Category: 766-84-7

766-84-7, Name is 3-Chlorobenzonitrile, molecular formula is C7H4ClN, belongs to nitriles-buliding-blocks compound, is a common compound. In a patnet, author is Gomaa, Mohsen A-M, once mentioned the new application about 766-84-7, Application In Synthesis of 3-Chlorobenzonitrile.

Background: The reactivity of 4-(dicyanomethylene)-3-methyl-l-phenyl-2-pyrazoline-5-one DCNP 1 and its derivatives makes it valuable as a building block for the synthesis of heterocyclic compounds like pyrazolo-imidazoles, – thiazoles, spiropyridines, spiropyrroles, spiropyrans and others. As a number of publications have reported on the reactivity of DCNP and its derivatives, we compiled some features of this interesting molecule. Objective: This article aims to review the preparation of DCNP, its reactivity and application in heterocyclic and dyes synthesis. Conclusion: In this review we have provided an overview of recent progress in the chemistry of DCNP and its significance in synthesis of various classes of heterocyclic compounds and dyes. The unique reactivity of DCNP offers unprecedentedly mild reaction conditions for the generation of versatile cynomethylene dyes from a wide range of precursors including amines, a-aminocarboxylic acids, their esters, phenols, malononitriles and azacrown ethers. We anticipate that more innovative transformations involving DCNP will continue to emerge in the near future.

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Reference:
Nitrile – Wikipedia,
,Nitriles – Chemistry LibreTexts

Reference of 766-84-7,Some common heterocyclic compound, 766-84-7, name is 3-Chlorobenzonitrile, molecular formula is C7H4ClN, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

To a 400 L glass lined vessel was charged 1,3-dibromo-5,5-dimethyl-hydantoin (DBH) (10.88 kg, 38.6 mol), followed by methane sulfonic acid (111.4 kg). The resulting slurry was warmed to 35 C. to form a DBH solution. [0306] To a separate 400 L vessel was charged 3-chlorobenzonitrile 1-1 (8.050 kg, 58.5 mol, Acros, Lancaster) melt and cyclohexane (1.8 L total), followed by methanesulfonic acid (47.6 kg) to form a benzonitrile solution, which was warmed to 25-30 C. to dissolve any solids. The DBH solution was added to the benzonitrile solution over a period of about 30 minutes with fast agitation while maintaining a batch temperature of <30 C. The empty DBH solution containing vessel was rinsed with methane sulfonic acid (5.0 kg) and the rinse was added to the reaction mixture. The reaction was aged at 30 C. for 1 to 2 hours to affect reaction conversion >95 area % (tracked via HPLC assay). The reaction was then cooled to about 14 C. and slowly quenched with water (80.5 L) to maintain a temperature of <30 C. The reaction was then re-cooled to 20 C. and MTBE was added (208.5 kg) at <30 C. under agitation. The mixture was allowed to settle, the layers were separated and the aqueous layer was extracted with 101 kg of MTBE at 30 C., followed by 30 kg of MTBE. The organic layers were combined and washed with 50 kg 1.6 N NaOH, and 54 kg water, and then concentrated to 48 L, cooled and seeded (10 g of seed). Once a slurry formed, the concentration was resumed until a batch volume of 40 L was achieved. The resulting slurry was aged at 20 C. for 1.5 hours and then filtered. The cake was washed with 12 kg of 1:1 MTBE:cyclohexane (in 2 drops). The wet solids were dried in a filter dryer to give 1-2. 1H NMR (CDCl3, 400 MHz) delta 7.39 (d, J=2.2 Hz, 1H), 7.22 (dd, J=2.3, 8.4 Hz, 1H), 7.16 (d, J=8.5 Hz, 1H) The synthetic route of 766-84-7 has been constantly updated, and we look forward to future research findings. Reference:
Patent; Boice, Genevieve N.; Conrad, Karen M.; Corley, Edward G.; Matty JR., Louis; Murry, Jerry A.; Savarin, Cecile G.; US2004/181070; (2004); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 766-84-7, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 766-84-7 name is 3-Chlorobenzonitrile, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

