Category: 3598-13-8

Adding a certain compound to certain chemical reactions, such as: 3598-13-8, name is 2-(4-Chlorophenoxy)acetonitrile, 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 3598-13-8, HPLC of Formula: C8H6ClNO

2-(3-(hydroxymethyl)-6-nitro-2,3-dihydrobenzo[b][l,4]dioxin-5-yl)acetonitrile: A solution of racemic (7-nitro-2,3-dihydrobenzo[b][l,4]dioxin-2-yl)methanol (1.00 g, 4.73 mmol) and 4-chlorophenoxyacetonittauile (827 mg, 4.94 mmol) in DMF (12 mL) was added dropwise to a solution of potassium tert-butoxide (2.12 g, 18.9 mmol) in DMF (20 mL) at -5- 00C. After the addition was complete (7 minutes), the reaction mixture was stirred for 1 hour at -5-00C. The reaction mixture was acidified with 1 N HCl before drowning into water (200 mL). The mixture was extracted with EtOAc (3 x 100 mL) and the combined organic layers were washed with IN NaOH (3 x 50 mL) to remove most of the 4-chlorophenol. After removal of solvent, the residue was purified by flash chromatography on silica gel, gradient elution using 2:3, 1 :1, 3:2, 100:0 ethyl acetate/hexane, to give 139 mg, 14% recovered starting material and 804 mg, 68% yield of the title compound as a solid. 1H NMR (CDCl3) 5 7.77 (IH, d, J=9.12 Hz); 7.01 (IH, d, J=9.12 Hz); 4.50-4.40 (2H, m); 4.30-3.91 (5H, m); 2.25-2.21 (IH, m). 13C NMR (CDCl3) 5 148.07, 141.71, 141.55, 119.44, 117.07, 116.96, 115.71 , 74.36, 65.31, 61.18, 14.89.

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, 2-(4-Chlorophenoxy)acetonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; WYETH; WO2007/139998; (2007); A2;,
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. 3598-13-8, name is 2-(4-Chlorophenoxy)acetonitrile, A new synthetic method of this compound is introduced below., name: 2-(4-Chlorophenoxy)acetonitrile

Intermediate 2; 7-methoxy-3-piperidin-4-yl-1,3,4,5-tetrahydro-1,3-benzodiazepin-2-one; Step 1: (5-methoxy-2-nitrophenyl)-acetonitrile; 24.0 g (214 mmol) potassium-tert-butoxide in 100 mL DMF were slowly added dropwise to a solution of 13.2 g (86.0 mmol) 4-nitroanisole and 18.0 g (107 mmol) of 4-chlorophenoxy-acetonitrile in 50 mL DMF. The reaction mixture was stirred for 30 min at -10 C. and then poured into 300 g of a 1:1 mixture of conc. HCl and ice. After extraction with EtOAc the organic phase was washed with water, dried and evaporated down i. vac. The residue was treated with a 1:1 mixture PE/EtOAc and the product that crystallised out was suction filtered. After washing with a 1:1 mixture of petroleum ether/EtOAc the crystals were dried in the air.Yield: 6.5 g (39% of theoretical)ESI-MS: m/z=210 (M+NH4)+ Rf: 0.45 (silica gel; PE/EtOAc=1:1)

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; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2010/324028; (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. 3598-13-8, name is 2-(4-Chlorophenoxy)acetonitrile, This compound has unique chemical properties. The synthetic route is as follows., Safety of 2-(4-Chlorophenoxy)acetonitrile

(5-Chloro-2-nitrophenyl)acetonitrile was prepared from 4-chloronitrobenzene and 4-chlorophenoxyacetonitrile according to procedure known in the art (M. Makosza, J. Wimiarski, J. Org. Chem. 1984, 49, 1494). To a suspension of 13.8 g (0.1 mol) anhydrous potassium carbonate in 100 ml acetonitrile were added 100 mg 18-crown-6, 3.93 g (20.0 mmol) of (5-chloro-2-nitrophenyl)acetonitrile, and 4.15 g (21.95 mmol) 3-fluorobenzyl bromide, successively. It was stirred at room temperature overnight, and the solids were removed by filtration. The filtrate was concentrated under reduced pressure, and the residue was stirred with a small amount of ethanol to give the pale yellow crystalline title compound, which was collected by filtration, washed with cold ethanol, and dried in vacuo. yield: 4.9 g (80%)

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 3598-13-8.

Reference:
Patent; Takeuchi, Kumiko; Jirousek, Michael Robert; Paal, Michael; Ruhter, Gerd; Schotten, Theo; US2004/9976; (2004); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 3598-13-8, A common heterocyclic compound, 3598-13-8, name is 2-(4-Chlorophenoxy)acetonitrile, molecular formula is C8H6ClNO, 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.

A. (5-Amino-2-chloro-4-pyridyl) acetonitrile To a stirred solution of potassium t-butoxide (24.69 g, 220 mmol, 2.2 eq) in anhydrous tetrahydrofuran (150 ml) at -50C under nitrogen, a solution of 2-chloro-5-nitropyridine (15.85 g, 100 mmol) and (4-chlorophenoxy)acetonitrile (E. Grochowski et al., Bull. Acad. Pol. Sci. Ser. Sci. Chim ., 11 , 443 (1963)) (18.44 g, 110 mmol, 1.1 eq) in anhydrous tetrahydrofuran (150 ml) was added dropwise at such a rate that the reaction temperature was maintained at -40 to -50C with cooling in a dry ice/acetone bath. The resultant purple colored reaction mixture was then stirred at -78C under nitrogen for 1 hour, at which time glacial acetic acid (20 ml, 0.35 mol, 3.5 eq) was added to the reaction, and the mixture was allowed to warm to room temperature. A solution of 5% HCl (100 ml) was added to the reaction mixture and this aqueous mixture was extracted with ethyl ether (100 ml) and then with methylene chloride (2×100 ml). The extracts were combined, dried over magnesium sulfate, and passed through a silica gel filter (approximately 150 g) followed by methylene chloride (1200 ml). This filtrate was evaporated under reduced pressure, and the residual oil was chromatographed using silica gel (approximately 300 g) and eluted with 25% hexanes in methylene chloride to afford an oil (Rf=0.52 in methylene chloride) which was triturated in cold anhydrous ether to afford 6-chloro-3-nitro-2-pyridyl acetonitrile (1.37 g, 7%) as a white crystalline solid: mp, 121.5-123.5C.

The synthetic route of 3598-13-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER INC.; EP436333; (1991); A2;,
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 3598-13-8 as follows. Formula: C8H6ClNO

Starting Material 7: (6-Nitro-2-phenyl-benzoxazole-7-yl)-acetonitrile STR24 To a stirred suspension of potassium tert-butoxide (701 mg, 6.25 mmol) in DMF (6 mL) was added a solution of 6-nitro-2-phenyl-benzoxazole (500 mg, 2.08 mmol)(Starting Material 3) and 4-chlorophenoxyacetonitrile (366 mg, 2.19 mmol) (Aldrich) in DMF (20 mL) at -30 C. The mixture was then stirred at this temperature for 3 h and neutralized with aqueous 1N hydrochloric acid solution at 0 C. The aqueous layer was extracted with ethyl acetate. The combined extracts were dried over anhydrous magnesium sulfate and concentrated in vacuo to give a yellow solid. The crude product was purified by silica gel chromatography. (Yield 520 mg, 90%).

According to the analysis of related databases, 3598-13-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Hoffmann-La Roche Inc.; US6153634; (2000); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 3598-13-8, A common heterocyclic compound, 3598-13-8, name is 2-(4-Chlorophenoxy)acetonitrile, molecular formula is C8H6ClNO, 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.

Preparation 1: [0033] Step A: (2-Nitro-1-naphthyl)acetonitrile [0034] Prepare a solution of 53.5 g (0.477 mol) of potassium tert.-butanolate in 400 ml of dimethylformamide. Cool the resulting solution to -10[deg.] C. and add thereto, over the course of about 1 hour, a solution of 40 g of 4-chlorophenoxyacetonitrile (0.24 mol) and 37 g of 2-nitronaphthalene (0.213 mol) in 200 ml of dimethylformamide. After 2 hours at -5[deg.] C., pour the mixture into 4 litres of water containing 1 litre of concentrated hydrochloric acid and extract the aqueous phase with 3*500 ml of dichloromethane. Wash the organic phase with 300 ml of water, dry it over magnesium sulphate, filter and then evaporate off the solvent. [0035] 65 g of product are obtained. [0036] Recrystallise that 65 g from a mixture of cyclohexane/ethyl acetate: 50/50.

The synthetic route of 3598-13-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Lavielle, Gilbert; Muller, Olivier; Millan, Mark; Gobert, Alain; US2003/199555; (2003); 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. 3598-13-8, name is 2-(4-Chlorophenoxy)acetonitrile, This compound has unique chemical properties. The synthetic route is as follows., category: nitriles-buliding-blocks

Starting Material 6: (5-Nitro-2-phenyl-benzothiazole4-yl)-acetonitrile STR23 5-Nitro-2-phenyl-benzothiazole (1.52 g, 5.94 mmol)(Starting Material 1) and 4-chlorophenoxyacetonitrile (1.05 g, 6.26 mmol) (Aldrich) were mixed in dimethylsulfoxide (20 mL). Powdered potassium hydroxide (1.40 g, 25 mmol) was added, and the mixture was stirred at room temperature for 8 hours. The mixture was poured into ice water and acidified with concentrated hydrochloric acid. The mixture was extracted with ethyl acetate (3*). The combined organic layers were washed with water (2*), brine and dried over anhydrous magnesium sulfate. The solvent was concentrated in vacuo and the residue was crystallized from ethyl acetate/hexanes to give the product. (Yield 0.64 g, 37%).

