Tag: M.W=100-200

Electric Literature of 3598-14-9,Some common heterocyclic compound, 3598-14-9, name is Phenoxyacetonitrile, molecular formula is C8H7NO, 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) In a 1L hydrogenation tank, 100g of phenoxyacetonitrile and 3g of Raney-Ni, 400mL of ethanol are added and H2 is continuously charged, so that the pressure of the system during the reaction is always maintained at 7MPa. After the reaction was performed at a reaction temperature of 90C for 1 hour, the temperature was lowered. After the temperature in the reactor was lowered to room temperature, the mixture was purged, and phenoxyethylamine (purity of 99% or more) was obtained by filtration and recrystallization. The yield was 93% by weight.

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

Reference:
Patent; Sinopec Corporation; Sinopec Yangzi Petrochemical Co., Ltd.; Sun Hailong; Wei Yanyu; Gao Yilong; Chen Xinhua; Miao Jun; Li Na; Kan Lin; Bai Jiye; Chen Shaohui; Yang Aiwu; Xu Yuexing; (84 pag.)CN104557610; (2018); B;,
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Reference of 40497-11-8, 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. 40497-11-8, name is Ethyl 2,3-dicyanopropanoate belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Into a 500 ml three-necked glass bottle, 30.4 g (0.2 mol) of ethyl 2,3-dicyanopropionate (1E) and 300 g of water were sequentially added.The temperature of the reaction solution was lowered to 0 10 with stirring;Add 32g (0.2mol) bromine (Br2) to the reaction solution dropwise, and control the drop rate so that the solution temperature does not exceed 10 ;At the end of the dropwise addition, continue to hold at 0-10 C and stir the reaction for 4h.Then, let stand and dispense. Sampling the organic layer for gas chromatography analysis,The results showed that the content of ethyl 2-bromo-2,3-dicyanopropionate (1F), the target product of this reaction, was 91.22%, and it could be directly put into the next reaction.

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, Ethyl 2,3-dicyanopropanoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Jiangsu Guangyu Chemical Co., Ltd.; Shi Haibing; Song Qifa; Cai Yichao; (8 pag.)CN111004250; (2020); A;,
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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. 149793-69-1, name is 3-Fluoro-5-(trifluoromethyl)benzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Safety of 3-Fluoro-5-(trifluoromethyl)benzonitrile

Synthesis of Intermediate (1)Molecular Weight: 189.1 Molecu lar Weight: 247.2[00495] In a 3-neck 100 mL round-bottomed flask, to a solution of propan-2-ol (1.6 mL, 1 eq.) in DMF (25 mL, 5 V) at 0 C was added 60 % NaH in mineral oil (1.5 g, 3 eq.). The reaction mixture was stirred at 0 C for 1 h and then 3-fluoro-5-(trifluoromethyl)benzonitrile (5 g, 1.25 eq.) was added and reaction was heated to 60 C for 2 h an further stirred for 12 h at room temp. Reaction completion was monitored on TLC using ethyl acetate: hexane (2:8) as mobile phase. The reaction mixture was quenched into the ice-water slurry (250 mL) and was extracted with ethyl acetate (50 mL x 3). Organic layer was washed with brine solution (50 mL x 3). The organic layer was dried using anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to provide the 5.8 g crude titled compound, yield (96 %). This crude material was directly used for next step without purification.

According to the analysis of related databases, 149793-69-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; KARYOPHARM THERAPEUTICS, INC.; SHECHTER, Sharon; KAUFFMAN, Michael; SANDANYAKA, Vincent, P.; SHACHAM, Sharon; WO2011/109799; (2011); A1;,
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Related Products of 38469-83-9, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 38469-83-9 name is 4-Methoxy-2-nitrobenzonitrile, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Intermediate 3 : 2-Iodo-4-methoxybenzonitrile; To a solution of 4-methoxy-2-nitrobenzonitrle (5.00 g, 22.46 mmol) in EtOH (93 mL) was added 5% Pd-C (0.500 g) under nitrogen atmosphere. The resulting mixture was hydrogenated at 1 atm. After stirring for 1 O h, the mixture was filtered through celite, washed with EtOAc/MeOH. The combined filtrates were concentrated in vacuo and the residue was purified by column chromatograph on SiO2 using 80 to 100 % gradient of EtOAc in hexanes to afford 4-methoxy-2-amiobenzonitrle (3.23 g, 99%). 4-Methoxy-2-aminobenzonitrle (1.0 g, 6.58 mmol) was dissolved in a mixture of H2O (7 niL), acetic acid (7 niL), and cone. HCl at rt, followed by addition of a solution Of NaNO2 (0.513 g, 7.43 mmol) in H2O (2 niL) at 0 0C for 5 min. To the above mixture KI (2.18 g, 13.2 mmol) was added and after stirring for 10 h at rt, the resulting mixture was treated with solid NaHSO3 and diluted with water. The product portion was extracted with CH2Cl2, washed with satd. NaHCO3, brine, dried (Na2SO4), filtered, and concentrated in vacuo. The residue was purified by column chromatography on SiO2 using 10 to 50% gradient of EtOAc in hexane to provide the example intermediate (1.0 g, 59%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Methoxy-2-nitrobenzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; MYRIAD GENETICS, INC.; WO2009/65035; (2009); A1;,
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Reference of 6574-99-8, These common heterocyclic compound, 6574-99-8, name is 3,4-Dichlorobenzonitrile, 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: Hydrogen chloride gas was passed through a solution of 4-chlorobenzonitrile (9b, 25.0 g) in chloroform (350 mL) and ethanol (100 mL) at -78 C for 0.5 h. Then the solution was warmed up to room temperature, and stirred at room temperature overnight. The solution was evaporated in vacuo, and the resulting residue was dissolved with ethanol (500 mL). To the solution was added ammonium carbonate (90.0 g), and the reaction mixture was stirred at room temperature for 3 days. To the mixture was added water (300 mL), and ethanol was removed by concentration in vacuo. The resulting solid was collected by filtration, washed with water and dried in vacuo to give 12b (25.4 g, 71%) as a white solid.

Statistics shows that 3,4-Dichlorobenzonitrile is playing an increasingly important role. we look forward to future research findings about 6574-99-8.

Reference:
Article; Negoro, Kenji; Yonetoku, Yasuhiro; Misawa-Mukai, Hana; Hamaguchi, Wataru; Maruyama, Tatsuya; Yoshida, Shigeru; Takeuchi, Makoto; Ohta, Mitsuaki; Bioorganic and Medicinal Chemistry; vol. 20; 17; (2012); p. 5235 – 5246;,
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Adding a certain compound to certain chemical reactions, such as: 939-79-7, name is 4-Methyl-3-nitrobenzonitrile, 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 939-79-7, Computed Properties of C8H6N2O2

A mixture of 3-nitro-p-tolunitrile (9.30 g, 57.4 mmol, 1 equiv) and 10% Pd/C (4.00 g, 3.76 mmol, 0.066 equiv) in ethanol (100 mL) was stirred under a hydrogen balloon at 23 0C for 20 h. The catalyst was filtered onto a pad a celite and washed with EtOAc (300 mL). The filtrate was concentrated to give 3- amino-4-methylbenzonitrile (1-2) as an off-white solid. 1H NMR (300 MHz, CDCl3) delta 7.10 (d, IH, J= 7.6 Hz), 6.98 (dd, IH, J = 7.9, 1.5 Hz), 6.89 (d, IH, J= 1.5 Hz), 3.78 (br s, 2H), 2.20 (s, 3H). LRMS m/z (M+H + CH3CN) 174.2 found, 174.1 required

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-Methyl-3-nitrobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK SHARP & DOHME LIMITED; WO2007/88400; (2007); A1;,
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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. 22364-68-7, name is 2-(o-Tolyl)acetonitrile, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C9H9N

Add dichloroethane (60g),Potassium hydroxide (0.15mol, 9.6g, content 90%),After stirring, the temperature was lowered to 15 C, and o-methylphenylacetonitrile (0.1 mol, 13.1 g) was added in one portion. Isoamyl nitrite (0.16mol, 18.7g) was added dropwise to the system, and after holding for 1 hour after the completion of the infiltration, 2-methyl-a-cyanobenzoxime potassium was obtained by suction filtration and dried. The yield was 96 %, The content is 93.5%.

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 22364-68-7.

Reference:
Patent; Jingbo Agrochemical Technology Co., Ltd.; Wang Shuaishuai; Cao Tongbo; Wang Xiangchuan; Li Hongxia; Cheng Guohua; Wang Jiangang; Ma Falu; Yu Lianyou; Wang Xue; (12 pag.)CN110396054; (2019); A;,
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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. 177476-76-5, name is 4-Amino-3-methoxybenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 177476-76-5

To a solution of 1 (3.46g, 10mmol) in 2-methoxyethanol (20mL) was charged 4-amino-3-methoxybenzonitrile or 4-amino-3-isopropoxybenzonitrile (11mmol) in 2-methoxyethanol (10mL), and the mixture was then heated to 100C, after which methanesulfonic acid (0.64mL, 0.96g, 11mmol) was added dropwise over 5min below 110C, and then the mixture was heated at 110C for 12h. The slurry was cooled to below 10C. The resulting solids were isolated by filtration and washed with cold 2-methoxyethanol until the filtrate was clear to obtain 2a or 2b. 4.1.1.1 4-((5-chloro-4-((2-(isopropylsulfonyl)phenyl)amino)pyrimidin-2-yl)amino)-3-methoxybenzonitrile (2a) (0025) Yield: 63.2%; MS (ESI) m/z: 458.3 [M+H]+.

According to the analysis of related databases, 177476-76-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Wang, Yu; Chen, Shaowei; Hu, Gang; Wang, Jiao; Gou, Wenfeng; Zuo, Daiying; Gu, Yucheng; Gong, Ping; Zhai, Xin; European Journal of Medicinal Chemistry; vol. 143; (2018); p. 123 – 136;,
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Reference of 67832-11-5, The chemical industry reduces the impact on the environment during synthesis 67832-11-5, name is 4-Bromo-2-methylbenzonitrile, I believe this compound will play a more active role in future production and life.

Intermediate 24a) Methyl magnesium bromide (3 M in tetrahydrofuran) was added at rt drop wise to a solution of 4-bromo-2- methylbenzonitrile (4 g) in dry THF (15 mL) and was then heated to reflux for 2 h and then stirred at rt for 3 d. The mixture was chilled in an ice bath, saturated aqueous ammonium chloride solution (100 mL) was added and the mixture was extracted with EtOAc. The combined organic layers were concentrated under reduced pressure and the remaining residue was treated with 4 N HCI at 0 C and was stirred at rt for 18 h. The mixture was extracted with EtOAc and the organic layer was washed with water, dried and the solvent was removed under reduced pressure to yield the desired product (88% yield).

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-Bromo-2-methylbenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GRUeNENTHAL GMBH; NORDHOFF, Sonja; WACHTEN, Sebastien; KLESS, Achim; VOSS, Felix; RITTER, Stefanie; WO2014/108337; (2014); 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. 19472-74-3, name is 2-Bromophenylacetonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C8H6BrN

General procedure: Step 1: To an 8-mL culture tube with stir bar was added lithium chloride (1.1 equiv) and the flask was flame-dried under vacuum and cooled under an atmosphere of N2. THF (1.0 M) was added, followed by the appropriate nitrile (1.0 equiv). While stirring, methylmagnesium bromide (1.1 equiv of a solution in Et2O) was added dropwise at r.t., and the solutionwas stirred at r.t. for 30 min under an atmosphere of N2. A 1.1M stock solution of dimethylmanononitrile (DMMN) or dibenzylmalononitrile (DBMN) inTHF was prepared and added at r.t. (1.1 equiv of a 1.1M solution inTHF, reaction volume 0.50M with respect to nitrile starting material). The reaction was stirred at 80 C for 6 h under an atmosphere of N2. Step 2: The reaction was cooled to r.t. and DMF was added to bring the reaction solvent to a 1:1 THF/DMF ratio (0.25Mof a 1:1 THF/DMF mixture with respect to nitrile starting material). The desired electrophile (1.2 equiv) was added in a single portion. Ifthe electrophile was a solid, it was added with the DMF as a 0.60Mstock solution. The reaction was stirred at 80 C for 16 h, or until complete conversion was achieved as judged by TLC. The reaction was cooled to r.t., opened to air, quenched with 1M aq. HCl, and extracted with EtOAc (3). The organic fractions were combined,dried over MgSO4, and concentrated. The crude residue was purified by flash column chromatography to yield the desired malononitrile.

The synthetic route of 19472-74-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Mills, L. Reginald; Rousseaux, Sophie A.L.; Tetrahedron; vol. 75; 32; (2019); p. 4298 – 4306;,
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