119-27-7

Usage

Uses

Used in Dye Industry:
2,4-Dinitroanisole is used as a dye ingredient for its ability to provide color and enhance the visual appeal of various products.
Used in Munitions:
2,4-Dinitroanisole is used as an insensitive nitroaromatic ingredient in the munitions industry. It serves as a replacement for 2,4,6-trinitrotoluene (TNT) due to its relatively safer and more stable nature, making it a preferred choice for explosive applications.

Flammability and Explosibility

Notclassified

Safety Profile

Poison by ingestion. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx. See also NITRO COMPOUNDS of AROMATIC HYDROCARBONS and NITRATES.

Purification Methods

Purify the anisole by repeated crystallisation from EtOH, MeOH or H2O and dry it in a vacuum desiccator over P2O5. The naphthalene complex has m 69o (from EtOH). [Beilstein 6 III 869, 6 IV 1385.

Upstream product

• 67-56-1 methanol 
• 2734-78-3 1-(benzyloxy)-2,4-dinitrobenzene 
• 529-28-2 4-iodoanisol 
• 610-54-8 2,4-dinitro-1-ethoxybenzene 
• 124-41-4 sodium methylate 
• 89-41-8 4-methoxy-3-nitrobenzoic acid 
• 10202-94-5 3-methoxy-2,6-dinitrobenzaldehyde 
• 70-34-8 2,4-Dinitrofluorobenzene 
• 121-44-8 triethylamine 
• 100-66-3 methoxybenzene 
• 97-00-7 1-chloro-2,4-dinitro-benzene 
• 610-31-1 1,2,4-trinitrobenzene 
• 29418-59-5 4-(4'-nitrophenylazo)anisole 
• 51-28-5 2,4-Dinitrophenol 

Downstream Products

• 51-28-5 2,4-Dinitrophenol 
• 10242-17-8 1-propoxy-2,4-dinitrobenzene 
• 2831-60-9 2-(2,4-dinitrophenoxy)ethanol 
• 40742-19-6 3-(2,4-dinitro-phenoxy)-propane-1,2-diol 
• 13417-44-2 n-Butyl 2,4-dinitrophenyl ether 
• 626-67-5 N-methylcyclohexylamine 
• 67-56-1 methanol 
• 839-93-0 1-(2,4-dinitrophenyl)piperidine 
• 15302-91-7 1,1-dimethyl-piperidinium 
• 20350-26-9 2,4-dinitrophenolate 
• 92241-28-6 1-Benzenesulfonylmethyl-5-methoxy-2,4-dinitro-benzene 
• 14314-69-3 potassium 2,4-dinitrophenolate 
• 84845-89-6 3.5-Bis-aci-nitro-2-methoxy-cyclohexen-⁽¹⁾ 
• 99-59-2 3-amino-4-methoxynitrobenzene 

Relevant academic research and scientific papers

Alkoxyphosphonium Salts. 3. Kinetics and Thermodynamics in Alkylation by Alkoxyphosphonium Salts

Several methoxyphosphonium trifluoromethanesulfonates (triflates) are characterized by the rates of methyl transfer to the 2,4-dinitrophenoxide ion.In acetone at 25 deg C, the measured second-order rate constants range from about 0.2 to about 40 M-1s-1, putting substances of this class among the most powerful methylating agents.The methylating power is confirmed by the measurement of the equilibrium extent of methylation of the counterion, the triflate ion.The Arbuzov rearrangement of trimethyl phosphite is slow with the catalyst methyl iodide but is fast enough with the cata lyst methyltrimethoxyphosphonium triflate to allow calorimetric measurement for the conversion of trimethyl phosphite to dimethyl methylphosphonate; ΔH = -24 +/- 2 kcal/mol.An earlier error in the measurement of the rate of this reaction is corrected, so that the mechanism of the methyl iodide catalyzed Arbuzov reaction of trimethyl phosphite is no longer in question; the first step is rate-determining.

