89-58-7

Usage

Chemical Properties

pale yellow liquid

Synthesis Reference(s)

Synthesis, p. 690, 1978 DOI: 10.1055/s-1978-24859

General Description

Clear pale yellow to amber liquid.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

2,5-Dimethylnitrobenzene is incompatible with strong oxidizers and strong bases .

Fire Hazard

2,5-Dimethylnitrobenzene is probably combustible.

InChI:InChI=1/C8H9NO2/c1-6-3-4-7(2)8(5-6)9(10)11/h3-5H,1-2H3

Upstream product

• 106-42-3 para-xylene 
• 3460-29-5 4-nitro-2,5-xylidine 
• 67-56-1 methanol 
• 54874-33-8 (E)-1,4-dimethyl-4-nitrocyclohexa-2,5-dien-1-ol 
• 54874-32-7 (E)-1,4-dimethyl-4-nitrocyclohexa-2,5-dienyl acetate 
• 54874-31-6 1,4-dimethyl-c-4-nitrocyclohexa-2,5-dien-r-1-yl acetate 
• 7697-37-2 nitric acid 
• 75-52-5 nitromethane 
• 95-72-7 2-chloro-1,4-dimethyl-benzene 
• 780820-44-2 3,6-dimethyl-2-(trimethylsilyl)phenyl triflate 
• 7325-46-4 1,4-phenylenediacetic acid 
• 1455471-51-8 2,2'-(2-nitro-1,4-phenylene)diacetic acid 
• 108-24-7 acetic anhydride 

Downstream Products

• 610-29-7 2-nitroterephthalic acid 
• 95-78-3 2,5-Dimethylaniline 
• 609-92-7 2,5-dimethyl-1,3-dinitrobenzene 
• 711-41-1 2,3-dinitro-p-xylene 
• 3096-64-8 N-(2,5-dimethylphenyl)hydroxylamine 
• 3096-71-7 2,5-dimethyl-4-amino phenol 
• 103264-29-5 (4-methyl-2-nitro-phenyl)-pyruvic acid 
• 18102-22-2 1-(chloromethyl)-2,5-dimethyl-3-nitrobenzene 
• 31684-75-0 4-benzoyl-2,5-dimethylaniline 
• 18714-08-4 N-(2,5-Dimethyl-phenyl)-imidophosphorsaeure-triethylester 
• 22846-97-5 (2,5-Dimethyl-phenyl)-phosphoramidic acid diethyl ester 
• 109277-81-8 1-amino-2-(β-hydroxyethyl)-5-methylbenzene 
• 65813-72-1 2-(4-methyl-2-nitrophenyl)ethanol 
• 102781-38-4 2-(4-methyl-2-nitrophenyl)-1,3-propanediol 

Relevant academic research and scientific papers

One-pot process for preparing acetic acid -2, 5 -dimethylphenyl ester and 2,5 -dimethylnitrobenzene (by machine translation)

The method comprises the following steps of: adding acetic anhydride in a single-mouth flask; adding additional p-xylene; adding the reaction solution obtained in Step III to a separatory funnel; stirring the reaction; cooling to room temperature; and quenching the reaction solution obtained in the step three steps: adding deionized water, stirring the reaction and cooling to room temperature; and quenching the reaction solution in step three steps: adding deionized water, stirring the reaction and cooling to room temperature; and thirdly, distilling the reaction solution obtained in the step three steps into dichloromethane to volatilize to obtain a product, namely acetic acid -2 -2, 5 - 5 -dimethylphenyl ester 2,5 - and 2,5 -dimethylnitrobenzene. To the method, nitrate is used as an oxidant and a nitrate agent, the price is low,2-dimethylnitrobenzene can be obtained while the acetic acid 5 - and 2,5 -dimethylphenyl ester are obtained, two products can be obtained through one-step reaction, and the utilization rate of the raw material is improved. (by machine translation)

Method and device for preparing methylnitro-benzene by channelization

The invention discloses a method and a device for preparing methylnitro-benzene by channelization. The device comprises a storage tank, a nitrogen dioxide cylinder, an ozone generator, a flow pump, agas flowmeter, a reaction pipeline filled with a catalyst, a mixing pipeline, two T-shaped mixed joints, a cooling system, a heating system, a back pressure valve and a receiving tank. The method specifically comprises the following steps: opening the cooling system and the heating system; opening the ozone generator; arranging the flow pump and the gas flowmeter; and mixing raw materials liquid methyl benzene and nitrogen dioxide through the first T-shaped mixing joint and feeding the mixture into the mixing pipeline, then mixing the mixture with ozone in the second T-shaped mixing joint, feeding the mixture into the reaction pipeline filled with the catalyst for a nitrifying reaction, and post-treating a reaction liquid to obtain methylnitro-benzene. The method is controlled precisely and automatically, and is simple to operate, mild in reaction condition, simple in post treatment, quick to transfer mass and heat, high in safety and good in economical benefit.

Hydrophobic WO3/SiO2 catalyst for the nitration of aromatics in liquid phase

WO3/SiO2 solid acid catalyst synthesized using sol gel method has shown promising activity (up to 65% conversion) for aromatic nitration in liquid phase using commercial nitric acid (70%) as nitrating agent without using any sulfuric acid. The water formed during the reaction as well as water from dilute nitric acid (70%) was removed azeotropically, however due to the hydrophilic nature of the catalyst, some water gets strongly adsorbed on catalyst surface forming a barrier layer between catalyst and organics. This prevents effective adsorption of substrate on catalyst surface for its subsequent reaction. To improve the activity further, the hydrophilic/hydrophobic nature of the catalyst was altered by post modification by grafting with commercial short chain organosilane (Dynasylan 9896). The modified 20% WO3/SiO2 catalyst when used for o-xylene nitration in liquid phase, showed significant increase in the conversion from 65% to 80% under identical reaction conditions. Catalyst characterization revealed decrease in the surface area of 20% WO3/SiO2 from 356 m2/g to 302 m2/g after grafting with Dynasylan 9896. The fine dispersion of WO3 particles (2–5 nm) on silica support was not affected due to modification. NMR and FTIR study revealed the decrease in surface hydroxyl groups imparting hydrophobicity to the catalyst. Interestingly the total acidic sites of the catalyst remained almost unaltered (0.54 mmol NH3/g) even after modification. Even though, the acidity and other characteristics of the catalyst did not change appreciably, there was a considerable increase in the o-xylene conversion which can be ascribed to the hydrophobic nature of the catalyst.

MOF Decomposition and Introduction of Repairable Defects Using a Photodegradable Strut

Photoswitchable components can modulate the properties of metal organic frameworks (MOFs); however, photolabile building blocks remain underexplored. A new strut NPDAC (2-nitro-1,4-phenylenediacetic acid) that undergoes photodecarboxylation has been prepared and incorporated into a MOF, using post-synthetic linker exchange (PSLE) from the structural analogue containing PDAC (p-phenylenediacetic acid). Irradiation of NPDAC-MOF leads to MOF decomposition and concomitant formation of amorphous material. In addition to complete linker exchange, MOFs containing a mixture of PDAC and NPDAC can be obtained through partial linker exchange. In NPDAC30-MOF, which contains approximately 30 % NPDAC, the MOF retains crystallinity after irradiation, but the MOF contains defect sites consistent with loss of decarboxylated NPDAC linkers. The defect sites can be repaired by exposure to additional PDAC or NPDAC linkers at a much faster rate than the initial exchange process. The photoremoval and replacement process may lead to a more general approach to customizable MOF structures.

HNO3/HFIP: A Nitrating System for Arenes with Direct Observation of π-Complex Intermediates

This report describes an efficient nitrating system for the nitration of arenes at room temperature by using an equivalent of nitric acid in HFIP (1,1,1,3,3,3-hexafluoroisopropanol). The π-complex intermediate of an arene with a nitronium ion stabilized by HFIP can be directly observed by UV-vis spectra and is supported by theoretical calculations.

Nucleophilic Nitration of Arynes by Sodium Nitrite and its Multicomponent Reaction Leading to Double-Functionalized Arenes

An unusual nucleophilic nitration of arynes by NaNO2 in the presence of water has been developed, and the concept was further demonstrated to accomplish a double functionalization of arynes using a multicomponent reaction protocol to synthesize pharmaceutically important (2-nitrophenyl)methanol derivatives. Such substitution ortho to -NO2 is difficult by other means. The reaction conditions are mild and avoid the use of strong acids, expensive transition metal catalysts, and additives.

Poly(4-vinylpyridine)-nitrating mixture complex (PVP-NM): Solid nitrating mixture equivalent for safe and efficient aromatic nitration

Friedel-Crafts type aromatic nitration has served as an indispensable reaction within both industrial and academic applications. However, growing concern over the use of copious amounts of strong acids has prompted the search for more environmentally friendly alternatives. Polymer-bound Bronsted acids, on the other hand, have been shown useful as convenient alternatives to liquid acids. Nitric acid and sulfuric acids have, therefore, been combined, both individually and as a mixture, with poly(4-vinylpyridine). The new solid acid systems have been used to nitrate both activated and deactivated arenes under mild conditions and proved to be effective nitrating agent.

Regioselective nitration of m-xylene catalyzed by zeolite catalyst

Nitration with nitric acid and acetic anhydride via acetyl nitrate as nitrating species is efficient with the substrate m-xylene as solvent. Zeolite Hβ with an SiO2/Al2O3 ratio of 500 was found to be the most active of the catalysts tried both in yield and regioselectivity in the nitration of m-xylene. The molecular volume of the reactants was calculated with the Gaussian 09 program at the B3LYP/6-311+G(2d, p) level and compared with the size of the zeolite Hβ channels. A range of other substrates were subjected to the nitrating system under the same conditions as those optimized for m-xylene and excellent selectivity was obtained.

Regioselective preparation of 4-nitro-o-xylene using nitrogen dioxide/molecular oxygen over zeolite catalysts. remarkable enhancement of para-selectivity

In the presence of molecular oxygen and zeolite H-β with Si/Al 2 = 500, o-xylene reacted regioselectively with liquid nitrogen dioxide at 35 °C to yield mononitro-o-xylenes as the main product, where the 4-nitro-o-xylene isomer predominated up to 89% and the 4-nitro-/3-nitro-o- xylene isomer ratio improved to 7.8. The process is eco-friendly, less expensive, and the zeolite could be easily regenerated by a simple workup to afford results similar to those obtained with the fresh catalyst.

Eco-friendly nitration of benzenes over zeolite-β-SBA-15 composite catalyst

Direct synthesis of microporous-mesoporous zeolite-β-SBA-15 (ZBS-15) composite catalyst from the synthetic precursors of SBA-15and zeolite-β seeds under acidic hydrothermal conditions through the simultaneous self-assembly of mesoporous silica SBA-15 and zeolite-β has been accomplished and characterized the ZBS-15 catalyst by XRD, N2 sorption, FT-IR, TPD of ammonia and SEM techniques. The activity of the ZBS-15 composite catalyst for the nitration of benzenes under solvent-free conditions has been investigated, which revealed that there is a significant synergistic influence of both zeolite-β and SBA-15 materials on the activity of the ZBS-15 catalyst.