89-39-4

Usage

Synthesis Reference(s)

Synthetic Communications, 16, p. 681, 1986 DOI: 10.1080/00397918608057740

InChI:InChI=1/C8H9NO4/c1-12-6-3-4-8(13-2)7(5-6)9(10)11/h3-5H,1-2H3

Upstream product

• 150-78-7 1,4-dimethoxybezene 
• 150-78-7 1,4-dimethoxybenzene radical cation 
• 102-56-7 2,5-dimethoxyaniline 
• 509-14-8 tetranitromethane 
• 67-56-1 methanol 
• 7697-37-2 nitric acid 
• 16090-33-8 2-nitrohydroquinone 
• 74-88-4 methyl iodide 
• 121-43-7 Trimethyl borate 
• 5081-36-7 3-methoxy-4-nitrobenzoic acid 
• 186581-53-3 diazomethane 
• 1568-70-3 4-methoxy-2-nitrophenol 

Downstream Products

• 103942-91-2 6,9-dimethoxyphenazine-1-carboxylic acid 
• 13860-45-2 1,4-Dimethoxy-phenazin 
• 67119-46-4 N-(2,5-Dimethoxyphenyl)hydroxylamin 
• 132370-32-2 (2,5-Dimethoxy-4-nitro-phenyl)-acetonitrile 
• 1568-70-3 4-methoxy-2-nitrophenol 
• 6319-28-4 bis-(2,5-dimethoxy-phenyl)-diazene 
• 501-60-0 1,2-di(p-tolyl)diazene 
• 107135-53-5 2-bromo-1,4-dimethoxy-3-nitrobenzene 
• 115929-62-9 3-bromo-2,5-dimethoxyaniline 
• 16169-28-1 4-methoxy-2-nitro-1-propoxy-benzene 
• 18468-36-5 1-methoxy-2-nitro-4-propoxy-benzene 
• 25445-13-0 2,5-dimethoxy-4-nitroacetanilide 
• 3467-59-2 2,5-dimethoxyacetanilide 
• 32065-63-7 N-(2,5-dimethoxyphenyl)-N'-phenylthiourea 

Relevant academic research and scientific papers

Metal-free Transformations of Nitrogen-Oxyanions to Ammonia via Oxoammonium Salt

Transformations of nitrogen-oxyanions (NOx?) to ammonia impart pivotal roles in sustainable biogeochemical processes. While metal-mediated reductions of NOx? are relatively well known, this report illustrates proton-assisted transformations of NOx? anions in the presence of electron-rich aromatics such as 1,3,5-trimethoxybenzene (TMB?H, 1 a) leading to the formation of diaryl oxoammonium salt [(TMB)2N+=O][NO3?] (2 a) via the intermediacy of nitrosonium cation (NO+). Detailed characterizations including UV/Vis, multinuclear NMR, FT-IR, HRMS, X-ray analyses on a set of closely related metastable diaryl oxoammonium [Ar2N+=O] species disclose unambiguous structural and spectroscopic signatures. Oxoammonium salt 2 a exhibits 2 e? oxidative reactivity in the presence of oxidizable substrates such as benzylamine, thiol, and ferrocene. Intriguingly, reaction of 2 a with water affords ammonia. Perhaps of broader significance, this work reveals a new metal-free route germane to the conversion of NOx to NH3.

New diarylsulfonamide inhibitors of Leishmania infantum amastigotes

New drugs against visceral leishmaniasis with mechanisms of action differing from existing treatments and with adequate cost, stability, and properties are urgently needed. No antitubulin drug is currently in the clinic against Leishmania infantum, the causative agent of visceral leishmaniasis in the Mediterranean area. We have designed and synthesized a focused library of 350 compounds against the Leishmania tubulin based on the structure-activity relationship (SAR) and sequence differences between host and parasite. The compounds synthesized are accessible, stable, and appropriately soluble in water. We assayed the library against Leishmania promastigotes, axenic, and intracellular amastigotes and found 0, 8, and 16 active compounds, respectively, with a high success rate against intracellular amastigotes of over 10%, not including the cytotoxic compounds. Five compounds have a similar or better potency than the clinically used miltefosine. 14 compounds showed a host-dependent mechanism of action that might be advantageous as it may render them less susceptible to the development of drug resistance. The active compounds cluster in five chemical classes that provide structure-activity relationships for further hit improvement and facilitate series development. Molecular docking is consistent with the proposed mechanism of action, supported by the observed structure-activity relationships, and suggests a potential extension to other Leishmania species due to sequence similarities. A new family of diarylsulfonamides designed against the parasite tubulins is active against Leishmania infantum and represents a new class of potential drugs with favorable cost, stability, and aqueous solubility for the treatment of visceral leishmaniasis (VL). These results could be extended to other clinically relevant species of Leishmania spp.

Methoxy and bromo scans on N-(5-methoxyphenyl) methoxybenzenesulphonamides reveal potent cytotoxic compounds, especially against the human breast adenocarcinoma MCF7 cell line

Thirty seven N-(5-methoxyphenyl)-4-methoxybenzenesulphonamide with methoxy or/and bromo substitutions (series 1-4) and with different substituents on the sulphonamide nitrogen have been synthesised. 21 showed sub-micromolar cytotoxicity against HeLa and HT-29 human tumour cell lines, and were particularly effective against MCF7. The most potent series has 2,5-dimethoxyanilines, especially the 4-brominated compounds 23–25. The active compounds inhibit microtubular protein polymerisation at micromolar concentrations, thus pointing at tubulin as the target. Co-treatment with the MDR inhibitor verapamil suggests that they are not MDR substrates. Compound 25 showed nanomolar antiproliferative potency. It severely disrupts the microtubule network in cells and arrests cells at the G2/M cell-cycle phase, thus confirming tubulin targeting. 25 triggered apoptotic cell death, and induced autophagy. Docking studies suggest binding in a distinct way to the colchicine site. These compounds are promising new antitumor agents acting on tubulin.

Electrochemical Nitration with Nitrite

Aromatic nitration has tremendous importance in organic chemistry as nitroaromatic compounds serve as versatile building blocks. This study represents the electrochemical aromatic nitration with NBu4NO2, which serves a dual role as supporting electrolyte and as a safe, readily available, and easy-to-handle nitro source. Stoichiometric amounts of 1,1,1-3,3,3-hexafluoroisopropan-2-ol (HFIP) in MeCN significantly increase the yield by solvent control. The reaction mechanism is based on electrochemical oxidation of nitrite to NO2, which initiates the nitration reaction in a divided electrolysis cell with inexpensive graphite electrodes. Overall, the reaction is demonstrated for 20 examples with yields of up to 88 %. Scalability is demonstrated by a 13-fold scale-up.

Nitration method for aryl phenol or aryl ether derivative

The invention relates to a nitration method for an aryl phenol or aryl ether derivative. The method comprises the steps of stirring an aryl phenol or aryl ether compound, nitrate, trimethylchlorosilane (TMSCl) and a copper salt in an acetonitrile solution in air at room temperature, simultaneously, monitoring extent of reaction through a TLC dot plate, removing a solvent from a mixture by a rotaryevaporator after a substrate is consumed completely, and carrying out purification through a silica-gel column, thereby obtaining a nitroolefin derivative. Meanwhile, the selective mono-nitration orbis-nitration of the substrate can be achieved through controlling equivalent weight of the nitrate. Compared with the prior art, the nitration method disclosed by the invention has the advantages that the consumption of strong-acid substances is avoided, the reaction conditions are mild, the yield is high, the applicable range of the substrate is wide, reaction activity is free of obvious attenuation after an amplified reaction, and an excellent yield is still obtained, so that the method has an obvious industrial application value.

3-(Ethoxycarbonyl)-1-(5-methyl-5-(nitrosooxy)hexyl)pyridin-1-ium cation: A green alternative to tert-butyl nitrite for synthesis of nitro-group-containing arenes and drugs at room temperature

Due to their remarkable properties, task-specific ionic liquids have turned out to be progressively popular over the last few years in the field of green organic synthesis. Herein, for the first time, we report that a new task-specific nitrite-based ionic liquid such as 3-(ethoxycarbonyl)-1-(5-methyl-5-(nitrosooxy)hexyl)pyridin-1-ium bis(trifluoromethanesulfonyl)imides (TS-N-IL) derived from biodegradable ethyl nicotinate indeed acted as an efficient and eco-friendly reagent for the synthesis of highly valuable nitroaromatic compounds and drugs including nitroxynil, tolcapone, niclofolan, flutamide, niclosamide and nitrazepam. The bridging of an ionic liquid with nitrite group not only increases the yield and rate of direct C[sbnd]N bond formation reaction but also allows easy product separation and recyclability of a byproduct. Nonvolatile nature, easy synthesis, merely stoichiometric need and mildness are a portion of the extra focal points of TS-N-IL while contrasted with tert-butyl nitrite an outstanding and highly-flammable reagent utilized largely in organic synthesis.

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.

Mechanical force under the action of the nitration of aromatic compounds of nitrate method (by machine translation)

The invention discloses a mechanical force under the action of the nitration of aromatic compounds of nitrate method. The invention provides a method for preparing aromatic nitro compounds, comprising the following steps: under the action of mechanical force, aromatic compound with a metal nitrate or its hydrate by the nitration reaction, to obtain the aromatic nitro compound; the mechanical fastener is machinery offers can cause material physical and/or chemical nature of the change of the external force. The mechanical force can be compression, shear, impact, friction, tensile, bending and vibration of any kind. The invention has the following advantages: without the use of any solvent, thereby avoiding the waste liquid produced; and without the use of the acidic substance, the reaction is complete after treatment is simple, without any damage to the apparatus; a very high conversion and selectivity, can be applied to the nitration of conventional aromatic compound. (by machine translation)

Rapid aerobic iodination of arenes mediated by hypervalent iodine in fluorinated solvents

Arenes are rapidly converted to the corresponding iodides by aerobic oxidative iodination at room temperature by treatment with iodine and catalytic quantities of nitrous acid in a fluorinated solvent. Dichloroiodic acid is proposed as the actual iodination reagent.

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.