Tag: M.W=100-200

Electric Literature of 654-70-6, The chemical industry reduces the impact on the environment during synthesis 654-70-6, name is 4-Cyano-3-trifluoromethylaniline, I believe this compound will play a more active role in future production and life.

A. 4-(2,5-Dioxo-2,5-dihydro-pyrrol-1-yl)-2-trifluoromethyl-benzonitrile (471A) A mixture of 3-trifluoromethyl-4-cyano-aniline (24.0 g, 129 mmol) and maleic anhydride (14.0 g, 143 mmol) in 50 mL of acetic acid was heated at 115 C. overnight. A precipitate was obtained during the heating period. The reaction was allowed to stand at rt for an additional overnight period. The solid was removed by filtration, the filter cake was washed with diethyl ether and dried to give 21 g (79 mmol, 61%) of compound 471A as an off white solid. HPLC: 100% at 2.11 min (retention time) (YMC S5 ODS column, 4.6*50 mm, eluding with 10-90% aqueous methanol over 4 min containing 0.2% phosphoric acid, 4 mL/min, monitoring at 220 nm).

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-Cyano-3-trifluoromethylaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Salvati, Mark E.; Balog, James Aaron; Pickering, Dacia A.; Giese, Soren; Fura, Aberra; Li, Wenying; Patel, Ramesh N.; Hanson, Ronald L.; Mitt, Toomas; Roberge, Jacques Y.; Corte, James R.; Spergel, Steven H.; Rampulla, Richard A.; Misra, Raj N.; Xiao, Hai-Yun; US2004/77605; (2004); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 96606-37-0,Some common heterocyclic compound, 96606-37-0, name is 2,4,6-Trifluorobenzonitrile, molecular formula is C7H2F3N, 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.

In one embodiment,The 6 mmol of the second reactant was dissolved in 15 ml to 25 ml of the first solvent tetrahydrofuran, and then 0.5 mmol to 2 mmol of the first additive sodium hydride was slowly added.The reaction is carried out for 20-50 minutes under room temperature conditions and under nitrogen.Then 2 second of the first reactant was added to continue the reaction for 12 hours.A mixture comprising the electroluminescent material is obtained.The mixture of the electroluminescent material is cooled to room temperature and poured into distilled water.Extraction with a second extraction solvent, and then washing with a second detergent,Drying with a second desiccant, and then performing chromatography,Obtaining a second crude product, and then eluting with a second eluent to obtain the electroluminescent material, wherein the electroluminescent material is a white solid,The yield was 54%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2,4,6-Trifluorobenzonitrile, its application will become more common.

Reference:
Patent; Wuhan Hua Xing Optoelectric Semiconductor Display Co., Ltd.; Jing Xiaofang; (40 pag.)CN110229094; (2019); A;,
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 1194-65-6 as follows. Quality Control of 2,6-Dichlorobenzonitrile

In the same manner as in the process of the fluorination step of Example 1 except for using 17.2 g of 2,6-dichlorobenzonitrile instead of 2,3,6-trichlorobenzonitrile, the reaction and refinement were carried out to obtain 9.5 g of 2,6-difluorobenzonitrile (yield: 68%).

According to the analysis of related databases, 1194-65-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Ishihara Sangyo Kaisha Ltd.; US4406841; (1983); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 134227-45-5,Some common heterocyclic compound, 134227-45-5, name is 3,4,5-Trifluorobenzonitrile, molecular formula is C7H2F3N, 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.

Potassium carbonate (1.38 g, 10 mmol) was added to a solution of 2,4-dihydro- 2,5-dimethyl-3H-pyrazol-3-one (0.70 g, 6.3 mmol) in N,N-dimethylformamide (15 mL). 3,4,5-Trifluorobenzonitrile (0.94 g, 6.0 mmol) was added, and the reaction mixture was heated at 75 C under a nitrogen atmosphere for 16 h, then allowed to cool. The reaction mixture was partitioned between water (60 mL) and ethyl acetate (30 mL). The organic phase was washed with water (2 x 30 mL) and brine (30 mL), dried over MgS04, and concentrated to give the title compound as a yellow oil (1.38 g).¾ NMR delta 7.36 (m, 2H), 5.24 (s, 1H), 3.78 (s, 3H), 2.16 (s, 3H).

The synthetic route of 134227-45-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; E. I. DU PONT DE NEMOURS AND COMPANY; LONG, Jeffrey, Keith; GREGORY, Vann; GUTTERIDGE, Steven; TAGGI, Andrew, Edmund; BEREZNAK, James, Francis; WO2012/31061; (2012); A2;,
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. 243128-37-2, name is 4-Fluoro-3-methoxybenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Product Details of 243128-37-2

To a stirred solution of trans-4-aminocyclohexanol (115 mg, [1] mmol) in DMF (5 mL) at 0 [C] was added 60% NaH in mineral oil (120 mg, 3 [MMOL).] The reaction mixture was stirred at 0 [C] for 1/2 hour and then 4-fluoro-3-methoxy-benzonitrile (182 mg, 1.2 mmol) was added. It was heated to 60 [C] for 2 hours and stirred for 12 hours at room temperature. The reaction mixture was diluted with ethyl acetate and washed with water (3 times) and brine. The organic layer was dried (sodium sulfate), filtered, and concentrated under reduced pressure to provide the titled compound. MS (DCI) [M/Z] 247 (M+H) [+.]

The synthetic route of 243128-37-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ABBOTT LABORATORIES; WO2004/26822; (2004); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 50712-68-0, A common heterocyclic compound, 50712-68-0, name is 4-Chloro-2-methylbenzonitrile, molecular formula is C8H6ClN, 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.

Step A 4-Chloro-2-(bromo-methyl)-benzonitrile 2 To a stirred solution 4-Chloro-2-methyl-benzonitrile 1(5.0 g, 33.0 mmol) in carbon tetrachloride (150 mL) was added N-bromosuccinamide (7.6 g, 42.9 mmol) and 2,2′-azobisisobutyronitrile (cat.). The reaction mixture was refluxed 6 hrs, filtered, concentrated, and partitioned between ether and water. The ether layer was dried, concentrated, and purified by silica gel chromatography (10% ether/hexanes) to yield a white solid (40%). 1H NMR (400 MHz, CDCl3) delta7.61 (d, J=8.3 Hz, 1 H, Ar), 7.57 (d, J=2.2 Hz, 1 H, Ar), 7.41 (dd, J=8.3, 2.0 Hz, 1 H, Ar), 4.59 (s, 2 H, CH2).

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; Merck & Co., Inc.; US6376530; (2002); B1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of 134227-45-5,Some common heterocyclic compound, 134227-45-5, name is 3,4,5-Trifluorobenzonitrile, molecular formula is C7H2F3N, 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.

(Methylsulfinyl) (methylthio) methane (7.26g, 0.0584 mol) was dissolved in 100 mL of dry THF under argon and was cooled [TO-78C.] Butyllithium in hexane (16 mL 1. 6M, 0.0256 mol) was added dropwise with stirring. The mixture was stirred for 15 min. Meanwhile, a solution of 3,4, 5-trifluorobenzonitrile (4.0 g, 0.025 mmol) in 100 [ML] of dry THF was cooled to-78C under argon and the former solution was added through a cannula to the latter solution over a period of 35 min. After 30 min, the cooling bath was removed and when the reaction had reached room temperature it was poured into 400 mL of water. The THF was evaporated and the remaining aqueous layer was extracted three times with diethyl ether. The combined ether phase was washed with water, dried [(NA2SO4)] and evaporated. Yield: 2.0 g (30%). ‘H NMR (500 MHz, [CDC13)] 8 7.4-7. 25 (m, 2H), 5.01 (s, [1H,] diasteromer), 4.91 (s, [1H,] diasteromer), 2.88 (s, 3H, diasteromer), 2.52 (s, 3H, diasteromer), 2.49 (s, 3H, diasteromer), 2.34 (s, 3H, diasteromer), 1.72 (broad, [1H)]

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3,4,5-Trifluorobenzonitrile, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; WO2003/101956; (2003); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 51762-67-5, name is 3-Nitrophthalonitrile, 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 51762-67-5, category: nitriles-buliding-blocks

General procedure: 8-hydroxyquinoline-5-sulfonic acid (1.30 g, 5.78 mmol) was dissolved in dry DMF (8.00 mL) at 45 C and anhydrous K2CO3(1.5 g, 11.56 mmol) was added. After stirring for 15 min, 3-nitrophthalonitrile (1) was added dropwise in 2 h with efficient stirring. The reaction mixture was stirred under nitrogen at 45C for 4 days. After being cooled to room temperature, the mixture was poured into ca. 200 mL ice-water media and 1 M HCl (50 mL)was added in it. After completion of the precipitation approximately in 0.5 h, the creamy precipitate that formed was filtered and then washed with ca. 100 mL water until the washings became neutral. Column chromatography with methanol/dichloromethane (5:1) eluent on silica gel was employed to obtain the pure product. As expected, the yellow products were soluble in DMF and DMSO. Yield of 1: 1.36 g (67%); m.p.: Anal. Calc. for C17H9N3O4S (Mw:351.34): C, 58.12; H, 2.58; N, 11.96. Found: C, 57.90; H, 2.56; N,11.81%. FT-IR (KBr disc) n/cm-1: 3082, 3027, 2980 (Ar H), 2240 (CN), 1590, 1574, 1550 (Ar), 1273 (ArOAr), 1191, 1154 (SO2),789, 774, 674. 1H NMR (DMSO-d6): d ppm = 7.10-9.50 (m, 8H, ArH). UV/vis (DMSO): lambdamax = 299, 259.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Article; Guensel, Arma?an; Bilgicli, Ahmet T.; Kirbac, Erkan; Gueney, Sevgi; Kandaz, Mehmet; Journal of Photochemistry and Photobiology A: Chemistry; vol. 310; (2015); p. 155 – 164;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

60710-80-7, name is 3-Amino-4-methylbenzonitrile, belongs to nitriles-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. category: nitriles-buliding-blocks

DIPEA (1 mL; 5.8 mmol) was added to a solution of 3-amino-4-methylbenzonitrile(661 mg; 5 mmol) and 2,4-dichloro-1,3,5-triazine (750 mg; 5 mmol) in ACN (30 mL).The reaction mixture was stirred overnight at room temperature. The solvent wasremoved by evaporation and the residue was partionned between water and EtOAc. The organic layer was decanted, washed with water, then brine, dried over MgSO4, filtered and evaporated to dryness. The residue was purified by chromatography over silica gel (irregular SiOH; mobile phase: gradient from 0% EtOAc, 100% petroleum ether to 50% EtOAc, 50% petroleum ether). The fractions containing the product were collectedand evaporated to dryness yielding 700 mg (57%) of intermediate 543.

The synthetic route of 60710-80-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; STANSFIELD, Ian; QUEROLLE, Olivier Alexis Georges; PONCELET, Virginie Sophie; GROSS, Gerhard Max; JACOBY, Edgar; MEERPOEL, Lieven; KULAGOWSKI, Janusz Jozef; MACLEOD, Calum; MANN, Samuel Edward; GREEN, Simon Richard; HYND, George; (477 pag.)WO2017/125530; (2017); 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. 13531-48-1, name is Methyl 3-cyanobenzoate, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of Methyl 3-cyanobenzoate

Into a 1000-mL round-bottom flask, was placed methyl 3-cyanobenzoate (20 g, 124.10 mmol, 1.00 equiv), methanol (200 mL), and 50% NH2OH (10 mL). The resulting solution was stirred for 1.5 h at 70 oC in an oil bath. The resulting mixture was concentrated under vacuum. This resulted in 24 g (100%) of methyl (Z)-3-(N’- hydroxycarbamimidoyl)benzoate as a tan solid.

According to the analysis of related databases, 13531-48-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; LYCERA CORPORATION; AICHER, Thomas, D.; PADILLA, Fernando; SKALITZKY, Donald, J.; TOOGOOD, Peter, L.; VANHUIS, Chad, A.; (172 pag.)WO2018/39539; (2018); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts