Author: Jessica.F

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;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of 179898-34-1, 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. 179898-34-1, name is 3-Bromo-5-fluorobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows.

A solution of 3-bromo-5-fluorobenzonitrile (LXXXIII) (44.0 g, 220.0 mmol, 1.0 eq) was dissolved in THF (30 mL). BH3-Me2S (33.43 g, 440.0 mmol, 2.0 eq) was added to the solution at 20C. Then it was stirred at 80C for 2 h, HCl (6 N, 100 mL) was added to the mixture slowly at 20C. The mixture was stirred at 80C for 1 h, then it was washed with EtOAc (300 mL). The water phase was basified with 50% aqueous NaOH and it was extracted with EtOAc (300 mL x 3). The combined organic layers were dried over anhydrous Na2S04 and concentrated in vacuo to produce (3-bromo-5-fluoro-phenyl)methanamine (LXXXIV) (24.0 g, 1 17.62 mmol, 53.5% yield). NMR (CDC13, 300 MHz) ppm 3.86 (s, 2H), 7.01 (d, J=8Hz, IH), 7.12 (d, J=8Hz, IH), 7.28 (s, IH); ESIMS found C7H7BrFN mlz 203.9 (Br79M+H).

The chemical industry reduces the impact on the environment during synthesis 3-Bromo-5-fluorobenzonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; SAMUMED, LLC; KC, Sunil Kumar; WALLACE, David Mark; CAO, Jianguo; CHIRUTA, Chandramouli; HOOD, John; (280 pag.)WO2017/23986; (2017); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 20099-89-2,Some common heterocyclic compound, 20099-89-2, name is 4-(2-Bromoacetyl)benzonitrile, molecular formula is C9H6BrNO, 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: A vial containing a mixture of 2-aminopyridine (1) (1 mmol), and alpha-bromoketone (2) (1 mmol) was placed in a microwave synthesiser. The vial was subjected to microwave irradiation programmed at 65 C, 120 W and 1 bar pressure. After 15-20 min of irradiation, the mixture was cooled to room temperature. The crude product (3) was subjected to column chromatography on alumina (solvent: dichloromethane) to obtain the pure products.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-(2-Bromoacetyl)benzonitrile, its application will become more common.

Reference:
Article; Kong, Dulin; Wang, Xianghui; Shi, Zaifeng; Wu, Mingshu; Lin, Qiang; Wang, Xin; Journal of Chemical Research; vol. 40; 9; (2016); p. 529 – 531;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 17823-40-4, name is 4-Bromo-2,3,5,6-tetrafluorobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of 4-Bromo-2,3,5,6-tetrafluorobenzonitrile

A mixture of Compound I (2.00 g, 4.59 mmol), 4-bromo-2,3,5,6-tetrafluorobenzonitrile (1 .19 g, 4.69 mmol), Pd(PPli3)4 (268 mg, 0.230 mmol), potassium carbonate (1.90 mg, 13.78 mmol) in degassed deionized water (6 mL) and degassed THF ( 18 mL) solution was stirred at 80 C under a nitrogen atmosphere for 18 h. After cooled to room temperature, the reaction mixture was filtered through a Ceiite pad rinsed by chloroform, and the resulting filtrate was evaporated in vacuo. The obtained residue was purified by column chromatography on silica gel using 3:2 (v/v) hexane/toluene as eluent to afford a white solid (0.962 g, 43.4%). HNMR (500 MHz, CDCb, d): 8.94 (d, J = 8 0 Hz, 1H), 8.86 (s, 1H), 8.77 (d, ./ = 8.0 Hz, 4H), 7.77 (f ./= 7.5 Hz, 1H), 7.70 (d, J= 7.5 Hz, 1H), 7 66-7 57 (m, 6H).

The synthetic route of 17823-40-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KYULUX, INC.; CHENG, Shuo-Hsien; CHO, Yong, Joo; SUZUKI, Yoshitake; YANG, Yu, Seok; NOTSUKA, Naoto; ENDO, Ayataka; KAKIZOE, Hayato; YOSHIZAKI, Makoto; AGUILERA-IPARRAGUIRRE, Jorge; (264 pag.)WO2019/191665; (2019); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts