluene over reusable zeolite Hβ

A nitration system comprising nitric acid, propanoic anhydride, and zeolite Hβ has been developed for dinitration of toluene to give 2,4-dinitrotoluene in 98% yield, with a 2,4-:2,6-dinitrotoluene ratio of over 120. This represents the most selective quantitative method for 2,4-dinitration of toluene; the catalyst is reusable, solvent is not needed, and an aqueous work-up is not required.

Probing the importance of ionic liquid structure: A general ionic liquid effect on an SNAr process

The effect of a range of ionic liquids, with systematic variations in the cation and anion, on the rate constant of an aromatic substitution process was investigated. Temperature-dependent kinetic data allowed calculation of activation parameters for the process in each solvent. These data demonstrate a generalised ionic liquid effect, with an increase in rate constant observed in each ionic solvent, though the microscopic origins of the rate constant enhancement differ with the nature of the ionic liquid.