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 
• 10442-39-4 tetra-n-butylammonium cyanide 
• 114650-59-8 C₁₂H₉FN₂S 
• 79-24-3 Nitroethane 
• 459-57-4 4-fluorobenzaldehyde 

Downstream Products

• 93593-10-3 (4-Fluoro-phenyl)-[2-(1-methyl-piperidin-4-ylamino)-phenyl]-methanone 
• 25117-74-2 4-ethoxybenzonitrile 
• 840-77-7 4-fluorobenzoic acid octyl ester 
• 1627148-44-0 1-(4-fluorophenyl)pentan-1-imine 
• 80529-17-5 4,4'-difluorobenzophenone imine 
• 444002-96-4 4-[2-oxopyridin-1(2H)-yl]benzonitrile 
• 25372-03-6 4-(1H-imidazol-1-yl)benzonitrile 
• 1999-00-4 ethyl 3-(4'-fluorophenyl)-3-oxopropionate 
• 55368-18-8 4'-Cyanacetophenon-<3-(4-cyanphenoxy)>-phenylhydrazon 
• 80498-64-2 4,4'-(1,4-Phenylendioxy)-dibenzamidin 
• 30202-93-8 4-(3-aminophenoxy)benzonitrile 
• 37507-06-5 Diphenylmethyl-2-nitro-4-cyano-phenolat 
• 96159-98-7 2-(4-Fluoro-phenyl)-3-methyl-4,5-dihydro-thiazol-3-ium; iodide 

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.

Development and Molecular Understanding of a Pd-Catalyzed Cyanation of Aryl Boronic Acids Enabled by High-Throughput Experimentation and Data Analysis

A synthetic method for the palladium-catalyzed cyanation of aryl boronic acids using bench stable and non-toxic N-cyanosuccinimide has been developed. High-throughput experimentation facilitated the screen of 90 different ligands and the resultant statistical data analysis identified that ligand σ-donation, π-acidity and sterics are key drivers that govern yield. Categorization into three ligand groups – monophosphines, bisphosphines and miscellaneous – was performed before the analysis. For the monophosphines, the yield of the reaction increases for strong σ-donating, weak π-accepting ligands, with flexible pendant substituents. For the bisphosphines, the yield predominantly correlates with ligand lability. The applicability of the designed reaction to a wider substrate scope was investigated, showing good functional group tolerance in particular with boronic acids bearing electron-withdrawing substituents. This work outlines the development of a novel reaction, coupled with a fast and efficient workflow to gain understanding of the optimal ligand properties for the design of improved palladium cross-coupling catalysts.

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.

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.

A new reagent for efficient synthesis of nitriles from aldoximes using methoxymethyl bromide

This study outlines an efficient, high-yielding, and rapid method by which to access diverse nitriles from aldoximes with methoxymethyl bromide (MOM-Br) in THF. It represents the first application of MOM-Br as a deoximation reagent to synthesize nitriles. The reaction was performed at reflux to ensure excellent yield (79-96%) of the nitriles within 20-45 minutes. Furthermore, this method has been successfully applied to the synthesis of the synthesis precursor of aromatic, heteroaromatic, cyclic, and acyclic aliphatic.

Facile dehydration of primary amides to nitriles catalyzed by lead salts: The anionic ligand matters

The synthesis of nitrile under mild conditions was achieved via dehydration of primary amide using lead salts as catalyst. The reaction processes were intensified by not only adding surfactant but also continuously removing the only by-product, water from the system. Both aliphatic and aromatic nitriles can be prepared in this manner with moderate to excellent yields. The reaction mechanisms were obtained with high-level quantum chemical calculations, and the crucial role the anionic ligand plays in the transformations were revealed.