143234-87-1

Basic information

• Product Name: p-Fluorobenzonitrile
• Synonyms: p-Fluorobenzonitrileradical ion(1+)
• CAS NO: 143234-87-1
• Molecular Formula: C7H4FN
• Molecular Weight: 121.1118
• EINECS: 214-784-9
• Mol File: 143234-87-1.mol

Chemical Properties

• Boiling Point: 189.6 °C at 760 mmHg
• Flash Point: 65.6 °C
• Appearance: /
• Density: 1.15 g/cm³
• CAS DataBase Reference: p-Fluorobenzonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: p-Fluorobenzonitrile(143234-87-1)
• EPA Substance Registry System: p-Fluorobenzonitrile(143234-87-1)

Safety Data

• Hazardous Substances Data: 143234-87-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
p-Fluorobenzonitrile is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its unique structure allows for the development of new drugs with specific therapeutic properties, contributing to the advancement of medicine.
Used in Agrochemical Industry:
In the agrochemical sector, p-Fluorobenzonitrile is employed as a crucial component in the production of pesticides and other crop protection agents. Its incorporation enhances the effectiveness of these products, ensuring better agricultural yields.
Used in Dye and Pigment Manufacturing:
p-Fluorobenzonitrile is utilized as an intermediate in the manufacturing process of dyes and pigments. Its presence contributes to the creation of vibrant colors and improved stability in various applications, such as textiles, plastics, and printing inks.
Safety Precautions:
It is essential to handle and store p-Fluorobenzonitrile with caution due to its hazardous nature if ingested, inhaled, or comes into contact with skin. Adhering to all safety guidelines and regulations is crucial to prevent any adverse effects on health and the environment.

Upstream product

• 623-03-0 4-Cyanochlorobenzene 
• 462-06-6 fluorobenzene 
• 460-19-5 ethanedinitrile 
• 2252-32-6 4-cyanophenyldiazonium tetrafluoroborate 
• 79-24-3 Nitroethane 
• 459-57-4 4-fluorobenzaldehyde 
• 114650-59-8 C₁₂H₉FN₂S 
• 100-47-0 benzonitrile 
• 98516-43-9 C₉H₁₀NS⁽¹⁺⁾*CH₃O₄S^(1-) 
• 459-23-4 (E)-4-fluorobenzaldehyde oxime 
• 75-05-8 acetonitrile 
• 873-74-5 4-Aminobenzonitrile 
• 619-72-7 4-nitrobenzonitrile 
• 459-23-4 4-fluorobenzaldoxime 

Downstream Products

• 59100-92-4 4-(1,1-Dimethyl-hexadecyloxy)-benzoic acid 
• 59100-89-9 4-(1,1-Dimethyl-dodecyloxy)-benzoic acid 
• 59100-91-3 4-(1,1-Dimethyl-tetradecyloxy)-benzoic acid 
• 59100-87-7 4-Cyclododecyloxy-benzoic acid 
• 64468-77-5 2-(4-cyanophenyl)furan 
• 156601-59-1 4-pentyl-N-(4-cyanophenyl)piperidine 
• 93593-10-3 (4-Fluoro-phenyl)-[2-(1-methyl-piperidin-4-ylamino)-phenyl]-methanone 
• 146328-87-2 2-fluoro-5-cyanobenzoic acid 
• 40507-24-2 2-(4-fluorobenzoyl)-N-isopropyl-5-methylaniline 
• 78649-81-7 2-(4-fluorobenzoyl)-N-isopropyl-3-methylaniline 
• 90178-98-6 5-Brom-2-<4-(4-cyanphenoxy)phenyl>-1-benzofuran 
• 90178-97-5 2-<4-(4-Cyanphenoxy)phenyl>-1-benzofuran-5-carbonitril 
• 122957-42-0 3-(4-cyanophenyl)-2-methylimidazo<4,5-c>pyridine 
• 122957-32-8 4-(2-methylimidazo[4,5-c]pyrid-1-yl)benzonitrile 

Relevant articles and documents

Nitrile Synthesis via Desulfonylative-Smiles Rearrangement

Herein, we designed a simple nitrile synthesis from N-[(2-nitrophenyl)sulfonyl]benzamides via base-promoted intramolecular nucleophilic aromatic substitution. The process features redox-neutral conditions as well as no requirement of toxic cyanide species and transition metals. Our process shows broad scope and various functional group compatibility, affording a variety of (hetero)aromatic nitriles in good to excellent yields.

