Tag: M.W=200-300

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. 1953-99-7, name is 3,4,5,6-Tetrachlorobenzene-1,2-dicarbonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C8Cl4N2

3,4,5,6-tetrachlorophthalonitrile (5 g), isoamyl alcohol (5.9 g), 1,8-diazabicycloundec-7-ene (3.898 g), and tetrahydrofuran (50 ml) are in a 100 ml flask and then stirred while heated at 50° C. When a reaction is complete, an extraction is performed with EA (ethyl acetate). After the extraction, a liquid column-purified through column chromatography with EA/hexane is concentrated to obtain a solid, and the solid is vacuum-dried, obtaining a compound according to Synthesis Example 4.

The synthetic route of 1953-99-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Samsung SDI Co., Ltd.; PAK, Chae Won; SEO, Hye Won; SHIN, Myoung Youp; JEONG, Eui Soo; CHOI, Seung Jib; (35 pag.)US2017/107224; (2017); A1;,
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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 79463-77-7 as follows. Safety of Diphenyl N-cyanocarbonimidate

A mixture of 4-(4-amino-2,6-dimethoxy-phenoxy)-piperidine-1-carboxylic acid benzyl ester (57.8 mg, 0.180 mmol) and diphenyl cyanocarbonimide (42.8 mg, 0.180 mmol) in toluene (1.0 mL) was heated at 100 C overnight. The mixture was concentrated and purified by silica gel column chromatograghy eluted with EtOAc:hexanes (40 to 60% EtOAc) to give the title compound (65.3 mg, 82%) as a colorless oil. MS (ES+): m/z = 531.2.

According to the analysis of related databases, 79463-77-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; WO2004/46120; (2004); A2;,
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70484-01-4, name is 4-Bromophthalonitrile, belongs to nitriles-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Recommanded Product: 4-Bromophthalonitrile

A stirrer,thermometer,condenser,A 100 mL four-necked glass flask equipped with a glass stopper was purged with nitrogen,The open end of the condenser was sealed with a gentle stream of nitrogen. Bis (dibenzylideneacetone) platinum (0) (6.6 mg, 0.01 mmol),4-Bromophthalonitrile (207 mg, 1.0 mmol) and N-methylpyrrolidone (4 mL) were charged,The flask contents were stirred at room temperature to dissolve the solids. Triethylamine (304 mg,3.0 mmol) was added,1, 1, 1, 3, 5, 5, 5-heptamethyltrisiloxane (178 mg, 0.8 mm pl) was slowly added and stirred at 19 to 22 C for 17 hours. Bis (dibenzylideneacetone) platinum (0) (6.6 mg, 0.01 mmol) was added,1,1,1,3,5,5,5-heptamethyltrisiloxane (178 mg, 0.8 mm pl)Was added slowly and stirring was continued at 19 to 22 C. for 12 hours. By gas chromatography mass spectrometry (GC-MS) of the reaction mixture,Formation of the target compound was confirmed.

The synthetic route of 70484-01-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SHIN-ETSU CHEMICAL COMPANY LIMITED; KIYOMORI, AYUMU; ITOH, YUSUKE; (49 pag.)JP2015/10084; (2015); A;,
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Reference of 79630-23-2, 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. 79630-23-2, name is 3-Bromo-4-fluorobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 82(3-Bromo-4-fluorophenviy4-methoxy-3-methylphenyl’)methanamine; Isopropylmagnesium bromide (IM in tetrahydrofuran, 8.87 mL, 8.87 mmol) was added drop wise to a stirred solution of 4-iodo-l~methoxy-2-methylbenzene (2 g, 8.06 mmol) in tetrahydrofuran (30 mL) at room temperature and under argon atmosphere, and the mixture was stirred for Ih. A solution of 3-bromo-4-fluorobenzonitrile (1.613 g, 8.06 mmol) in tetrahydrofuran (12 mL) was then added and the reaction was stirred overnight at 500C. After cooling to room temperature dry methanol (10 mL) was added and stirring was continued for 30-40 min. The mixture was cooled to 0 C and sodium borohydride (0.397 g, 10.48 mmol) was added in portions and the reaction mixture was stirred overnight at room temperature. Saturated aqueous ammonium chloride (40 mL) was carefully added, the mixture was concentrated and the water layer extracted with dichloromethane. The organic layer was dried over sodium sulfate, concentrated, and the crude product was added to a silica gel column and eluted with methanol (0.1% 7N ammonia) in dichloromethane (0-10%) to give 1.24 g (47%) of the title compound. MS (ES) m/z 324 [M+l]+.

The synthetic route of 3-Bromo-4-fluorobenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; ASTEX THERAPEUTICS LTD; WO2007/145571; (2007); A1;,
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Electric Literature of 877131-92-5, 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. 877131-92-5 name is 2-(4-Bromo-2-(trifluoromethyl)phenyl)acetonitrile, 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.

To a stirred solution of (4-bromo-2-trifluoromethyl-phenyl)-acetonitrile (3.33 g, 12.61 mmol) from step 2 of example A(141), benzyltriethylammoniym chloride (0.057 g, 0.25 mmol) and 1-bromo-2-chloroethane (1.57 g, 10.94 mmol), was added dropwise a solution of NaOH 40% ( 3 ml_). The reaction mixture was stirred 6 hours at 50 C. After this time the reaction was quenched with 1 N HCI (30 ml) and extracted with EtOAC (3 x 30 ml_). The organic phase was dried over Na2SO4 and evaporated. The crude organic product was purified by flash column chromatography (10% EtOAc in hexanes) to give the product (3.1 g, 86%) as a clear oil. 1H NMR (400 MHz, CDCI3) 6 1.4-1.44 (m, 2H), 1.76-1.80 (m, 2H), 7.44 (d, J=8.3 Hz, 1 H), 7.69 (dd,J=8.3, 2 Hz, 1 H), 7.84 (d, J=2 Hz, 1 H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-(4-Bromo-2-(trifluoromethyl)phenyl)acetonitrile, and friends who are interested can also refer to it.

Reference:
Patent; PFIZER INC.; WO2006/18725; (2006); A1;,
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Reference of 5866-98-8, 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. 5866-98-8, name is 2,6-Dichloro-3-nitrobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows.

To a stirred solution of 2,6-dichloro-3-nitrobenzonitrile (750.0 g, 3.45 mol, 1.0 equiv.) in ethanol (7.5 L, 10.0 V) at 15-20 C. was slowly added hydrazine hydrate (519.0 g, 10.36 mol, 3.0 equiv.) while maintaining the reaction mass below 25 C (Observation: Addition is slightly exothermic and solid formation will begin upon addition). The reaction mixture temperature was slowly raised to room temperature and then the mixture was stirred for 3 h (Observation: the quantity of solids will increase during this time). After completion of the reaction (monitored by TLC), the mixture was diluted with water (7.5 L, 10.0 V) and further stirred for 1 h at room temperature. The solids were isolated via filtration and then were washed with water (2.25 L, 3.0 V). The wet solid was washed with a 1 : 1 ratio mixture of acetone (1.875 L, 2.5 V) and hexanes (1.875 L, 2.5 V). Bulk residual water was removed from the solids by maintaining vacuum filtration for 60-90 min. The wet solid was finally dried in a hot air oven for 7-8 h at 50 C (until moisture content reaches below 1.5%) to get the dried product, 4-chloro-7-nitro-li/-indazol-3 -amine (549.0 g, 75% yield) as a brick red- colored solid. NMR (400 MHz, CDCL): d 10.36 (bs, 1H), 8.20 (d, J= 8.4 Hz, 1H), 7.07 (d, J= 8.40 Hz, 1H), 4.73 (bs, 2H).

The chemical industry reduces the impact on the environment during synthesis 2,6-Dichloro-3-nitrobenzonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; VIIV HEALTHCARE UK (NO.5) LIMITED; IWUAGWU, Christiana; PEESE, Kevin M.; (0 pag.)WO2020/58844; (2020); A1;,
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Adding a certain compound to certain chemical reactions, such as: 499983-13-0, name is 4-Bromo-3-fluorophenylacetonitrile, 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 499983-13-0, COA of Formula: C8H5BrFN

A solution of 4-bromo-3-fluorophenylacetonitrile (Ig, 4.6 mmoles) in toluene (4 ml) is added with 0.6 ml (7 mmoles) of 1,2-dibromoethane, a 50% NaOH aqueous solution (4 ml) and tetrabutylammonium bromide (0.32 g, 1 mmoles). The mixture is kept under stirring at room temperature for 4 hours, then diluted with water and extracted with ethyl acetate. The organic phase is recovered and solvent is eliminated under vacuum to give a brown solid, which is subjected to silica gel chromatography purification, to afford an orange to yellow product in the solid form (I g, yield 90%).

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-fluorophenylacetonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CHIESI FARMACEUTICI S.P.A.; PIVETTI, Fausto; FORNARETTO, Maria Gioia; RE, Marco; WO2011/15287; (2011); A2;,
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Reference of 68385-95-5, These common heterocyclic compound, 68385-95-5, name is 2-Amino-3,5-dibromobenzonitrile, 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.

Bromine (110 mmol, 5.6 mL) was added dropwise to an acetic acid solution (150 mL) of 2-aminobenzonitrile (50 mmol, 5.9 g) in an argon atmosphere, and the mixture was stirred at room temperature for 5 hours. The reaction solution was poured into ice water (200 mL), and the resulting solid was collected by filtration and washed with water.The residue was recrystallized from ethyl acetate to obtain 2-amino-3,5-dibromobenzonitrile (6.9 g, yield 50%).The obtained 2-amino-3,5-dibromobenzonitrile (10.0 mmol, 2.75 g), tetrabutylammonium fluoride trihydrate (5.0 mmol, 1.58 g), trimethylsilyl azide (TMSN3) (15 0.0 mmol, 2.0 mL) was stirred at 85 C. for 2 hours under an argon atmosphere. Ethyl acetate was added to the reaction solution, and the mixture was extracted 3 times with 1M hydrochloric acid (5 mL), and then the organic layer was dried over magnesium sulfate and dried under reduced pressure.Ethyl acetate was distilled off. The residue was subjected to silica gel column chromatography (ethyl acetate: ethanol = 10: 1), and 2,4-dibromo-6- (1H-tetrazol-5-yl) aniline (1.40 g, yield 44%) was white. Obtained as a solid.

The synthetic route of 68385-95-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Tohoku University; Uozumi, Nobuyuki; Arisawa, Mieko; Suzuki, Futoshi; Endo, Akira; Hamamoto, Susumu; Ikenokami, Yoshiaki; (20 pag.)JP2019/137678; (2019); A;,
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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. 179898-34-1, name is 3-Bromo-5-fluorobenzonitrile, A new synthetic method of this compound is introduced below., Computed Properties of C7H3BrFN

To a solution of 3,5-dibromofluorobenzene in diethyl ether (100 cm3) at -78 C. was added n-butyl lithium (2.5 M, 8 cm3, 20 mmol) dropwise. After 30 min. the mixture was treated with DMF (20 cm3) in diethyl ether (10 cm3) and stirring was continued at -78 C. After 30 min. the mixture was quenched with dilute HCl aq., separated and the aqueous layer was extracted with EtOAc. The combined organic layers were combined, washed with water, brine, dried (MgSO4) and evaporated to give 3-fluoro-5-bromobenzaldehyde (4.0 g, 19.7 mmol, 100%) as an oil: 1H NMR (CDCl3) delta inter alia 7.50-7.53 (m, 2H), 7.82 (s, 1H) and 9.93 (m, 1H); MS (EI) m/z 202, 204 [M+]. To a solution of the last cited compound (4.0 g, 19.7 mmol) in ethanol:water (8:2, 50 cm3), was added sodium acetate (1.72 g, 21 mmol) and hydroxylamine hydrochloride (1.45 g, 21 mmol), and the mixture was heated under reflux. After 30 min., the mixture was cooled, evaporated and the residue partitioned between water and EtOAc. The aqueous layer was re-extracted with EtOAc and the combined organic layers were washed with water, saturated sodium hydrogen carbonate solution, brine, dried (MgSO4) and evaporated to give 3-fluoro-5-bromobenzaldehyde oxime (3.76 g, 17.24 mmol, 87%) which was used without further purification: 1H NMR (CDCl3) delta 7.24-7.27 (m, 2H), 7.50 (s, 1H), 7.68 (s, 1H) and 8.04 (s, 1H); MS (EI) m/z 217 [M+]. The above oxime (3.76 g, 17.24 mmol) and copper (II) acetate (370 mg) were dissolved in acetonitrile (100 cm3) under nitrogen and heated under reflux. After 5 h, the mixture was evaporated, the residue taken into EtOAc, washed with sulfuric acid (1N), water, brine, dried (MgSO4) and evaporated to give 3-fluoro-5-bromobenzonitrile (3.08 g, 15.39 mmol, 89%) which was used without further purification. The above bromide (3.0 g, 15 mmol) and tetrakis(triphenylphosphine)palladium (0) (0.86 g, 0.75 mmol) were dissolved in dimethoxyethane (130 cm3) under nitrogen. After 15 min. (2′-oxo-2,3-dihydrospiro[cyclohexane-1,3′-[3H]indol]-5′-yl) boronic acid (2.82 g, 11.5 mmol) and sodium carbonate (3.1 g, 29.3 mmol) dissolved in water (40 cm3) were added, and the mixture heated under reflux. After 8 h the mixture was cooled, poured into water and extracted with EtOAc (×3). The combined organic layers were then washed with water, dried (MgSO4) and evaporated. The residue was then purified by column chromatography (EtOAc:hexane, gradient elution), and the product recrystallized from methanol to give 3-(1,2-Dihydro-2-oxospiro[cyclohexane-1,3-[3H]indol]-5-yl)-5-fluorobenzonitrile (1.78 g, 5.55 mmol, 48%): mp 199-205 C.; 1H NMR (CDCl3) delta 1.64-2.03 (m, 10H), 7.03 (d, 1H, J=8 Hz), 7.31 (dt, 1H, J=7.7 and 1.6 Hz), 7.41 (dd, 1H, J=8, 1.7 Hz), 7.49 (dt, 1H, J=9.6, 2 Hz), 7.58 (d, 1H, J=2 Hz), 7.64 (s, 1H) and 8.37 (s, 1H): MS (EI) m/z 320 [M+].

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; American Home Products Corporation; Ligand Pharmaceuticals, Inc.; US6355648; (2002); B1;,
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Related Products of 1953-99-7,Some common heterocyclic compound, 1953-99-7, name is 3,4,5,6-Tetrachlorobenzene-1,2-dicarbonitrile, molecular formula is C8Cl4N2, 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 A 3,4,5,6-Tetrafluorophthalonitrile Anhydrous potassium fluoride (11.0 kg) is added to a 50 gallon stainless steel reactor. The salt is dried under 28 inches vacuum at 115°-138° C. for 48 hours. The salt is cooled to 100° C. and tetramethylenesulfone (19 liters) added followed by tetrachlorophthalonitrile (4.74 kg). The mixture is heated with stirring to 156° C. over a 30 minute period. Heating with vigorous agitation is continued for another 2.5 hours at 135°-162° C. The mixture was cooled to 31° C. (15 minutes) and ice (69 kg) and demineralized water (119 liters) were added. The resulting mixture was stirred 1.5 hours before centrifuging to collect crude product which was washed with demineralized water (120 liters). The crude product was transferred back into the 50 gallon stainless steel still and demineralized water (100 liters) added. The mixture was steam distilled until 80 liters of distillate were collected. The distillate was cooled to 0°-5° C. and the product collected on a centrifuge. The crystals were washed with demineralized water (2*90 liters) to give 2.82 kg wet product: LOD 6.4percent; calculated yield: 74percent. A small sample was dried under vacuum for two days at room temperature; mp 81°-83° C.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3,4,5,6-Tetrachlorobenzene-1,2-dicarbonitrile, its application will become more common.

Reference:
Patent; Warner-Lambert Company; US4782180; (1988); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts