119-10-8

Usage

Uses

Used in Chemical Synthesis:
4-Methyl-2-nitroanisole is used as a synthetic intermediate for the production of various organic compounds. Its reactivity in nucleophilic substitution reactions makes it a valuable building block in the synthesis of complex molecules.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4-Methyl-2-nitroanisole is used as a key component in the synthesis of certain pharmaceuticals. Its ability to undergo nucleophilic substitution reactions allows for the creation of new drug candidates with potential therapeutic applications.
Used in the Synthesis of 1-Dibromomethyl-4-Methoxy-2-Nitrobenzene:
4-Methyl-2-nitroanisole is used as a starting material for the synthesis of 1-dibromomethyl-4-methoxy-2-nitrobenzene, which is an important compound in the development of new chemical entities with potential applications in various fields, including pharmaceuticals and materials science.
General Description:
Nucleophilic substitution reactions of 4-methyl-2-nitroanisole in neat cyclohexylamine and piperidine have been reported. These reactions highlight the compound's reactivity and its potential use in the synthesis of various organic compounds, particularly those with pharmaceutical or industrial applications.

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

Upstream product

• 104-93-8 p-methylanizole 
• 67-56-1 methanol 
• 89-60-1 1-chloro-4-methyl-2-nitro-benzene 
• 119-33-5 4-methyl-2-nitrophenol 
• 77-78-1 dimethyl sulfate 
• 186581-53-3 diazomethane 
• 67-63-0 isopropyl alcohol 
• 108-93-0 cyclohexanol 
• 622-60-6 1-ethoxy-4-methylbenzene 
• 7697-37-2 nitric acid 
• 64-19-7 acetic acid 
• 56-23-5 tetrachloromethane 
• 108-88-3 toluene 
• 106-43-4 para-chlorotoluene 

Downstream Products

• 21043-02-7 4-methoxy-1-methyl-phenazine 
• 119-33-5 4-methyl-2-nitrophenol 
• 55315-09-8 Cyclohexyl-(4-methyl-2-nitro-phenyl)-amine 
• 61010-34-2 3-nitro-4-methoxybenzyl bromide 
• 190908-10-2 7-methoxy-2,4-dimethylindole 
• 35485-95-1 bis-(2-methoxy-5-methyl-phenyl)-diazene 
• 141600-28-4 5,5'-dimethoxy-2,2'-dimethyl-benzidine 
• 120-71-8 Cresidine 
• 6376-14-3 2-methoxy-5-methyl-4-chloroaniline 
• 142596-53-0 1-Methoxy-3,4-dimethyl-2-nitro-benzene 
• 168766-14-1 2-(4-methoxy-3-nitrophenyl)ethanol 
• 185062-89-9 (2-methoxy-5-methyl-3-nitrophenyl)methanol 
• 1330633-85-6 (Z)-2',4',6'-trimethoxystyryl-4-methoxy-3-nitrobenzyl sulfide 
• 1427278-44-1 C₁₉H₂₁NO₇S 

Relevant academic research and scientific papers

Interaction between Electron Donor and Acceptor Groups in Some Trisubstituted Benzenes. Part 1. Relative Reactivities of 4-Substituted 1,2-Dinitrobenzenes towards Sodium Methoxide

In an effort to study the effects of 'through conjugation' on the properties of some 1,2,4-trisubstituted benzenes, the rates of reaction of a series of four 4-substituted 1,2-dinitrobenzenes with sodium methoxide in methanol have been studied.Although reactivities at the 2-position were qualitatively in the order to be expected from inductive effects, those at the 1-position were highly sensitive to the influence of mesomeric donor action of the 4-substituent.Relatively large effects were seen for the 4-alkyl derivatives; and C-H hyperconjugation appeared to be stronger than C-C hyperconjugation.

ipso-Nitration: Formation of Nitronium Acetate Adducts in the Nitration of p-Acetamido-, p-Halogeno-, and p-Methoxy-toluenes, and α-p-Tolyloxyisobutyric acid

Low-temperature nitration of the title compounds in acetic anhydride gives 1,2-nitronium acetate adducts, except p-fluorotoluene which gives both 1,2 and 1,4 adducts and α-p-tolyloxyisobutyric acid which gives a spiro adduct.

Direct Acetoxylation of Arenes

Acetoxylation of arenes is an important reaction and an unmet need in chemistry. We report a metal-free, direct acetoxylation reaction using sodium nitrate under an anhydrous environment of trifluoroacetic acid, acetic acid, and acetic anhydride. Arenes (31 examples), with oxidation potentials (Eox, in V vs SCE) lower than benzene (2.48 V), were acetoxylated with good yields and regioselectivity. A stepwise, single electron-transfer mechanism is proposed.

Eco-Friendly Methodology for the Formation of Aromatic Carbon–Heteroatom Bonds by Using Green Ionic Liquids

A new sustainable method is reported for the formation of aromatic carbon–heteroatom bonds under solvent-free and mild conditions (no co-oxidant, no strong acid and no toxic reagents) by using a new type of green ionic liquid. The bromination of methoxy arenes was chosen as a model reaction. The reaction methodology is based on only using natural sodium bromine, which is transformed into an electrophilic brominating reagent within an ionic liquid, easily prepared from the melted salt FeCl3 hexahydrate. Bromination reactions with this in-situ-generated reagent gave good yields and excellent regioselectivity under simple and environmentally friendly conditions. To understand the unusual bromine polarity reversal of sodium bromine without any strong oxidant, the molecular structure of the reaction medium was characterised by Raman and direct infusion electrospray ionisation mass spectroscopy (ESI-MS). An extensive computational investigation using density functional theory methods was performed to describe a mechanism that suggests indirect oxidation of Br? through new iron adducts. The versatility of the methodology was successively applied to nitration and thiocyanation of methoxy arenes using KNO3 and KSCN in melted hexahydrated FeCl3.

Direct nitration method of electron-enriched aromatic hydrocarbons

The invention discloses a direct nitration method of electron-enriched aromatic hydrocarbons, and belongs to the field of organic synthesis. The direct nitration method is a novel green free radical nitration method; aromatic hydrocarbons are taken as raw materials, acetonitrile, dichloromethane, chloroform, or acetone is taken as a reaction solvent, at room temperature conditions, the raw materials and green nitration reagent tert-butyl nitrite (TBN) are subjected to free radical nitration so as to obtain nitro-aromatic compounds. According to the direct nitration method, no metal is adoptedin reaction, tert-butyl nitrite is directly adopted in nitration reaction. Electron-donating groups such as OMe are introduced, the electron density of aromatic compounds is increased, the nitration reaction possibility is increased. The using amount of tert-butyl nitrite is reduced; only a product and tert-butyl alcohol are generated, environment pollution is reduced. The direct nitration methodis promising in application prospect in the field of nitro-aromatic compound synthesis, green nitration is realized, and a novel idea is provided for large-scale industrialized nitro-aromatic compoundproduction.

4-METHOXYACRIDINE-1-CARBOXAMIDE DERIVATIVES AND THE PHENAZINE AND OXANTHRENE ANALOGS AS PDE4-INHIBITORS FOR THE TREATMENT OF ASTHMA AND CHRONIC PULMONARY DISEASE (COPD)

The present invention relates to new Phosphodiesterase type 4 (PDE4) inhibitors of the formula (1) for treatment of asthma: Ar is a substituted or unsubstituted aryl, substituted or unsubstituted arylalkyl, substituted or unsubstituted heterocyclic ring or substituted or unsubstituted heteroaryl ring; each occurrence of L is O, S or NR 3; X and A are independently-CRaRb-,-CRa-,-C(=B)-, O, S(O)m, N or NR3; each occurrence of m is 0, 1, or 2; n is 0-4; p is 0-2; Y is-C(=B)C(=D)NR 4 or-C(=B)NR4 B is O, S or NRa; D is O, S or NRa; The other substituents are defined in the claims.

Steroid and nitro phenol esters from Bignonia unguis-cati roots

Two new esters, β-sitosterol cerotate 1 and 2-(4-hydroxy-3-nitrophenyl)ethyl stearate 2 have been isolated from the roots of Bignonia unguis-cati (Bignoniaceae) and their structures are elucidated by spectroscopic and chemical studies.

Electrophilic nitration of aromatics in ionic liquid solvents

Potential utility of a series of 1-ethyl-3-methylimidazolium salts [emim][X] with X = OTf-, CF3COO-, and NO3- as well as [HNEtPri2][CF3COO] (protonated Huenig's base) ionic liquids were explored as solvent for electrophilic nitration of aromatics using a variety of nitrating systems, namely NH4NO3/TFAA, isoamyl nitrate/BF3·Et2O, isoamyl nitrate/TfOH, Cu(NO3)/TFAA, and AgNO3/Tf2O. Among these, NH4NO3/TFAA (with [emim][CF3COO], [emim][NO3]) and isoamyl nitrate/BF3·Et2O, isoamyl nitrate/TfOH (with [emim][OTf]) provided the best overall systems both in terms of nitration efficiency and recycling/reuse of the ionic liquids. For [NO2][BF4] nitration, the commonly used ionic liquids [emim][AlCl4] and [emim][Al2Cl7] are unsuitable, as counterion exchange and arene nitration compete. [Emim][BF4] is ring nitrated with [NO2][BF4] producing [NO2-emim][BF4] salt, which is of limited utility due to its increased viscosity. Nitration in ionic liquids is surveyed using a host of aromatic substrates with varied reactivities. The preparative scope of the ionic liquids was also extended. Counterion dependency of the NMR spectra of the [emim][X] liquids can be used to gauge counterion exchange (metathesis) during nitration. Ionic liquid nitration is a useful alternative to classical nitration routes due to easier product isolation and recovery of the ionic liquid solvent, and because it avoids problems associated with neutralization of large quantities of strong acid.

Nighttime tropospheric chemistry: Kinetics and product studies in the reaction of 4-Alkyl- and 4-Alkoxytoluenes with NO3 in gas phase

Alkylbenzenes are important constituents of gasoline and industrial solvents and contribute to the formation of tropospheric ozone. The removal of these compounds from the troposphere is due to reaction with OH during the day and with NO3 during the night. Five para-substituted toluenes are reacted with the nitrate radical in gas phase. Samples to be used for product analysis were preconcentrated and analyzed by GC-MSD analysis with the use of a reference curve. The yields of methanol, ethanol, and formaldehyde were determined by FTIR analysis of the reaction mixture in the chamber. Carbonyl compounds, benzyl alcohols, and nitroderivatives were formed. In the case of the alkoxytoluenes, products were also an alkanol, benzyl alcohols, and nitrophenols. Indirect rate constants measurements were performed by comparing by FTIR measurements the decay of the aromatic compound under investigation to that of a reference compound, with a known rate constant for the reaction with NO3 added to the gas mixture. Wall loss constants were evaluated by FTIR. A Hammett correlation with ρ = - 4.3 ± 0.6; r2-= 0.87 was obtained. This and the kinetic isotope effect of 1.5-1.8 suggest a reaction mechanism occurring via an addition-elimination pathway.

Transformations of arylcyclopropanes under the action of dinitrogen tetroxide

p-Bromophenylcyclopropane, 1- and 2-methylphenylcyclopropanes, and 1,2-di-p-tolyl- and l,2-bis(p-methoxyphenyl)cyclopropanes react with N2O4with opening of the three-membered ring. Reactions of p-methoxyphenylcyclopropane, 6-cyclopropyl-l,4-benzodioxane, and 2-cyclopropylfluorene yield the corresponding nitroaromatic derivatives with conservation of the cyclopropane ring. The nitration of p-methoxyphenylcyclopropane is accompanied by demethylation. 2-Nitro- and 4-nitrophenylcyclopropanes, as well as l-chloro-2-phenylcyclopropane, do not react with N2O4 under the same conditions. The differences in the behavior of arylcyclopropanes in reactions with N2O4 are explained by the different action of nitrosonium ion in the first reaction step: It acts as either electrophilic species capable of initiating opening of the cyclopropane ring or one-electron oxidant converting the initial arylcyclopropanes into the corresponding radical cations which are precursors of Wheland σ complexes responsible for aromatic nitration. copy;1998 MAHK "Hayka/Interperiodica".