Product selectivity controlled by manganese oxide crystals in catalytic ammoxidation

The performances of heterogeneous catalysts can be effectively tuned by changing the catalyst structures. Here we report a controllable nitrile synthesis from alcohol ammoxidation, where the nitrile hydration side reaction could be efficiently prevented by changing the manganese oxide catalysts. α-Mn2O3 based catalysts are highly selective for nitrile synthesis, but MnO2-based catalysts including α, β, γ, and δ phases favour the amide production from tandem ammoxidation and hydration steps. Multiple structural, kinetic, and spectroscopic investigations reveal that water decomposition is hindered on α-Mn2O3, thus to switch off the nitrile hydration. In addition, the selectivity-control feature of manganese oxide catalysts is mainly related to their crystalline nature rather than oxide morphology, although the morphological issue is usually regarded as a crucial factor in many reactions.

Selective oxidation of alcohols to nitriles with high-efficient Co-[Bmim]Br/C catalyst system

An efficient method for catalyzing the ammoxidation of aromatic alcohols to aromatic nitriles was developed, in which a new heterogeneous catalyst based on transition metal elements was employed, the new catalyst was named Co-[Bmim]Br/C-700 and then characterized by X-ray photo-electronic spectroscopy, transmission electron microscope and X-ray diffraction. The reaction was carried out by two consecutive dehydrogenations under the catalysis of Co-[Bmim]Br/C-700, which catalytically oxidized the alcohol to the aldehyde, and then the aldehyde was subjected to ammoxidation to the nitrile. The catalyst system was suitable for a wide range of substrates and nitriles obtained in high yields, especially, the conversion rate of benzyl alcohol, 4-methoxybenzyl alcohol, 4-chlorobenzyl alcohol and 4-nitrobenzyl alcohol reached 100%. The substitution of ammonia and oxygen for toxic cyanide to participate in the reaction accords with the theory of green chemistry.

Preparation method of aromatic nitrile compound

The invention discloses a preparation method of an aromatic nitrile compound, which comprises the following steps: stirring benzyl alcohol, ammonia water and a transition metal doped MCM-48 molecular sieve supported bis-imidazole ionic liquid in a reaction vessel, introducing oxygen, and reacting at 20-90 DEG C for 1-12 hours to obtain the target aromatic nitrile compound. The functionalized transition metal doped MCM-48 molecular sieve supported bis-imidazole ionic liquid is adopted as the catalyst, and the catalyst is high in activity, high in catalytic efficiency, good in stability, easy to recover and capable of being well recycled. The method has the advantages of high ammoxidation reaction selectivity, high product yield and simple system operation, is a green and efficient method for preparing the aromatic nitrile compound, and is beneficial to industrial production.

Cu2O-Catalyzed Conversion of Benzyl Alcohols Into Aromatic Nitriles via the Complete Cleavage of the C≡N Triple Bond in the Cyanide Anion

Nitrogen transfer from cyanide anion to an aldehyde is emerging as a promising method for the synthesis of aromatic nitriles. However, this method still suffers from a disadvantage that a use of stoichiometric Cu(II) or Cu(I) salts is required to enable the reaction. As we report herein, we overcame this drawback and developed a catalytic method for nitrogen transfer from cyanide anion to an alcohol via the complete cleavage of the C≡N triple bond using phen/Cu2O as the catalyst. The present condition allowed a series of benzyl alcohols to be smoothly converted into aromatic nitriles in moderate to high yields. In addition, the present method could be extended to the conversion of cinnamic alcohol to 3-phenylacrylonitrile.

