606-27-9

Usage

Chemical Properties

clear yellow to orange-brownish liquid

Uses

Methyl 2-nitrobenzoate may be used in chemical synthesis studies.

Synthesis Reference(s)

Chemical and Pharmaceutical Bulletin, 29, p. 1475, 1981 DOI: 10.1248/cpb.29.1475

InChI:InChI=1/C8H7NO4/c1-13-8(10)6-4-2-3-5-7(6)9(11)12/h2-5H,1H3

Upstream product

• 93-58-3 benzoic acid methyl ester 
• 67-56-1 methanol 
• 552-16-9 ortho-nitrobenzoic acid 
• 186581-53-3 diazomethane 
• 610-14-0 2-nitrobenzyl chloride 
• 63133-13-1 N-methoxy-2-nitrobenzamide 
• 75-91-2 tert.-butylhydroperoxide 
• 552-89-6 2-nitro-benzaldehyde 
• 612-25-9 2-Nitrobenzyl alcohol 
• 67-68-5 dimethyl sulfoxide 
• 4731-65-1 tris(o-methoxyphenyl)phosphine 
• 610-15-1 2-nitrobenzamide 
• 609-73-4 o-nitroiodobenzene 
• 98-95-3 nitrobenzene 

Downstream Products

• 58165-13-2 Methyl,2-N-Hydroxylamino Benzoate 
• 3342-77-6 N-formylanthranilic acid 
• 118-92-3 anthranilic acid 
• 19354-50-8 3-methoxy-1-benzothiophene-2-carboxylic acid 
• 39264-16-9 2-nitrophenyl-2'-thiazolylketone 
• 40017-83-2 3-(2-Nitrophenyl)-3-oxopropionsaeurenitril 
• 1355966-15-2 C₁₃H₁₃N₃O₃ 
• 1355966-19-6 C₁₁H₈N₄O₂ 
• 1355966-22-1 C₁₁H₁₀N₄ 
• 50998-74-8 methyl N-tosylanthranilate 
• 552-16-9 ortho-nitrobenzoic acid 
• 98-95-3 nitrobenzene 
• 117375-30-1 2-nitrobenzoic acid 1-hexyl ester 
• 491-36-1 4-quinazolinol 

Relevant academic research and scientific papers

Direct C–H Carboxylation Forming Polyfunctionalized Aromatic Carboxylic Acids by Combined Br?nsted Bases

CO2 fixation into electron-deficient aromatic C–H bonds proceeds with the combined Br?nsted bases LiO-t-Bu and LiO-t-Am/CsF/18-crown-6 (t-Am = CEtMe2) under a CO2 atmosphere to afford a variety of polyfunctionalized aromat

Oxidative esterification of alcohols by a single-side organically decorated Anderson-type chrome-based catalyst

The direct esterification of alcohols with non-noble metal-based catalytic systems faces great challenges. Here, we report a new chrome-based catalyst stabilized by a single pentaerythritol decorated Anderson-type polyoxometalate, [N(C4H9)4]3[CrMo6O18(OH)3C{(OCH2)3CH2OH}], which can realize the efficient transformation from alcohols to esters by H2O2oxidation in good yields and high selectivity without extra organic ligands. A variety of alcohols with different functionalities including some natural products and pharmaceutical intermediates are tolerated in this system. The chrome-based catalyst can be recycled several times and still keep the original configuration and catalytic activity. We also propose a reasonable catalytic mechanism and prove the potential for industrial applications.

Light-induced carboxylation of aryl derivatives with cooperative COF as an active photocatalyst and Ni(ii) co-catalyst

The photocatalytic carboxylation of aryl derivatives was demonstrated under CO2at atmospheric pressure using a mesoporous covalent organic framework (COF) as the active photocatalyst with triethylamine (TEA) as a sacrificial electron source under visible light. A yield of greater than 91% of the isolated product was achieved with 5 mg of catalyst. The reaction cycle is dependent on the use of the Ni(dmg)2co-catalyst and the sacrificial electron donor (TEA). The reaction does not occur in the absence of light (445 nm) even at elevated reaction temperature. We have also demonstrated that a yield of 32% of the isolated product could be obtained with the use of sunlight in the catalytic cycle. Additionally, this heterogeneous catalytic system was recyclable and reusable for several cycles.

The Highly Effective Cobalt Based Metal–Organic Frameworks Catalyst for One Pot Oxidative Esterification Under Mild Conditions

The cobalt-based metal organic frameworks (Co-MOFs) catalyst has been prepared with using terephthalic acid and 4,4′-bipyridine as organic linkers by facile solvothermal method for one pot oxidative esterification. The prepared catalyst was pyrolysed at different temperature and then applied for oxidation of aldehyde using molecular oxygen as benign oxidant under mild conditions. The Co-MOFs pyrolysed at 800?°C (denoted as Co-MOFs-800) catalyst exhibited excellent catalytic activity, selectivity and recyclability toward the oxidative esterification of benzaldehydes. Furthermore, it can be reused up to 5 runs without significant loss of activity. Graphic Abstract: [Figure not available: see fulltext.]

Nitration of aromatics with dinitrogen pentoxide in a liquefied 1,1,1,2-tetrafluoroethane medium

Regardless of the sustainable development path, today, there are highly demanded chemical productions still operating that bear environmental and technological risks inherited from the previous century. The fabrication of nitro compounds, and nitroarenes in particular, is traditionally associated with acidic wastes formed in nitration reactions exploiting mixed acids. However, nitroarenes are indispensable for industrial and military applications. We faced the challenge and developed a greener, safer, and yet effective method for the production of nitroaromatics. The proposed approach comprises the application of an eco-friendly nitrating agent, namely dinitrogen pentoxide (DNP), in the medium of liquefied 1,1,1,2-tetrafluoroethane (TFE) - one of the most non-hazardous Freons. Importantly, the used TFE is not emitted into the atmosphere but is effortlessly recondensed and returned into the process. DNP is obtainedviathe oxidation of dinitrogen tetroxide with ozone. The elaborated method is characterized by high yields of the targeted nitro arenes, mild reaction conditions, and minimal amount of easy-to-utilize wastes.

COMPOUNDS AND METHODS FOR TREATING CANCER

Substituted cinnamamide compounds and analogs, methods of making such compounds, pharmaceutical compositions and medicaments comprising such compounds, and methods of using such compounds to treat, prevent or ameliorate cancer are provided.

Synthesis, antifungal and antibacterial activity of calix[4]arene-based 1,3,4-oxadiazole derivatives

We describe the synthesis of some novel p-tert-butylcalix[4]arene-based (5-aryl-1,3,4-oxadiazol-2-yl)2-chloroethanethioate derivatives (4a–e). These compounds were synthesized by the reaction of tetra-tert-butyl calix[4]arene (1) with (5-aryl-1,3,4-oxadiazol-2-yl)2-chloroethanethioate (3a–e) in the presence of potassium carbonate as a weak base and dry acetone as the solvent. All the newly synthesized calix[4]arene derivatives were characterized by elemental analysis and various spectroscopic methods such as FT-IR, 1H NMR,13C NMR, DEPT, and ESI-MS. The synthesized compounds were tested in vitro for their antibacterial and antifungal activities against Escherichia coli and Aspergillus fumigates in comparison with enrofloxacin and amphotericin as reference drugs, which are normally used for treating such infections. The synthesized compounds showed different inhibition zones against the tested bacteria and fungi. Compound 4c was found to be most effective against A. fumigates, whereas compound 4e was found to be equally effective against E. coli and A. fumigates.

Pd-Colloids-Catalyzed/Ag2O-Oxidized General and Selective Esterification of Benzylic Alcohols

Palladium colloids obtained from the degradation of Hermann–Beller palladacycle proved to be an efficient catalytic system in combination with silver oxide as a selective oxidant for the oxidative esterification of differently substituted benzyl alcohols in MeOH as solvent. Excellent reactivity exhibited by the catalytic system also allowed the alcoholic coupling partner to be changed from MeOH to a wide range of alcohols having diverse functionalities. The mildness of the developed protocol also made it possible to employ propargyl alcohol as the coupling partner without any observation of any interference of the terminal alkyne. Selective oxidative coupling of a primary alcoholic functional group over secondary in the case of glycols and glycerols was also made possible using the developed catalyst system. To test the relevancy of Pd/Ag combined catalysis mixed Pd/Ag colloids were synthesized, characterized by TEM, XRD and XPS and applied to oxidative-esterification successfully.

1,3-Dibromo-5,5-dimethylhydantoin as a Precatalyst for Activation of Carbonyl Functionality

Activation of carbonyl moiety is one of the most rudimentary approaches in organic synthesis and is crucial for a plethora of industrial-scale condensation reactions. In esterification and aldol condensation, which represent two of the most important reactions, the susceptibility of the carbonyl group to nucleophile attack allows the construction of a variety of useful organic compounds. In this context, there is a constant need for development of and improvement in the methods for addition-elimination reactions via activation of carbonyl functionality. In this paper, an advanced methodology for the direct esterification of carboxylic acids and alcohols, and for aldol condensation of aldehydes using widely available, inexpensive, and metal-free 1,3-dibromo-5,5-dimethylhydantoin under neat reaction conditions is reported. The method is air- and moisture-tolerant, allowing simple synthetic and isolation procedures for both reactions presented in this paper. The reaction pathway for esterification is proposed and a scale-up of certain industrially important derivatives is performed.