350-46-9

Usage

Uses

Used in Chemical Synthesis:
4-Fluoronitrobenzene is used as a key intermediate in the chemical synthesis industry for the production of a wide range of compounds. Its unique structure allows for versatile reactions and the creation of various derivatives, making it a valuable component in the synthesis of pharmaceuticals, dyes, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4-Fluoronitrobenzene is utilized as a pharmaceutical intermediate. Its properties enable the development of new drugs with potential therapeutic applications, contributing to the advancement of medical treatments.
Used in Hair Dye Industry:
4-Fluoronitrobenzene is also used as a component in the hair dye industry. Its incorporation into hair dye formulations can enhance the color properties and improve the overall performance of the product, providing consumers with better hair coloring experiences.
Used in Polymer Industry:
In the polymer industry, 4-Fluoronitrobenzene is used for the preparation of novel soluble aromatic polyimides, such as 1,3,5-Tris(4-aminophenoxy)benzene (TAB). These polyimides exhibit unique properties, such as high thermal stability and excellent mechanical strength, making them suitable for various applications, including aerospace, electronics, and automotive industries.

Synthesis Reference(s)

Journal of the American Chemical Society, 78, p. 6034, 1956 DOI: 10.1021/ja01604a022Tetrahedron, 52, p. 23, 1996 DOI: 10.1016/0040-4020(95)00867-8Tetrahedron Letters, 30, p. 7199, 1989 DOI: 10.1016/S0040-4039(01)93933-4

Flammability and Explosibility

Nonflammable

Purification Methods

Crystallise it from EtOH. [Beilstein 5 H 241, 5 IV 719.]

InChI:InChI=1/C6H4FNO2/c7-5-1-3-6(4-2-5)8(9)10/h1-4H

Upstream product

• 462-06-6 fluorobenzene 
• 591-09-3 nitro acetate 
• 598-58-3 methyl nitrate 
• 54480-44-3 N,N-dimethyl-N'-(4-methoxyphenyl)-1,4-phenylendiamine 
• 118-74-1 hexachlorobenzene 
• 34467-53-3 p-fluoronitrobenzene anion 
• 98-95-3 nitrobenzene 
• 352-34-1 4-fluoro-1-iodobenzene 
• 100-25-4 para-dinitrobenzene 
• 100-00-5 4-chlorobenzonitrile 
• 1849-36-1 para-nitrobenzenethiol 
• 220405-40-3 2,2-difluoro-1,3-dimethyl-imidazolidine 
• 1040922-31-3 Pd(CH₃COO)(C₅H₅N)(C₅H₄NC₆H₄NSO₂C₆H₄NO₂) 
• 5122-94-1 4-biphenylboronic acid 

Downstream Products

• 3665-80-3 N-Ethyl-4-nitroanilin 
• 1965-54-4 N-(2-hydroxyethyl)-4-nitroaniline 
• 16365-27-8 2-(4-nitrophenoxy)ethanol 
• 2216-15-1 1-diethylamino-4-nitrobenzene 
• 58259-34-0 N-butyl-4-nitroaniline 
• 13788-94-8 3,5-dimethyl-1-(4-nitrophenyl)pyrazole 
• 87787-17-5 4-(2,2-ethylenedioxy-1-methylcyclohexylmethoxy)nitrobenzene 
• 103788-68-7 2-Methyl-4-[2-(4-nitro-phenoxy)-ethyl]-thiazole 
• 85002-52-4 4-<2-(2-pyridyl)ethoxy>nitrobenzene 
• 85583-51-3 4-[2-(5-methyl-pyridin-2-yl)ethoxy]nitrobenzene 
• 85583-54-6 4-[2-(5-ethyl-2-pyridyl)ethoxy]nitrobenzene 
• 14960-95-3 1-(4-nitro-phenyl)-4-phenyl-piperazine 
• 23309-18-4 2,4-dimethyl-1-(4-nitrophenyl)-1H-imidazole 
• 117847-19-5 [4-(4-Nitro-phenylamino)-phenyl]-phenyl-methanone 

Relevant academic research and scientific papers

Method for synthesizing nitro (hetero) aromatic hydrocarbon

The invention discloses a method for synthesizing nitro (hetero) aromatic hydrocarbon, and belongs to the field of organic synthesis. According to the method, simple (hetero) aromatic hydrocarbon is taken as an initial raw material and is stirred and reacted in an organic solvent at 40-100 DEG C under the action of a nitration reagent, a lewis acid catalyst and protective gas, and nitro (hetero) aromatic hydrocarbon can be obtained. The method provided by the invention has the advantages of cheap and easily available raw materials, mild reaction conditions, simple preparation process, good chemical selectivity, wide substrate application range, easy amplification and the like, has great application potential, and lays a good foundation for industrial production.

The polyhedral nature of selenium-catalysed reactions: Se(iv) species instead of Se(vi) species make the difference in the on water selenium-mediated oxidation of arylamines

Selenium-catalysed oxidations are highly sought after in organic synthesis and biology. Herein, we report our studies on the on water selenium mediated oxidation of anilines. In the presence of diphenyl diselenide or benzeneseleninic acid, anilines react with hydrogen peroxide, providing direct and selective access to nitroarenes. On the other hand, the use of selenium dioxide or sodium selenite leads to azoxyarenes. Careful mechanistic analysis and 77Se NMR studies revealed that only Se(iv) species, such as benzeneperoxyseleninic acid, are the active oxidants involved in the catalytic cycle operating in water and leading to nitroarenes. While other selenium-catalysed oxidations occurring in organic solvents have been recently demonstrated to proceed through Se(vi) key intermediates, the on water oxidation of anilines to nitroarenes does not. These findings shed new light on the multifaceted nature of organoselenium-catalysed transformations and open new directions to exploit selenium-based catalysis.

Nucleophilic Fluorination of Heteroaryl Chlorides and Aryl Triflates Enabled by Cooperative Catalysis

Aryl and heteroaryl fluorides are growing to be dominant motifs in pharmaceuticals and agrochemicals, yet they are rare in both nature and commodity chemicals. As a consequence, there is an increasingly urgent need to develop mild, cost-effective, and scalable methods for fluorination. The most straightforward route to synthesize aryl fluorides is through the halide exchange "halex"reaction, but conditions, cost, and atom economy preclude most available methods from large-scale manufacturing processes. We report a new approach that leverages the cooperative action of 18-crown-6 ether and tetramethylammonium chloride to catalytically access the reactivity of tetramethylammonium fluoride and achieve halex fluorinations under mild conditions with operational ease. The described methodology readily converts both heteroaryl chlorides and aryl triflates to their corresponding (hetero)aryl fluorides in high yields and purities.

Ipso Nitration of Aryl Boronic Acids Using Fuming Nitric Acid

The ipso nitration of aryl boronic acid derivatives has been developed using fuming nitric acid as the nitrating agent. This facile procedure provides efficient and chemoselective access to a variety of aromatic nitro compounds. While several activating agents and nitro sources have been reported in the literature for this synthetically useful transformation, this report demonstrates that these processes likely generate a common active reagent, anhydrous HNO3. Kinetic and mechanistic studies have revealed that the reaction order in HNO3 is >2 and indicate that the ?NO2 radical is the active species.

Method for pipeline continuous fluorination with fluorine salt as fluorine source

The method comprises the following steps: dissolving a fluorine salt in an aqueous polar aprotic solvent as reaction liquid A, dissolving an aryl (heterocyclic) chloride in a polar aprotic solvent as reaction liquid B, and reacting a polar aprotic solvent in the reaction liquid A with a polar aprotic solvent of the reaction liquid B. The reaction medium consisting of the preheated reaction liquid A and the preheated reaction liquid B enters the reaction coil for a fluorination reaction, and the resulting product from the reaction coil is subjected to post-treatment to obtain the product. The method has the characteristics of no need of adding a phase transfer catalyst, continuous production, low production cost and the like.

Method for efficiently synthesizing fluorine-containing compound

The invention discloses a method for efficiently synthesizing a fluorine-containing compound, and relates to the field of fluorine-containing compound synthesis. The method is a method for generating a corresponding fluorine atom substituted fluorine-containing compound by reacting aromatic chloride or activated chloride serving as a raw material with potassium fluoride under the action of a novel catalyst. The method disclosed by the invention has the advantages of good product selectivity, high efficiency, mild reaction conditions, simplicity and convenience in operation, convenience in application and the like.

Preparation method of fluorine-containing aryl compound

The invention relates to the field of organic synthesis, and especially relates to a preparation method of a fluorine-containing aryl compound. The invention provides a preparation method of a compound as shown in a formula 1. The preparation method comprises the following steps: fluorination reaction: reacting a compound as shown in a formula 2 with alkali metal fluoride in the presence of a phase transfer catalyst to prepare the compound as shown in the formula 1. According to the preparation method of the fluorine-containing aryl compound provided by the invention, a reaction system does not contain a solvent, the boiling point of the phase transfer catalyst is relatively high, solvent interference is avoided during rectification or short steaming after the reaction is finished, the distillation yield is high, and the product purity is good.

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.

Photoinduced Iron-Catalyzed ipso-Nitration of Aryl Halides via Single-Electron Transfer

A photoinduced iron-catalyzed ipso-nitration of aryl halides with KNO2 has been developed, in which aryl iodides, bromides, and some of aryl chlorides are feasible. The mechanism investigations show that the in situ formed iron complex by FeSO4, KNO2, and 1,10-phenanthroline acts as the light-harvesting photocatalyst with a longer lifetime of the excited state, and the reaction undergoes a photoinduced single-electron transfer (SET) process. This work represents an example for the photoinduced iron-catalyzed Ullmann-type couplings.

Radical Decarboxylative Carbometalation of Benzoic Acids: A Solution to Aromatic Decarboxylative Fluorination

Abundant aromatic carboxylic acids exist in great structural diversity from nature and synthesis. To date, the synthetically valuable decarboxylative functionalization of benzoic acids is realized mainly by transition-metal-catalyzed decarboxylative cross couplings. However, the high activation barrier for thermal decarboxylative carbometalation that often requires 140 °C reaction temperature limits both the substrate scope as well as the scope of suitable reactions that can sustain such conditions. Numerous reactions, for example, decarboxylative fluorination that is well developed for aliphatic carboxylic acids, are out of reach for the aromatic counterparts with current reaction chemistry. Here, we report a conceptually different approach through a low-barrier photoinduced ligand to metal charge transfer (LMCT)-enabled radical decarboxylative carbometalation strategy, which generates a putative high-valent arylcopper(III) complex, from which versatile facile reductive eliminations can occur. We demonstrate the suitability of our new approach to address previously unrealized general decarboxylative fluorination of benzoic acids.