Tag: M.W=100-200

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. 326-62-5 name is 2-(2-Fluorophenyl)acetonitrile, 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. 326-62-5

General procedure: A solution of aryl acetonitrile 2 (50 mg), and triethylamine (1.1 equiv.) in dimethylformamide dimethyl acetal (0.5 mL, 3.76 mmol) was heated in a microwave reactor at 120 C for 20 minutes. The mixture was cooled to RT, and solvents were then evaporated. To the resulting crude product 3 was added hydrazine mono-hydrobromide (3.0 equiv.), 200 proof EtOH (1.0 mL), and H2O (0.3 mL). The mixture was heated in a microwave reactor at 120 C for 20 minutes. The mixture was cooled to RT and concentrated in vacuo. The resulting residue was subjected to liquid-liquid extraction using saturated NaHCO3 (aq) and CH2Cl2. The organic layer was collected, dried over anhydrous MgSO4, filtered and removed under vacuum to afford 4.The resulting crude product 4 and 2-arylsubstitutedmalondialdehydes or 1,1,3,3tetramethoxypropane (1.0 equiv.) were dissolved in glacial AcOH (1.0 mL) and 200 proof EtOH (1.5 mL). The mixture was heated in a microwave reactor at 120 C for 20 minutes. After cooling on ice, the precipitate was collected on a fine scintered-glass frit and washed with icecold EtOH (2 x 1.0 mL). The resulting crystals 5-32 were dried and collected.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-(2-Fluorophenyl)acetonitrile, and friends who are interested can also refer to it.

Reference:
Article; Singleton, Justin D.; Dass, Reuben; Neubert, Nathaniel R.; Smith, Rachel M.; Webber, Zak; Hansen, Marc D.H.; Peterson, Matt A.; Bioorganic and Medicinal Chemistry Letters; vol. 30; 2; (2020);,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 1194-02-1, The chemical industry reduces the impact on the environment during synthesis 1194-02-1, name is 4-Fluorobenzonitrile, I believe this compound will play a more active role in future production and life.

Preparation of BB8: 4-Fluoro-N-hydroxy-benzamidine; To a solution of the 4-fluoro-benzonitrile (10.0 g, 52.9 mmol) in ethanol (200 mL), the solution of NH2OH-HCl (4.0 g, 58.2 mmmol) in H20 (4 mL) was added dropwise. The mixture was stirred vigorously at about 65 C and stood overnight. The analysis by TLC indicated the complete consumption of starting material. The solution was concentrated to remove the solvent. The residue was dissolved in DCM and washed with water, brine, dried over Na2S04 and concentrated in vacuum to afford 4-Fluoro-N-hydroxy-benzamidine as pale- yellow solid (BB8).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 4-Fluorobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ABBOTT LABORATORIES; CUSACK, Kevin, P.; BREINLINGER, Eric, C.; FIX-STENZEL, Shannon, R.; STOFFEL, Robert, H.; WOLLER, Kevin, R.; WO2011/71570; (2011); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 29509-06-6, A common heterocyclic compound, 29509-06-6, name is 4-Methyl-3-oxopentanenitrile, molecular formula is C6H9NO, 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.

Hydroxylamine hydrochloride (10.3 g, 148 mmol) was slowly added to an ice cold solution of NaOH (25.9 g, 645 mmol) in water (73 mL) and the resulting solution was poured into a solution of crude 3-oxo-4-methylpentanenitrile while stirring. The resulting yellow solution was heated at 50 C for 2.5 hours to produce a less dense yellow oil. The warm reaction mixture was immediately extracted with CHCl3 (3 x 100 mL) without cooling. The combined organic layers were dried (MgSO4), and concentrated in vacuo. The resulting oily yellow solid was filtered through a pad of silica (10% acetone/90% CH2Cl2) to afford the desired isoxazole as a yellow solid (11.3 g, 70%): mp 63-65 C; TLC Rf (5% acetone/95% CH2Cl2) 0.19; 1H-NMR (DMSO-d6) d 1.12 (d, J=7.0 Hz, 6H), 2.72 (sept,J=7.0 Hz, 1H), 4.80 (s, 2H), 6.44 (s, 1H); FAB-MS m/z (rel abundance) 127 ((M+H)+; 67%).

