Category: 4592-94-3

Adding a certain compound to certain chemical reactions, such as: 4592-94-3, name is 3-(4-Bromophenyl)-3-oxopropanenitrile, 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 4592-94-3, Safety of 3-(4-Bromophenyl)-3-oxopropanenitrile

General procedure: A mixture of 1,2-bis(bromomethyl)benzene (1.0 mmol), alpha-cyanoacetophenone (1.0 mmol) and Cs2CO3 (3.0 mmol) in DMSO (5 mL) was stirred at 80 C for 4 h till almost full conversion of the substrates by TLC analysis. The resulting mixture was dropped into 100 mL 1 M HCl (aq) and extracted with EtOAc three times (3×50 mL). The organic extract was dried with Na2SO4, filtered and concentrated. The crude product was purified by column chromatography on silica gel (eluent: petroleum ether/EtOAc=50/1) to afford the product 3aa as a white solid.

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; Wang, Jungang; Xiang, Jiachen; Wang, Miao; Guan, Jie; Wu, Anxin; Tetrahedron; vol. 70; 7; (2014); p. 1412 – 1417;,
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. 4592-94-3, name is 3-(4-Bromophenyl)-3-oxopropanenitrile, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C9H6BrNO

General procedure: A mixture of ethyl 3-oxo-3-phenylpropanoate (2a) (1.73 mL,10.00 mmol) and allylamine [(3.75 mL, 50.00 mmol) neutralized with acetic acid (2.86 mL, 50.00 mmol)] in ethanol (10 mL) was heated to reflux for 3 h. The resulting mixture was concentrated and the residue was taken up in CH2Cl2. The organic layer was washed with 5% HCl and water, dried over MgSO4 and concentrated. Purification of the crude product by flash column chromatography (silica gel; petroleum ether/ethyl acetate95:5) afforded 3a (2.08 g, 9.00 mmol) in 90% yield as a colourless liquid. When treated with 2c, it afforded 3c instead of 3-(allylamino)-3-(2-fluorophenyl) acrylonitrile.

According to the analysis of related databases, 4592-94-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Zhai, Sheng-Xian; Dong, Hong-Ru; Chen, Zi-Bao; Hu, Yi-Ming; Dong, Heng-Shan; Tetrahedron; vol. 70; 44; (2014); p. 8405 – 8412;,
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. 4592-94-3, name is 3-(4-Bromophenyl)-3-oxopropanenitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Product Details of 4592-94-3

General procedure: To a solution of 0.45 g of 3-(4-bromophenyl)-3-oxopropanenitrile (6a, 2.0 mmol) in 25 mL of ethanol, 0.165 g of benzothiazolylhydrazine (5a, 1.0 mmol) and 0.058 g of propionaldehyde (8a, 1.0 mmol) were added along with 2 drops of conc. HCl. The reaction mixture was heated to reflux for 45 minutes until the formation of a solid product in the reaction mixture. The hot reaction mixture was filtered at the vacuum pump and washed with hot ethanol to afford the pure compound 7a. All other compounds (7b-i) were synthesized according to the procedure mentioned for 7a using heteroarylhydrazines (5a-c), different 3-aryl-3-oxopropanenitriles (6a-d) and aldehydes (8a-d). 1-(Benzo[d]thiazol-2-yl)-4,7-dihydro-4-ethyl-3,6-di(4-bromophenyl)-1H-pyrazolo[3,4-b]pyridine-5-nitrile (7a). Yield 62%; M.p. 240-245 C; IR (KBr, cm-1): 2208 (CN), 3340 (N-H); 1H NMR (400 MHz, CDCl3): delta 0.87-0.90 (t, 3H, CH3, J 6.8 Hz), 1.71-1.89 (m, 2H, CH2), 4.44-4.46 (t, 1H, 4-H, J 4 Hz), 7.38-7.42 (m, 1H, 6?-H), 7.48-7.51 (m, 1H, 5′-H), 7.62-7.69 (m, 6H, Ph-H), 7.72-7.74 (m, 2H, 2??-H), 7.78-7.80 (d, 1H, 7′-H, J 8.0 Hz), 7.86-7.88 (d, 1H, 4′-H, J 8.0 Hz), 9.1 (s, 1H, exchangeable with D2O, 7-H); 13C NMR (75 MHz, CDCl3): delta 8.8, 28.2, 36.6, 84.7, 99.5, 121.7, 121.9, 123.4, 125.1, 125.4, 126.8, 128.7, 129.3, 130.9, 131.5, 132.0, 132.6, 139.9, 148.4, 150.3, 160.7; MS: m/z 615.97 [M+1]+, 617.97 [M+1+2]+, 619.97 [M+1+4]+, (1:2:1); Elemental analysis: Calcd. for C28H19Br2N5S: C, 54.47; H, 3.10; N, 11.34; Found: C, 53.35; H, 2.63; N, 11.12.

The synthetic route of 4592-94-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Aggarwal, Ranjana; Kumar, Suresh; Singh, Gulshan; Synthetic Communications; vol. 49; 7; (2019); p. 973 – 985;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 4592-94-3, name is 3-(4-Bromophenyl)-3-oxopropanenitrile, 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 4592-94-3, Computed Properties of C9H6BrNO

1.0 g (2.1 mmol) of N(4-(4,4,5 ,5-tetramethyl- 1,3 ,2-dioxaborolane-2-yl)- 1 -tosyl- 1 H-pyffolo [2,3-b jpyridin-6-yl)cyclopropanecarboxamide prepared from the reaction formula 3 above was dissolved in DMF/H 20 = 2:1 solution, and then 0.6 g (2.5 mmol) of 3-(4-bromophenyl)-3-oxopropanenitrile, 0.2 g (0.2 mmol) of Pd(PPh ) and 0.15 mL of 2M K 2C0 aqueous solution were inserted thereinto and stuffed at 100 – 110C for 2 hours. Once the reaction was completed, the said mixture was cooled down at room temperature, then water was added thereto, and then an extraction using ethyl acetate was performed. After that, a solution extracted therefrom was dried by means of magnesium sulfate anhydrous and concentrated under reduced pressure, from which a residue was accordingly obtained. The residue was separated via NH-silica gel column chromatography (n-hexane / ethyl acetate = 5: 1), and N(4-(4-(2-cyanoacetyl)phenyl)- 1 -tosyl- 1 H-pyrrolo [2,3-b jpyridin-6-yl)cyclopropanecarboxamide was synthesized. A synthesized material was dissolved in MeOH/THF (1:1) solution, and then 2N sodium hydroxide aqueous solution was added thereto and stirred at 30 – 40C for 4 hours. Once the reaction was completed, the said mixture was cooled down to room temperature, and saturated ammonium chloride aqueous solution was added thereto while being stirred. A produced solid was filtered out, and finally a product, i.e., N(4-(4-(2-cyanoacetyl)phenyl)- 1 H-pyrrolo [2,3-b jpyridin-6-yl)cyclopropanecarboxamide was accordingly obtained.MS(ESI+) mlz 345 (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-(4-Bromophenyl)-3-oxopropanenitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CJ HEALTHCARE CORPORATION; LEE, Hyuk Woo; JI, Mi Kyung; KIM, Seung Chan; YU, Ha Na; JUNG, Soo Yeon; PARK, Ji-Yeon; LEE, Ye-Lim; LEE, Ho-Youl; KI, So Young; KIM, Dongkyu; KIM, Myeongjoong; (410 pag.)WO2019/78619; (2019); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of 4592-94-3, 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 4592-94-3 as follows.

General procedure: A microwave tube was charged with ketonitrile (2.0 mmol), methanol (1 mL), and hydrazine monohydrate (2.6 mmol) and subjected to microwave irradiation (100 W, 150 C) for 5 minutes. Volatiles were subsequently removed under reduced pressure. The residue was purified by either trituration with cold methanol or cyclohexane, or by using column chromatography to give the final product.

According to the analysis of related databases, 4592-94-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Kelada, Mark; Walsh, John M. D.; Devine, Robert W.; McArdle, Patrick; Stephens, John C.; Beilstein Journal of Organic Chemistry; vol. 14; (2018); p. 122 – 1228;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 4592-94-3, 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. 4592-94-3, name is 3-(4-Bromophenyl)-3-oxopropanenitrile, This compound has unique chemical properties. The synthetic route is as follows.

A solution of 3-(4-bromophenyl)-3-oxopropanenitrile (1.0 g, 4.5 mmol) in THF (89 mL) was heated to reflux. Borane-THF complex (13 mL of 1 M solution, 13 mmol) was added dropwise. After 3.5 h the mixture was cooled to room temperature, then MeOH (20 mL) was added. The volatiles were evaporated to give a white residue, which was then dissolved in MTBE. The clear solution was treated with a 1 M ethereal HCl solution. The solvents were evaporated and the residue was partitioned between water and DCM. The organic phase was set aside. The aqueous phase was neutralized with a 50% aqueous sodium hydroxide solution, and then extracted with DCM (thrice). The combined organic phase was washed with brine and dried over sodium sulfate. The solvent was evaporated to give the title compound in impure form as a colorless oil (0.85 g) which was used without further purification. Exact mass calculated for C9H12BrNO: 229.0, found: LCMS m/z = 230.3 [M+H]+.

The chemical industry reduces the impact on the environment during synthesis 3-(4-Bromophenyl)-3-oxopropanenitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; ARENA PHARMACEUTICALS, INC.; WO2009/58300; (2009); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 4592-94-3, 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. 4592-94-3 name is 3-(4-Bromophenyl)-3-oxopropanenitrile, 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.

General procedure: To the 1 mol eq. of 3-aryl-3-oxopropanonitrile (2) was added1 mol eq. of hydrazine hydrate (1) in Toluene/EtOH (9:1) and thereaction mixture was refluxed for 30 min then another 1 mol eq. ofdifferent 3-aryl-3-oxopropanonitrile (2) and catalytic amount ofPTSA (0.01 mol eq.) was added. Again reaction mixture wasrefluxed up to 4 h. On completion of the reaction, excess solvent was distilled off. The solid so obtained was filtered and washedwith cold ethanol. Solid was neutralised with aq. sodium bicarbonatesolution and again filtered. Compound thus obtained wasair dried and recrystallized from ethanol.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-(4-Bromophenyl)-3-oxopropanenitrile, and friends who are interested can also refer to it.

Reference:
Article; Aggarwal, Ranjana; Singh, Gulshan; Kaushik, Pawan; Kaushik, Dhirender; Paliwal, Deepika; Kumar, Ajay; European Journal of Medicinal Chemistry; vol. 101; (2015); p. 326 – 333;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Some common heterocyclic compound, 4592-94-3, name is 3-(4-Bromophenyl)-3-oxopropanenitrile, molecular formula is C9H6BrNO, 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. Formula: C9H6BrNO

General procedure: Method C: Almac CRED (200 mg) andNADP or NAD (10 mg) were measured into a 250 mL roundbottomedflask then dissolved in 0.1 M potassium phosphate buffer(pH 7, ca. 50 mL). IPA (7 mL) was added, followed by a solutionof ketone (900-1700 mg) in DMSO (2.5-5 mL, depending on solubility).This was stirred at 35 C under 500 mbar reduced pressureto aid removal of acetone formed by IPA oxidation. Standardwork-up procedure: The pH of the reaction mixture was adjustedif necessary (basic or acidic depending on estimated pKa of alcoholproduct) with either 1 M NaOH or 1 M HCl. The reaction mixturewas then extracted with MTBE (3 100 mL).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4592-94-3, its application will become more common.

Reference:
Article; Rowan, Andrew S.; Moody, Thomas S.; Howard, Roger M.; Underwood, Toby J.; Miskelly, Iain R.; He, Yanan; Wang, Bo; Tetrahedron Asymmetry; vol. 24; 21-22; (2013); p. 1369 – 1381;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Some common heterocyclic compound, 4592-94-3, name is 3-(4-Bromophenyl)-3-oxopropanenitrile, molecular formula is C9H6BrNO, 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 C9H6BrNO

General procedure: To a solution of catalyst 4 (0.01mmol), 3,5-(NO2)2C6H3CO2H (0.02mmol), and alpha,beta-unsaturated aldehyde 2 (0.10mmol) in toluene (1.0mL) was added alpha-cyanoketones 1 (0.15mmol) at 0C. The resulting solution was then stirred for 48h. After complete consumption of the aldehyde (as monitored by TLC), the reaction mixture was evaporated and then loaded onto silica gel (ethyl acetate/petroleumether=1:10 to 1:7) and the products 3a-n were obtained by column chromatography. 4.2.1 (4S)-6-(4-Bromophenyl)-2-hydroxy-4-phenyl-3,4-dihydro-2H-pyran-5-carbonitrile 3a The title compound was obtained according to the general procedure (87% yield) as a mixture of two diastereoisomers (major and minor). Yellow solid; [alpha]D30 = +22.6 (c 1.30, CHCl3); mp = 146-147 C; 1H NMR (400 MHz, CDCl3): delta 7.67 (d, J = 8.8 Hz, 2H; both diastereoisomers), 7.56 (d, J = 8.8 Hz, 2H; both diastereoisomers), 7.41-7.37 (m, 2H; both diastereoisomers), 7.32-7.29 (m, 3H; both diastereoisomers), 5.63 (s, 1H; major), 5.56 (s, 1H; minor), 3.94 (dd, J = 9.6, 6.4 Hz, 1H; major), 3.88 (dd, J = 10.0, 6.8 Hz, 1H; minor), 3.62 (s, 1H), 2.51-2.45 (m, 1H; minor), 2.29-2.23 (m, 1H; major), 2.09-2.03 (m, 1H; both diastereoisomers); 13C NMR (100 MHz, CDCl3): delta 162.1, 140.9, 132.0, 131.7, 129.8, 129.7, 129.2, 129.1, 127.9, 127.7, 127.5, 125.3, 119.0, 96.0, 92.6, 88.2, 40.3, 37.5, 36.6, 35.4 ppm; (additional peaks are observed due to diastereoisomers). IR (KBr): nu 3377.5, 2207.1, 1608.5, 1588.4, 1488.0, 1454.0, 1145.0, 1010.7, 954.9, 867.9, 829.8, 728.3, 700.9 cm-1; d.r.: trans/cis = 3.63/1; ESI-MS (m/z): 354.1 (M-H)-; HRMS(ESI): calcd for ([C18H14NO2BrNa+]): 378.0100. Found: 378.0086; enantiomeric excess: 96%, determined by HPLC (Chiralcel OD-H column, hexane/i-PrOH 80:20, flow rate 0.7 mL/min; lambda = 254 nm, tmajor = 17.5 min, tminor = 11.0 min).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4592-94-3, its application will become more common.

Reference:
Article; Niu, Zhiqiang; He, Xinwei; Shang, Yongjia; Tetrahedron Asymmetry; vol. 25; 10-11; (2014); p. 796 – 801;,
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. 4592-94-3, name is 3-(4-Bromophenyl)-3-oxopropanenitrile, This compound has unique chemical properties. The synthetic route is as follows., Safety of 3-(4-Bromophenyl)-3-oxopropanenitrile

General procedure: A dry 50 mL round flask equipped with a magnetic stirring bar was charged with a solution of 3-oxo-3-phenylpropanenitrile (0.87 g, 6.0 mmol), benzaldehyde (0.61 mL, 6.0 mmol), piperidine (0.12 mL, 0.2 equiv), and acetic acid (0.069 mL, 0.2 equiv) in toluene (20 mL). The mixture was heated at 60 C for 12 h. After cooling to room temperature, the mixture was washed with water (10 mL) and the aqueous phase was extracted with ethyl acetate (3×10 mL). The crude mixture was subjected to column chromatography (PE/EA 98:2) to yield 0.68 g (2.9 mmol, 48%) of the desired product as a white solid.

According to the analysis of related databases, 4592-94-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Liu, Wen; Zhou, Jing; Zheng, Changwu; Chen, Xingkuan; Xiao, Hua; Yang, Yingquan; Guo, Yinlong; Zhao, Gang; Tetrahedron; vol. 67; 10; (2011); p. 1768 – 1773;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts