Tag: M.W=200-300

Adding a certain compound to certain chemical reactions, such as: 186517-05-5, name is 2,3-Difluoro-6-(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 186517-05-5, Computed Properties of C8H2F5N

Example 13 2,3-difluoro-6-trifluoromethylbenzaldehyde (Compound No. 44) STR30 2.0 g of 2,3-difluoro-6-trifluoromethylbenzonitrile was dissolved in 20 ml of anhydrous dichloromethane and the resultant solution was cooled down to -78 C. under a nitrogen atmosphere. To the solution was then gradually added dropwise with 7.1 ml of 1.5 M toluene solution of diisobutyl aluminium hydride (DIBAL) over 30 minutes. After stirring the solution at -78 C. for 1 hour, the solution was allowed to room temperature. The solution was then added with 7 ml of saturated aqueous solution of ammonium chloride, stirred for 30 minutes and subsequently added with 33 ml of 5% sulfuric acid. The mixture was then extracted with ether, and the organic layer obtained was washed with saturated saline solution and was then dried over anhydrous magnesium sulfate. After a process for the concentration, the organic solution was purified by using silica gel column chromatography to obtain 1.36 g of the title compound (nD 20.6-1.4357). The aldehyde compound obtained here was easily oxidized if it is left in the air and was converted to the corresponding benzoic acid (Compound No. 14).

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, 2,3-Difluoro-6-(trifluoromethyl)benzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Nippon Soda Co., Ltd.; US6054605; (2000); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 1835-49-0, name is Tetrafluoroterephthalonitrile, 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 1835-49-0, name: Tetrafluoroterephthalonitrile

[Comparative Example 1]; The same operations as in Example 1 were carried out, except that the amount of the catalyst used was changed from 0.25 g to 0.05 g on a dry weight basis. After a lapse of 7.0 hours, absorption of hydrogen ceased. The quantity of hydrogen absorbed was 83% of the theoretical quantity of hydrogen absorbed. Treatment of the reaction solution was carried out in the same manner as in Example 1. EPO From the toluene extract, a small amount of a sample was withdrawn, and it was subjected to GC analysis. As a result of the analysis, the tetrafluoroterephthalonitrile as a raw material remained in an amount of 21.0 mol%, and tetrafluoroterephthalaldehyde was obtained in an amount of only 5.0 mol%. The amount of 2, 3, 5, 6-tetrafluorobenzene was 0.65 mol%, the amount of 2,3,5,6- tetrafluorobenzonitrile was 0.53 mol%, and 1-cyano- 2, 3, 5, 6-tetrafluorobenzaldehyde wherein a nitrile group on only one side had reacted was obtained in an amount of 63.1 mol%. On the other hand, the aqueous phase was neutralized and then subjected to GC analysis. As a result of the analysis, presence of 2.88 mol% of 2,3,5,6- tetrafluorobenzylamine was confirmed. The results are set forth in Table 2.; [Comparative Example 3]; The same operations as in Example 1 were carried out, except that the amount of sulfuric acid used was changed from 20.6 g to 5.15 g (50 mmol). After a lapse of 4.2 hours, absorption of hydrogen ceased. The quantity of hydrogen absorbed was 47% of the theoretical quantity of hydrogen absorbed. Treatment of the reaction solution was carried out in the same manner as in Example 1.From the toluene extract, a small amount of a sample was withdrawn, and it was subjected to GC analysis. As a result of the analysis, a peak of the tetrafluoroterephthalonitrile as a raw material was below EPO the detection limit, and tetrafluoroterephthalaldehyde was obtained in an amount of only 14.5 mol%. The amount of 2, 3, 5, 6-tetrafluorobenzene was 0.81 mol%, the amount of 2, 3, 5, 6-tetrafluorobenzonitrile was 0.67 mol%, and 1- cyano-2, 3, 5, 6-tetrafluorobenzaldehyde wherein a nitrile group on only one side had reacted was obtained in an amount of 54.0 mol%. On the other hand, the aqueous phase was neutralized and then subjected to GC analysis. As a result of the analysis, presence of 0.04 mol% of 2,3,5,6- tetrafluorobenzylamine was confirmed. The results are set forth in Table 2.

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

Reference:
Patent; SHOWA DENKO K.K.; WO2006/137347; (2006); A2;,
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. 90110-98-8, name is 3-Bromo-4-(hydroxymethyl)benzonitrile, A new synthetic method of this compound is introduced below., COA of Formula: C8H6BrNO

A solution of compound B (211 mg, 1.0 mmol) and triisopropyl borate (282 mg, 1.5 mmol) in anhydrous THF (10 mL) at N2 atmosphere was cooled to -78C. n- BuLi (0.9 mL, 2.25 mmol) was added dropwise at -78C. Then the mixture was allowed to warm to room temperature and stirr at room temperature for 1 h. The mixture was qunched with IN HCl and extracted with ethyl acetate (25 mL*3). The combined organic layers were washed with brine (20 mL), dried (Na2SO4) and concentrated under vacuum. The residue was purified by column chromatography (eluting with CH3OH and EtOAc =1 :1) on silica gel to give the desired compound C as a yellow solid (80 mg, 50 %).1H NMR (300 MHz, CDCl3): delta 9.50 (s, IH), 8.08 (s, IH), 7.83-7.92 (m, IH), 7.61-7.66 (m, IH), 5.06 (s, 2H). LC-MS: 160 (M + I)+.

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; ANACOR PHARMACEUTICALS, INC.; JACOBS, Robert; ORR, Matthew; WRING, Stephen; CHEN, Daitao; ZHOU, Huchen; DING, Dazhong; FENG, Yiqing; YE, Long; HERNANDEZ, Vincent, S.; ZHANG, Yong-Kang; PLATTNER, Jacob J.; WO2010/45503; (2010); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 1735-53-1, 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. 1735-53-1, name is 4-Bromo-3-(trifluoromethyl)benzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 485A/-(5-(6-(4-cvano-2-(trifluoromethyl)phenyl)imidazori ,2-blpyridazin-2-yl)-2- methylphenvDpivalamideA 200 mL flask is charged with 2-(4-methyl-3-pivalamidophenyl)imidazo[1 ,2-6]pyridazin-6- ylboronic acid (1 1 .4 g, 0.0325 mol), 4-bromo-3-(trifluoromethyl)benzonitrile (10.16 g, 0.04 mol), K2C03 (8.98 g, 0.065 mol), palladium acetate (0.510 g, 2.28 mmol), 2- dicyclohexylphosphino-2′,6′-dimethoxy-1 , 1 ‘-biphenyl (1.868 g, 4.55 mmol) and a solution of isopropanol-water (3:1 , 80 mL). The mixture is degassed by bubbling N2 through and heated at 90 C for 5 hours. The mixture is then cooled and filtered through celite, concentrated and purified by silica gel chromatography (0-100% EtOAc in CH2CI2). The desired fractions are combined and stirred for 24 hours with QuadraSil MP (a mercaptopropyl bound silica gel, 20 g) to scavenge the palladium, filtered and concentrated to give desired title compound (7.5 g). LCMS (m/z) = 478.6 [M+H]+, fR = 2.97 min.

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-3-(trifluoromethyl)benzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PAMLICO PHARMACEUTICAL INC.; ATKINSON, Robert N.; OMMEN, Andy J.; VEAL, James M.; HUANG, Kenneth H.; SMITH, Emilie, D.; WO2012/88411; (2012); A1;,
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. 179897-89-3, name is 5-Bromo-2-fluorobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. COA of Formula: C7H3BrFN

A mixture of 1-15 (3.0 g, 14.99 mmcl), 1-Boc-piperizine(3.33 g, 17.99 mmcl) and Cs2003 (9.68 g, 29.98 mci) in DMSO(60 ml) was stirred at 12000 for 1 hour. The reaction mixture was diluted with water (100 mL) and extracted with diethyl ether (100 ml x 3) . The organic layer was dried over anhydrous Na2SO4 and concentrated under reduced pressure to give thedesired product 1-16 (2.5 g, 44%) as yellow solid which wasused in the next step without purification; LCMS: m/z 312 [MtBu+1]

The synthetic route of 179897-89-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; KOUL, Summon; KURHADE, Suresh; NAIK, Keshav; SALUNKHE, Videsh; KULKARNI, Rakesh; PARDESHI, Vishwajeet; BHUNIYA, Debnath; KULKARNI, Bheemashankar; MOOKHTIAR, Kasim Abbaas; (274 pag.)WO2017/38909; (2017); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 330792-69-3, 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. 330792-69-3, name is 2-(Methoxy(4-phenoxyphenyl)methylene)malononitrile, This compound has unique chemical properties. The synthetic route is as follows.

l,l-Dicyano-2-methoxy-2-(4-phenoxyphenyl)ethene (22.5 g) and 1 , 1 -dicyano-2-methoxy-2- (4-phenoxyphenyl)ethene oil (15 g) are treated with a solution of hydrazine hydrate (18 mL) in ethanol (25 mL) and heated on the steambath for 1 h. Ethanol (15 mL) is added followed by water (10 mL). The precipitated solid is collected and washed with ethanol: water (4:1) and then dried in air to give 3-amino-4- cyano-5-(4-phenoxyphenyl)pyrazole as a pale orange solid.

The chemical industry reduces the impact on the environment during synthesis 2-(Methoxy(4-phenoxyphenyl)methylene)malononitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; PHARMACYCLICS, INC.; CHEN, Wei; LOURY, David, J.; MODY, Tarak, D.; WANG, Longcheng; WO2013/10136; (2013); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 886498-08-4, The chemical industry reduces the impact on the environment during synthesis 886498-08-4, name is 2-Fluoro-5-(trifluoromethoxy)benzonitrile, I believe this compound will play a more active role in future production and life.

xxvii) 5-(Trifluoromethoxy)benzo[d]isoxazol-3-amine I63 To a solution of acetohydroxamic acid (2.2 g, 0.029 mol) in DMF (50 ml.) was added t-BuOK (3.28 g, 0.029 mol) and the mixture was stirred RT for 1 hour. 2-Fluoro-5-(trifluoromethoxy)benzonitrile (2 g, 9.75 mmol) was then added and the mixture was heated at 60 C overnight. The mixture was diluted with water and extracted with EtOAc. The organic extract was concentrated under reduced pressure to give the title compound (1.6 g, 75%) as a yellow solid. LCMS-D: Rt2.43 min; m/z 219.0 [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, 2-Fluoro-5-(trifluoromethoxy)benzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CTXT PTY LIMITED; STUPPLE, Paul, Anthony; LAGIAKOS, Helen, Rachel; MORROW, Benjamin, Joseph; FOITZIK, Richard, Charles; HEMLEY, Catherine, Fae; CAMERINO, Michelle, Ang; BOZIKIS, Ylva, Elisabet, Bergman; WALKER, Scott, Raymond; (321 pag.)WO2019/243491; (2019); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 179898-34-1, These common heterocyclic compound, 179898-34-1, name is 3-Bromo-5-fluorobenzonitrile, 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.

Step 1 A solution of 3-bromo-5-fluorobenzonitrile (CIV) (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 20 C. Then it was stirred at 80 C. for 2 h, HCl (6 N, 100 mL) was added to the mixture slowly at 20 C. The mixture was stirred at 80 C. 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*3). The combined organic layers were dried over anhydrous Na2SO4 and concentrated in vacuo to produce (3-bromo-5-fluoro-phenyl)methanamine (CV) (24.0 g, 117.62 mmol, 53.5% yield). 1H NMR (CDCl3, 300 MHz) 3.86 (s, 2H), 7.01 (d, J=8 Hz, 1H), 7.12 (d, J=8 Hz, 1H), 7.28 (s, 1H); ESIMS found C7H7BrFN m/z 203.9 (Br79M+H).

Statistics shows that 3-Bromo-5-fluorobenzonitrile is playing an increasingly important role. we look forward to future research findings about 179898-34-1.

Reference:
Patent; Samumed, LLC; KC, Sunil Kumar; Wallace, David Mark; Cao, Jianguo; Chiruta, Chandramouli; Hood, John; (264 pag.)US2016/68550; (2016); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

These common heterocyclic compound, 57381-37-0, name is 2-Bromo-5-chlorobenzonitrile, 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. Product Details of 57381-37-0

To a solutionof 2-bromo-5-chlorobenzonitrile (20 g, 93 mmol) in THF (200 mL) was added cyclopropylmagnesiumbromide (558 mL, 279 mmol) at 0 C. The resulting reaction – 151 -mixture was stirred at 0-5 C for 5 hours before MeOH (100 mL) was added and stirring continued at room temperature for 15 min. NaBH4 (7.1 g, 186 mmol) was added subsequently and the reaction mixture was stirred at room temperature overnight. Water was added and reaction mixture was exacted with AcOEt (300 mL x 3). The combined organic layers were concentrated in vacuo to give a crude product which was then purified by chromatography to give (2-bromo-5-chlorophenyl)(cyclopropyl)methanamine (8.2 g, yield 34%).

The synthetic route of 2-Bromo-5-chlorobenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; AEBI, Johannes; AMREIN, Kurt; CHEN, Wenming; HORNSPERGER, Benoit; KUHN, Bernd; LIU, Yongfu; MAERKI, Hans P.; MAYWEG, Alexander V.; MOHR, Peter; TAN, Xuefei; WANG, Zhanguo; ZHOU, Mingwei; WO2013/79452; (2013); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 13544-06-4, 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 13544-06-4 as follows.

Step 1. Preparation of 2-Methyl-2-(2-nitro-4- trifluoromethyl-phenyl) -propionitrile; The title compound was synthesized according to a method described in Prasad, G. , J. Org. Chem. 1991,56, 7188-7190. To a yellow-brown solution of (2-Nitro-4-trifluoromethyl- phenyl) -acetonitrile (2.5 g, 11 mmol), 18-crown-6 (0.72 g, 2.7 mmol), and methyl iodide (1.5 mL, 24 mmol) in dry THF under nitrogen at-78 degrees C was added potassium tert- butoxide (2.7 g, 24 mmol) in one portion. The reaction immediately became a deep purple color. The reaction was allowed to stir for 2 h at-78 degrees C, and was then warmed to ambient temperature. A water-cooled reflux condenser was added and the solution heated to 70 degrees C under nitrogen. Over 40 minutes, the color changed from dark purple to cloudy gray. The mixture was allowed to cool to room temperature, and was concentrated in vacuo. The resulting material was partitioned between 1 N HCI and EtOAc. The organic layer was washed once with brine, dried over sodium sulfate, filtered, and concentrated in vacuo to give a brown oil which was judged to be primarily monoalkylated nitrile. The crude material was resubjected to the reaction conditions using 18-crown-6 (0.72 mg, 2.7 mmol), methyl iodide (0.75 mL, 12 mmol), and potassium tert- butoxide (1.4 g, 12 mmol) as before, with the following modifications: the reaction was allowed to stir only 10 min. at-78 degrees C before being warmed to room temperature, and the reaction vessel was sealed and heated to 70 degrees C for 2 h. Upon cooling to room temperature, the reaction was quenched and worked up as before. Purification by flash chromatography afforded the desired product as a light brown solid. MS (M+H) + = 259; Calc’d 258.20 for C11H9F3N2O2.

According to the analysis of related databases, 13544-06-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AMGEN INC.; WO2005/113494; (2005); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts