610-34-4

Usage

Uses

Used in Organic Chemistry:
Ethyl 2-nitrobenzoate is used as a synthetic intermediate for the production of various organic compounds. Its versatility in chemical reactions makes it a valuable component in the synthesis of pharmaceuticals, dyes, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical sector, ethyl 2-nitrobenzoate serves as a key precursor in the synthesis of drugs. Its ability to undergo various chemical transformations allows for the creation of a wide range of medicinal agents, contributing to the development of new treatments and therapies.
Used in Dye Industry:
Ethyl 2-nitrobenzoate is also utilized as a starting material in the manufacture of dyes. Its chemical properties facilitate the production of diverse colorants used in various applications, including textiles, plastics, and printing inks.
Used in Environmental Management:
Given its potential environmental hazard, ethyl 2-nitrobenzoate is involved in the development and implementation of proper disposal methods. This application ensures that the compound is managed responsibly to mitigate any negative impacts on the environment, adhering to local regulations and best practices in waste management.

InChI:InChI=1/C9H9NO4/c1-2-14-9(11)7-5-3-4-6-8(7)10(12)13/h3-6H,2H2,1H3

Upstream product

• 64-17-5 ethanol 
• 552-16-9 ortho-nitrobenzoic acid 
• 100881-12-7 (2-nitro-phenyl)-(toluene-4-sulfonyloxy)-acetonitrile 
• 141-52-6 sodium ethanolate 
• 591-09-3 nitro acetate 
• 93-89-0 benzoic acid ethyl ester 
• 108-24-7 acetic anhydride 
• 552-89-6 2-nitro-benzaldehyde 
• 64-67-5 diethyl sulfate 
• 31042-59-8 phenyl 2-nitrobenzoate 
• 88356-11-0 o-nitrobenzaldehyde diethylacetal 
• 7697-37-2 nitric acid 
• 610-14-0 2-nitrobenzyl chloride 
• 201230-82-2 carbon monoxide 

Downstream Products

• 573-79-5 2,2'-azoxy-di-benzoic acid 
• 57892-27-0 ethyl 2-nitrosobenzoate 
• 38476-40-3 ethyl 2-(hydroxyamino)benzoate 
• 87-25-2 2-ethoxycarbonylaniline 
• 134-20-3 2-carbomethoxyaniline 
• 27542-75-2 2-nitro-benzoic acid menthyl ester 
• 612-25-9 2-Nitrobenzyl alcohol 
• 29091-47-2 phenyl N-(2-nitrophenyl)carbamate 
• 1134-10-7 2-nitrobenzoyl azide 
• 26707-36-8 2-nitro-benzoic acid-(1-p-tolyl-ethylidenehydrazide) 
• 29091-48-3 p-Methoxyphenyl-N-(o-nitrophenyl)carbamat 
• 29091-49-4 (2-nitro-phenyl)-carbamic acid-(4-nitro-phenyl ester) 
• 19011-95-1 2-nitro-benzoic acid benzylidenehydrazide 
• 304479-42-3 3-(2-nitro-benzoylhydrazono)-butyric acid ethyl ester 

Relevant academic research and scientific papers

Nitration of deactivated aromatic compounds via mechanochemical reaction

A variety of deactivated arenes were nitrated to their corresponding nitro derivatives in excellent yields under high-speed ball milling condition using Fe(NO3)3·9H2O/P2O5 as nitrating reagent. A radical involved mechanism was proposed for this facial, eco-friendly, safe, and effective nitration reaction.

Design, Synthesis, and Study of the Insecticidal Activity of Novel Steroidal 1,3,4-Oxadiazoles

A series of novel steroidal derivatives with a substituted 1,3,4-oxadiazole structure was designed and synthesized, and the target compounds were evaluated for their insecticidal activity against five aphid species. Most of the tested compounds exhibited potent insecticidal activity against Eriosoma lanigerum (Hausmann), Myzus persicae, and Aphis citricola. Compounds 20g and 24g displayed the highest activity against E. lanigerum, showing LC50 values of 27.6 and 30.4 μg/mL, respectively. Ultrastructural changes in the midgut cells of E. lanigerum were detected by transmission electron microscopy, indicating that these steroidal oxazole derivatives might exert their insecticidal activity by destroying the mitochondria and nuclear membranes in insect midgut cells. Furthermore, a field trial showed that compound 20g exhibited effects similar to those of the positive controls chlorpyrifos and thiamethoxam against E. lanigerum, reaching a control rate of 89.5% at a dose of 200 μg/mL after 21 days. We also investigated the hydrolysis and metabolism of the target compounds in E. lanigerum by assaying the activities of three insecticide-detoxifying enzymes. Compound 20g at 50 μg/mL exhibited inhibitory action on carboxylesterase similar to the known inhibitor triphenyl phosphate. The above results demonstrate the potential of these steroidal oxazole derivatives to be developed as novel pesticides.

PROCESS FOR THE PREPARATION OF QUINOLONE BASED COMPOUNDS

The present invention relates to an improved process for the preparation of quinolone based compounds of general formula (I) using intermediate compound of general formula (XII). Invention also provides an improved process for the preparation of compound of formula (I-a) using intermediate compound of formula (XII-a) and some novel impurities generated during process. Compounds prepared using this process can be used to treat anemia.

N-(5-Methyl-1,3-Thiazol-2-yl)-2-{[5-((Un)Substituted- Phenyl)1,3,4-Oxadiazol-2-yl]Sulfanyl}acetamides. Unique Biheterocycles as Promising Therapeutic Agents

An electrophile, 2-bromo-N-(5-methyl-1,3-thiazol-2-yl)acetamide, was synthesized by the reaction of 5-methyl-1,3-thiazol-2-amine and bromoacetyl bromide in an aqueous medium. In a parallel scheme, a series of (un)substituted benzoic acids was converted sequentially into respective esters, acid hydrazides, and then into 1,3,4-oxadiazole heterocyclic cores. The electrophile was coupled with the aforementioned 1,3,4-oxadiazoles to obtain the targeted bi-heterocyles. Structural analysis of the synthesized compounds was performed by IR, EI-MS, 1H NMR, and 13C NMR. The enzyme inhibition study of these molecules was carried out against four enzymes, namely, acetylcholinesterase, butyrylcholinesterase, α-glucosidase, and urease. The interactions of these compounds with respective enzymes were recognized by their in silico study. Moreover, their cytotoxicity was also determined to find out their utility as possible therapeutic agents.

Synthesis, spectral analysis and antibacterial evaluation of 5-substituted-1,3,4-oxadiazol-2-yl 4-(4-methylpiperidin-1-ylsulfonyl)benzyl sulfides

Owing to valuable biological activities of 1,3,4-oxadiazole, sulfamoyl and piperidine functionalities, some new 1-(4-{[(5-substituted-1,3,4-oxadiazol-2-yl) thio]methyl}benzene sulfonyl)-4-methylpiperidine (6a-o) derivatives have been introduced. The target molecules were synthesized from different aralkyl/aryl carboxylic acids, 1a-o, through a series of steps. First the compounds, 1a-o, were converted to heterocyclic 1,3,4-oxadiazole nucleophiles, 4a-o. Second an electrophile as 1-(4-bromomethylbenzenesulfonyl)-4-methylpiperidine (5) was synthesized from 4-methylpiperidine. Finally the target compounds, 6a-o, were prepared by reacting 4a-o with 5 in DMF and LiH. The final compounds were structurally elucidated by spectral data of IR, 1H-NMR and EI-MS. All the compounds were screened for their antibacterial evaluation and found to exhibit valuable results.

Solvent- and Metal-free Oxidative Esterification of Aromatic Aldehydes Using Urea-2,2-dihydroperoxypropane as a New Solid Oxidant

Urea-2,2-dihydroperoxypropane as a noble and solid gem-dihydroperoxide derivative was used to transform various aromatic aldehydes to their corresponding benzoate derivatives in the presence of HBr under mild conditions at room temperature in high yields and short reaction times.

Polymer supported Zn-salen complexes: An effective one-pot oxidative esterification of aldehydes to carboxylic esters

Polymer-supported Zn-salen (PS-Zn-salen) complexes were synthesized, characterized and used as a catalyst for one-pot oxidative esterification of aldehydes with alcohols. The PS-Zn-salen heterogeneous catalyst exhibited a high-performance for the oxidative esterification of aldehydes to the corresponding methyl/ethyl esters using hydrogen peroxide as a green oxidant. Due to the synergistic effect of polymer support, the heterogeneous catalyst presented superior catalytic activity and afford 100% conversion of 3,4,5-trimethoxybenzaldehyde and 4-chlorobenzaldehyde to corresponding esters under optimized conditions. The different alcohol substrates study (viz. methyl alcohol, ethyl alcohol, allyl alcohol and benzyl alcohol) showed reasonable selectivity for esters, indicating the scope of the catalysts. Significantly, the synthesized complexes possess good hydrophobic/heterogeneous properties, which permit facile reclamation of the catalyst by using mere filtration. Moreover, the effect of counter anions of complex also studied which indicated that there is no appreciable influence on the conversion of product. The catalyst was reused up to 5th successive run with the average conversion of ester 87.4%. Mechanistic studies have recognized that this “one pot” direct oxidative esterification proceeds through acid formation, proven by a GC–MS. The catalyst is also found to be very stable, up to 280?°C, confirmed by the thermo gravimetric study.

Zinc Complexes with Cyanoxime: Structural, Spectroscopic, and Catalysis Studies in the Pivaloylcyanoxime-Zn System

Reaction of 2-hydroxyimino-4,4-dimethyl-3-oxo-pentanenitrile (common abbreviation HPiCO, pivaloyl-cyanoxime) with zinc sulfate in an aqueous solution results in the formation of the two new complexes: [Zn(PiCO){H(PiCO)2}(H2O)] (I) and tetranuclear Zn complex [Zn4(μ3-OH)2(PiCO)6 (H2O)4] (II). Both complexes were characterized by elemental analysis, IR- and UV-visible spectra, DSC/TGA studies, and X-ray analysis. In complex II, the PiCO- cyanoxime anion adopts three bidentate binding modes: O-monodentate, chelating (κ2), and bridging (2) coordinations. Also, the ligand represents the mixture of two diasteromers (cis-anti and cis-syn) that form five- and six-membered chelate rings with Zn atoms and cocrystallize in one unit cell at population of 0.57-0.43. There are two crystallographically different Zn-centers in the ASU, and two μ3-bridging hydroxo-groups arrange via inversion center the formation of an elegant tetranuclear complex. Each Zn atom has a molecule of coordinated water and is in the distorted octahedral environment. Because of the structural flexibility and multidentate propensity of the pivaloyl-cyanoxime, complex II may act as a structural model of naturally occurring Zn-containing enzymes. Indeed, compound I exhibits an efficient catalytic performance for transesterification reaction of various esters in ethanol under mild reaction conditions. Therefore, obtained results allow assignment of observed activity as green catalysis.

Synthesis of oxadiazoline and quinazolinone derivatives and their biological evaluation as nitric oxide synthase inhibitors

The synthesis of two new families of compounds with oxadiazoline and quinazolinone structures and their in vitro biological evaluation as inhibitors of both neuronal and inducible nitric oxide synthases (nNOS and iNOS) are described. These derivatives have been obtained from cyclization of substituted benzohydrazides with acid anhydrides followed by reduction, using different synthetic procedures. Their structures were confirmed by high-resolution mass spectroscopy and 1H and 13C nuclear magnetic resonance data. In general, the assayed compounds show better inhibition values of nNOS than of iNOS, being 7d the most active derivative with a quinazolinone scaffold, and 6t the best oxadiazoline one and the best nNOS inhibitor of all tested compounds. The structure–activity relationships are discussed in terms of the effects of the substituents on both 2- and 3-positions of the heterocyclic rings.

Design, synthesis, pharmacological evaluation and molecular docking studies of substituted oxadiazolyl-2-oxoindolinylidene propane hydrazide derivatives

The manuscript describes design and synthesis of novel oxadiazolyl-2-oxoindolinylidene propane hydrazides as amide tethered hybrids of indole and oxadiazole and their evaluation for antiinflammatory and analgesic activity. The compounds were synthesized following five step reaction to yield fifteen derivatives as 3-(5-substituted-1,3,4-oxadiazol-2-yl)-N′-[2-oxo-1,2-dihydro-3Hindol-3-ylidene]propane hydrazides. The final derivatives 3-[5-(4-hydroxyphenyl)-1,3,4-oxadiazol-2-yl]-N′-[2-oxo-1,2-dihydro-3H-indol-3-ylidene]propane hydrazide and 3-[5-(4-methylphenyl)-1,3,4-oxadiazol-2-yl]-N′-[2-oxo-1,2-dihydro-3H-indol-3-ylidene]propane hydrazide were found to be highly promising molecules with severity index of 0.35 and 0.56, respectively, which is promising for an analgesic compound. The hydroxy and methyl substitution on phenyl ring system provided with active anti-inflammatory compounds having increase in reaction time of 84.11 and 83.17percent, respectively compared to standard drug at 85.84percent. Molecular docking studies exhibit comparable interaction with synthesized derivatives and standard drug having a dock score of -4.44 by the K-nearest neighbour genetic algorithm method.