According to the analysis of related databases, 3598-13-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Hoffmann-La Roche Inc.; US6153634; (2000); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 3598-13-8,Some common heterocyclic compound, 3598-13-8, name is 2-(4-Chlorophenoxy)acetonitrile, molecular formula is C8H6ClNO, 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. (5-Amino-2-chloro-4-pyridyl) acetonitrile To a stirred solution of potassium t-butoxide (24.69 g, 220 mmol, 2.2 eq) in anhydrous tetrahydrofuran (150 ml) at -50 C. under nitrogen, a solution of 2-chloro-5-nitropyridine (15.85 g, 100 mmol) and (4-chlorophenoxy)acetonitrile (E. Grochowski et al., Bull. Acad. Pol. Sci. Ser. Sci. Chim., 11, 443 (1963)) (18.44 g, 110 mmol, 1.1 eq) in anhydrous tetrahydrofuran (150 ml) was added dropwise at such a rate that the reaction temperature was maintained at -40 to -50 C. with cooling in a dry ice/acetone bath. The resultant purple colored reaction mixture was then stirred at -78 C. under nitrogen for 1 hour, at which time glacial acetic acid (20 ml, 0.35 mol, 3.5 eq) was added to the reaction, and the mixture was allowed to warm to room temperature. A solution of 5% HCl (100 ml) was added to the reaction mixture and this aqueous mixture was extracted with ethyl ether (100 ml) and then with methylene chloride (2*100 ml). The extracts were combined, dried over magnesium sulfate, and passed through a silica gel filter (approximately 150 g) followed by methylene chloride (1200 ml). This filtrate was evaporated under reduced pressure, and the residual oil was chromatographed using silica gel (approximately 300 g) and eluted with 25% hexanes in methylene chloride to afford an oil (Rf =0.52 in methylene chloride) which was triturated in cold anhydrous ether to afford 6-chloro-3-nitro-2-pyridyl acetonitrile (1.37 g, 7%) as a white crystalline solid: mp, 121.5-123.5 C.

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-Chlorophenoxy)acetonitrile, its application will become more common.

Reference:
Patent; Pfizer Inc; US5811432; (1998); 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. 3598-13-8, name is 2-(4-Chlorophenoxy)acetonitrile, This compound has unique chemical properties. The synthetic route is as follows., category: nitriles-buliding-blocks

To a solution of potassium tert-butoxide (1.72 g, 15.4 mmol) in DMF (15 ml) cooled at 30 C., was added dropwise a solution of 2-fluoro-4-nitro-benzyloxybenzene (1.73 g, 7 mmol) and 4-chlorophenoxyacetonitrile (1.29 g, 7.7 mmol) while maintaining the temperature below -25 C. After completion of addition, the mixture was stirred for 30 minutes at -20 C. and then poured onto a mixture of cold 1N hydrochloric acid and ether. The organic layer was separated, washed with 1N sodium hydroxide, followed by water, brine, dried (MgSO4). The volatiles were removed under vacuum and the residue was purified by column chromatography eluding with methylene chloride/petroleum ether (3/1) to give a mixture of 3-cyanomethyl-2-fluoro-4-nitrobenzyloxybenzene and 5-cyanomethyl-2-fluoro-4-nitrobenzyloxybenzene (1.2 g, 60%). 1H NMR Spectrum: (DMSOd6) 4.22 (s, 2H, 3-cyanomethyl isomer); 4.3 (s, 2H, 5-cyanomethyl isomer); 5.32 (s, 2H, 5-cyanomethyl isomer); 5.36 (s, 2H, 3-cyanomethyl isomer); 7.3-7.7 (m, 6H); 8.1 (d, 1H, 3-cyanomethyl isomer); 8.2 (d, 1H, 5-cyanomethyl isomer)

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 3598-13-8.

Some common heterocyclic compound, 3598-13-8, name is 2-(4-Chlorophenoxy)acetonitrile, molecular formula is C8H6ClNO, 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. Computed Properties of C8H6ClNO

Step 1 (5-methoxy-2-nitrophenyl)-acetonitrile 24.0 g (214 mmol) potassium-tert-butoxide in 100 mL DMF were slowly added dropwise to a solution of 13.2 g (86.0 mmol) 4-nitroanisole and 18.0 g (107 mmol) 4-chlorophenoxyacetonitrile in 50 mL DMF. The reaction mixture was stirred for 30 min at -10 C. and then poured into 300 g of a 1:1 mixture of conc. hydrochloric acid and ice. After extraction with EtOAc the organic phase was washed with water, dried and evaporated to dryness by rotary evaporation in vacuo with gentle heating. The residue was treated with a 1:1 mixture of petroleum ether/EtOAc and the product that crystallised out was suction filtered. After washing with a 1:1 mixture petroleum ether/EtOAc the crystals were dried in the air. Yield: 6.5 g (39% of theoretical) ESI-MS: m/z=210 (M+NH4)+

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3598-13-8, its application will become more common.