85-38-1

Usage

Uses

Used in Agriculture:
3-Nitrosalicylic acid is used as a soil and water conditioner to improve fertility. It binds to molybdenum, which is essential for the activity of nitrogenase, an enzyme involved in the nitrogen cycle and the conversion of atmospheric nitrogen into ammonia.
Used in Corrosion Inhibition:
3-Nitrosalicylic acid (3NSA) is used as a corrosion inhibitor. It can be used as a supporting electrolyte for the electrodeposition of pyrrole on zinc for corrosion protection. This application helps to prevent the corrosion of metal surfaces and extends the lifespan of materials used in various industries.
Used in Chelating Therapy:
3NSA can also be used as a ligand for the synthesis of complexes with iron and aluminum. These complexes are used in chelating therapy, which is a medical treatment that involves the administration of chelating agents to remove heavy metals from the body. This application is particularly useful in cases of heavy metal poisoning or in the treatment of certain diseases caused by metal imbalances.

InChI:InChI=1/C7H5NO5/c9-6-4(7(10)11)2-1-3-5(6)8(12)13/h1-3,9H,(H,10,11)/p-2

Upstream product

• 118-93-4 o-hydroxyacetophenone 
• 3970-35-2 2-chloro-3-nitrobezoic acid 
• 69-72-7 salicylic acid 
• 56-23-5 tetrachloromethane 
• 88-75-5 2-hydroxynitrobenzene 
• 482-89-3 1H,1H'-2,2'-Biindolylidene-3,3'-dione 
• 50-78-2 aspirin 
• 7697-37-2 nitric acid 
• 64-19-7 acetic acid 
• 7664-93-9 sulfuric acid 
• 90-02-8 salicylaldehyde 
• 28177-71-1 2-hydroxy-3-hydroxymethyl-1-nitrobenzene 
• 5274-70-4 3-nitrosalicylic aldehyde 
• 40751-88-0 2-methoxy-3-nitrobenzoic acid 

Downstream Products

• 90564-26-4 2-methoxy-3-nitro-benzoic acid methyl ester 
• 40751-88-0 2-methoxy-3-nitrobenzoic acid 
• 22621-41-6 2-hydroxy-3-nitro-benzoic acid methyl ester 
• 75024-21-4 3-nitro-2-propoxy-benzoic acid 
• 90564-38-8 2-Hydroxy-3-nitrobenzoesaeureethylester 
• 573-56-8 2,6-dinitrophenol 
• 609-99-4 3,5-dinitrosalicylic acid 
• 570-23-0 3-aminosalicylic acid 
• 22621-43-8 2-hydroxy-5-iodo-3-nitro-benzoic acid 
• 20294-48-8 diiodo-4,6 nitro-2 phenol 
• 35748-36-8 2-hydroxy-3-nitrobenzoyl chloride 
• 88-75-5 2-hydroxynitrobenzene 
• 68507-87-9 2-hydroxy-3-nitro-benzoic acid o-anisidide 
• 68507-88-0 4'-methoxy-2-hydroxy-3-nitrobenzanilide 

Relevant academic research and scientific papers

Continuous flow nitration of salicylic acid

Continuous flow nitration of salicylic acid using HNO3/AcOH was studied in the SS316 tubular microreactor. At specific reaction conditions, complete conversion of the reactant was achieved in less than 7 min. It yielded only mononitro derivatives with a higher selectivity of 5-nitrosalicylic acid. Presence of the lower amount of acetic acid in the reaction mixture was seen to be detrimental, leading to precipitation of the desired product (5-nitrosalicylic acid). Reaction at higher temperatures yielded byproducts. The continuous mode operation using the system comprising the microdevices was demonstrated for 2 h with consistent composition at the outlet

Method for selectively synthesizing 3-nitrosalicylic acid in continuous flow region

The invention provides a method for selectively synthesizing 3-nitrosalicylic acid in a continuous flow region. According to the method, salicylic acid and nitric acid are used as raw materials and react in a micro-channel reactor in the presence of a cat

Advanced Real-Time Process Analytics for Multistep Synthesis in Continuous Flow**

In multistep continuous flow chemistry, studying complex reaction mixtures in real time is a significant challenge, but provides an opportunity to enhance reaction understanding and control. We report the integration of four complementary process analytical technology tools (NMR, UV/Vis, IR and UHPLC) in the multistep synthesis of an active pharmaceutical ingredient, mesalazine. This synthetic route exploits flow processing for nitration, high temperature hydrolysis and hydrogenation reactions, as well as three inline separations. Advanced data analysis models were developed (indirect hard modeling, deep learning and partial least squares regression), to quantify the desired products, intermediates and impurities in real time, at multiple points along the synthetic pathway. The capabilities of the system have been demonstrated by operating both steady state and dynamic experiments and represents a significant step forward in data-driven continuous flow synthesis.

