4-Fluoroaniline CAS 371-40-4

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4-Fluoroaniline is an important organic synthetic intermediate, existing in the form of a pale yellow transparent oily liquid with a characteristic aromatic odor. The molecular formula of this compound is C₆H₆FN, and its structure results from the substitution of the hydrogen atom at the meta position of the benzene ring in the aniline molecule by a fluorine atom. This unique molecular structure endows it with excellent reactivity and stability. In industrial applications, 4-fluorobenzenamine plays an irreplaceable key role, being widely used in the synthesis of fluorine-containing medicines, efficient pesticides, and high-performance dyes and other important fine chemicals. It is an important cornerstone in constructing fluorine-containing functional molecules in modern chemical industry. Its preparation process has been highly mature, and it can be produced on a large scale through various routes such as nitrobenzene reduction method and p-chloronitrobenzene fluorination method, providing stable and reliable raw material guarantees for downstream industries. With its clear physical and chemical properties and outstanding synthetic value, 4-fluorobenzenamine continues to contribute significantly in the cutting-edge fields such as pharmaceutical innovation, crop protection, and materials science.

4-fluoroaniline is a light colored oily liquid, a mixture of three isomers, insoluble in water and denser than water. As a derivative of aniline, the hydrogen at position 4 is replaced by fluorine, making it a primary aromatic amine and fluoroaniline with wide applications in various fields.

In the field of dyes, it also has a wide range of application value. It can endow dyes with unique color and properties, enhancing the quality and application range of dyes.

Color enhancement

The introduction of product can enhance the color expression ability of dye molecules. By adjusting its dosage and reaction conditions, dye products with different colors and color fastness can be prepared. These dye products can meet the color requirements of different industries, such as textiles, leather, plastics, etc.

Performance optimization

In addition to improving color, it can also optimize the performance of dyes. For example, by introducing, the light resistance, water resistance, and chemical resistance of dyes can be improved. These performance improvements make dye products more durable and stable, capable of meeting higher requirements in application environments.

Pre treat activated carbon with different HNO3 concentrations (1-14M) at 366K for 5 hours. Filter the solution. Rinse the solution in distilled water until the pH value becomes neutral. Dry the solution at 383 K for 10 hours. Pre treat activated carbon with different KI concentrations (2.5M) at 333K for 6 hours. Filter the mixture. Rinse the filtrate with distilled water until there is no precipitate in the filtrate. Add AgNO3 solution to activated carbon. Dry the mixture at 383 K for 10 hours. Add a certain volume of H2PdCl4 aqueous solution to the aqueous suspension of pre treated activated carbon at 353 K. Stir the mixture for 6 hours. Add 10% NaOH solution dropwise to the suspension and maintain the pH within the range of 9-10 for 30 minutes. Clean the catalyst formed. Use hydrazine hydrate to reduce the precipitated Pd (OH) 2. Filter Pd/C catalyst. Rinse the filtrate with distilled water until the pH value reaches 7. Evacuate the mixture under vacuum at 383K for 10 hours. The title compound product was purified by silica gel column. The synthesis route is shown in Figure 1.

Mix an aqueous solution of RhCl3 · 3H2O (2.25 mL, 0.05 mmol/mL) and nickel acetylacetonate (9.6 mg) with a solution containing 2 g of ODA. Heat the obtained mixture to 120 ° C to form a transparent solution. Inject 8 g of ODA at 250 ° C, stir vigorously, and age for 1.5 minutes at 230 ° C. Wash the precipitate with ethanol several times and dry it. Disperse the obtained Rh3Ni1 BNP in n-hexane for future use. By adjusting the amount of metal precursor through a similar program, other RhxNiyBNP and Rh NPs were prepared. Add the catalyst (containing 0.3 mol% metal relative to the substrate) to a solution of the substrate (0.5 mmol) in 3mL solvent in a 25mL round flask. Degasse the reaction mixture twice, using hydrogen instead of vacuum each time. Stir at room temperature under H2. After the reaction is complete, the catalyst is recovered by centrifugation. Analyze the supernatant obtained from GC. The title compound 4-fluoroaniline was purified by silica gel chromatography using a suitable eluent for 1H NMR testing. The synthesis route is shown in Figure 1.

Traditional methods for synthesizing 4-FA (e.g., nitration-reduction, diazotization-fluorination, and nucleophilic aromatic substitution) often rely on toxic reagents (e.g., HF, ClF₃), high temperatures, and multi-step processes, leading to low atom economy and high waste generation. Future research should prioritize eco-friendly alternatives:

► Biocatalytic Fluorination

Enzymatic Fluorination: Explore florinases (e.g., Streptomyces cattleya fluorinase) or haloperoxidases to catalyze C-F bond formation under mild conditions (aqueous media, room temperature).

Microbial Synthesis: Engineer E. coli or Saccharomyces cerevisiae to express fluorinating enzymes, enabling whole-cell biotransformation of aniline derivatives to 4-FA.

Advantages: High selectivity, reduced energy consumption, and minimal hazardous waste.

► Electrochemical Synthesis

Direct Electrochemical Fluorination: Use renewable electricity to drive fluorination via anodic oxidation (e.g., fluoride ions as fluorine sources).

Paired Electrolysis: Combine fluorination with hydrogen evolution or CO₂ reduction to improve overall efficiency.

Case Study: Recent studies demonstrate electrochemical C-H fluorination of anilines with >80% yield under mild conditions.

► Photocatalytic Synthesis

Visible-Light-Driven Fluorination: Utilize metal-organic frameworks (MOFs) or organocatalysts (e.g., eosin Y) to activate fluorine sources (e.g., NFSI, Selectfluor®) under solar irradiation.

Mechanistic Insights: Investigate radical pathways or ion-pair intermediates to optimize reaction conditions.

Potential: Scalable, low-cost, and compatible with flow chemistry systems.

1. What is its specific role in crystal engineering?
When 4-fluorobenzenamine crystallizes at low temperatures, it forms a unique molecular packing pattern. The crystal structure contains both strong hydrogen bonds (N-H···F, N-H···π) and weak interactions involving fluorine atoms (C-F···H, C-F···π). Studies have shown that the introduction of fluorine atoms significantly alters the cooperative interaction network between molecules, making it an ideal model system for studying supramolecular chemistry of organic fluorine compounds. Moreover, it can form co-crystals with energetic materials (such as HMX) to regulate the crystal structure and properties of explosives.
2. What value does it have in the research of environmental microbial degradation?
As a representative of fluorinated aromatic amines, 4-fluorobenzenamine is often used as a model pollutant to study the microbial degradation mechanism of fluorinated organic compounds. The research found that it takes approximately 26 days for a mixed bacterial population to completely degrade 4-fluorobenzenamine, and the maximum specific degradation rate can reach 22.48 mg/(g VSS·h). Interestingly, as the number of fluorine substitutions on the benzene ring increases (from mono-fluorine to tri-fluorine), the time required for bacterial enrichment and acclimatization significantly increases, while the degradation rate decreases accordingly. This provides important reference data for evaluating the environmental fate of different fluorinated compounds.
3. How is it used in isotope labeling studies?
The deuterated derivative 4-fluorobenzenamine-d₄ (where four hydrogen atoms on the benzene ring are replaced by deuterium) is an important tool in nuclear magnetic resonance spectroscopy and reaction mechanism studies. Through catalytic hydrogenation of 4-fluoronitrobenzene-d₄ or by adopting the directed adjacent metalation (DoM) strategy, highly isotopically pure (over 98%) labeled products can be obtained. These deuterated compounds are often used to trace chemical reaction pathways, study drug metabolism processes, and serve as internal standards for mass spectrometry analysis.

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