Tag: M.W=100-200

Electric Literature of 133116-83-3, 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. 133116-83-3, name is 2-Fluoro-6-(trifluoromethyl)benzonitrile, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 2-fluoro-6-(trifluoromethyl)benzonitrile (1.0 g, 5.29 mmol) and K2C03 (1.46 g, 10.58 mmol) in DMF (5 mL) was added 2-(trimethylsilyl)ethanethiol (1.01 ml, 6.35 mmol). The mixture was stirred at room temperature for 4 hours. The TLC indicated complete consumption of starting material. The mixture was filtered and evaporated to dryness in vacuo. The crude was adsorbed onto silica gel, and purified by hexane and ethyl acetate to afford the desired compound. LC/MS [M+H]+:304.

The chemical industry reduces the impact on the environment during synthesis 2-Fluoro-6-(trifluoromethyl)benzonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MANDAL, Mihir; TANG, Haifeng; XIAO, Li; SU, Jing; LI, Guoqing; YANG, Shu-Wei; PAN, Weidong; TANG, Haiqun; DEJESUS, Reynalda; HICKS, Jacqueline; LOMBARDO, Matthew; CHU, Hong; HAGMANN, William; PASTERNAK, Alex; GU, Xin; JIANG, Jinlong; DONG, Shuzhi; DING, Fa-Xiang; LONDON, Clare; BISWAS, Dipshikha; YOUNG, Katherine; HUNTER, David, N.; ZHAO, Zhiqiang; YANG, Dexi; WO2015/112441; (2015); A1;,
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Reference of 145689-34-5,Some common heterocyclic compound, 145689-34-5, name is 2-(2,3-Difluorophenyl)acetonitrile, molecular formula is C8H5F2N, 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.

(35′,5^-3-Amino-5-(23-difluorophenyl)-l-(2,2,2-trifluoroethyl piperidin-2-one hydrochloride; Step A: Ethyl 4-cvano-4-f2,3-difluorophenyl)butanoate; To a mixture of (2,3-difluorophenyl)acetonitrile (40.5 g, 265 mmol), ethyl acrylate (24 mL, 221 mmol), and hydroquinone (50 mg, 0.45 mmol) was added OH (2 M in MeOH, 2.0 mL, 4.0 mmol) and the resulting mixture was heated at 160 C for 16 h and then allowed to cool to ambient temperature. The crude mixture was purified by silica gel chromatography, eluting with a gradient of hexanes: EtOAc – 100:0 to 50:50, to give the title compound. MS: miz = 207.9 (M – OEt).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(2,3-Difluorophenyl)acetonitrile, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; BELL, Ian, M.; BELARDI, Justin; WO2012/129013; (2012); A1;,
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Electric Literature of 7251-09-4, 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. 7251-09-4, name is 4-Amino-2-methoxybenzonitrile, This compound has unique chemical properties. The synthetic route is as follows.

A suspension of 6-chloro-7-hydroxy-2-oxo-l,2-dihydroquinoline-3- carbaldehyde (58.0 mg, 0.259 mmol) and 4-amino-2-methoxybenzonitrile (48.0 mg, 0.324 mmol) in DCM (4.0 mL) was treated with acetic acid (0.07 mL, 1.223 mmol) and stirred 10 minutes. Sodium triacetoxyborohydride (84.0 mg, 0.396 mmol) was added. The mixture was stirred at room temperature overnight. The mixture was diluted with EtOAc (50 mL), washed with water (2×50 mL) and brine (50 mL), dried (Na2S04), filtered, and evaporated under reduced pressure. The residue was dissolved in methanol, treated with silica gel, and evaporated. The material was chromatographed by Biotage MPLC (10 g silica gel column) with 20 to 100% EtOAc in hexanes to provide the title compound 1-57 (18.6 mg, 0.052 mmol, 20.2 % yield) as a peach-coloured solid. 1H NMR (300 MHz, DMSO-d6): delta ppm 11.82 (s, 1 H), 10.89 (s, 1 H), 7.70 (s, 1 H), 7.63 (s, 1 H), 7.28 (d, J=8.50 Hz, 1 H), 7.12 (dd, J=6.00, 6.00 Hz, 1 H), 6.91 (s, 1 H), 6.32 (d, J=1.76 Hz, 1 H), 6.22 (dd, J=8.60, 1.60 Hz, 1 H), 4.17 (d, J=5.60 Hz, 2 H), 3.78 (s, 3 H). LCMS (Method 4): Rt 1.17 min., m/z 356.1 [M+H]+.

The chemical industry reduces the impact on the environment during synthesis 4-Amino-2-methoxybenzonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; FORMA THERAPEUTICS, INC.; ASHWELL, Susan; CAMPBELL, Ann-Marie; CARAVELLA, Justin Andrew; DIEBOLD, R. Bruce; ERICSSON, Anna; GUSTAFSON, Gary; LANCIA, David R.; LIN, Jian; LU, Wei; WANG, Zhongguo; (141 pag.)WO2016/44782; (2016); A1;,
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Related Products of 123-06-8, The chemical industry reduces the impact on the environment during synthesis 123-06-8, name is Ethoxymethylenemalononitrile, I believe this compound will play a more active role in future production and life.

3.2 5-Amino-4-cyano-1-phenyl-1H-pyrazole (3a) A solution of phenylhydrazine (2d) (0.45 mL, 4.2 mmol) and ethoxymethylenemalononitrile (1b) (0.51 g, 4.2 mmol) in EtOH (4 mL) was irradiated at 120 C for 45 min in a sealed, pressure-rated Pyrex tube (10 mL) using a CEM Discover microwave synthesizer by moderating the initial power (100 W). After cooling in a flow of compressed air, the solvent was evaporated in vacuo. Purification by column chromatography on silica, eluting with light petroleum/EtOAc (5:1 v/v), gave the title compound (0.738 g, 95%) as a light brown solid, mp 137-139 C (lit. 29 mp 137 C) (found: 185.0827. C10H9N4 [MH] requires 185.0822); FTIR (KBr)/cm-1 numax 3302 (NH), 3240 (NH), 2230 (CN), 1577, 1530, 1368; 1H NMR (400 MHz; CDCl3) delta 7.58 (1H, s, H-3), 7.49-7.37 (5H, Ph), 4.52 (2H, br s, exch. D2O, NH2); 13C NMR (100 MHz, CDCl3) delta 141.9 (CH), 135 (C), 129.3 (C), 125.5 (CH), 124.1 (CH), 121.3 (CH), 115.6 (C), 86.2 (C); LRMS (APcI) m/z (rel intensity) 226 ([M+MeCNH]+, 100), 185 (MH+, 64).

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, Ethoxymethylenemalononitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Bagley, Mark C.; Baashen, Mohammed; Paddock, Victoria L.; Kipling, David; Davis, Terence; Tetrahedron; vol. 69; 39; (2013); p. 8429 – 8438;,
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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. 143879-77-0, name is 2,6-Difluoro-3-nitrobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 143879-77-0

6-Fluoro-3-nitro-2-phenylaminobenzonitrile LiHMDS (1.0M in THF, 38 mL, 38.0 mmol) was added dropwise to a stirred solution of aniline (1.86 g, 19.9 mmol) in anhydrous THF (30 mL) under a nitrogen atmosphere at -78 C. After 10 min stirring at -78 C., a solution of 2,6-difluoro-3-nitrobenzonitrile (3.5 g, 19.0 mmol) in THF (15 mL) was added and stirring at -78 C. continued for 30 min. The crude mixture was quenched with water and diluted with EtOAc. The resulting emulsion was filtered through a pad of Celite and the organic fraction separated, washed with brine, dried (MgSO4) and concentrated in vacuo. The resulting residue was purified by column chromatography (Si-PCC, gradient 0-100% EtOAc in cyclohexane) to afford the title compound (2.7 g, 55%). 1H NMR (CDCl3, 400 MHz): delta 9.94 (1H, br s), 8.51 (1H, dd, J=9.50, 5.88 Hz), 7.51-7.21 (5H, m), 6.68 (1H, dd, J=9.50, 7.46 Hz).

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 143879-77-0.

Reference:
Patent; Heald, Robert; Price, Stephen; Safina, Brian; Savy, Pascal Pierre Alexandre; Seward, Eileen Mary; Sutherlin, Daniel P.; Waszkowycz, Bohdan; US2012/202785; (2012); A1;,
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Related Products of 29509-06-6,Some common heterocyclic compound, 29509-06-6, name is 4-Methyl-3-oxopentanenitrile, molecular formula is C6H9NO, 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 B22 To a stirring suspension of 6-aminobenzothiazole (0.500 g, 3.33 mmol) in cone. HCl (5 ml) at 0-5 C. was added a solution of NaNO2 (0.276 g, 3.99 mmol) in H2O (5 ml). The mixture was stirred at 0-5 C. for 75 min until a clear yellow solution was obtained. To this was then added a solution of SnCl2.2H2O (2.76 g, 13.3 mmol) in conc. HCl (5 ml). After completing the addition, the suspension was stirred at RT for 2 h. 4-Methyl-3-oxopentanenitrile (0.444 g, 3.99 mmol) and EtOH (50 ml) were added and the reaction was stirred with heating at 75 C. After 18 h, the completed reaction was cooled to RT and concentrated to an aqueous residue. This was chilled thoroughly in ice and made strongly basic (pH 12-13) by the addition of 6M NaOH. While still cold the mixture was extracted with EtOAc (2*). The combined organics were washed with H2O (2*), brine (1*), dried (MgSO4), filtered and evaporated to afford crude 1-(benzo[d]thiazol-6-yl)-3-isopropyl-1H-pyrazol-5-amine (0.8 g, 93% yield) as an oil which was used as is in the next reaction. 1H NMR (400 MHz, DMSO-d6) delta 9.36 (s, 1H), 8.30 (d, J=2.4 Hz, 1H); 8.10 (d, J=8.8 Hz, 1H), 7.74 (dd, J=2.4 and 8.8 Hz, 1H), 5.36 (s, 1H), 5.33 (brs, 2H), 2.76 (septet, J=6.8 Hz, 1H), 1.17 (d, J=6.8 Hz, 6H); MS (ESI) m/z: 259.0 (M+H+).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Methyl-3-oxopentanenitrile, its application will become more common.

Reference:
Patent; Deciphera Pharmaceuticals, LLC; US2008/90856; (2008); A1;,
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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. 14447-18-8, name is Benzyl cyanoacetate belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Quality Control of Benzyl cyanoacetate

General procedure: A 100-mL round-bottom flask equipped with a stir bar is charged with dimethyl malonate (2.0 g, 15.0 mmol), crotonaldehyde (1.3 mL, 15.0 mmol), piperidine (0.2 mL, 3.0 mmol), benzoic acid (0.4 g, 3.0 mmol) and toluene (50 mL). The reaction mixture is heated at reflux using a Dean-Stark apparatus for 2 h. The toluene solution is washed with water, dried over Na2SO4 and concentrated in vacuo. The crude product is purified by silica gel column chromatography eluting with hexanes/ethyl acetate (20/1) to afford 1a (1.7 g, 60% yield) as a red liquid.

The synthetic route of 14447-18-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhang, Wei; Ghiviriga, Ion; Grenning, Alexander J.; Tetrahedron; vol. 73; 29; (2017); p. 4076 – 4083;,
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Reference of 53312-81-5, 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. 53312-81-5, name is 5-Amino-2-fluorobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Intermediate 9: 5- 5-(Benzyloxy)pyrimidin-2-ylamino]-2-fluoro-benzonitrileA suspension of 2-chloro-5-benzyloxypyrimidine (2.0g, 9.074mmol), 5-amino-2- fluorobenzonitrile (1.24g, 9.074mmol), in’5,(dibenzylideneacetone)palladium(0) (415 mg, 0.45mmol), 4,5-bi5,(diphenylphosphino)-9,9-dimethylxanthene (525 mg, 0.90 mol) and cesium carbonate (5.9g, 18.1mmol) in de-gassed 1,4-dioxane (15mL) was heated at 80 C for 2 days. The reaction mixture was diluted with dichloromethane and washed with water and brine. The organic phase was dried (MgS04) and the solvent removed under reduced pressure. The crude product was purified by flash chromatography, using 0-5% ethyl acetate:hexane as eluent, to give 5- [5- (benzyloxy)pyrimidin-2-ylamino]-2-fluoro-benzonitrile (2.88g) as yellow solid.Mass: (ES+) 321(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, 5-Amino-2-fluorobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SENEXIS LIMITED; HORWELL, David; SCOPES, David; WO2011/144577; (2011); A1;,
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Some common heterocyclic compound, 50594-78-0, name is 5-Fluoro-2-nitrobenzonitrile, molecular formula is C7H3FN2O2, 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. HPLC of Formula: C7H3FN2O2

[0593] (a) Preparation of 5-[((2S)-1-methylpyrrolidin-2-yl)methoxy]-2-nitrobenzenecarbonitrile. To a slurry of 60% NaH (956 mg, 24 mmol) in THF (100 mL) was added (S)-(-)-1-methyl-2-pyrolidinemethanol (Aldrich) (2.8 mL, 24 mmol) resulting in gas evolution. After 30 min, 5-fluoro-2-nitrobenzonitrile (Combi Blocks) (3.3 g, 20 mmol) was added. After 3 h the reaction solvent was removed in vacuo and the residue was partitioned between CH2Cl2 and H2O. The aqueous layer was extracted with CH2Cl2 and the combined organics were dried over Na2SO4 and concentrated in vacuo to give a red oil. MS m/z: 262 (M+1). Calc’d for C13H15N3O3-261.11.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 50594-78-0, its application will become more common.

Reference:
Patent; Huang, Qi; Kaller, Matthew; Nguyen, Thomas; Norman, Mark H.; Rzasa, Robert; Wang, Hui-Ling; Zhong, Wenge; US2003/229068; (2003); A1;,
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Reference of 4421-09-4, 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. 4421-09-4, name is 3,4-(Methylenedioxy)benzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Description 2: (Z)-N’ -hydroxybenzo[d][l,3]dioxole-5-carboximidamide To a solution of benzo[d][l,3]dioxole-5-carbonitrile (15 g, 102 mmol), hydroxylamine hydrochloride (14.17 g, 204 mmol) in Ethanol (500 mL) was added Na2C03 (54.0 g, 510 mmol) in one charge. The reaction mixture was stirred at 80C for 5 hr. Then the solvent was removed under reduced pressure, the residual was washed with DCM (1L><4), filtered and the combined filtrate was concentrated under reduced pressure to afford (Z)-N'-hydroxy benzo[d][l,3]dioxole-5-carboximidamide as a yellow solid (15 g, 73.5%). MS(ES+) m/z 181.1 (MH+). The synthetic route of 3,4-(Methylenedioxy)benzonitrile has been constantly updated, and we look forward to future research findings. Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; WANG, Rong; LU, Hongtao; WO2013/107336; (2013); A1;,
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