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:
Patent; Bayer Pharmaceuticals Corp.; EP1047418; (2005); B1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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 51762-67-5 as follows. Recommanded Product: 51762-67-5

3-nitrophthalonitrile (0.500 g, 2.888 mmol) was dissolved in anhydrous dimethylformamide (75 mL) under Ar and hydroxymethyl-EDOT (0.500 g, 2.903 mmol) was added. After stirring for 10 min, finely ground anhydrous K2CO3 (1.200 g, 8.682 mmol) was added in portions over 2 h with efficient stirring. The reaction mixture was stirred at room temperature for 120 h under Ar. Then the solution was poured into ice-water. The resulting white solid was collected by filtration and washed first with water and then with hexane. Yield 0.493 g (57%). Mp: 192 C. FT-IR: numax, cm-1 3116.56 (CH, aromatic), 2963.20 (CH, aliphatic), 2230.15 (C?N). 1H NMR (400 MHz, DMSO-d6, 298 K): delta, ppm 7.88-7.69 (3H, benzene -CH), 6.64 (2H, thiophene -CH), 4.63-4.13 (5H, -CH and -CH2). 13C NMR (400 MHz, CDCl3, 298 K): delta, ppm 160.38, 141.00, 140.83, 135.87, 126.21, 118.72, 115.71, 115.35, 113.48, 103.10, 100.16, 71.49, 68.00, 64.77. GC-MS: m/z 298 [M]+. C15H10N2O3S (298.04): calcd. C 60.39, H 3.38, N 9.39; found C 60.37, H 3.37, N 9.40.

According to the analysis of related databases, 51762-67-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Karada?, Sebahattin; Bozo?lu, Ceyda; Kasim ?ener; Koca, Atif; Dyes and Pigments; vol. 100; 1; (2014); p. 168 – 176;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 1080-74-6,Some common heterocyclic compound, 1080-74-6, name is 2-(3-Oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile, molecular formula is C12H6N2O, 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 degassed solution of intermediate 1 (0.13 g, 0.1 1 mmol) and 3- (dicyanomethylidene)indan-l -one (1 .5 g, 0.77 mmol) in chloroform (12 cm3) is added pyridine (0.6 cm3, 8 mmol). The mixture is then degassed with nitrogen for 30 minutes and then heated at 70 C for 15 hours. The reaction mixture allowed to cool to 23 C and the solvent removed in vacuo. The crude is purified by column chromatography (40-60 petrol :chloroform; 1 : 1 ) to give compound 75 (1 .1 g, 65%) as a dark blue crystalline solid. 1H NMR (400 MHz, CDCIs) 8.87 (2H, s), 8.69 (2H, d, J 7.6), 7.91 (2H, d, J 7.1 ), 7.68 – 7.79 (6H, m), 7.08 – 7.18 (16H, m), 2.60 (8H, t, J 7.7), 1 .62 (8H, q, J 7.1 Hz), 1 .21 – 1 .39 (40H, m), 0.88 (12H, t, J 6.5).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(3-Oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile, its application will become more common.

Reference:
Patent; MERCK PATENT GMBH; MORSE, Graham; NANSON, Lana; MITCHELL, William; KROMPIEC, Michal; D’LAVARI, Mansoor; PRON, Agnieszka; (327 pag.)WO2018/65350; (2018); A1;,
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. 16588-02-6, name is 2-Chloro-5-nitrobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Product Details of 16588-02-6

3-Cyano-4-chloroaniline 2-Chloro-5-nitrobenzonitrile (25 g, 137 mmol) was dissolved in ethanol (275 mL). Stannous chloride dihydrate (154.5 g, 0.685 M) was added and the mixture stirred at 70 C. for 30 min. The mixture was then cooled to room temperature and poured into crushed ice. The mixture was made basic with solid sodium hydroxide. This mixture was extracted with ethyl acetate (3*100 mL). The extracts were combined, washed with brine, dried (MgSO4), concentrated and the residue dried under vacuum and recrystallized from ethanol to yield light brown needles (10.6 g, 51%).

The synthetic route of 16588-02-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chapdelaine, Marc; Davenport, Timothy; Haeberlein, Markus; Horchler, Carey; McCauley, John; Pierson, Edward; Sohn, Daniel; US2004/110745; (2004); 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. 1009-35-4, name is 4-Fluoro-3-nitrobenzonitrile, A new synthetic method of this compound is introduced below., HPLC of Formula: C7H3FN2O2

Potassium hexamethyldisilazane [0.5 M in toluene] (12.04 mL, 24.08 mmol) was added to a solution of isopropanol (0.921 mL, 12.04 mmol) in tetrahydrofuran (20 mL) at 0° C. and stirred for 10 minutes. The resulting solution was added dropwise to a solution of commercially available 4-fluoro-3-nitrobenzonitrile at room temperature and stirred for several hours. Water was added and the product was extracted with ethyl acetate, dried with sodium sulfate and evaporated in vacuo to give the title compound

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:
Patent; WANG, Aihua; Zhang, Yan; Leonard, Kristi Anne; Hawkins, Michael; Tounge, Brett Andrew; Maharoof, Umar S.M.; Barbay, Joseph Kent; US2012/129811; (2012); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of 13531-48-1, These common heterocyclic compound, 13531-48-1, name is Methyl 3-cyanobenzoate, 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.