The appropriate quantity of stock solution A was added to a 4 mL vial containing the aryl chloride (1.00 mmol) and NaOtBu (230 mg, 2.40 mmol), unless otherwise stated, in 1.5 mL of DME. The thiol (1.00 mmol) was then added, and the vial sealed with a cap containing a PTFE septum. The mixture was heated at 110 0C until the chloroarene was consumed, as determined by GC. Silica gel (0.5 g) was added, and the solvents were evaporated under reduced pressure. The crude residue was purified by column chromatography on silica gel using hexane or mixtures of hexane and ethyl acetate as eluent. Aryl sulfides were isolated in the yields reported in Tables 5 and 6.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Chlorobenzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; YALE UNIVERSITY; WO2007/64869; (2007); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

These common heterocyclic compound, 766-84-7, name is 3-Chlorobenzonitrile, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Quality Control of 3-Chlorobenzonitrile

To a solution of 3-chlorobenzonitrile (10 g, 72.7 mmol) in 367 ml ethanol was added hydroxylammonium chloride (7.58 g, 109.0 mmol) and triethylamine (9.56 g, 94.5 mmol) and then the reaction mixture was stirred overnight at 50 C. After cooling to RT, the solvent was evaporated and the crude was solved in ethyl acetate and extracted with water. The organic phase was dried over magnesium sulfate, filtered and evaporated under vacuum to yield the title compound (10.77 g, 81% of theory, 93 % purity). The compound was used without further purification. LC-MS (method 2B): RT = 1.64 min, m/z = 171 (M+H)+

The synthetic route of 3-Chlorobenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; ELLERMANN, Manuel; VALOT, Gaelle; CANCHO GRANDE, Yolanda; HAssFELD, Jorma; KINZEL, Tom; KOeBBERLING, Johannes; BEYER, Kristin; ROeHRIG, Susanne; SPERZEL, Michael; STAMPFUss, Jan; MEYER, Imke; KOeLLNBERGER, Maria; BURKHARDT, Nils; SCHLEMMER, Karl-Heinz; STEGMANN, Christian; SCHUHMACHER, Joachim; WERNER, Matthias; HEIERMANN, Joerg; HENGEVELD, Willem Jan; (764 pag.)WO2016/71216; (2016); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 766-84-7,Some common heterocyclic compound, 766-84-7, name is 3-Chlorobenzonitrile, molecular formula is C7H4ClN, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Preparation of N-(2-butyryl-4-chlorophenyl)trifluoromethanesulfonamide (Formula 29A) a) To a stirred solution of 3-chlorobenzonitrile (2.0g, 14.54 mmol) and n-propylmagnesium chloride (2M in Et2O) (8.0 mL, 15.99 mmol) in THF (40 mL) was added CuCl (29 mg, 0.29 mmol), and the mixture was refluxed for 30 minutes. After cooling to RT, cold 1N HCl (10 mL) was added cautiously, the THF removed under reduced pressure, further 1N HCl (30 mL) added and the reaction heated at 90 C. for 1 hour. To the cooled reaction mixture was added water (20 mL) and CH2Cl2 (50 mL), the phases separated, and the aqueous phase again extracted with CH2Cl2. The combined organics were washed with water, dried over MgSO4 and the solvent evaporated under vacuum. The residue was filtered through a pad of silica (eluting with CH2Cl2) to afford 1-(3-chlorophenyl)butan-1-one 26A (3.14 g, 97%), as a yellow liquid.

The synthetic route of 766-84-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Meyer, Adam Gerhard; Winzenberg, Kevin Norman; Sawutz, David G.; Liepa, Andris Juris; US2006/63841; (2006); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 766-84-7, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 766-84-7 as follows.

General procedure: An equimolar mixture of 2-aminoethanol (1.0 mmol) and sulfur(1.0 mmol) was heated under solvent-free condition at 50C. Nitrile (1.0 mmol) was then added to reaction mixture and refluxed at 80C. The progress of the reaction was monitored through TLC (n-hexane: EtOAc, 8:2). After completion of the reaction, excess of water was added, and the product was filtered (for solid). Further chromatographic purification afforded pure product. All the compounds were characterizedby infrared (IR) and 1H NMR and 13C NMR spectroscopic data, as well as by comparison with data of reported compounds.

According to the analysis of related databases, 766-84-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Bansal, Shivani; Gupta, Poonam; Halve; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 191; 7; (2016); p. 971 – 974;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 766-84-7, name is 3-Chlorobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Quality Control of 3-Chlorobenzonitrile

General procedure: A 5 mL reaction tube was charged with Phen-MCM-41-CuBr (36 mg, 0.025 mmol), 2-aminopyridine 1 (0.6 mmol), nitrile 2 (0.5 mmol), ZnI2 (16 mg, 0.05 mmol), and 1,2-dichlorobenzene (1.5 mL) under an air atmosphere. The reaction tube was sealed and placed in an oil bath at r.t. The reaction mixture was stirred at 130 C for 24 h. After cooling to r.t., the reaction mixture was diluted with EtOAc (10 mL) and filtered. The supported copper catalyst was washed with water (2 5 mL) and acetone (2 5 mL), and reused in the next run. The filtrate was concentrated in vacuo and the residue was purified by flash column chromatography on silica gel (hexane/EtOAc, 3:2) to provide the desired product 3.

The synthetic route of 766-84-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Xia, Jianhui; Huang, Xue; Cai, Mingzhong; Synthesis; vol. 51; 9; (2019); p. 2014 – 2022;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 766-84-7,Some common heterocyclic compound, 766-84-7, name is 3-Chlorobenzonitrile, molecular formula is C7H4ClN, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

General procedure: To a solution of 0.01 mol of nitrile in 200 mL of ethanol was added a solution of 0.695 g (0.01 mol) of hydroxylamine hydrochloride in 10 mL of water, followed by the further addition of 0.420 g (0.005 mol) of sodium carbonate in 10 mL of water. The reaction mixture was stirred overnight at rt. The mixture was then concentrated to small volume under vacuum, diluted with cold water, and placed in refrigerator overnight. The precipitate that formed was recovered and recrystallized from ethanol. All amidoximes were known and characterized by comparison of their physical data with those prepared in accordance with literature procedures.1

The synthetic route of 766-84-7 has been constantly updated, and we look forward to future research findings.

Chemistry is an experimental science, Application In Synthesis of 3-Chlorobenzonitrile, and the best way to enjoy it and learn about it is performing experiments.Introducing a new discovery about 766-84-7, Name is 3-Chlorobenzonitrile, molecular formula is C7H4ClN, belongs to nitriles-buliding-blocks compound. In a document, author is Nori, Valeria.

Triarylborane catalysed N-alkylation of amines with aryl esters

The ability of halogenated triarylboranes to accept a lone pair of electrons from donor substrates renders them excellent Lewis acids which can be exploited as a powerful tool in organic synthesis. Tris(pentafluorophenyl)borane has successfully demonstrated its ability to act as a metal-free catalyst for an ever-increasing range of organic transformations. Herein we report the N-alkylation reactions of a wide variety of amine substrates including diarylamines, N-methylphenyl amines, and carbazoles with aryl esters using catalytic amounts of B(C6F5)(3). This mild reaction protocol gives access to N-alkylated products (35 examples) in good to excellent yields (up to 95%). The construction of a C-N bond at the propargylic position has also been demonstrated to yield synthetically useful propargyl amines. On the other hand, unsubstituted 1H-indoles and 1H-pyrroles at the C3/C2 positions afforded exclusively C-C coupled products. Extensive DFT studies have been employed to understand the mechanism for this transformation.

Balanced chemical reaction does not necessarily reveal either the individual elementary reactions by which a reaction occurs or its rate law. In my other articles, you can also check out more blogs about 766-84-7. Application In Synthesis of 3-Chlorobenzonitrile.

Chemistry is the science of change. But why do chemical reactions take place? Why do chemicals react with each other? The answer is in thermodynamics and kinetics, 766-84-7, Name is 3-Chlorobenzonitrile, SMILES is N#CC1=CC=CC(Cl)=C1, belongs to nitriles-buliding-blocks compound. In a document, author is Chen, Hong-Wei, introduce the new discover, Application In Synthesis of 3-Chlorobenzonitrile.

Asymmetric Deoxygenative Cyanation of Benzyl Alcohols Enabled by Synergistic Photoredox and Copper Catalysis

. Summary of main observation and conclusion: An enantioselective deoxygenative cyanation of benzyl alcohols was accomplished for the first time through the synergistic photoredox and copper catalysis. This reaction features the use of organic photosensitizer and low-cost 3d metal catalyst, simple and safe operations, and extremely mild conditions. A variety of chiral benzyl nitriles were produced in generally good yields and high level of enantiocontrols from readily available feedstocks (22 examples, up to 93% yield and 92% ee).

The proportionality constant is the rate constant for the particular unimolecular reaction. the reaction rate is directly proportional to the concentration of the reactant. I hope my blog about 766-84-7 is helpful to your research. Application In Synthesis of 3-Chlorobenzonitrile.