Tetramethylammonium Fluoride Alcohol Adducts for SNAr Fluorination

Nucleophilic aromatic fluorination (SNAr) is among the most common methods for the formation of C(sp2)-F bonds. Despite many recent advances, a long-standing limitation of these transformations is the requirement for rigorously dry, aprotic conditions to maintain the nucleophilicity of fluoride and suppress the generation of side products. This report addresses this challenge by leveraging tetramethylammonium fluoride alcohol adducts (Me4NF·ROH) as fluoride sources for SNAr fluorination. Through systematic tuning of the alcohol substituent (R), tetramethylammonium fluoride tert-amyl alcohol (Me4NF·t-AmylOH) was identified as an inexpensive, practical, and bench-stable reagent for SNAr fluorination under mild and convenient conditions (80 °C in DMSO, without the requirement for drying of reagents or solvent). A substrate scope of more than 50 (hetero) aryl halides and nitroarene electrophiles is demonstrated.

Highly Efficient Oxidative Cyanation of Aldehydes to Nitriles over Se,S,N-tri-Doped Hierarchically Porous Carbon Nanosheets

Oxidative cyanation of aldehydes provides a promising strategy for the cyanide-free synthesis of organic nitriles. Design of robust and cost-effective catalysts is the key for this route. Herein, we designed a series of Se,S,N-tri-doped carbon nanosheets with a hierarchical porous structure (denoted as Se,S,N-CNs-x, x represents the pyrolysis temperature). It was found that the obtained Se,S,N-CNs-1000 was very selective and efficient for oxidative cyanation of various aldehydes including those containing other oxidizable groups into the corresponding nitriles using ammonia as the nitrogen resource below 100 °C. Detailed investigations revealed that the excellent performance of Se,S,N-CNs-1000 originated mainly from the graphitic-N species with lower electron density and synergistic effect between the Se, S, N, and C in the catalyst. Besides, the hierarchically porous structure could also promote the reaction. Notably, the unique feature of this metal-free catalyst is that it tolerated other oxidizable groups, and showed no activity on further reaction of the products, thereby resulting in high selectivity. As far as we know, this is the first work for the synthesis of nitriles via oxidative cyanation of aldehydes over heterogeneous metal-free catalysts.

Biomass chitosan-derived nitrogen-doped carbon modified with iron oxide for the catalytic ammoxidation of aromatic aldehydes to aromatic nitriles

Nitrogen-doped carbon catalysts have attracted increasing research attention due to several advantages for catalytic application. Herein, cost-effective, renewable biomass chitosan was used to prepare a N-doped carbon modified with iron oxide catalyst (Fe2O3@NC) for nitrile synthesis. The iron oxide nanoparticles were uniformly wrapped in the N-doped carbon matrix to prevent their aggregation and leaching. Fe2O3@NC-800, which was subjected to carbonization at 800 °C, exhibited excellent activity, selectivity, and stability in the catalytic ammoxidation of aromatic aldehydes to aromatic nitriles. This study may provide a new method for the fabrication of an efficient and cost-effective catalyst system for synthesizing nitriles.

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 AND REAGENT FOR DEOXYFLUORINATION

A safe, simple, and selective method and reagent for deoxyfluorination is disclosed. With the method and reagent disclosed herein, organic compounds such as carboxylic acids, carboxylates, carboxylic acid anhydrides, aldehydes, and alcohols can be fluorinated by using the most common nucleophilic fluorinating reagents and electron deficient fluoroarenes as mediators under mild conditions, giving corresponding fluoroorganic compounds in excellent yield with a wide range of functional group compatibility and easy product purification. For example, directly utilizing KF for deoxyfluorination of carboxylic acids provides the most economical and the safest pathway to access acyl fluorides, key intermediates for syntheses of peptide, amide, ester, and dry fluoride salts.