General procedure: To a round-bottom flask (25 mL) was added phenylhydrazine hydrochloride 1a (43 mg, 0.3 mmol), benzonitrile 2a (0.3 mL, 3 mmol), t-BuONO (53 muL, 0.45 mmol), I2 (38 mg, 0.15 mmol), the mixture was well stirred for 6 h at 25 oC (the whole process was closely monitored by TLC). Then the reaction mixture was purified by a flash silica gel column chromatography (eluent: Petroleum ether (PE)/Ethyl acetate (EA) = 10:1) to give N-phenylbenzamide 3a as a white solid (38 mg, 64%).

Statistics shows that Methyl 3-cyanobenzoate is playing an increasingly important role. we look forward to future research findings about 13531-48-1.

Reference:
Article; Zhang, Zhiguo; Li, Xiang; Li, Yinghua; Guo, Yan; Zhao, Xunan; Yan, Yan; Sun, Kai; Zhang, Guisheng; Tetrahedron; vol. 75; 26; (2019); p. 3628 – 3635;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 127946-77-4, name is 1-Amino-1-cyclopropanecarbonitrile hydrochloride, belongs to nitriles-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 127946-77-4, Product Details of 127946-77-4

To prepare (2S,4R)-4-[2-chloro-4-((5)-2,2,2-trifluoro-1-methyl-ethoxy)-benzenesulfonyl]-1-(1-trifluoromethyl-cyclopropanecarbonyl)-pyrrolidine-2-carboxylic acid (1-cyano-cyclopropyl)-amide, example 183c (200 mg) was dissolved in DMF (2.0 mL). HATU (420 mg), DIEA (143 mg) and 1-amino-1-cyclopropane carbonitrile hydrochloride were added to the solution. The obtained suspension was stirred at ambient temperature for 2 h. After that the solvent was evaporated under reduced pressure to dryness. The residue was dissolved in CH2Cl2 (25 ml), was extracted in succession with aqueous 0.5 NHCl-solution, aqueous 10% Na2CO3-solution and brine. The water layers were washed with totally CH2Cl2 (50 ml), the combined organic layers were dried over Na2SO4, filtered and evaporated. The residue was purified over silica gel chromatography with n-heptan: AcOEt to yield 130 mg (59%) of the title compound as colorless amorphous solid. MS (ESI): m/z=602.1 [M+H]+.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 1-Amino-1-cyclopropanecarbonitrile hydrochloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Sanchez, Ruben Alvarez; Banner, David; Ceccarelli, Simona M.; Grether, Uwe; Haap, Wolfgang; Hartman, Peter; Hartmann, Guido; Hilpert, Hans; Kuehne, Holger; Mauser, Harald; Plancher, Jean-Marc; US2010/267722; (2010); A1;,
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. 57381-51-8, name is 4-Chloro-2-fluorobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C7H3ClFN

General procedure: Into an oven-dried flask equipped with a magnetic stir bar was added aryl fluoride (1.00 g, 1.0 eq.), Na2S (1.1 eq.) and DMF (5 mL) under argon. The reaction mixture was stirred at room temperature for 1 h. Then 1 M NaOH (50 mL) was added and was washed with CH2Cl2 (2 x 25 mL). The aqueous layer was acidified to pH ~ 1-2 with 6 N HCl and extracted with CH2Cl2 (2 x 50 mL). The combined organic layer was washed with brine (50 mL), dried over MgSO4, filtered and concentrated under reduced pressure to provide a crude residue. To the residue was added 10% HCl (40 mL) and cooled with an ice-water bath. Then zinc dust (4 g) was added and the mixture was stirred for 1 h. Then EtOAc (100 mL) was added and the mixture was stirred for an additional 30 minutes. The organic layer was separated and washed with water (40 mL) and brine (40 mL), dried over MgSO4, filtered and concentrated to provide the desired product with satisfactory purity.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 57381-51-8.

Reference:
Article; Taldone, Tony; Patel, Pallav D.; Patel, Hardik J.; Chiosis, Gabriela; Tetrahedron Letters; vol. 53; 20; (2012); p. 2548 – 2551;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts