Category: 1080-74-6

1080-74-6, name is 2-(3-Oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile, 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

To a degassed mixture of compound 9-3 (192 mg, 0.14 mmol), anhydrous chloroform (15 cm3) and pyridine (0.77 cm3) was added 2-(3-oxo-indan-1 – ylidene)-malononitrile (185 mg, 0.95 mmol). The solution was then degassed for a further 10 minutes and then stirred at 23 C for 160 minutes. Methanol (300 cm3) was added and after stirring for 20 minutes the solid was collected by filtration. The solid was then washed with methanol (3 x 10 cm3), acetone (3 x 10 cm3) and diethyl ether (2 x 10 cm3) to give compound 9 (179 mg, 75%) as a solid. 1H-NMR (400 MHz, CDCIs) 0.80 – 0.90 (12H, m), 1.18 – 1.43 (72H, m), 1.49 – 1.64 (8H, m), 2.48 – 2.60 (8H, m), 7.06 – 7.19 (16H, m), 7.53 (2H, s), 7.70 (2H, s), 7.73 – 7.83 (4H, m), 7.90 – 7.95 (2H, m), 8.65 – 8.70 (2H, m), 8.81 (2H, s).

The synthetic route of 1080-74-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK PATENT GMBH; MORSE, Graham; HEARD, Kane; MITCHELL, William; KROMPIEC, Michal; D’LAVARI, Mansoor; PRON, Agnieszka; (260 pag.)WO2019/52935; (2019); A1;,
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Electric Literature of 1080-74-6, A common heterocyclic compound, 1080-74-6, name is 2-(3-Oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile, molecular formula is C12H6N2O, 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.

In the N2 environment, compound 3 (0.065 mmol) and 4 (0.390 mmol) were dissolved in 6 mL of chloroform solution.Three drops of pyridine solution were added dropwise, and the mixture was reacted at 75 C for 16 hours. The solvent was evaporated under reduced pressure and purified by residue column chromatography to yield white product NITI-1 (yield 86%).

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; Chinese Academy Of Sciences Chemical Institute; Zhu Xiaozhang; Xu Shengjie; Zhou Zichun; (23 pag.)CN109485635; (2019); A;,
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Related Products of 1080-74-6, These common heterocyclic compound, 1080-74-6, name is 2-(3-Oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile, 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: A mixture of dye 6 (1.18 g, 3 mmol) and indandione (0.438 g,3 mmol) or malononitrile (0.198 g, 3 mmol) or 3-dicyanovinylindan-1-one (0.582 g, 3 mmol) in basic ethanol solution (7 ml) was stirredat room temperature overnight, filtered off and purified by columnchromatography on silica gel using CHCl3 as the eluent, affordingdyes a or b or c, respectively Yield: 66.6%. Mp 208e210 C. 1H NMR (600 MHz, CDCl3) 1.31 (t,6H, J ? 7.2 Hz, N(CH2CH3)2), 3.56 (q, 4H, J ? 7.2 Hz, N(CH2CH3)), 3.92(s, 3H, OCH3), 6.78 (d, 2H, J ? 9.6 Hz, AreH), 7.08 (d, 2H, J ? 7.2 Hz,AreH), 7.76 (m, 4H, AreH), 7.93 (d, 1H, J ? 7.2 Hz, AreH), 8.03 (m,2H, AreH), 8.66 (d, 1H, J ? 7.8 Hz, AreH), 8.75 (s, 1H, CH]C). 13CNMR (125 MHz, CDCl3) d 12.80, 45.42, 55.49, 69.77, 113.90, 114.44,114.78, 123.85, 125.11, 125.80, 126.01, 132.47, 134.36, 135.15, 136.96,138.06, 139.94, 143.91, 153.39, 160.77, 161.68, 170.58, 183.00, 188.07.IR n/cm 1 2211, 1746, 1697, 1595, 1519, 1214, 1102, 1065. HRMS calcdfor C33H26N6O2S: 570.68. Found: 570.95.

Statistics shows that 2-(3-Oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile is playing an increasingly important role. we look forward to future research findings about 1080-74-6.

Reference:
Article; El-Shishtawy, Reda M.; Borbone, Fabio; Al-Amshany, Zahra M.; Tuzi, Angela; Barsella, Alberto; Asiri, Abdullah M.; Roviello, Antonio; Dyes and Pigments; vol. 96; 1; (2013); p. 45 – 51;,
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1080-74-6, Name is 2-(3-Oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile, 1080-74-6, 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.

Compound 4 (0.15 g, 0.1275 mmol) and 2-(3-oxo-2,3-dihydroinden-1-ylidene)malononitrile (0.371 g, 3.825 mmol) were dissolved inchloroform (15 mL). A drop of pyridine was added and the solution wasleft to stir at 65 C overnight. The reaction was dissolved in ethanol andstirred for another 10 min. The product was extracted with dichloromethaneand dried over MgSO4. After removal of the solvent, thecrude product was chromatographically purified on silica gel column(eluted with chlorobenzene) to afford dark purple solid (105 mg, 85%).1H NMR (500 MHz, CDCl3) delta: 8.95 (s, 3H), 8.75 (m, 3H), 8.50 (m, 3H),8.01 (m, 3H), 7.98 (m, 6H), 7.91 (s, 3H), 7.83 (m, 6H), 7.69 (d, 3H),3.04 (m, 6H), 2.28 (m, 6H), 0.95 (m, 36H), 0.62 (m, 30H). 13C NMR (125 MHz, CDCl3) delta: 187.44, 159.75, 159.54, 153.77, 145.88, 145.39,141.05, 139.05, 137.13, 136.97, 135.96, 135.41, 134.29, 133.62,130.51, 124.42, 124.40, 124.27, 123.99, 122.85, 121.62, 119.14,113.53, 113.46, 70.06, 56.40, 37.23, 31.63, 29.57, 24.22, 22.41, 14.02.MS (MALDI-TOF) calculated for C114H108N6O3S3, 1705.77; found,1705.94.

Statistics shows that 2-(3-Oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile is playing an increasingly important role. we look forward to future research findings about 1080-74-6.

Reference:
Article; Lin, Kaiwen; Xie, Boming; Wang, Zhenfeng; Xie, Ruihao; Huang, Yunping; Duan, Chunhui; Huang, Fei; Cao, Yong; Organic electronics; vol. 52; (2018); p. 42 – 50;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

1080-74-6, name is 2-(3-Oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile, 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. 1080-74-6

Take a two-necked round bottom flask, dissolve compound 8-1 in chloroform, and perform a Knoevenagel condensation reaction with malononitrile indanone ketone electronic unit under weakly basic conditions. After TLC monitors the reaction, directly use reaction oil The ether / dichloromethane eluent was passed through the column to obtain the final type of organic solar cell using diindenobisthiophene as the core; wherein, the compound 8-1, the electron-drawing unit, pyridine, and chloroform had a ratio of 0.2 to 2.2mmol: 0.3 3.0mmol: 0.01 0.5mmol: 10 50mL; yield is 84.7%;

Statistics shows that 1080-74-6 is playing an increasingly important role. we look forward to future research findings about 2-(3-Oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile.

Reference:
Patent; Xiamen University; Xie Suyuan; Zheng Shanyu; An Mingwei; Pei Yaqian; Deng Linlong; (31 pag.)CN110746440; (2020); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

1080-74-6, name is 2-(3-Oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile, 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. 1080-74-6

General procedure: Compound 4 (400 mg, 0.47 mmol) and INCN (458 mg, 2.36 mmol) were dissolved in anhydrous chloroform (CF, 25 mL) and 0.3 mL of pyridine was slowly injected into mixture solution. Thereaction was stirred under a nitrogen atmosphere at 65 C for 12 h. Subsequently, the reaction vessel was cooled to room temperature and extracted with chloroform several times. The extracted organic layer were dried over MgSO4, filtered, and evaporated to obtain a residue. The mixture compound was then purified with column chromatography using chloroform to afford a dark solid.

Statistics shows that 1080-74-6 is playing an increasingly important role. we look forward to future research findings about 2-(3-Oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile.

Reference:
Article; Lee, Seong Lim; Kim, Hee Su; Ha, Jong-Woon; Park, Hea Jung; Hwang, Do-Hoon; Bulletin of the Korean Chemical Society; vol. 41; 2; (2020); p. 143 – 149;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

1080-74-6, Name is 2-(3-Oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile, 1080-74-6, 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.

As shown in the above reaction formula,The formula (2-8-a-3) obtained in the above Preparation Example 1The compound shown (129 mg, 0.1 mmol),a compound of the formula (a-2-1) (92 mg, 0.4 mmol),Pyridine (0.8 mL, 0.96 mmol) and chloroform(30 mL) was added to the reaction vessel,Argon gas for 25 minutes,It was then refluxed at 65 C for 12 h.After cooling to room temperature (about 25 C),The reaction product was poured into 200 mL of methanol and filtered.The obtained precipitate was sieved on a silica gel column (using 200-300 mesh silica gel,The eluent is a petroleum ether/dichloromethane in a volume ratio of 1:2 for chromatographic separation.Obtained a blue solid (147 mg, yield: 89.1%).That is, the poly-fused ring conjugated macromolecule represented by the formula (1-8-a-3).

Statistics shows that 2-(3-Oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile is playing an increasingly important role. we look forward to future research findings about 1080-74-6.

Reference:
Patent; Peking University; Zhan Xiaowei; Zhu Jingshuai; Lin Yuze; (40 pag.)CN109651393; (2019); A;,
Nitrile – Wikipedia,
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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. 1080-74-6, name is 2-(3-Oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile, This compound has unique chemical properties. The synthetic route is as follows., 1080-74-6

A solution of 5′-bromo-3,4′-dihexyl-[2,2′-bithiophene]-5-carbaldehyde (1.39 g, 3.14 mmol), denatured ethanol (75 cm3), pyridine (5 drops) and 3- (dicyanomethylidene)indan-1-one (0.61 g, 3.1 mmol) was stirred at 23 C for 20 minutes. Additional denatured ethanol (50 cm3) was added and the suspension heated at 80 C for 1 hour. The suspension was cooled to 23 C and the solid collected by filtration. The solid was washed with ethanol (50 cm3) then methanol (50 cm3) to give intermediate 5 (1.73 g, 89%) as a dark solid.1H NMR (400 MHz, CD2Cl2) 8.75 (1H, s), 8.62 – 8.70 (1H, m), 7.87 – 7.96 (1H, m), 7.73 – 7.86 (2H, m), 7.64 (1H, s), 7.23 (1H, s), 2.72 – 2.82 (2H, m), 2.60 – 2.68 (2H, m), 1.62 – 1.77 (4H, m), 1.32 – 1.51 (12H, m), 0.86 – 1.02 (6H, m).13C NMR (100 MHz, CD2Cl2) 188.1, 160.2, 147.6, 147.0, 143.6, 140.9, 139.9, 137.2, 136.9, 135.1, 134.6, 134.5, 134.3, 128.9, 125.2, 123.7, 122.9, 114.6, 114.5, 112.6, 69.9, 31.6, 31.6, 30.0, 29.6, 29.5, 29.2, 29.1, 28.9, 22.6, 13.9, 13.8.

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Reference:
Patent; MERCK PATENT GMBH; MITCHELL, William; WANG, Changsheng; D’LAVARI, Mansoor; (163 pag.)WO2020/48939; (2020); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

1080-74-6, A common heterocyclic compound, 1080-74-6, name is 2-(3-Oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile, molecular formula is C12H6N2O, 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.

To a solution of intermediate 27 (370 mg, 0.24 mmol) in anhydrous chloroform (26 cm3) is added pyridine (1 .4 cm3, 17 mmol). The mixture is then degassed with nitrogen before 3-(dicyanomethylidene) indan-1 -one (280 mg, 1 .4 mmol) is added. The solution is then further degassed and stirred at 23 C for 20 minutes. The mixture is stirred at 40 C for 2 hours and then the solvent is removed in vacuo. The crude is triturated with ethanol (200 cm3) to produce a heavy suspension which is collected by filtration and the solid washed with acetone (50 cm3). The crude is dissolved in dichloromethane (20 cm3) added precipitated into acetone (250 cm3) to form a suspension. The solid collected by filtration to give compound 90 (437 mg, 96%) as a gray solid. 1H NMR (400 MHz, CDCIs) 8.87 (2H, s), 8.63 – 8.74 (2H, m), 8.13 (2H, s), 7.87 – 7.97 (2H, m), 7.68 – 7.82 (4H, m), 7.23 (8H, d, J 8.8), 6.90 (8H, d, J 9.0), 3.92 (8H, t, J 6.5), 1 .69 – 1 .84 (8H, m), 1 .16 – 1 .52 (72H, m), 0.80 – 0.97 (12H, m).

The synthetic route of 1080-74-6 has been constantly updated, and we look forward to future research findings.

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,
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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. 1080-74-6, name is 2-(3-Oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile, A new synthetic method of this compound is introduced below., 1080-74-6

A solution of compound 2 (0.28 mmol, 50 mg) in ethanol (5 mL) was added 2-(1,2-dihydro-1-oxoinden-3-ylidene)malononitrile (0.28 mmol, 54 mg) and the mixture was stirred for 4 days at room temperature. The precipitate obtained was filtered and the product was recrystallized from ethanol which gave the pure compound 3c. 2-(((2-(1H-Pyrrol-1-yl)thiazol-5-yl)methylene)-1,2-dihydro-1- oxoinden-3-ylidene)malononitrile 3c. Orange solid (75 mg, 87%). Mp 294-295 C. 1H NMR (CDCl3) delta 6.43-6.45 (m, 2H, 3”-H and 4”-H), 7.50-7.51 (m, 2H, 2”-H and 5”-H), 7.80-7.85 (m, 2H, 4-H and 7-H), 7.96 (dd, 1H, J 6.8 and J 0.6 Hz, 6-H), 8.19 (s, 1H, 40-H), 8.74 (dd, 1H, J 6.8 and J 0.6 Hz, 5-H), 8.87 (s, 1H, C=CH). 13C NMR (CDCl3) delta108.2, 112.4, 114.1, 114.2, 120.1, 122.5, 123.0, 124.1, 125.6, 127.4, 134.9, 135.8, 135.9, 136.7, 140.1, 158.5, 159.5, 170.4. lambdamax (dioxane)/ nm 465 ( 3/dm3 mol-1 cm-1 36,130). IR (CHCl3): 2224, 1700, 1590, 1571,1554,1503,1398,1307,1290,1275,1253,1226,1189,1044, 988, 919 cm-1. MS (EI) m/z (%) 354 ([M], 87), 2891 (19), 288 (100), 263 (10), 262 (50), 234 (24), 218 (10), 207 (11), 189 (17), 164 (15), 163 (61); HMRS: m/z (EI) for C20H10N4OS: calcd 354.0575; found: 354.0570.

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:
Article; Castro, M. Cidalia R.; Belsley; Raposo, M. Manuela M.; Dyes and Pigments; vol. 128; (2016); p. 89 – 95;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts