Tag: M.W=100-200

Electric Literature of 1885-29-6, A common heterocyclic compound, 1885-29-6, name is 2-Aminobenzonitrile, molecular formula is C7H6N2, 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 mixture of 2-aminobenzonitrile (5 g, 42.3 mmol) and NBS (16.57g, 93.1 mmol, 2.2 equiv) was refluxed in MeCN (80 mL) for 3 h. After cooling, the precipitate formed was filtered, washed with H2O (3 × 60 mL), and dried in a vacuum drying oven (desiccator cabinet). Recrystallization from propan-2-ol gave 1 as a brown solid; yield: 8.9 g (77%); mp 158 C (Lit.14 mp 156 C). 1H NMR (200 MHz, CDCl3): delta = 4.91 (s, 2 H, NH2), 7.47 (d, J = 2.1Hz, 1 H, H-4), 7.71 (d, J = 2.1 Hz, 1 H, H-6). 13C NMR (50 MHz, CDCl3): delta = 97.9, 108.2, 109.7, 115.6, 133.6,139.4, 146.2.

The synthetic route of 1885-29-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kabri, Youssef; Crozet, Maxime D.; Redon, Sebastien; Vanelle, Patrice; Synthesis; vol. 46; 12; (2014); p. 1613 – 1620;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 766-84-7,Some common heterocyclic compound, 766-84-7, name is 3-Chlorobenzonitrile, molecular formula is C7H4ClN, 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 of N-(2-butyryl-4-chlorophenyl)trifluoromethanesulfonamide (Formula 29A) a) To a stirred solution of 3-chlorobenzonitrile (2.0g, 14.54 mmol) and n-propylmagnesium chloride (2M in Et2O) (8.0 mL, 15.99 mmol) in THF (40 mL) was added CuCl (29 mg, 0.29 mmol), and the mixture was refluxed for 30 minutes. After cooling to RT, cold 1N HCl (10 mL) was added cautiously, the THF removed under reduced pressure, further 1N HCl (30 mL) added and the reaction heated at 90 C. for 1 hour. To the cooled reaction mixture was added water (20 mL) and CH2Cl2 (50 mL), the phases separated, and the aqueous phase again extracted with CH2Cl2. The combined organics were washed with water, dried over MgSO4 and the solvent evaporated under vacuum. The residue was filtered through a pad of silica (eluting with CH2Cl2) to afford 1-(3-chlorophenyl)butan-1-one 26A (3.14 g, 97%), as a yellow liquid.

The synthetic route of 766-84-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Meyer, Adam Gerhard; Winzenberg, Kevin Norman; Sawutz, David G.; Liepa, Andris Juris; US2006/63841; (2006); 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. 1572-52-7, name is 2-Methylenepentanedinitrile, This compound has unique chemical properties. The synthetic route is as follows., name: 2-Methylenepentanedinitrile

a. 426 g (4 moles) of 2-methyleneglutaronitrile, 264 g (4 moles) of cyclopentadiene, 4 g of hydroquinone and 500 ml of benzene are heated in a pressure autoclave at 160 and under a maximum pressure of 3 bars, with stirring, for 10 hours. The mixture obtained after cooling is concentrated in vacuo (ca. 12 Torr), the residue twice extracted with 1.5 liters of petroleum ether each time and then extracted in high vacuum. The crude product is obtained as colourless oil, B.P. 115-128/0.03 Torr, which is dissolved in 300 ml of ethanol. On storage of this solution in a refrigerator overnight, there crystallises 2-exo-cyano-5-norbornene-2-endo-propionitrile, M.P. 40-42.

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 1572-52-7.

Reference:
Patent; Ciba-Geigy Corporation; US4015007; (1977); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 6621-59-6, 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. 6621-59-6, name is 6-Bromohexanenitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A solution of the corresponding precursor (4-chlorobutyronitrile for compounds 1, 5-chlorovaleronitrile for compounds 3 and 6-bromohexanenitrile for compounds 6) (2.5 mmol) in dimethylformamide (1 mL) was added during 1.5 h to a mixture of the arylamine (2.5 mmol), Cs2CO3(2.5 mmol) and KI (5 mmol) in dimethylformamide (2.5mL). The mixture was stirred at the indicated temperature and time. After completion of the reaction, as indicated by TLC, the mixture was treated with ethyl ether (50 mL) and water (10 mL). The aqueous phase was separated and extracted with ethyl ether (30 mL). The combined organic layers were dried over anhydrous sodium sulfate and filtered. The solvent was evaporated in vacuo. The crude product was purified by column chromatography (silica gel, hexane:DCM).

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, 6-Bromohexanenitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Diaz, Jimena E.; Mollo, Maria C.; Orelli, Liliana R.; Beilstein Journal of Organic Chemistry; vol. 12; (2016); p. 2026 – 2031;,
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. 1009-35-4, name is 4-Fluoro-3-nitrobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C7H3FN2O2

To a solution of methyl 4-aminocyclohexane carboxylate hydrochloride (1.5 g, 7.74 mmol) and 4-fluoro-3-nitrobenzonitrile (1.28 g, 7.74 mmol) in acetonitrile (50 ml) was added N,N-diisopropylethylamine (2.69 ml, 15.49 mmol) at ambient temperature. The resulting reaction mixture was stirred for 18 hours at room temperature. Acetonitrile was removed under reduced pressure and the crude solid was dissolved in dichloromethane and the dichloromethane layer was washed with water, dried over magnesium sulfate, filtered and then concentrated under reduced pressure. The crude solid product was washed with cold methanol and used in the next step without any further purification. Yield 1.8 g.77percent MS (ESI) m/z for C15H17N3O4 = 303.12 (calcd) 304.2 ([M + H]+, found)

According to the analysis of related databases, 1009-35-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; OSLO UNIVERSITY HOSPITAL HF; FORSCHUNGSVERBUND BERLIN E.V.; UNIVERSITY OF OULU; KRAUSS, Stefan; NAZARE, Marc; ANUMALA, Upendra Rao; LEHTIO, Lari; WAALER, Jo; HOLSWORTH, Dan; WEGERT, Anita; LEENDERS, Ruben Gerardus George; (99 pag.)WO2018/118868; (2018); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 455-18-5, name is 4-(Trifluoromethyl)benzonitrile, 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 455-18-5, Safety of 4-(Trifluoromethyl)benzonitrile

-Trifluoromethyl-thiobenzamide A solution of oc, a, [A-TRIFLUORO-P-TOLUNITRILE] (603.5 g, 3.53 mol) in dry DMF (2 L) under N2 was heated at [70C] and the Thioacetamide (505 g, 1.9 eq. ) was added. The reaction mixture was treated with HCI gas before 15 minutes and was stirred at [95C] for 6 hours. This treatment was operated 3 times and the mixture was stirred at rt for 24 hours. After cooling at [0C,] water was added and the residue was extracted with diethyl ether (4*1 L). The organic layer was washed with water (3*1 L), dried over [NA2SO4] and then evaporated off. The brownish powder was washed with pentane (3 L) to give the title compound (530.3 g, 2.59 mol) as brown solid in a 73% yield. GC/MS: [M+ C8H6F3NS] 205

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, 4-(Trifluoromethyl)benzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2004/785; (2003); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 1558-82-3, A common heterocyclic compound, 1558-82-3, name is Ethyl N-cyanoacetimidate, molecular formula is C5H8N2O, 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 7 Preparation of 6-cyano-3,4-dihydro-2,2-dimethyl-trans-4-[N-methyl-(N-cyano-acetimidoyl)amino]-2H-benzo[b]pyran-3-ol To 2.80 g of ethyl N-cyanoacetimidate, 4.65 g of 6-cyano-3,4-dihydro-2,2-dimethyl-trans-4-methylamino-2H-benzo[b]pyran-3-ol was added, and the mixture was reacted under stirring at a temperature of from 100 to 120 C. for 2 hours. The reaction mixture was cooled, then dissolved in 100 ml of ethyl acetate, washed twice with a saturated sodium chloride aqueous solution and then dried over anhydrous sodium sulfate. Then, ethyl acetate was distilled off under reduced pressure. The residual solid was recrystallized from ethanol to obtain 2.34 g of the above identified compound in the form of crystals. Melting point: 250-251 C.

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; Kaken Pharmaceutical Co., Ltd.; US5095016; (1992); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 766-84-7, 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 766-84-7 as follows.

General procedure: An equimolar mixture of 2-aminoethanol (1.0 mmol) and sulfur(1.0 mmol) was heated under solvent-free condition at 50C. Nitrile (1.0 mmol) was then added to reaction mixture and refluxed at 80C. The progress of the reaction was monitored through TLC (n-hexane: EtOAc, 8:2). After completion of the reaction, excess of water was added, and the product was filtered (for solid). Further chromatographic purification afforded pure product. All the compounds were characterizedby infrared (IR) and 1H NMR and 13C NMR spectroscopic data, as well as by comparison with data of reported compounds.

According to the analysis of related databases, 766-84-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Bansal, Shivani; Gupta, Poonam; Halve; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 191; 7; (2016); p. 971 – 974;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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

As shown in the above reaction formula,The compound of the formula (2-9-1) obtained in the above Preparation Example 2 (157.4 mg,0.1mmol),a compound of the formula (a-2-1) (78 mg, 0.4 mmol; purchased from TCI),Pyridine (0.8 mL, 0.96 mmol)Add chloroform (30 mL) to the reaction vessel and pass argon for 25 min.It was then refluxed at 65 C for 15 h.After cooling to room temperature (about 25 C), the reaction product was poured into 200 mL of methanol and filtered, and the resulting precipitate was chromatographed on silica gel (using 200-300 mesh).Separation of silica gel with eluent in a volume ratio of 1:2 petroleum ether/dichloromethane to give a blue solid(173.6 mg, yield 90.1%)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1080-74-6, its application will become more common.

Reference:
Patent; Peking University; Zhan Xiaowei; Wang Jiayu; (33 pag.)CN108794504; (2018); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 60899-34-5,Some common heterocyclic compound, 60899-34-5, name is 1-Oxo-2,3-dihydro-1H-indene-4-carbonitrile, molecular formula is C10H7NO, 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 the stirred mixture of 50.0 gm of 4-cyano-l-indanone (Formula 3) (0.318 moles) and 500 ml of heptane, 60 gm of (S)-(-)-l-(4-methoxyphenyl)ethylamine (Formulal3) (0.398 moles, 1.25eq.) was added at ambient temperature. The resulting mixture was heated to 100-105C and water was removed azeotropically. After 15.0 hrs, the reaction mass was cooled to 25-30C and stirred for 1.0 hr. The product was filtered, washed with heptane and dried to obtain a light brown solid of compound of Formulal4(84.0 g, 90.93% yield) with HPLC purity 94.35% & SOR -72 (c=0.1 in CHC13at 20C).MR: 130.4-132.1C; IR (KBr, cm”1): 2226, 1661, 1611, 1513, 1245, 1030; 1H- NMR(CDC13): delta 8.11-8.09 (d, 1H, J=7.74Hz), 7.66-7.64 (d, 1H, J=7.47Hz),7.41-7.89 (m, 3H), 6.89-6.87 (d, 2H, J=8.50Hz), 4.66-4.61 (q, 1H, J=6.46, 12.96 Hz), 3.79 (s, 3H), 3.26-3.21 (m, 2H), 2.90-2.88 (m, 1H), 2.78-2.73 (m, 1H), 1.56-1.55 (d, 3H, J=6.49Hz);13C-NMR(CDCl3): 169.99, 158.48, 152.56, 141.66, 137.59, 134.28, 127.72, 127.66 (2C),127.15,117.12, 113.87(2C), 109.93, 61.56, 55.32, 27.85, 27.67, 24.77;MS (m/z): 291.1 [M+l]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Oxo-2,3-dihydro-1H-indene-4-carbonitrile, its application will become more common.

Reference:
Patent; SUVEN LIFE SCIENCES LIMITED; CHINNAPILLAI, Rajendiran; PERIYANDI, Nagarajan; JASTI, Venkateswaralu; (33 pag.)WO2019/58290; (2019); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts