Category: 19472-74-3

Reference of 19472-74-3,Some common heterocyclic compound, 19472-74-3, name is 2-Bromophenylacetonitrile, molecular formula is C8H6BrN, 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.

A 100 mL round bottom flask was evacuated and back-filled byargon 3 times, and charged with 0.84 mL of o-bromophenylacetonitrile(6.5 mmol) and 25 mL of toluene under a positive pressure ofargon. After being cooled in an ice bath for 5 min, 7.5mL of a solutionof NaHMDS in THF (1 M, 7.5 mmol) was added to this toluenesolution, and the ice bath was removed. After 30 min, 0.47mL of 2-chloropyridine (5.0 mmol) was added, and the mixture was heatedin a 70 C oil bath for 6 h. The progress of reactionwas monitored byTLC. Upon completion, reaction was quenched by adding 50 mL ofsaturated aqueous ammonium chloride solution reaction, then extracted by 30 mL of ethyl acetate for three times. The combinedorganic extract was dried (anhydrous sodium sulfate), filtered(celite plug), and concentrated under a reduced pressure. A silicagel column chromatography purification (9:1 Hexanes/EtOAc)afforded 0.84 g of 1h in 64% yield.1h: 1H NMR (400 MHz, CDCl3) delta ppm 8.63-8.62 (1H, m),7.70-7.59 (m, 3H), 7.59e7.35 (m, 1H), 7.38-7.20 (m, 3H), 5.80 (s,1H). 13C NMR (101 MHz, CDCl3) delta ppm 153.95, 150.23, 137.38, 134.17,133.40, 130.44, 130.26, 128.40, 123.70, 123.27, 122.51, 118.53, 44.74.13C-DEPT 135 NMR (101 MHz, CDCl3) delta ppm 150.23, 137.37, 133.39,130.43, 130.24, 128.39, 123.26, 122.50, 44.72.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Bromophenylacetonitrile, its application will become more common.

Reference:
Article; Chuentragool, Padon; Li, Zhou; Randle, Katrina; Mahchi, Faraj; Ochir, Ishmael; Assaf, Shadi; Gevorgyan, Vladimir; Journal of Organometallic Chemistry; vol. 867; (2018); p. 273 – 277;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 19472-74-3, A common heterocyclic compound, 19472-74-3, name is 2-Bromophenylacetonitrile, molecular formula is C8H6BrN, 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.

2-(2-bromophenyl)acetonitrile (5.00 g, 25.5 mmol), 4-chlorophenylboronic acid (4.30 g, 27.5 mmol), and tetrakis(triphenylphosphine)palladium(0) (0.48 g 0.42 mmol) were mixed with toluene (57 ml) in a 250 ml 3-necked flask. A reflux condenser was attached and the flask was purged with nitrogen. Aqueous solution of Na2CO3 (2M, 29 ml, 58 mmol) was added by syringe, and the atmosphere was evacuated and replaced with nitrogen. The reaction mixture was heated at reflux overnight, and then allowed to cool at ambient temperature. The mixture was partitioned between saturated aq. NH4Cl and EtOAc (200 ml each). The organic phase was separated, dried (MgSO4), filtered through diatomaceous earth and the filtrate was evaporated under reduced pressure. The residue was purified by column chromatography (ISCO, 120 g silica gel column, 0?20% EtOAc/hexanes) to give the tile compound (5.44 g, yield: 94%). 1H NMR (400 MHz, DMSO-d6) delta ppm 3.91 (s, 2H), 7.26-7.33 (m, 1H), 7.36-7.49 (m, 4H), 7.50-7.59 (m, 3H). LCMS: (ESI) m/z 228 [M+H]+.

The synthetic route of 19472-74-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; US2012/35134; (2012); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 19472-74-3, name is 2-Bromophenylacetonitrile, A new synthetic method of this compound is introduced below., Recommanded Product: 19472-74-3

To a solution of compound 5a (500 mg, 2.12 mmol) and 2-Bromophenylacetonitrile (538 mg, 2.76 mmol) in TMEDA (3 mL) and H2O (0.1 mL) was added Na2PdCl4 (6.23 mg, 0.02 mmol), CuI (7.62 mg, 0.04mmol) and 2-(Di-tert-butylphosphino)-1-phenylindole (13.5 mg, 0.04mmol). Under Ar, the mixture was warmed to 80 C and stirred for 3 h. After the mixture was cooled to warm temperature, water was added. The resulting solution was extracted with ethyl acetate and washed with water and brine. The organic solution was dried over sodium sulfate, concentrated in vacuo. The residue was purified by silica gel chromatography (petroleum/ethyl acetate 5:1) to give 462 mg of compound 6 (yield: 62%) as a colorless liquid. 1H NMR (400 MHz, CDCl3): delta 7.50 – 7.44 (m, 2H), 7.38 (td, 1H, J = 7.6, 1.3 Hz), 7.30 (t, 1H, J = 7.5 Hz), 7.15 (t, 1H, J = 8.7 Hz), 6.78 – 6.70 (m, 2H), 4.93 (s, 2H), 3.72 (s, 3H), 3.79 (s, 2H), 2.95 – 2.89 (m, 2H), 2.60 (t, 2H, J = 7.6 Hz). MS (EI) m/z: 351 (M+).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Article; Huang, Jing; Guo, Bin; Chu, Wen-Jing; Xie, Xin; Yang, Yu-She; Zhou, Xian-Li; Chinese Chemical Letters; vol. 27; 1; (2016); p. 159 – 162;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 19472-74-3, name is 2-Bromophenylacetonitrile, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C8H6BrN

2-Bromophenylacetonitrile (20.0 g, 0.1 mol) was dissolved in THF (100 mL), iced water,1 M borane tetrahydrofuran solution (200 mL, 0.2 mol) was added dropwise, and the mixture was dropped.Slowly warm to 80 C, stir for 24 h, place the cooled ice bath after cooling.Methanol (50 mL), 3N hydrochloric acid (30 mL) were slowly added dropwise, and the temperature was raised to 80 C.Stir for 4 h, concentrate and dilute with water (100 mL) and wash with diethyl ether (50 mL×2).The aqueous phase is adjusted to pH=10 with saturated sodium carbonate solution.Extracted with EA (50 mL×2), dried and concentrated.17.4 g (85.2%) of a pale yellow oily liquid was obtained.

According to the analysis of related databases, 19472-74-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Chinese Academy Of Medical Sciences Pharmaceutical Institute; Liu Zhanzhu; Shen Zhufang; Sun Zhaozhu; Pan Xuan; Zhou Tian; Huan Yi; Guan Baohe; (76 pag.)CN110294744; (2019); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 19472-74-3, name is 2-Bromophenylacetonitrile, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 19472-74-3

Step 1 : Nitrtle 19 (1.0 g, 5.10 mmol) was dissolved in DMF (20 mL) and was cooled to 0 C. NaH (60% in mineral oil, 449 mg, 11.22 mmol) was added and the reaction was warmed to 23 C and was stirred for 10 min. Dichloride {5, 1.3 g, 5.36 mmol) was added and the reaction was heated at 80 C overnight. The reaction was cooled to 23 C and was quenched with aqueous sat’d NH4CI (5 mL). The mixture was extracted with EtOAc (3x). The organic layers were washed with brine (1x), dried over MgS04, filtered and concentrated. The crude residue was recrystallized with EtOAc hexanes to obtain pure ferf-butyl 4-(2- bromophenyl)-4-cyanopiperidine-1-carboxylate as an off-white solid (20, 1.1 g, 59% yield). 1H NMR (400 MHz, CDCI3): delta 7.70-7.68 (m, 1 H), 7.39-7.37 (m, 2H), 7.25-7.21 (m, 2H), 4.31-4.27 (m, 2H), 3.29 (bt, 2H), 2.58-2.52 (m, 2H), 1.98 {td, 2H), 1.48 (s, 9H).

According to the analysis of related databases, 19472-74-3, the application of this compound in the production field has become more and more popular.

Chemo-enzymatic cascade processes are invaluable due to their ability to rapidly construct high-value products from available feedstock chemicals in a one-pot relay manner. In an article, author is Yang, Hongzhi, once mentioned the application of 19472-74-3, Name is 2-Bromophenylacetonitrile, molecular formula is C8H6BrN, molecular weight is 196.0439, MDL number is MFCD00001896, category is nitriles-buliding-blocks. Now introduce a scientific discovery about this category, Recommanded Product: 19472-74-3.

Photoinduced, strain-promoted cycloadditions of trans-cycloheptenones and azides

An unprecedented photoinduced azide-alkene cycloaddition has been developed, the key elements of which include the photoisomerization of cis-cycloheptenone to trans-cycloheptenone, strain-promoted 1,3-dipolar cycloaddition of trans-cycloheptenone with azide, and aerobic oxidative aromatization of the resulting 1,2,3-triazoline. The newly developed photoclick reactions display several appealing features including high overall efficiency, broad substrate scope, environmentally benign conditions, and operational simplicity, which provide an enabling tool for accessing structurally diverse 1,2,3-triazoles. In addition, the photoisomerization-cycloaddition strategy could also be extended to the 1,3-dipolar cycloadditions of trans-cyclooctenone with azide andtrans-cycloheptenone with nitrile oxide. More appealingly, the title reaction has been successfully applied as a bioconjugation tool for in vitro protein labeling.

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19472-74-3, Name is 2-Bromophenylacetonitrile, molecular formula is C8H6BrN, belongs to nitriles-buliding-blocks compound, is a common compound. In a patnet, author is Gore, Babasaheb Sopan, once mentioned the new application about 19472-74-3, Name: 2-Bromophenylacetonitrile.

De Novo Protocol for the Construction of Benzo[a]fluorenes via Nitrile/Alkene Activation

Unprecedented chemo- and regioselective synthesis of benzo[a]fluorenes and naphthamide-substituted benzo[a]fluorenes were constructed from the reaction of (E)-2-aroyl-3-(2-(arylalkynes/alkenes)aryl)acrylonitrile scaffolds under metal-free conditions via the activation of nitriles and alkenes, respectively. A tentative reaction mechanism was proposed for this homofunctionalization of nitriles. Control experiments showed that the reaction proceeds via selective nitrile or alkene protonation, depending upon the substrates. Additionally, we demonstrated an alternative expeditious route for the synthesis of disubstituted benzo[a]fluorenes in the presence of TfOH alone.

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Related Products of 19472-74-3, As an important bridge between the micro and macro material world, chemistry is one of the main methods and means for humans to understand and transform the material world. 19472-74-3, Name is 2-Bromophenylacetonitrile, SMILES is C1=C(C(=CC=C1)CC#N)Br, belongs to nitriles-buliding-blocks compound. In a article, author is Feberero, Claudia, introduce new discover of the category.

Experimental and Computational Study of the 1,5-O -> N Carbamoyl Snieckus-Fries-Type Rearrangement

The reactions of o-lithiated O-aryl N,N-diethylcarbamates with different C-N multiple bond electrophiles have been thoroughly studied. A 1,5-O -> N carbamoyl shift, a new variation of the anionic Fries-type rearrangement, takes place when nitriles, imines, or alkylcarbodiimides are employed. In these cases, the carbamoyl group plays a dual role as a directing group, building up a variety of functional groups through the 1,5-O -> N carbamoyl migration. On the other hand, the use of iso(thio)cyanates and arylcarbodiimides led to non-rearranged o-functionalized O-arylcarbamates. This reactivity was further computationally explored, and the governing factor could be traced back to the relative basicity of the alternative products (migrated vs nonmigrated substrates). This exploration also provided interesting insights about the degree of complexation of the lithium cations onto these substrates. A new access to useful 2-hydroxybenzophenone derivatives has also been developed.

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Catalysts are substances that increase the reaction rate of a chemical reaction without being consumed in the process. 19472-74-3, Name is 2-Bromophenylacetonitrile, SMILES is C1=C(C(=CC=C1)CC#N)Br, belongs to nitriles-buliding-blocks compound. In a document, author is Shere, Henry, introduce the new discover, Product Details of 19472-74-3.

Reactivity of a magnesium diboranate with organic nitriles

A series of complexes generated through reactions of the beta-diketiminato magnesium diboranate species, [(BDI)Mg{(n-Bu)pinB-Bpin}] (BDI = HC{(Me)CNDipp}(2); Dipp = 2,6-di-iso-propylphenyl), and a variety of organic nitriles are reported. Although, in every case, the diboranate anion acts as a surrogate source of the {Bpin} nucleophile, resulting in B-C bond formation at the electrophilic sp-hydridised nitrile carbon, the resultant compounds display a variable propensity to undergo subsequent reaction with additional nitrile equivalents. This behaviour is rationalised to be a consequence of substituent-dependent modulation in the basicity and resultant electrophilicity of magnesium-coordinated nitrile intermediates.

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 19472-74-3 is helpful to your research. Product Details of 19472-74-3.

Enzymes are biological catalysts that produce large increases in reaction rates and tend to be specific for certain reactants and products. 19472-74-3, Name is 2-Bromophenylacetonitrile, molecular formula is C8H6BrN, belongs to nitriles-buliding-blocks compound. In a document, author is Pipim, George Baffour, introduce the new discover, Computed Properties of C8H6BrN.

Computational exploration of the 1,3-dipolar cycloaddition reaction of 7-isopropylidenebenzonorbornadiene with nitrile oxide and cyclic nitrone derivatives

The synthesis of isoxazolidine and isoxazole derivatives, versatile building blocks for the construction of a wide range of complex heterocyclic architectures in synthetic organic and medicinal chemistry, is efficiently achieved via the 1,3-dipolar cycloaddition reaction (1,3-DC). Herein, we report an extensive theoretical study on the peri-, regio-, stereo, and enantio-selectivities of 1,3-DC of 7-isopropylidenebenzonorbornadiene with nitrile oxide and cyclic nitrone derivatives using density functional theory calculations. Acetophenone-substituted nitrile oxide periselectively adds across the endocyclic olefinic bond of the dipolarophile to furnish the exo-cycloadduct as the major product, a reaction that has a rate constant of 1.88 x 10(9) s(-1). The endo approach of this periselective path is the closest competing pathway with a rate constant of 4.59 x 10(7) s(-1). Different substituents on the nitrile oxide do not affect the peri- and stereo-selectivity of the reaction. Diethyl ether solvation has no substantial effect on the energetic patterns observed in the gas phase computation. Also, we report a novel 1,3-DC between cyclic nitrone derivatives and 7-isopropylidenebenzonorbornadiene as an efficient way to generate isoxazolidine derivatives. Even though the reactions of the cyclic nitrone derivatives have slightly higher activation barriers than the acyclic nitrile oxide derivatives, the former is more enantioselective than the latter. Whereas electron-donating groups (EDGs) on the cyclic nitrone favor the formation of the exo-cycloadduct, electron-withdrawing groups (EWGs) favor the formation of the endo-cycloadduct. Both 1,3-dipoles add across the dipolarophile via a concerted asynchronous mechanism.

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 19472-74-3. Computed Properties of C8H6BrN.