Reactions in Strongly Basic Media. Part 9. Correlation of the Rates of Methoxide-catalysed Methanolysis of 1-Substituted 2,4-Dinitrobenzenes and 2-Substituted 5-Nitropyridines in Methanolic Dimethyl Sulphoxide with an Acidity Function. Details of the Mechanistic Pathway

The rate coefficients for the methoxide-catalised methanolysis of a series of 1-substituted 2,4-dinitrobenzenes and 2-substituted 5-nitropyridines have been measured in methanolic DMSO at 20.0 or 21.0 deg C.For the 2-substituted 5-nitropyridines and for the 1-substituted 2,4-dinitrobenzenes below ca. 55 mol percent DMSO, the rates have been correlated with an acidity function of the medium.The slopes of these linear relations are discussed.The 1-substituted 2,4-dinitrobenzenes above ca. 55 mol percent DMSO give rise to Meisenheimer complexes as intermediates and/or as the product of the reaction.The product of the reaction then becomes the 1,1-Meiseheimer complex of methoxide and 2,4-dinitroanisole.For the 1-fluoro substrate the formation of the latter becomes rate determining.For other 1-substituted substrates the decomposition of a 1,3-Meisenheimer complex becomes rate determining.

Nitration of aromatics with dinitrogen pentoxide in a liquefied 1,1,1,2-tetrafluoroethane medium

Regardless of the sustainable development path, today, there are highly demanded chemical productions still operating that bear environmental and technological risks inherited from the previous century. The fabrication of nitro compounds, and nitroarenes in particular, is traditionally associated with acidic wastes formed in nitration reactions exploiting mixed acids. However, nitroarenes are indispensable for industrial and military applications. We faced the challenge and developed a greener, safer, and yet effective method for the production of nitroaromatics. The proposed approach comprises the application of an eco-friendly nitrating agent, namely dinitrogen pentoxide (DNP), in the medium of liquefied 1,1,1,2-tetrafluoroethane (TFE) - one of the most non-hazardous Freons. Importantly, the used TFE is not emitted into the atmosphere but is effortlessly recondensed and returned into the process. DNP is obtainedviathe oxidation of dinitrogen tetroxide with ozone. The elaborated method is characterized by high yields of the targeted nitro arenes, mild reaction conditions, and minimal amount of easy-to-utilize wastes.

Ipso Nitration of Aryl Boronic Acids Using Fuming Nitric Acid

The ipso nitration of aryl boronic acid derivatives has been developed using fuming nitric acid as the nitrating agent. This facile procedure provides efficient and chemoselective access to a variety of aromatic nitro compounds. While several activating agents and nitro sources have been reported in the literature for this synthetically useful transformation, this report demonstrates that these processes likely generate a common active reagent, anhydrous HNO3. Kinetic and mechanistic studies have revealed that the reaction order in HNO3 is >2 and indicate that the ?NO2 radical is the active species.

Process for synthesizing 2-amino-4-acetylaminoanisole

The invention discloses a process for synthesizing 2-amino-4-acetylaminoanisole. The process comprises the steps of preparing 2,4-dinitroanisole from 2,4-dinitrochlorobenzene, which serves as a raw material, in methanol, in the presence of sodium hydroxide or potassium hydroxide, carrying out reduction in the presence of action of Pd/C catalyst by taking hydrazine monoformate as a hydrogen sourceso as to prepare a 2,4-diaminoanisole-methanol solution, and then, subjecting 2,4-diaminoanisole and acetic anhydride to a partial acylation reaction in the presence of an acid binding agent, therebypreparing the 2-amino-4-acetylaminoanisole. According to the process disclosed by the invention, the energy consumption is low, the cost is low, the volume of solid waste and waste liquid is small, the process is environmentally friendly, the operation is simple, the reaction conditions are mild, the industrial safety coefficient is big, the total yield of a target compound is 85% or more (by initial reactants), the HPLC purity is 99.0% or more, and the target compound is high in yield and good in quality, so that the process is more applicable to industrial production.

2 - Amino - 4 - acetamido anisole novel synthesis process (by machine translation)

The present invention provides a novel 2 - amino - 4 - acetamido anisole synthesis process, the usage of palladium bi-metal catalysts and the palladium/carbon catalyst to replace Rany - Ni catalyst, to the anisole on the nitro-selective catalytic hydrogenation, which not only reduces use Rany - Ni catalyst of post-industrial risks, while at the same time, the resulting 2 - amino - 4 - acetyl anisole purity higher, greater yield. (by machine translation)

Synthesis process of 2-amidogen-4-acetamido anisole

The invention discloses a synthesis process of 2-amidogen-4-acetamido anisole. The synthesis process of the 2-amidogen-4-acetamido anisole comprises the steps of adopting p-methoxyaniline as a raw material, carrying out partial acylation reaction on the p-methoxyaniline and acetic anhydride, and preparing to obtain p-acetamido anisole; then carrying out nitration reaction, carrying out one-pot method'reaction to obtain 2-nitro-4-acetamido anisole, and under the action of a Pd/C catalyst, reducing the 2-nitro-4-acetamido anisole by adopting hydrazine monoformate as a hydrogen source to preparethe 2-amidogen-4-acetamido anisole. The synthesis process provided by the invention is low in energy consumption, low in cost, less in solid wastes and waste liquids, green and environmentally friendly, simple to operate, mild in reaction conditions, and high in industrial safety coefficient, the total yield of the target compound is 85 percent or above (on the basis of an initial reaction raw material), the HPLC (High Performance Liquid Chromatography) purity is 99.0 percent or above, the target compound is high in yield and good in quality, and the synthesis process is more suitable for industrial production.

Synthesis process of 4-acetamino-2-aminoanisol

The invention belongs to the field of fine chemical engineering, and discloses a synthesis process of 4-acetamino-2-aminoanisol. The synthesis method comprises the following steps: step one, adding 0.25 mol of 2,4-dinitrochlorobenzene and 100 ml of methyl alcohol, carrying out heating to 35-45 DEG C, adding a sodium hydroxide solution with a mass fraction of 20% with a decreasing speed, carrying out heating to 55-65 DEG C, carrying out filtering, diluting the filter cake with water, and carrying out drying under reduced pressure to obtain 2,4-nitroanisole; step two, preparing 200 ml of a sodium disulfide solution with a concentration of 20%, adding 0.25 mol of the 2,4-dinitroanisole, carrying out heating to a reflux temperature, then carrying out cooling to 80 DEG C, carrying out standing,washing a filter cake by using cold water, and carrying out drying under reduced pressure to obtain 2,4-diaminophenyl ether; and step three, adding 0.25 mol of 2,4-diaminoanisole, 50 ml of acetic acid and 0.1 mol of a catalyst, carrying out ice bath, adding 0.25 mol of acetic anhydride, adding 125 ml of ice water, carrying out filtering, washing a filter cake with a solution of sodium dithionite,and carrying out drying under reduced pressure to obtain the 4-acetamino-2-aminoanisol. The invention aims at providing the synthesis process of 4-acetamino-2-aminoanisol, and the synthesis method has the advantages of high recovery rate, simple process and low cost.

A 2, 4 - dinitrobenzene synthesizing method (by machine translation)

The invention discloses a 2, 4 - dinitrobenzene synthesizing method. The method of the invention to 2, 4 - dinitro chlorobenzene as raw materials, the use of methanol as a solvent, under mild conditions, and sodium methoxide reaction synthesis of 2, 4 - dinitro anisole. And the reported 2, 4 - dinitrobenzene ether synthesis method comparison, this invention has low cost of material, mild reaction conditions, the operation is simple, high reaction efficiency, without side reaction product purity and the like. (by machine translation)

Convenient, metal-free ipso-nitration of arylboronic acids using nitric acid and trifluoroacetic acid

A feasible protocol for the direct ipso-nitration of arylboronic acids using trifluoroacetic acid and nitric acid as nitration reagent has been developed. Various aromatic nitro compounds are produced in moderate to good yields under the metal-free conditions. The method is operationally simple and regioselective, and might have potential application in industry.