2 nitroaniline

Manufactured by Merck Group

Sourced in United States, Germany

2-nitroaniline is a chemical compound used as a precursor in the production of various pharmaceutical and agricultural products. It is a yellow crystalline solid that is soluble in organic solvents. 2-nitroaniline serves as a building block in the synthesis of various heterocyclic compounds, dyes, and other specialty chemicals.

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2,4-Nitroaniline

9 protocols using 2 nitroaniline

Reagent Sources for Immunoassay Development

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NIC, 4-nitroaniline, 2-nitroaniline, 3-nitroaniline, N-(4-nitrophenyl) propionamide, H-Val-pNA HCl, L-argininep-nitroanilide dihydrochloride, 4-nitrophenethylamine hydrochloride, N-methyl-4-nitrophenethylamine hydrochloride, H-Ala-pNA HCl, N, N-dimethyl-4-nitroaniline, H-Glu-pNA, halofuginone, toltrazuril, 1,3-diphenylguanidine, ronidazole, and dinitolmide were obtained from Sigma-Aldrich (St. Louis, MO, USA) (Figure 1). The coating antigen (DNC-4-BSA) and mAb 3B4 were acquired from China Agricultural University (Qianqian Tang May 2018). For other reagents materials were shown in the Supplementary Materials part.

Zou M., Yin Y., Guo L., Zhang Q., Li J., Zhang H., Song Q., Li Z., Wang L., Ao X, & Liang X. (2023). A Europium Nanosphere-Based Time-Resolved Fluorescent Immunochromatographic Assay for the Rapid Screening of 4,4′-Dinitrocarbanilide: Aiming at Improving Strip Method Performance. Biosensors, 13(5), 518.

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Analytical Comparison of Mass Spectrometry Techniques

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For our investigation, we used the same compounds as for Paper-LTPI^{28 (link)} and in a comparison between Paper-LTPI, ESI and APCI^{27 (link)}: 3-aminophenol, 2-fluoro aniline, 3-fluoro aniline, 4-fluoro aniline, 2-methoxy aniline (o-anisidine), 3-methoxy aniline (m-anisidine), 4-methoxy aniline (p-anisidine), 2-nitro aniline, 3-nitro aniline, 4-nitro aniline, 3-methyl aniline (m-toluidine), 3-aminoaniline (m-phenylenediamine), 4-amino aniline (p-phenylenediamine), 2-aminobenzonitrile, 3-aminobenzonitrile and 4-aminobenzonitrile from Sigma Aldrich (Taufkirchen, Germany); 2-methylaniline (o-toluidine), 4-methylaniline (p-toluidine) from Fluka (Buchs, Switzerland) and aniline from Acros (Geel, Belgium). Acetonitrile (ACN, LC–MS grade) was from VWR (Dresden, Germany) and water (LC–MS grade) from BIOSOLVE (Valkenswaard, Netherlands). 2-aminoaniline (o-phenylenediamine), 2-aminopyridine, 3-aminopyridine, 4-aminopyridine, 2-aminophenol, 4-aminophenol, 2-aminobenzoic acid, 3-aminobenzoic acid, 4-aminobenzoic acid, sulfanilic acid and 4-chloroaniline were kindly provided by Prof. em. S. Berger (University of Leipzig, Germany).

Kiontke A., Roudini M., Billig S., Fakhfouri A., Winkler A, & Birkemeyer C. (2021). Surface acoustic wave nebulization improves compound selectivity of low-temperature plasma ionization for mass spectrometry. Scientific Reports, 11, 2948.

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Ionic Liquid-Based Polymer Biosensor

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4-Nonylphenol and 2,2’-azobisisobutyronitrile (AIBN) were obtained from Aladdin Industrial Corporation (Shanghai, China). Ethylene glycol dimethacrylate (EGDMA), 1-vinylimidazole, 1,4-dibromobutane, 2-nitroaniline, 3-nitroaniline, and 4-nitroaniline were procured from Sigma-Aldrich (St. Louis, MO, USA). IL [V₂C₄(mim)₂]Br₂ was prepared in our laboratory. Chitosan was procured from Sinopharm Chemical Regent Co., Ltd. (Shanghai, China). Phosphate buffer was prepared using NaH₂PO₄ and Na₂HPO₄. Deionized water of 18 MΩ cm was applied in the experiments.

Hu J., Dai H., Zeng Y., Yang Y., Wang H., Zhu X., Li L., Zhou G., Chen R, & Guo L. (2019). A Cross-Linker-Based Poly(Ionic Liquid) for Sensitive Electrochemical Detection of 4-Nonylphenol. Nanomaterials, 9(4), 513.

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Synthesis of Nanomaterials and Nanocomposites

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For synthesis of nanomaterials and nanocomposites, cetyl-trimethyl ammonium bromide (CTAB, 99%), ethanol (99%), graphite flakes (size 100 micron, 99.5%), hydrochloric acid (HCl, 36.5%), hydrogen peroxide (H₂O₂, 30% w/v), potassium permanganate (KMnO₄, 99.5%), phosphoric acid (H₃PO₄, 85%), sulfuric acid (H₂SO₄, 98%), silver nitrate (AgNO₃, 99.9%) were used. The acetate buffer (pH 3.6), 2,4,6-tripyridyl-s-triazine (TPTZ) and FeCl₃·6H₂O (97%) are used for preparing FRAP (ferric reducing/antioxidant power) reagent. All other chemicals required for the experiments were of analytical grades and procured from Sigma (St. Louis MO, USA). The following chemicals are purchased from Sigma-Aldrich, Milwaukee (USA): 4-nitrophenol (4-NP) (C₆H₅NO₃, 99%), 2-nitroaniline (2-NA) (C₆H₆N₂O₂, 98%), 3-nitroaniline (3-NA) (C₆H₆N₂O₂, 98%), 4-nitroaniline (4-NA) (C₆H₆N₂O₂, 99%), and sodium borohydride (NaBH₄, 98%). Microbes namely Escherichia coli (NCLM2832) and Staphylococcus aureus (NCLM2602) procured from National Chemical Laboratory Pune were used for this study. The stock cultures were maintained on nutrient agar slants at 37 °C. The freshly discharged liquid metabolic waste (urine) of healthy and fully vaccinated Gir (Bos taurus indicus) (A-2) cow. The cow urine was donated from the owner of the cattle, Mr Dhanaji parasharam sarvalkar, A/P kaneriwadi, Dist. Kolhapur, Maharashtra, India 416234.

Kumbhar G.S., Patil S.V., Sarvalkar P.D., Vadanagekar A.S., Karvekar O.S., Patil S.S., Rane M.R., Sharma K.K., Kurhe D.N, & Prasad N.R. (2022). Synthesis of a Ag/rGO nanocomposite using Bos taurus indicus urine for nitroarene reduction and biological activity. RSC Advances, 12(55), 35598-35612.

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Synthesis of Heterocyclic Compounds

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All experiments were carried out in an atmosphere of dry argon, and flasks were flame dried. Solvents were dried by usual methods (diphenyl ether, diethyl ether, and THF over benzophenone ketyl, CHCl₃, and CH₂Cl₂ over P₄O₁₀, hexane over sodium-potassium alloy) and distilled. Chromatographic purification was carried out on silica gel 60 (0.15–0.3 mm, Macherey-Nagel GmbH & Co. KG, Düren, Germany). Sodium hydride (dry, 95%), potassium tert-butoxide, trimethyl orthoformate, 2-iso-propylaniline, 2-(tert-butyl)aniline, 2-nitroaniline, phosphoryl chloride, 9H-carbazole, Meldrum’s acid, acrolein, and crotonaldehyde were purchased from Sigma-Aldrich (Poznań, Poland), and were used without further purification.

Wantulok J., Swoboda D., Nycz J.E., Książek M., Kusz J., Małecki J.G, & Kubíček V. (2021). Direct Amination of Nitroquinoline Derivatives via Nucleophilic Displacement of Aromatic Hydrogen. Molecules, 26(7), 1857.

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Synthesis and Characterization of Hybrid Microgels

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Styrene (STY), N-isopropylmethacrylamide (NIPM) (98%), N,N-methylenebisacrylamide (MBIS) (99%), ammonium per sulfate (APs) (99%), sodium dodecyl sulfate (SDS) (98%), sodium borohydride (NaBH₄) (98%), 2-nitrophenol (2NP), 4-nitrophenol (4NP), 3-nitrophenol (3NP), 4-chloronitrobenzene (4NCB), 2-nitroaniline (2NA), 3-nitroaniline (3NA), 4-nitroaniline (4NA), 2-amino-4-nitroanisole (2A4NA), 4-nitrophenylhydrazine (4NPH), 2,4-dinitrophenylhydrazine (2,4DNPH), and tetrachloroauric(iii) acid trihydrate (HAuCl₄·3H₂O) were obtained from Sigma Aldrich (Germany). No further purification of the chemicals was done except STY. STY was purified via vacuum filtration by passing it through alumina (Al₂O₃) to remove the inhibitor. Deionized water was used in all the experimental work. The membrane for dialysis (cut off = 12 000–14 000) was obtained from Scharlu and was used for the removal of unreacted reactants from the microgel and hybrid microgel dispersions.

Arif M., Shahid M., Irfan A., Nisar J., Wu W., Farooqi Z.H, & Begum R. (2022). Polymer microgels for the stabilization of gold nanoparticles and their application in the catalytic reduction of nitroarenes in aqueous media. RSC Advances, 12(9), 5105-5117.

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Biogenic ZnO Nanoparticles Synthesis

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Zinc nitrate hexahydrate (Zn(NO₃)₂·6H₂O), 30 wt% Ammonia solution, Silver nitrate (AgNO₃), Methylene Blue (MB) and Crystal Violet (CV) dye, Analytical grade 4-Nitrophenol (C₆H₅NO₃) (4-NP), 2-Nitroaniline (C₆H₆N₂O₂) (2-NA), 3-Nitroaniline (C₆H₆N₂O₂) (3-NA), 4-Nitroaniline (C₆H₆N₂O₂) (4-NA), and Sodium Borohydride (NaBH₄) chemicals are procured form Sigma-Aldrich, Milwaukee (USA). The fresh Zingiber officinale rhizome is procured from the local market in India (N-16.67.35, E-74.25.32).

Karvekar O.S., Sarvalkar P.D., Vadanagekar A.S., Singhan R.D., Jadhav S.M., Nimbalkar M.S, & Prasad N.R. (2022). Biogenic synthesis of silver anchored ZnO nanorods as nano catalyst for organic transformation reactions and dye degradation. Applied Nanoscience, 12(7), 2207-2226.

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Fluorescent Dye Binding Assay

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ThT was purchased from Acros Organics (Fair Lawn, New Jersey). Lipids [dioleoylphosphatidylglycerol (DOPG) and dioleoylphosphatidylcholine (DOPC)] were purchased from Avanti Polar Lipids, Inc. (Alabaster, Al). The 96-well plates (coated, non-binding surface, black, flat bottom) were bought from Greiner Bio-One (Monroe, NC). All of the chemicals were purchased from commercial suppliers and used without further purification. Silica plates (w/UV254, aluminum backed, 200 micron) and silica gel (standard grade, particle size = 40–63 micron, 230 × 400 mesh) for flash column chromatography were purchased from Sorbent Technologies (Atlanta, GA). Dry solvents were purchased from Sigma Aldrich (St. Louis, MI) or VWR (Bridgeport, NJ). Triethylamine (dry), 2-chloro-1-methylpyridinium iodide, tert-Butyl bromoacetate, 2-nitroaniline, dimethylacetylene dicarboxylate, and polyphosphoric acid were purchased from Sigma Aldrich (St. Louis, MI).

Kumar S., Brown M.A., Nath A, & Miranker A.D. (2014). Folded Small Molecule Manipulation of Islet Amyloid Polypeptide. Chemistry & biology, 21(6), 775-781.

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Synthesis and Characterization of Substituted Anilines

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The analytical grades of ethyl 4-aminobenzoate, sodium nitrite (NaNO₂), phenol, 1-bromohexane, 1,3-dicyclohexylcarbodiimide (DCC), 4-(N,N-dimethyl amino)pyridine (DMAP), 4-fluoro aniline, 2-fluoro aniline, 2-nitro aniline, 2-trifluoromethyl aniline, 2,4-dinitro aniline, potassium carbonate (K₂CO₃), sodium hydroxide (NaOH), potassium hydroxide (KOH), potassium iodide (KI) were procured from Sigma Aldrich and Spectrochem. For column chromatography silica gel 60-120 and neutral alumina were procured from Thomas baker. Acetone, hexane, ethyl acetate and dichloromethane were dried over phosphorus pentaoxide and calcium hydride, respectively. These solvents were distilled using standard methods when required for the experiment. Thin-layer chromatography (TLC) were performed on aluminium sheet precoated with silica gel-60 F₂₅₄ (Merck). Infrared (IR) spectra were recorded using a PerkinElmer 1000 spectrometer. Proton nuclear magnetic resonance (¹H NMR) spectra were recorded on a 400 MHz Bruker NMR spectrometer, using CDCl₃ as a solvent and tetramethyl silane (TMS) as an internal standard.

Sunil B.N., Behera P.K., Achalkumar A.S., Shanker G, & Hegde G. (2020). Influence of inter- and intramolecular H-bonding on the mesomorphic and photoswitching behaviour of (E)-4-((4-(hexyloxy)phenyl)diazenyl)-N-phenyl benzamides. RSC Advances, 10(34), 20222-20230.

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