2-Methyl-1,3-disulfoimidazolium polyoxometalate hybrid catalytic systems as equivalent safer alternatives to concentrated sulfuric acid in nitration of aromatic compounds

Ionic liquid-derived polyoxometalate salts [mdsim]3[PM12O40] (where M?=?W and Mo) of two heteropolyacids H3PW12O40.nH2O and H3PMo12O40.nH2O were synthesized using 2-methyl-1,3-disulfoimidazolium chloride ([mdsim][Cl]) ionic liquid and the corresponding heteropolyacids. Three equivalents of [mdsim][Cl] were treated with the respective Keggin-structured heteropolyacids (one equivalent) in aqueous medium at room temperature to afford the water-stable ionic polyoxometalates as acidic solids. They were completely characterized using spectroscopic and other analytical techniques including thermal analysis and Hammett acidity studies. The inherent Br?nsted acidic properties of ─SO3H group of these polyoxometalate salts were studied for the nitration of aromatic compounds with 69% HNO3 at normal temperature and 80°C without use of any external concentrated sulfuric acid. These strongly acidic polyoxometalates display good recyclability and efficient reusability.

Improved synthesis of 3-nitrosalicylic acid

Nitration of salicylic acid using 2-propyl nitrate/sulfuric acid/tetrabutylammonium hydrogensulfate/dichloromethane/water yielded a mixture of 3-nitro and 5-nitrosalicylic acids in the ratio 56:44. Pure potassium 3-nitrosalicylate was crystallized and converted to 3-nitrosalicylic acid in 30% overall yield. Copyright

A simple and practical copper-catalyzed approach to substituted phenols from aryl halides by using water as the solvent

Water surprise! A simple and practical copper-catalyzed approach to substituted phenols by hydroxylation of aryl halides has been developed by using environmentally benign water as the solvent (see scheme). The method proceeds under mild conditions and is tolerant towards various functional groups in the substrates.

Fast and efficient nitration of salicylic acid and some other aromatic compounds over H3PO4/TiO2-ZrO2 using nitric acid

TiO2-ZrO2 (1/1)-surf with Ti and Zr molar ratio of 1/1 was prepared with surfactant through a sol-gel method. The optimum experimental condition was investigated for nitration of salicylic acid. Then, a number of nitration reactions were carried out with a variety of aromatic compounds in the optimum condition. The 25 wt% H3PO4/TiO2-ZrO2 (1/1)-surf catalyst showed good selectivity and yield in a short time for the nitration of salicylic acid and some other aromatic compounds.

NITRATION OF ACTIVATED AROMATICS IN MICROREACTORS

The invention relates to the nitration of aromatic or heteroaromatic compounds, wherein an activated aromatic or heteroaromatic compound and a nitration agent, optionally in the presence of a solvent, are mixed intensely in a microreactor, and wherein the proportion of the nitration agent to the activated aromatic or heteroaromatic compound, the concentration of nitration agent in the reaction mixture, and the temperature are selected at levels such high that the nitration begins autocatalytically, and wherein the nitration product is obtained after leaving the microreactor and, optionally after an after-reaction time outside the microreactor.

Synthesis, structural investigations, hydrogen-deuterium exchange studies, and molecular modeling of conformationally stablilized aromatic oligoamides

Biasing the conformational preferences of aromatic oligoamides by internally placing intramolecular hydrogen bonds has led to a series of stably folded molecular strands. This article presents the results from extensive solid-state, solution, and computational studies on these folding oligomers. Depending on its backbone length, an oligoamide adopts a crescent or helical conformation. Surprisingly, despite the highly repetitive nature of the backbone, the internally placed, otherwise very similar intramolecular hydrogen bonds showed significantly different stabilities as demonstrated by hydrogen-deuterium exchange data. It was also observed that the hydrogen-bonding strength can be tuned by adjusting the substituents attached to the exterior of the aromatic backbones. Examining the amide hydrogen-deuterium exchange rates of trimers revealed that a six-membered hydrogen bond nearing the ester end is the weakest among all the four intramolecular hydrogen bonds of a molecule. This observation was verified by ab initio quantum mechanical calculations at the level of B3LYP/6-31G. Such a "weak point" creates the "battle of the bulge" where backbone twisting is centered, which is consistently observed in the solid-state structures of the four trimer molecules studied. In the solid state, the oligomers assemble into interesting one-dimensional structures. A pronounced columnar packing of short oligomers (i.e., dimers, trimers, and tetramer) and channel-like, potentially ion-conducting stacks of longer oligomers (i.e., tetramer, pentamer, and hexamer) were observed.

Helical organization in foldable aromatic oligoamides by a continuous hydrogen-bonding network

Introduction of a continuous internal hydrogen-bonding network suppressed the conformational flexibility of a series of oligoaromatic foldamers with a lengthened backbone. The helical ordering over up to six aromatic repeating units was established in solution by a 2D NOESY study and in the solid state by an X-ray diffraction method. Computational molecular modeling further corroborates the experimentally observed helical propagation in this class of foldable molecular strands.