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

• 459-23-4 (E)-4-fluorobenzaldehyde oxime 
• 108-24-7 acetic anhydride 
• 680-31-9 N,N,N,N,N,N-hexamethylphosphoric triamide 
• 623-03-0 4-Cyanochlorobenzene 
• 462-06-6 fluorobenzene 
• 460-19-5 ethanedinitrile 
• 75-75-2 methanesulfonic acid 
• 79664-67-8 4-(3,3-diethyltriaz-1-en-1-yl)benzonitrile 
• 824-75-9 p-fluorobenzamide 
• 2252-32-6 4-cyanophenyldiazonium tetrafluoroborate 
• 79-24-3 Nitroethane 
• 459-57-4 4-fluorobenzaldehyde 
• 114650-59-8 C₁₂H₉FN₂S 
• 100-47-0 benzonitrile 

Downstream Products

• 59100-90-2 4-(1,1-Dimethyl-tridecyloxy)-benzoic acid 
• 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 
• 56714-60-4 4-(1-adamantyloxy)benzoic acid 
• 59100-88-8 4-(Adamantan-2-yloxy)-benzoic acid 
• 59100-93-5 4-(1-Ethyl-1-methyl-pentadecyloxy)-benzoic acid 
• 59100-87-7 4-Cyclododecyloxy-benzoic acid 
• 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 

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.

Synthesis and Characterization of Bidentate (P^N)Gold(III) Fluoride Complexes: Reactivity Platforms for Reductive Elimination Studies

A new family of cationic, bidentate (P^N)gold(III) fluoride complexes has been prepared and a detailed characterization of the gold-fluoride bond has been carried out. Our results correlate with the observed reactivity of the fluoro ligand, which undergoes facile exchange with both cyano and acetylene nucleophiles. The resulting (P^N)arylgold(III)C(sp) complexes have enabled the first study of reductive elimination on (P^N)gold(III) systems, which demonstrated that C(sp2)?C(sp) bond formation occurs at higher rates than those reported for analogous phosphine-based monodentate systems.

Pd@CeO2-catalyzed cyanation of aryl iodides with K4Fe(CN)6·3H2O under visible light irradiation

Cyanation of aryl iodides is still challenging work for chemical researchers because of harsh reaction conditions and toxic cyanide sources. Herein, we have developed a new protocol based on the combination of the catalyst Pd@CeO2, nontoxic cyanide source K4[Fe (CN)6]·3H2O, and driving force visible light irradiation. The reaction is operated at relatively moderate temperature (55°C) and exhibits good catalytic efficiency of product aryl nitriles (yields of 89.4%). Moreover, the catalyst Pd@CeO2 possesses good reusability with a slight loss of photocatalytic activity after five consecutive runs. The reaction system based on the above combination shows a wide range of functional group tolerance under the same conditions. Reaction conditions such as temperature, time, the component of catalyst, and solutions are optimized by studying cyanation of 1-iodo-4-nitrobenzene as model reaction. According to these results, the possible mechanism of Pd@CeO2-catalyzed cyanation of aryl iodides under visible light irradiation is proposed based on the influence of visible light on the catalyst and reactant compounds. In all, we provided an environmental and economic method for preparation of aryl nitriles from cyanation of aryl iodides based on the goal of green chemistry for sustainable development.

CuO-catalyzed conversion of arylacetic acids into aromatic nitriles with K4Fe(CN)6 as the nitrogen source

Readily available CuO was demonstrated to be effective as the catalyst for the conversion of arylacetic acids to aromatic nitriles with non-toxic and inexpensive K4Fe(CN)6 as the nitrogen source via the complete cleavage of the C[tbnd]N triple bond. The present method allowed a series of arylacetic acids including phenylacetic acids, naphthaleneacetic acids, 2-thiopheneacetic acid and 2-furanacetic acid to be converted into the targeted products in low to high yields.

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.

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.

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.