Month: February 2021

Related Products of 2469-99-0, These common heterocyclic compound, 2469-99-0, name is 3-Oxobutanenitrile, 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 B: 5-Methyl-2-phenyl-2H-pyrazol-3-ylamine Into a 1000-mL 3-necked round bottom flask, was placed a solution of 3-oxobutanenitrile (23 g, 277.11 mmol, 1.00 equiv) in ethanol (400 mL), 1-phenylhydrazine (30 g, 277.78 mmol, 1.00 equiv). The resulting solution was heated to reflux overnight in an oil bath. The resulting mixture was then concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:10-1:5) to yield 3-methyl-1-phenyl-1H-pyrazol-5-amine as a yellow solid.

The synthetic route of 2469-99-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ZHANG, Xuqing; ABAD, Marta G.; GIBBS, Alan C.; KUO, Gee-Hong; KUO, Lawrence C.; SONG, Fengbin; SUI, Zhihua; US2011/263559; (2011); A1;,
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Adding a certain compound to certain chemical reactions, such as: 14533-86-9, name is Methyl (E)-2-Cyano-3-phenylacrylate, 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 14533-86-9, name: Methyl (E)-2-Cyano-3-phenylacrylate

(E)-methyl-2-cyano-3-phenylacrylate 30a (1.40 g, 7.48mmol, 1.0 equiv) and zinc powder (7.83 g, 119.7 mmol,16.0 equiv) were dissolved in 50 mL glacial acetic acid and the solution was stirred for 2.5 h at 100 C. The reaction mixture was filtered through a celite pad and washed with 100 mL EtOAc. The filtrate was neutralised with aq. NaHCO3 solution and the organic layer was separated,washed with brine (2 ¡Á 25 mL), dried over Na2SO4 and the solvent removed under reduced pressure. The crude product was further purified on a silica column with a solvent mixture of 1:9 (EtOAc/hexane) with the desired nitrile isolated as a colourless oil. 6 Isolated yield: 0.583 g (41%, 7.48 mmol),

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, Methyl (E)-2-Cyano-3-phenylacrylate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Mallia, Carl J.; Englert, Lukas; Walter, Gary C.; Baxendale, Ian R.; Beilstein Journal of Organic Chemistry; vol. 11; (2015); p. 875 – 883;,
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Related Products of 58633-04-8, These common heterocyclic compound, 58633-04-8, name is 4-Amino-3,5-dibromobenzonitrile, 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.

EXAMPLE 26 PREPARATION OF 3,5-DIBROMOBENZONITRILE STR38 To a stirred solution of t-butylnitrite (53.5 muL, 0.449 mmoles) in 1 ml sieve dried dimethylformamide at 50 C. under an atmosphere of nitrogen was added a solution of 4-amino-3,5-dibromobenzonitrile (50 mg, 0.179 mmoles) in 1 mL of DMF. The mixture was stirred at 50 C. for 0.5 hour and partitioned between diethyl ether, ice-water, and ammonium chloride. The organic phase was separated, washed with water and brine, dried over anhydrous sodium, filtered, and evaporated. Purification by plate layer chromatography using hexane-ethyl acetate (9:1) as the eluant provided 28 mg (59%) of white, crystalline product. NMR (CDCl3) delta:7.7 (d, J=1.8Hz, 2H), 7.9 (t, J=1.8Hz, 1H).

Statistics shows that 4-Amino-3,5-dibromobenzonitrile is playing an increasingly important role. we look forward to future research findings about 58633-04-8.

Reference:
Patent; Merck & Co. Inc.; US5455239; (1995); A;,
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Application of 628-20-6, 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. 628-20-6, name is 4-Chlorobutyronitrile, This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 1 Preparation of cyclopropylnitrile (2 molar scale) STR2 A stirred mixture of 4-chlorobutyronitrile (213.4 g, 2.0 mole), sodium chloride (58.0 g, 0.5 mole) and 2.0 g of water in 200 g of dimethylsulfoxide is heated to 80 C., treated with ground solid sodium hydroxide (88 g, 2.2 mole) over a 3 hour period and held at 80 C. for about 1 additional hour. The reaction mixture is cooled to room temperature neutralized to about pH6.8 with concentrated HCl (37% aqueous solution), diluted with 200 ml water (readjusted pH to 6.8 with 37% HCl) and azeotropically distilled with a Dean Stark trap to remove the cyclopropylnitrile/water azeotrope. The aqueous layer is continuously returned to the distillation pot to give the initial product as the distillate cyclopropylnitrile, 133.5 g. A 121.5 g sample of this cyclopropylnitrile is azeotropically distilled using a Dean Stark trap (to remove water) and continuous return of the organic layer to give the final productproduct cyclopropylnitrile, 106.6. g, 87.8% yield, 98% pure by GLC analysis and 0.04% H2 O by Karl Fischer titration.

The chemical industry reduces the impact on the environment during synthesis 4-Chlorobutyronitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; American Cyanamid Company; US5380911; (1995); A;,
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Application of 19472-74-3, 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. 19472-74-3, name is 2-Bromophenylacetonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

(2-Methylpyridin-3-yl)boronic acid (550 mg, 3.2 mmol), 2-(2-bromophenyl)acetonitrile (597 mg, 3.05 mmol), Pd(PPh3)4 (176 mg, 0.15 mmol) and K2C03 (176 mg, 0.15 mmol) were dissolved in /’PrOH (5 mL) and water (2 mL) and the mixture was heated at 80 C under N2 for 5h. The mixture was filtered and the solid was washed with DCM (20 mL). The filtrate was washed with brine, dried over sodium sulfate and concentrated. Column chromatography (DCM/MeOH = 100:0 – 20:1) gave the product (300 mg, 45% yield) as a yellow solid. LCMS (ES-API): Rt 0.44 min; m/z 209.1 [M+H]+.

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

Reference:
Patent; CTXT PTY LIMITED; MORROW, Benjamin Joseph; FOITZIK, Richard Charles; CAMERINO, Michelle Ang; LAGIAKOS, Helen Rachel; WALKER, Scott Raymond; BOZIKIS, Ylva Elisabet Bergman; STEVENSON, Graeme Irvine; CUZZUPE, Anthony Nicholas; STUPPLE, Paul Anthony; (313 pag.)WO2019/43139; (2019); A1;,
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Application of 42872-73-1, 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. 42872-73-1, name is 2-Bromo-4-methylbenzonitrile, This compound has unique chemical properties. The synthetic route is as follows.

To a stirred solution of Int4.1 (500 mg) in toluene (7.5 ml) was added 2-bromo-4-methylbenzonitrile (1.2 g), Pd2dba3 (140 mg) and rac-BINAP (191 mg). The flask was twice degased and backfilled with argon. The mixture was stirred at r.t. for 5 minutes. Caesium carbonate (2.5 g) was added, the flask was twice degased and backfilled with argon and the mixture was heated to reflux for 4h. Further Pd2dba3 (140 mg) and rac-BINAP (191 mg) was added, the flask was twice degased and backfilled with argon and the mixture was heated to reflux for 2h. Water was added and the reaction mixture was extracted with a mixture of dichloromethane and methanol (10:1). The combined organic phases were washed with saturated sodium chloride solution, dried (sodium sulfate) and the solvent was removed in vacuum. Silica gel chromatography gave 205 mg of the title compound. 1H-NMR (400MHz, DMSO-d6): delta [ppm]= 1.46 (s, 9H), 2.35 (s, 3H), 6.96 (dd, 1H), 7.54 (d, 2H), 7.57 – 7.63 (m, 2H), 7.66 (d, 2H), 7.79 (s, 1 H), 7.87 (dd, 1 H), 9.04 (dd, 1 H), 9.34 (s, 1 H), 9.47 (s, 1H).

The chemical industry reduces the impact on the environment during synthesis 2-Bromo-4-methylbenzonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Bayer Schering Pharma AG; EP2343295; (2011); A1;,
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Electric Literature of 914637-31-3,Some common heterocyclic compound, 914637-31-3, name is 2-(3-Fluoro-5-methoxyphenyl)acetonitrile, molecular formula is C9H8FNO, 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 solution of 2-(3-fluoro-5-methoxyphenyl)acetonitrile (2.62 g, 16 mmol) in MeOH:H20 (1 :1; 15 mL), NaOH (1.28 g, 32 mmol) was added. Then the mixture was stirred at 65 C for 4 h. The mixture was cooled to room temperature, and 4M aqueous HCl solution was added until the pH was adjusted to 4~5. The mixture was filtered and the solid obtained was washed with H20 (2 x 5 mL) to give 2.33 g of 2-(3-fluoro-5-methoxyphenyl)acetic acid. H NMR (CDC13): delta 6.52-6.62 (m, 3H), 3.78 (s, 3H), 3.59 (s, 2H).

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-Fluoro-5-methoxyphenyl)acetonitrile, its application will become more common.

Reference:
Patent; ARAGON PHARMACEUTICALS, INC.; KAHRAMAN, Mehmet; GOVEK, Steven, P.; NAGASAWA, Johnny, Y.; SMITH, Nicholas, D.; WO2011/156518; (2011); A2;,
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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. 67515-59-7, name is 4-Fluoro-3-(trifluoromethyl)benzonitrile, This compound has unique chemical properties. The synthetic route is as follows., category: nitriles-buliding-blocks

In a screw cap pressure tube, 4-fluoro-3-(trifluoromethyl)-benzonitrile (425 mg, 1.70 mmol) and 2-(3,6-dihydro-2Eta-pyran-4-yl)-4,4,5,5-tetramethyl- 1,3,2- dioxaborolane (357.1 mg, 1.70 mmol) were dissolved in dimethoxyethane. Na2CO3 (2 M aq. sin, 2.5 ml) and LiCl (216.4 mg, 5.1 mmol) were added. N2 was bubbled through the mixture for 5 minutes. Pd(PPtLs)4 (39.3 mg, 0.03 mmol) was added. The tube was sealed and the mixture heated to reflux for 20 h. The mixture was allowed to cool. H2O was added and the product extracted with EtOAc. The combined organic extracts were dried (MgSO4), filtered and concentrated. The crude product was purified by flash chromatography; Pet. Ether, EtOAc (4:1) affording 254 mg (59%) the title compound. 1H NMR (CDCl3) delta 7.97 (d, IH), 7.80 (dd, IH), 7.40 (d, IH), 5.72 (m, IH), 4.29 (dd, 2H), 3.92 (t, 2H), 2.36 (m, 2H).

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 67515-59-7.

Reference:
Patent; RESPIRATORIUS AB; JOHANSSON, Martin; THORNQVIST-OLTNER, Viveca; TOFTERED, Joergen; WENSBO, David; DALENCE, Maria; WO2010/97410; (2010); A1;,
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Reference of 170572-49-3,Some common heterocyclic compound, 170572-49-3, name is 3-Fluoro-4-methylbenzonitrile, molecular formula is C8H6FN, 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.

Method B The reaction was carried out with the aid of a washer filled with sodium hypochlorite solution. 3-Fluoro-4-methylbenzonitrile (200 g, 1479.9 mmol) was initially charged in DMF (1.5 liters) and warmed to 40 C., and sodium methanethiolate (altogether 126.8 g, 1627.9 mmol) was added a little at a time (about 25 g per portion). During the addition, the temperature increased to 100 C. The reaction mixture was stirred initially at a bath temperature of 175 C. for 1.5 h and then at room temperature overnight. The reaction mixture was then poured into water (7.5 liters) and extracted twice with ethyl acetate (1875 ml each). The combined organic phases were washed with saturated sodium chloride solution (1875 ml) and concentrated on a rotary evaporator, and the residue was chromatographed on silica gel (mobile phase: petroleum ether/ethyl acetate 95:5, about 30 liters). Removal of the solvent on a rotary evaporator and drying under high vacuum gave 172 g (71% of theory) of the desired compound. GC-MS (Method 1): Rt=5.25 min; MS (ESIpos): m/z (%)=163.0 (100) [M]+ 1H-NMR (400 MHz, DMSO-d6): delta=2.30 (s, 3H), 2.54 (s, 3H), 7.38 (d, 1H), 7.52 (dd, 1H), 7.58 (br. s, 1H).

The synthetic route of 170572-49-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER SCHERING PHARMA AKTIENGESELLSCHAFT; US2011/34433; (2011); A1;,
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Electric Literature of 42872-74-2, 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. 42872-74-2, name is 3-Bromo-4-methylbenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a stirred solution of 3-bromo-4-methyl-benzonitrile (2 g, 10.2014 mmol, 100 mass%) in carbon tetrachloride (20 ml_, 100 mass%) under argon, was added NBS (2.2 g., 12.2417 mmol, 99 mass%) and benzoyl peroxide (0.123 g., 0.5101 mmol, 100 mass%). The mixture was heated to 85C for 18h. The reaction mass was diluted with water (50 ml) and extracted with ethyl acetate. Organics were washed again with water and brine, dried and evaporated to afford 3-bromo-4-(bromomethyl) benzonitrile (1.2 g, 4.4 mmol, 90 mass%, 95% Yield) as an off white solid solid. H NMR (400 MHz, chloroform-c) delta ppm 3.89 – 4.01 (m, 2 H) 6.61 – 6.77 (m, 1 H) 6.92 – 7.07 (m, 2 H) LCMS: RT 1.12-1.49 Min 274 [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, 3-Bromo-4-methylbenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; RAJAN, Ramya; STIERLI, Daniel; BEAUDEGNIES, Renaud; RENOLD, Peter; (79 pag.)WO2016/113303; (2016); A1;,
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