Tag: M.W=100-200

Synthetic Route of 118431-88-2, 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. 118431-88-2, name is 3-Cyclopropyl-3-oxopropanenitrile, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a cooled solution of potassium ieri-butylate (91.6mmol, 1.1 equiv.) in THF (260ml) was added a solution of 3-cyclopropyl-3-oxo-propionitrile (83.2mmol, 1.0 equiv.) in THF (130ml) over 30 minutes, while maintaining the temperature at 0C. After stirring for an additional hour at 0C, the solution was cooled to -20C. The respective isothiocyanate (83.2mmol, 1.0 equiv.) was dissolved in THF (130ml) and added to the orange solution over 25 minutes. The reaction mixture was allowed to warm to room temperature. TLC indicated complete conversion of starting material. The clear solution was poured onto ice-cold IN HCl (1L), extracted with dichloromethane (1L), dried over Na2SO4 and evaporated to dryness. The resulting raw-solid was recrystallized from MTBE.

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

Reference:
Patent; ALGIAX PHARMACEUTICALS GMBH; HASSE, Birgit; KOOPMANS, Guido; (41 pag.)WO2015/140081; (2015); A1;,
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Application of 873-74-5, A common heterocyclic compound, 873-74-5, name is 4-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.

EXAMPLE 1 Preparation of 4-Amino-3,5-dibromobenzonitrile STR15 To a stirred solution of 100 mg (0.847 mmoles) of p-aminobenzonitrile in 3.6 mL dioxane chilled in an ice-bath was added sequentially 356 muL (1.78 mmoles) of 5 N sodium hydroxide solution and 284 mg (1.78 mmoles) of bromine. The ice-water bath was removed and the reaction mixture was stirred further for 1.5 hours. After this time, 21.8 muL (0.423 mmoles) of bromine was added to drive the reaction to completion and stirring was continued for 10 minutes. The mixture was partitioned between ethyl acetate and ice-water and the organic phase was separated. It was washed with brine, dried over anhydrous sodium sulfate, filtered, and evaporated. Purification by plate layer chromatography using hexane-ethyl acetate (7:3) as eluant provided 175 mg (74%) of the entitled product. NMR(CDCl3) delta: 5.1 (bs, 2H), 7.66 (s, 2H).

The synthetic route of 873-74-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck & Co., Inc.; US5192758; (1993); A;,
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Synthetic Route of 139152-08-2, A common heterocyclic compound, 139152-08-2, name is 4,5-Dichlorophthalonitrile, molecular formula is C8H2Cl2N2, 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 mixture of 9-phenanthrol (1) (0.97 g, 5 mmol) and4,5-dichlorophthalonitrile (2) (0.985 g, 5 mmol) in 50 mLof DMSO at 25 C was added lithium hydroxide monohydrate(0.21 g, 5 mmol) within 0.5 h. The mixture was stirred for 24 h at same temperature and then it was pouredinto 100 mL of water. Then extracted with chloroform(2 × 100 mL), washed with water (1 × 100 mL), brine(1×100 mL) and dried over Na2SO4. The solvent wasremoved under reduced pressure. The resulting residuewas purified by silica-gel column chromatography usingethyl acetate:hexane (1:9) as an eluent to obtain a lightyellow solid, yield (1.45 g, 82%). 1H NMR (600 MHz,CDCl3: delta 8.79 (d, J = 82 Hz, 1H), 8.73 (d, J = 82 Hz,1H), 7.95 (s, 1H), 7.91-7.84 (m, 2H), 7.81-7.62 (m, 4H),7.44 (s, 1H), 7.06 (s , 1H) ppm; 13C NMR (150 MHz,CDCl3: delta 157.10, 146.53, 134.58, 131.30, 130.13, 128.32,128.10, 127.47, 127.24, 126.65, 126.56, 126.27, 124.28,122.46, 121.90, 120.65, 119.66, 115.24, 114.65, 113.25,108.98, 28.67 ppm; IR (KBr tablet) max/cm-1: 3104,3040, 2900, 2233, 1628, 1584, 1510, 1303, 1198, 1128;ESI-MS: 354 [M]+.

The synthetic route of 139152-08-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kim, Changkyeom; Kumar, Rangaraju Satish; Mergu, Naveen; Jun, Kun; Son, Young-A; Journal of Nanoscience and Nanotechnology; vol. 18; 5; (2018); p. 3192 – 3205;,
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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. 72115-09-4, name is 5-Amino-2-bromobenzonitrile, A new synthetic method of this compound is introduced below., Recommanded Product: 5-Amino-2-bromobenzonitrile

Step A: tert-Butyl 2-(4-amino-2-cyanophenyl)acetate: To a solution of 5-amino-2- bromobenzonitrile (400 mg, 2.03 mmol) in THE (8 mL) were added Pd2(dba)3 (149 mg, 0.162 mmol), X-Phos (116 mg, 0.244 mmol). The reaction mixture was degassed and filled with nitrogen, followed by addition of 2-(tert-butoxy)-2-oxoethyzink chloride (10.15 mL, 5.08 mmol). The reaction mixture was heated at 60 C overnight, cooled to RT, quenched with satNH4C1, and extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4, and concentrated. The residue was purified with preparative TLC (1500 uM, hex/EA=7/3) to give tert-butyl 2-(4-amino-2-cyanophenyl)acetate.LCIMS: [(M+23)] = 255.2

The synthetic route of 72115-09-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; PASTERNAK, Alexander; DEJESUS, Reynalda, Keh; FRIE, Jessica, L.; PIO, Barbara; TANG, Haifeng; WALSH, Shawn, P.; WO2014/99633; (2014); A2;,
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Some common heterocyclic compound, 1194-02-1, name is 4-Fluorobenzonitrile, molecular formula is C7H4FN, 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: C7H4FN

27.1 g (197 mmol) of K2CO3, 12.13 g (100.3 mmol) of 4-fluorobenzonitrile of formula (IV), 34.2 g (98.3 mmol) of 1-bromo-4-trimethylsilanoxy-2-trimethylsilanoxymethyl benzene of formula (III), obtained as described in Example 2, and 60 mL of DMSO are placed under nitrogen in a previously anhydrified flask. The reaction mixture is heated to 105 C. and kept at the same temperature for 2 hours. Then, 120 mL of toluene and 240 mL of H2O are added, the phases are separated and the organic phase is washed with a solution of 10% K2CO3. The organic phase is allowed to cool down to room temperature and the product is allowed to crystallize providing 19.7 g 4-(4-bromo-3-hydroxymethyl-phenoxy)-benzonitrile of formula (II) with a yield of 66%. 1H-NMR (DMSO-d6, 300 MHz) delta (ppm): 7.85-7.80 (2H, m) 7.62 (1H, d, J=8.4 Hz), 7.22 (1H, d, J=3.0 Hz), 7.13-7.11 (2H, m) 6.98 (1H, dd, J=3.0, J=8.4 Hz), 4.47 (2H, s)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1194-02-1, its application will become more common.

Reference:
Patent; DIPHARMA FRANCIS S.R.L.; Santillo, Niccolo’; Attolino, Emanuele; Brenna, Davide; Vladiskovic, Chiara; Lombardo, Alessandro; Razzetti, Gabriele; US2019/241585; (2019); A1;,
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Synthetic Route of 4553-07-5, 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 4553-07-5 as follows.

General procedure: To a solution of methyleneindolinone (0.1 mmol, 1equiv) and isocyanide 1a (0.15 mmol, 1.5 equiv) in DCM (0.2 mL) was added catalyst VI (0.01 mmol, 0.1 equiv). The resulting mixture was stirred at room temperature (23 C). After thereaction completed, the mixture was quenched with water (5 mL) and extracted with DCM (2 x 5mL). The combined organic layer was washed with brine and dried over Na2SO4. The solvent was then removed under reduced pressure. The product was afforded by silica gel flash chromatography using gradient elution (EtOAc/Hexane = 1:10 to 1:6).

According to the analysis of related databases, 4553-07-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Tan, Bin; Zhang, Xuan; Zhong, Guofu; ARKIVOC; vol. 2014; 3; (2014); p. 124 – 142;,
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Synthetic Route of 6575-00-4, 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 6575-00-4 as follows.

Step 1 To a 250 ML round bottom flask charged with 3,5-dichlorobenzonitrile (130a, 7.31 g; 34.90 mmol) and maintained under an argon atmosphere was added DMF (70 ML).The flask was cooled to 0 C. and powdered sodium methoxide (1.88 g; 34.90 mmol) was added in two portions 15 m apart.The homogeneous mixture was allowed to warm to room temperature and stirred for 24 h.The solution was cooled to 0 C. and aqueous 10% HCl (20 ML) was added dropwise via an addition funnel after which the reaction was warmed to RT. The mixture was extracted with EtOAc and the combined extracts washed sequentially with water and brine.The organic phase was dried (Na2SO4), filtered, and volatile solvents were removed in vacuo.The resulting solid was recrystallized from hexanes to afford 3-chloro-5-methoxybenzonitrile (130b, 4.2 g; 72%).

According to the analysis of related databases, 6575-00-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Roche Palo Alto LLC; US2004/198736; (2004); A1;,
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Adding a certain compound to certain chemical reactions, such as: 68119-31-3, name is 2-(2,2-Difluorobenzo[d][1,3]dioxol-5-yl)acetonitrile, 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 68119-31-3, Formula: C9H5F2NO2

288 g of water and 67 g of triethylamine were placed in the reaction tank.Stir well, add 4g of tetraoctyl ammonium bromide and 44g of 2,2-difluoro pepper acetonitrile.80 g of 1-bromo-2-chloroethane was added dropwise at 35 C, and the reaction was kept at 35 C for 1 h, and the reaction was completed, and the solid product was directly filtered to obtain the target product, which was 48 g after drying.After HPLC purification,The content of 1-(2,2-difluorobenzo[D][1,3]dioxol-5-yl)cyclopropylcarbonitrile is 99.6%,The yield was 96.3%.

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, 2-(2,2-Difluorobenzo[d][1,3]dioxol-5-yl)acetonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Fuxin Aoruikai New Materials Co., Ltd.; Liu Min; Yang Yinxing; Chen Li; Liu Chunyu; Liu Wei; Qin Wenyi; (7 pag.)CN105130949; (2019); B;,
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Adding a certain compound to certain chemical reactions, such as: 1129-35-7, name is Methyl 4-cyanobenzoate, 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 1129-35-7, SDS of cas: 1129-35-7

To a stirred solution of methyl 4-cyanobenzoate (0.9 g, 5.6 mmol) in methanol (12 mL), sodium bicarbonate (0.5 g, 6.1 mmol) and hydroxylamine hydrochloride (0.4 g, 5.6 mmol) were added. The resulting reaction mixture was heated to reflux for 4 h. After completion of the reaction, the reaction mixture was cooled to 25 oC and filtered. The filtrate was concentrated under reduced pressure to obtain methyl-4-(N’-hydroxycarbamimidoyl)benzoate (0.9 g, 4.6 mmol, 83 % yield).

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

Reference:
Patent; PI INDUSTRIES LTD.; BHUJADE, Paras Raybhan; PAWAR, Rajesh; NAIK, Maruti N; POTLAPALLY, Rajender Kumar; TEMBHARE, Nitin Ramesh; AUTKAR, Santosh Shridhar; GARG, Ruchi; VENKATESHA, Hagalavadi M; KLAUSENER, Alexander G.M.; RAMAKRISHNA, Visannagari; ADHAV, Nilesh Bharat; TRIVEDI, Pooja; (138 pag.)WO2019/150219; (2019); A2;,
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Reference of 6609-56-9, A common heterocyclic compound, 6609-56-9, name is 2-Methoxybenzonitrile, molecular formula is C8H7NO, 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 37 5-Bromo-2-(methyloxy)benzonitrile Bromine (13.7 g, 86.0 mmol) in CHCl3 (20 mL) was added to the solution of 2-(methyloxy)benzonitrile (10.9 g, 81.9 mmol) in CHCl3 (50 mL). The mixture was refluxed for 29 h. The reaction was allowed to cool to room temperature, and washed with saturated sodium bisulfite (50 mL), and brine (50 mL). The organic layer was dried over anhydrous sodium sulfate. Evaporation of the solvent afforded 5-bromo-2-(methyloxy)benzonitrile (12.4 g, 71percent).

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; Glaxo Group Limited; US2009/197871; (2009); A1;,
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