4 fluoroaniline

Manufactured by Merck Group

Sourced in Germany, Belgium

4-fluoroaniline is a chemical compound that serves as a raw material or intermediate for various pharmaceutical and industrial applications. It is a colorless to pale yellow liquid with a characteristic amine-like odor. 4-fluoroaniline is used in the synthesis of a range of organic compounds, such as pharmaceuticals, agrochemicals, and specialty chemicals. Its core function is to provide a fluorinated aniline building block for further chemical transformations.

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Lab products found in correlation

2 fluoroaniline, by Merck Group (3 mentions) 3 fluoroaniline, by Merck Group (2 mentions) Cyclohexylamine, by Merck Group (2 mentions) Triethylamine, by Tedia (2 mentions) Dimethylformamide, by Carlo Erba (2 mentions) Sulfaguanidine, by Tokyo Chemical Industry (2 mentions) Morpholine, by Tokyo Chemical Industry (2 mentions) 4 nitroaniline, by Johnson & Johnson (2 mentions) M toluidine, by Merck Group (2 mentions) 4 chloroaniline, by Merck Group (2 mentions) 4 bromoaniline, by Merck Group (2 mentions) N hexane, by Carlo Erba (2 mentions) Ethanol, by Carlo Erba (2 mentions) Acetone, by Carlo Erba (2 mentions) Chloroform, by Carlo Erba (2 mentions) Dimethyl sulfoxide (dmso), by Carlo Erba (2 mentions) 2 nitroaniline, by Merck Group (2 mentions) Phenyl isocyanate, by Merck Group (1 mentions) 3 chloroaniline, by Merck Group (1 mentions) Aniline, by Merck Group (1 mentions)

8 protocols using 4 fluoroaniline

Synthesis of Functionalized Adamantanes

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Triethylamine (BioUltra ≥ 99.5%, CAS 121-44-8), 3-chloro aniline (99%, CAS 108-42-9), cyclohexyl isocyanate (98%, CAS 3173-53-3), phenyl isocyanate (98%, CAS 103-71-9) manufactured by Sigma-Aldrich (St. Louis, MO, USA) were used without purifying.
4-(Trifluoromethoxy) isocyanate (97%, CAS 35037-73-1), aniline (99+%, CAS 62-53-3), 2-fluoroaniline (99%, CAS 348-54-9), 3-fluoroaniline (98%, CAS 372-19-0), 4-fluoroaniline (99%, CAS 371-40-4) produced by the AlfaAesar (Ward Hill, MA, USA) were used without additional purification.
Diethyl ether was purified by well-known methods. trans-4-Amino-(cyclohexyloxy)benzoic acid 7a [2 (link)], 1,3-dehydroadamantane 2a [12 (link)], 1,3-dehydro-5,7-dimethyladamantane 2b [12 (link)], 2-(adamantane-1-yl)-2-phenylacetic acid ethyl ester 3a [15 (link)], 2-(adamantane-1-yl)-2-phenylacetic acid 4a, 1-(isocyanato(phenyl) methyl)adamantane 5a [10 (link)] were obtained by well-known methods.

D’yachenko V., Danilov D., Kuznetsov Y., Moiseev S., Mokhov V., Burmistrov V, & Butov G. (2023). Synthesis and Properties of 1,3-Disubstituted Ureas Containing (Adamantan-1-yl)(phenyl)methyl Fragment Based on One-Pot Direct Adamantane Moiety Inclusion. Molecules, 28(8), 3577.

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Synthesis and Characterization of Sulfonamides

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All the solvents used were analytically pure. The reagents 5-isopropyl-2-methylphenol (carvacrol), chlorosulfonic acid, morpholine, 4-fluoroaniline, pyridin-2-yl methanamine, 2-hydroxyaniline, 2,4-dichloroaniline were obtained from Sigma Aldrich.
The synthesis sulfonamides S1–S5, as already described in the literature (de Oliveira et al., 2016 (link)) was performed in two steps: firstly, the synthesis of 4-hydroxy-2-isopropyl-5-methylbenzene-1-sulfonyl chloride (ChS) was performed, subsequently, the ChS was used in reactions with different amines (Scheme 1). ChS was obtained from the reaction of carvacrol to six equivalents of chlorosulfonic acid. The sulfonamides obtained in this study were prepared from ChS with two equivalents of amine added slowly. Reactions were followed by thin layer chromatography (TLC). All sulfonamides were purified by acid-base extraction and the compounds were duly characterized by spectroscopic and spectrometric techniques.

de Oliveira A.S., Llanes L.C., Nunes R.J., Nucci-Martins C., de Souza A.S., Palomino-Salcedo D.L., Dávila-Rodríguez M.J., Ferreira L.L., Santos A.R, & Andricopulo A.D. (2021). Antioxidant Activity, Molecular Docking, Quantum Studies and In Vivo Antinociceptive Activity of Sulfonamides Derived From Carvacrol. Frontiers in Pharmacology, 12, 788850.

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Synthesis and Characterization of Benzothiazole Derivatives

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All reagents, catalysts,
and chemicals utilized in the study were of analytical quality and
supplied by commercial providers. The chemicals used in this study
were sourced from various suppliers. 2-Aminobenzothiazole (Sigma-Aldrich,
99%), sulfapyridine (NENTECH, U.K., 99%), sulfaguanidine (Tokyo Chemical
Industry, Japan, 98%), piperazine (Central Dreug House, India, 99%),
benzylamine (Loba Chemi, India, 99%), cyclohexylamine (Sigma-Aldrich,
99%), 3,4 dimethylaniline (GCC, U.K., 98%), 4-chloroaniline (Sigma-Aldrich,
98%), 4-bromoaniline (Sigma-Aldrich, 90%), 4-fluoroaniline (Sigma-Aldrich,
99%), 4-nitroaniline (Janssen, Belgium, 98%), diethylamine (GCC, U.K.,
98%), m-toluidine (Sigma-Aldrich, 99%), morpholine
(Tokyo Chemical Industry, Japan, 99%), dimethylformamide (DMF) (Carlo
Erba, France, 99.9%), acetone (Carlo Erba, France, 99%), triethylamine
(TEA) (TEDIA, 99%), ethanol (Carlo Erba, France, 98%), n-hexane (Carlo Erba, France, 95%), sodium bicarbonate (NaHCO₃) (GCC, U.K., 99.5%), sodium hydroxide (NaOH) (GCC, U.K.,
99.5%), chloroform (Carlo Erba, France, 99.9%), and dimethyl sulfoxide
(DMSO) (Carlo Erba, France, 99%) and monochloroacetyl chloride (α
Chemika, India) were used.

Salih O.M., Al-Sha’er M.A, & Basheer H.A. (2024). Novel 2-Aminobenzothiazole Derivatives: Docking, Synthesis, and Biological Evaluation as Anticancer Agents. ACS Omega, 9(12), 13928-13950.

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Synthesis and Characterization of Aniline Derivatives

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4-aminophenylacetic acid, 4-aminophenethyl alcohol, 4-fluoroaniline, 4-(heptadecafluorooctyl)aniline, 4-aminoantipyrine, 4-(4-aminophenyl)butyric acid, and 3,4,5-trimethoxyaniline, sodium nitrite, hydrogen peroxide 30%, sodium chloride, sodium citrate, and citric acid were obtained from Sigma-Aldrich (Taufkirchen, Germany). CuSO₄ anhydrous 98% was purchased from Alfa Aesar (Karlsruhe, Germany). Hydrochloric acid (37%) was obtained from Carl Roth (Karlsruhe, Germany). Sulphuric acid (98%) was purchased from Merck Millipore (Darmstadt, Germany). Chemically pure acetonitrile, ethanol, and purified water (18 MΩ cm⁻¹, Millipore Darmstadt, Germany) were used to prepare solutions.

Chira A., Bucur B, & Radu G.L. (2017). Electrodeposited Organic Layers Formed from Aryl Diazonium Salts for Inhibition of Copper Corrosion. Materials, 10(3), 235.

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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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Synthesis and Characterization of Sulfanilamide Derivatives

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All of the reagents and
chemicals were of analytical grade and purchased from commercial suppliers.
Sulfapyridine (NENTECH, U.K., 99%), sulfaguanidine (Tokyo Chemical
Industry, Japan, 98%), cyanuric chloride (Acros Organics, China, 99%),
aniline (GCC, U.K., 99.5%), benzylamine (LobaChemi, India, 99%), cyclopropylamine
(Sigma-Aldrich, 98%), cyclohexyl amine (Sigma-Aldrich, 99%), diethylamine
(GCC, U.K., 98%), m-toluidine (Sigma-Aldrich, 99%),
3,4-dimethylaniline (GCC, U.K., 98%), 4-chloroaniline (Sigma-Aldrich,
98%), 4-bromoaniline (Sigma-Aldrich, 90%), 4-fluoroaniline (Sigma-Aldrich,
99%), 4-nitroaniline (Janssen, Belgium, 98%), morpholine (Tokyo Chemical
Industry, Japan, 99%), acetone (Carlo Erba, France, 99%), ethanol
(Carlo Erba, France, 98%), dimethylformamide (DMF) (Carlo Erba, France,
99.9%), n-hexane (Carlo Erba, France, 95%), sodium
bicarbonate (NaHCO₃) (GCC, U.K., 99.5%), sodium hydroxide
(NaOH) (GCC, U.K., 99.5%), triethylamine (TEA) (TEDIA, 99%), chloroform
(Carlo Erba, France, 99.9%) and dimethyl sulfoxide (DMSO) (Carlo Erba,
France, 99%).

Alelaimat M.A., Al-Sha’er M.A, & Basheer H.A. (2023). Novel Sulfonamide–Triazine Hybrid Derivatives: Docking, Synthesis, and Biological Evaluation as Anticancer Agents. ACS Omega, 8(15), 14247-14263.

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Synthesis of Podophyllotoxin Derivatives

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All chemicals, reagents, and solvents were of analytical grade and used directly without extra purification. Chloroform, methanol, cyclohexane, ethylacetate, dichloromethane (DCM), and triethylamine (TEA) were purchased from Fisher Scientific (UK) and Tedia Company (USA). Podophyllotoxin, chlorosulfonic acid, ammonia, 2-picolylamine(2-aminomethyl pyridine), 2-(2-aminoethyl)pyridine, 2-amino pyridine, 4-fluoroaniline, and 2-amino anthracene were purchased from Sigma-Aldrich (Germany).

Bader A., Bkhaitan M.M., Abdalla A.N., Abdallah Q.M., Ali H.I., Sabbah D.A., Albadawi G, & Abushaikha G.M. (2021). Design and Synthesis of 4-O-Podophyllotoxin Sulfamate Derivatives as Potential Cytotoxic Agents. Evidence-based Complementary and Alternative Medicine : eCAM, 2021, 6672807.

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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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