371-40-4

Usage

Uses

Used in Pharmaceutical Industry:
4-Fluoroaniline is used as an intermediate in the manufacture of pharmaceuticals, contributing to the development of various medications.
Used in Analytical Chemistry:
4-Fluoroaniline serves as an analytical reagent in the enzymic detection of glucose, playing a crucial role in the accurate measurement of blood sugar levels.
Used in Agriculture:
As an intermediate, 4-Fluoroaniline is utilized in the production of herbicides and plant growth regulators, helping to control weeds and promote plant growth in the agricultural sector.
Used in Environmental Research:
4-Fluoroaniline may be employed as one of the target pollutants during the investigation of biodegradability of fluorinated compounds under aerobic conditions, aiding in understanding the environmental impact of such compounds.
Used in Material Science:
4-Fluoroaniline is used for the synthesis of luminescent and cationic monocyclometalated gold(III) monoaryl complexes, which have potential applications in various material science and technology fields.
Used in Ezetimibe Degradation:
4-Fluoroaniline is a degradation product of Ezetimibe (E975000), a medication used to lower cholesterol levels. Understanding its formation and properties can contribute to the assessment of the drug's long-term effects and safety.

Preparation

The better process in the one-step process is the nitrobenzene method, which is obtained by deoxygenation, hydrogenation and fluorination. With PdCl2-V2O5 as the catalyst and carbon monoxide as the reducing agent, the reaction was carried out at 160°C for 3h, and the yield of 4-fluoroaniline could reach 90%, with another 10% of aniline as a by-product. With PtO2 as the catalyst, BF3-HF as the fluorinating agent and hydrogen as the reducing agent, the reaction was carried out at 42℃ for 12.5h, with 100% conversion and 95% yield.

Synthesis Reference(s)

Journal of the American Chemical Society, 70, p. 654, 1948 DOI: 10.1021/ja01182a065The Journal of Organic Chemistry, 26, p. 4014, 1961 DOI: 10.1021/jo01068a089

Hazard

Toxic material.

Flammability and Explosibility

Notclassified

Safety Profile

Poison by ingestion. Mutation data reported. A severe skin and eye irritant. When heated to decomposition it emits very toxic fumes of NOx and F-.

InChI:InChI:1S/C6H6FN/c7-5-1-3-6(8)4-2-5/h1-4H,8H2

Upstream product

• 352-33-0 1-Chloro-4-fluorobenzene 
• 456-22-4 4-Fluorobenzoic acid 
• 100-65-2 N-Phenylhydroxylamine 
• 98-95-3 nitrobenzene 
• 350-46-9 4-Fluoronitrobenzene 
• 363-02-0 4,4’-difluorobenzophenone oxime 
• 71-43-2 benzene 
• 103-82-2 phenylacetic acid 
• 53477-44-4 C₇H₈FN₃ 
• 462-06-6 fluorobenzene 
• 117872-31-8 (4-Fluoro-phenyl)-carbamic acid 2-piperidin-1-yl-ethyl ester; hydrochloride 
• 106-50-3 1,4-phenylenediamine 
• 110-83-8 cyclohexene 
• 3296-02-4 p-azidofluorobenzene 

Downstream Products

• 780-05-2 (Z)-4-((4-fluorophenyl)amino)-4-oxobut-2-enoic acid 
• 348-45-8 N-(4-fluorophenyl)benzo[d]thiazol-2-amine 
• 2369-32-6 6-methyl-N-(4-fluorophenyl)benzo[d]thiazol-2-amine 
• 494-26-8 2,5-bis-(4-fluoro-anilino)-[1,4]benzoquinone-bis-(4-fluoro-phenylimine) 
• 327-23-1 (6-bromo-benzothiazol-2-yl)-(4-fluoro-phenyl)-amine 
• 391-91-3 2-cyano-3-[1-(4-fluoro-phenyl)-pyrrol-2-yl]-acrylic acid methyl ester 
• 314-53-4 4,5,6,7-tetrachloro-2-(4-fluoro-phenyl)-isoindoline-1,3-dione 
• 1494-14-0 (2-methyl-6-oxo-6,7-dihydro-1H-purin-8-ylmercapto)-acetic acid-(4-fluoro-anilide) 
• 457-77-2 ethyl 4-fluorophenylcarbamate 
• 351-83-7 4'-fluoroacetanilide 
• 448-39-5 N-(4-fluoro-2-nitrophenyl)acetamide 
• 331-98-6 N-benzylidene-4-fluoroaniline 
• 366-75-6 N-(4-fluorophenyl)benzamide 
• 330-98-3 N-(4-fluorophenyl)-N'-phenyl-urea 

Related news

Determination of the second-order 1H NMR parameters for the aromatic protons in 4-Fluoroaniline (cas 371-40-4) and application to the analysis of the 1H NMR spectra for the aromatic protons in N4-(4′-fluorophenyl)succinamic acid and in N4-(4′-fluorophenyl)-3,3-difluorosuccinamic acid07/21/2019

Four studies of the 1H NMR spectrum for the aromatic protons of 4-fluoroaniline between 1958 and 1974 give three very different solutions to the second-order, AA′BB′X, spectrum. A re-evaluation of the second-order spectrum was done at 300 MHz. Simultaneous simulations of the 1H NMR spectrum an...detailed

Relevant academic research and scientific papers

Reduction of nitrobenzene derivatives using sodium borohydride and transition metal sulfides

Reported here is the reduction of aromatic nitro compounds using sodium borohydride and transition metal sulfides as catalysts. The reaction conditions were optimized using the reduction of nitrobenzene as a model reaction. The catalysts studied were iron sulfide (Fe3S4), copper sulfide (CuS), zinc sulfide (ZnS), cobalt sulfide (Co3S4), and nickel sulfide (NiS). The reduction was monitored using gas chromatography. Quantitative conversions were achieved using Co3S4 and NiS, representing a ten-fold increase in reactivity compared to the non-catalyzed reaction. Fe3S4 and ZnS had no apparent effect on the reduction of nitrobenzene while the reduction using CuS showed a marginal increase. The reduction method was applied to several aryl-nitro derivatives containing either electron-withdrawing or electron-donating groups. Halogen containing aryl-nitro compounds were reduced without dehalogenation. The reduction had no effect on other functional groups such as carboxylic acids, esters, amides, or alkenes, indicating that the reduction is highly chemoselective.

Dihydro-2H-thiopyran-3(4H)-one-1,1-dioxide–a new cyclic ketomethylenic reagent for the Dimroth-type 1,2,3-triazole synthesis

A series of 1,5,6,7-tetrahydrothiopyrano[2,3-d][1,2,3]triazole 4,4-dioxides, new triazole-based bicyclic ring system, were prepared via base-mediated click reaction of organic azides with the readily available dihydro-2H-thiopyran-3(4H)-one-1,1-dioxide. The reaction proceeded at room temperature in 5-12 h with catalysis by base-solvent system K2CO3/DMSO. High purity products were isolated by simple filtration and no formation of side products was observed. The key structure was confirmed by an X-ray study.

Hydrogen Sulfide Donors Activated by Reactive Oxygen Species

Hydrogen sulfide (H2S) exhibits promising protective effects in many (patho)physiological processes, as evidenced by recent reports using synthetic H2S donors in different biological models. Herein, we report the design and evaluation of compounds denoted PeroxyTCM, which are the first class of reactive oxygen species (ROS)-triggered H2S donors. These donors are engineered to release carbonyl sulfide (COS) upon activation, which is quickly hydrolyzed to H2S by the ubiquitous enzyme carbonic anhydrase (CA). The donors are stable in aqueous solution and do not release H2S until triggered by ROS, such as hydrogen peroxide (H2O2), superoxide (O2?), and peroxynitrite (ONOO?). We demonstrate ROS-triggered H2S donation in live cells and also demonstrate that PeroxyTCM-1 provides protection against H2O2-induced oxidative damage, suggesting potential future applications of PeroxyTCM and similar scaffolds in H2S-related therapies.

Nickel Boride Catalyzed Reductions of Nitro Compounds and Azides: Nanocellulose-Supported Catalysts in Tandem Reactions

Nickel boride catalyst prepared in situ from NiCl2 and sodium borohydride allowed, in the presence of an aqueous solution of TEMPO-oxidized nanocellulose (0.01 wt%), the reduction of a wide range of nitroarenes and aliphatic nitro compounds. Here we describe how the modified nanocellulose has a stabilizing effect on the catalyst that enables low loading of the nickel salt pre-catalyst. Ni-B prepared in situ from a methanolic solution was also used to develop a greener and facile reduction of organic azides, offering a substantially lowered catalyst loading with respect to reported methods in the literature. Both aromatic and aliphatic azides were reduced, and the protocol is compatible with a one-pot Boc-protection of the obtained amine yielding the corresponding carbamates. Finally, bacterial crystalline nanocellulose was chosen as a support for the Ni-B catalyst to allow an easy recovery step of the catalyst and its recyclability for new reduction cycles.

Synthesis method of o-bromo-p-fluoroacetyl aniline

The invention relates to a synthesis method of o-bromo-p-fluoroacetyl aniline, and belongs to the technical field of synthesis of chemical intermediates. According to the preparation method, potassium fluoride and parachloronitrobenzene are taken as starting raw materials, halogen exchange, reduction, acylation reaction and bromination reaction are carried out, then the o-bromo-p-fluoroacetyl aniline is prepared, and the synthesis method which is high in operability, high in product yield and high in purity is provided for synthesis of the o-bromo-p-fluoroacetyl aniline.

Selective Carbon-Carbon Bond Amination with Redox-Active Aminating Reagents: A Direct Approach to Anilines?

Amines are among the most fundamental motifs in chemical synthesis, and the introduction of amine building blocks via selective C—C bond cleavage allows the construction of nitrogen compounds from simple hydrocarbons through direct skeleton modification. Herein, we report a novel method for the preparation of anilines from alkylarenes via Schmidt-type rearrangement using redox-active amination reagents, which are easily prepared from hydroxylamine. Primary amines and secondary amines were prepared from corresponding alkylarenes or benzyl alcohols under mild conditions. Good compatibility and valuable applications of the transformation were also displayed.

Room-temperature copper-catalyzed electrophilic amination of arylcadmium iodides with ketoximes

We started our study by preparation two ketoximes. Later, there were studies to reveal these ketoximes' effects in the electrophilic amination reaction with organocadmium reagents. Primarily, it was observed that arylcadmium iodides could not be reacted with ketoximes at room temperature in the absence of a catalyst. CuCN was a suitable catalyst for this electrophilic amination reaction of arylcadmium iodides and allowed the preparation of functionalized aniline derivatives in good yields under mild reaction conditions. We obtained the results indicated that the yield of primary arylamines was strongly dependent on the steric and electronic effects of organocadmium reagent and amination agent. In the case of both amination reagents, meta-substituted arylamines were obtained in higher yields than para-substituted arylamines. We observed that acetone O-(4-chlorophenylsulfonyl)oxime, 1, as an aminating agent, was more successful than acetone O-(2-Naphthylsulfonyl)oxime, 2, in the synthesis of functionalized arylamines by electrophilic amination of corresponding aryl cadmium iodides. In this method, there is no cadmium release to the environment.

High yielding electrophilic amination with lower order and?higher order organocuprates: Application of acetone O-(4-Chlorophenylsulfonyl)oxime in the construction of the C?N bond at room temperature

Electrophilic amination reaction was performed with lower order and?higher order organocuprates using acetone O-(4-Chlorophenylsulfonyl)oxime (1). It was proceeded smoothly at room temperature in the presence of organocuprates to provide the corresponding primary amines in good yields with 10 and 60 min, respectively. The primary amine yields of the electrophilic amination of bromomagnesium organocyanocuprates and dibromomagnesium diorganocyanocuprates were obtained 52–72% and 58–83%, respectively. We observed that higher order organocuprates were more successful than lower order organocuprates in the synthesis of functionalized arylamines by electrophilic amination.

4 - Fluorine substituted aryl amine compound and synthesis method thereof

The invention discloses a synthesis method of 4 -fluorine substituted aryl amine compound, which comprises the following steps: 1) taking acyl-protected phenylhydroxylamine as a substrate, and generating 4 -fluorine substituted aniline compound under basic conditions by taking sulfonyl fluoride as a fluorine source in a polar solvent. 2) The deprotection is carried out under dilute acid conditions or Pd by catalytic hydrogenation to give the 4 - fluorine-substituted aryl amine compound. 4 - Fluorine substituted aniline compounds which are synthesized by the invention greatly increase the lipophilic property due to the introduction of fluorine atoms, and can be widely applied to preparation of fluorine-containing drugs and pesticide and dye intermediates. , The adopted raw materials are industrial products, are cheap and easily available, and are commercially available. 4 - Fluoroaryl aniline prepared by the method is high in yield, and the product with the purity 90% can be obtained in a yield of more than ≥ 99%. The method is simple to operate and low in cost, is very suitable for industrialization, and can be widely popularized and used.

Method for preparing amine through catalytic reduction of nitro compound by cyclic (alkyl) (amino) carbene chromium complex

The cyclic (alkyl) (amino) carbene chromium complex is prepared from corresponding ligand salt, alkali and CrCl3 and used for catalyzing pinacol borane to reduce nitro compounds in an ether solvent under mild conditions to generate corresponding amine. The method for preparing amine has the advantages of cheap and accessible raw materials, mild reaction conditions, wide substrate application range, high selectivity and the like, and is simple to operate.