Category: 31643-49-9

31643-49-9, Name is 4-Nitrophthalonitrile, 31643-49-9, 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.

This synthesis is a modified version of the method described previously [24] and [25]. 4-Nitrophthalonitrile (8.7 g, 50 mmol) and an excess of 3-hydroxypyridine (1) (7.13 g, 75 mmol) were dissolved in 100 mL of dry DMSO under inert gas. A portion of dry potassium carbonate (13.8 g, 100 mmol) was added. After 48 h stirring at room temperature next portion of potassium carbonate was added (10 g, 72 mmol). After 72 h the mixture was poured to 500 mL of water. Precipitate was washed thoroughly with water. The isolated and dried product was dissolved in hot ethanol and active charcoal was added. After filtration ethanol solution was poured into water. Precipitate was filtered, washed with water and dried. Chromatography on silica gel with CH2Cl2 afforded solid product that was dissolved in Ac and slowly poured to water. The white crystals of high purity were obtained. Yield 8.73 g (80%). M = 221.22 g mol-1, C13H7N3O. IR (KBr): nu, cm-1 = 3107, 3070, 3039, 2228 (CN), 1596, 1574, 1566, 1487, 1424, 1314, 1280 (Ar-O-Ar), 1253 (Ar-O-Ar), 1216, 1084, 1025, 956, 892, 854, 820, 706, 615, 527. 1H NMR (200 MHz, DMSO-d6): delta = 8.52 (m, 1H), 8.40 (s, 1H), 8.12 (d, 1H), 7.9 (dd, 1H), 7.71 (m, 1H), 7.54 (m, 1H), 7.49 (dd, 1H). EI-MS (200 C, 70 eV): m/z 221 [M]+, 127 [M+ – C5H4NO], 78 [C5H4N]+.

Statistics shows that 4-Nitrophthalonitrile is playing an increasingly important role. we look forward to future research findings about 31643-49-9.

Reference:
Article; Mantareva, Vanya; Angelov, Ivan; Kussovski, Veselin; Dimitrov, Roumen; Lapok, Lukasz; Woehrle, Dieter; European Journal of Medicinal Chemistry; vol. 46; 9; (2011); p. 4430 – 4440;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

31643-49-9,Some common heterocyclic compound, 31643-49-9, name is 4-Nitrophthalonitrile, molecular formula is C8H3N3O2, 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.

4-nitrophthalonitrile (1.00 g, 5.78 mmol) and 4-hydroxybenzaldehyde (0.71 g, 5.78 mmol) were dissolved inN,N-dimethylformamide (15 mL) and degassed with argon ina dual-bank vacuum-gas manifold system. After stirring for15 min, finely ground anhydrous potassium carbonate (2 g,14.45 mmol) was added portion-wise within 2 h period withthe efficient stirring. The progress of the reaction was monitoredby TLC using DCM / hexane (3/1) solvent system. Thestirring of the suspension was maintained at room temperaturefor further 24 h. The resulting mixture was poured into aniced-water/acetone mixture (5/1: v/v). The occured precipitatewas collected by filtration, washed several times with ethanoland dried in vacuo. The desired pure compound (1) was obtainedas a yellowish powder in sufficient purity. Yield 1.30 g,90 %. m.p. 154 C. FT-IR (PIKE MIRacleTM ATR) nu max/cm-1: 3105-3041(Ar, C-H), 2805-2764 (OC-H), 2237 (C?N),1691 (C=O), 1587-1506 (Ar, C=C), 1489-1309 (C-C), 1255(Ar-O-Ar), 1209, 1155, 1111, 1087, 950, 858, 839, 821. 1HNMR(CDCl3) delta (ppm) : 10.03 (s, 1H, OCH)), 8.01 (d, 2H,ArH), 7.81 (d, 1H, ArH), 7.41-7.34(m, 2H, ArH), 7.23 (d, 2H,ArH). 13C-NMR (CDCl3) delta (ppm): 190.7, 160.3, 159.1,135.9, 134.1, 132.6, 123.0, 122.9, 120.59, 118.2, 115.3,114.9, 110.6.

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

Reference:
Article; Sen, Pinar; Atmaca, Goeknur Ya?a; Erdo?mu?, Ali; Dege, Necmi; Genc, Hasan; Atalay, Yusuf; Yildiz, S. Zeki; Journal of Fluorescence; vol. 25; 5; (2015); p. 1225 – 1234;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts