Category: 2620-76-0

Reference of 2620-76-0, These common heterocyclic compound, 2620-76-0, name is 2-(4-Bromophenyl)-1-phenyl-1H-benzoimidazole, 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.

(1-7) Synthesis of Compound (1); Into a 300 ml three-necked flask, 2.0 g (5.0 mmole) of Intermediate 6, 3.9 g (11 mmole) of 2-(4-bromophenyl)-1-phenylbenzimidazole, 0.23 g (0.20 mmole) of tetrakis(triphenylphosphine)palladium(0), 50 ml of 1,2-dimethoxyethane and 15 ml (30 mmole) of a 2 M aqueous solution of sodium carbonate were placed under the stream of argon, and the resultant mixture was heated under the refluxing condition for 8 hours. After the reaction was completed, the organic layer was washed with water and dried with magnesium sulfate, and the solvent was removed by distillation using a rotary evaporator. The obtained crude crystals were washed with 50 ml of toluene and 100 ml of methanol, and 3.4 g of a light yellow powder substance was obtained. The obtained substance was identified to be Compound (1) by the measurement of the field desorption mass spectrum (FD-MS) (the yield: 80percent).

The synthetic route of 2620-76-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Idemitsu Kosan Co., Ltd.; US8058450; (2011); B2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 2620-76-0,Some common heterocyclic compound, 2620-76-0, name is 2-(4-Bromophenyl)-1-phenyl-1H-benzoimidazole, molecular formula is C19H13BrN2, 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.

A 500 mL four-neck round-bottomed flask (RBF) equipped with an overhead stirrer, a nitrogen inlet, a 125 mL addition funnel, and a thermocouple was purged with anhydrous nitrogen for 10 min. The flask was charged with 2- (4-bromophenyl) -1-phenyl-1 H-benzo [d] imidazole (25.0 g, 71.59 mmol) and THF (250.0 mL) , and then cooled to -71? of internal temperature. 1.6 M n-butyl lithium solution (67.0 mL, 107.2 mmol) in hexane was added dropwise into the flask via an addition funnel for 30 min, and the mixture was further stirred at an internal temperature of -72oC of for 30 min. 2-Isopropoxy-4, 4, 5, 5-tetramethyl-1, 3, 2-dioxaborolane (32.0 mL, 171.99 mmol) was added to the resulting dark red solution via an addition funnel for 30 min while maintaining the temperature of below -70oC. After removing a cooling bath, the brown slurry was warmed to room temperature and stirred for 16 hrs. The reactants were concentrated by using a rotary evaporator, dissolved in dichloromethane (350.0 mL) , and washed with water (200.0 mL) to obtain a cloudy mixture. The aqueous layer was extracted with dichloromethane (2 X 150.0 mL) , and the combined organic layers were dried with MgSO4, filtered, and concentrated by using a rotary evaporator. The resulting yellow solid was washed with hexane (100.0 mL) and tan colored solids (22.2 g) were obtained by mostly removing the color. The solids were divided into two crops and recrystallized from acetonitrile (? 180.0 mL per crop) to obtain pale orange crystalline solids as a title compound (16.5 g, 41.6 mmol, 58percent) .

The synthetic route of 2620-76-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DOW GLOBAL TECHNOLOGIES LLC; ROHM AND HAAS ELECTRONIC MATERIALS KOREA LTD.; CHO, Sang Hee; NA, Hong Yeop; TANG, Zhengming; FENG, Shaoguang; MOON, Doo-Hyeon; (43 pag.)WO2017/156698; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 2620-76-0, name is 2-(4-Bromophenyl)-1-phenyl-1H-benzoimidazole, belongs to imidazoles-derivatives 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 2620-76-0, HPLC of Formula: C19H13BrN2

[0104] Compound 26: A mixture of Compound 25 (4- (diphenylamino)phenyl)boronic acid (900 mg, 3.1 mmol), Compound 9 (1.09 g, 3.1 mmol), Pd(PPh3)4 (180 mg, 0.16 mmol) and K2CO3 (1.38 g, 10 mmol) in 1,4- dioxane/H2O (25 mL/5 mL) was degassed and the resulting mixture was heated at about 100 0C overnight under an argon atmosphere. After cooling to room temperature, the resulting mixture was poured into water, extracted with ethyl acetate (100 mL x 2). The organic phase was dried over Na2SO4 and filtered. After addition of hexanes (100 mL), a yellow precipitate formed after about one hour. Filtration gave a yellow solid (760 mg) and the filtrate was absorbed on silica gel and purified by flash chromatography to give a yellow solid (200 mg). The total amount of product (Compound 26) was 960 mg in 62% 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, 2-(4-Bromophenyl)-1-phenyl-1H-benzoimidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NITTO DENKO CORPORATION; ZHENG, Shijun; CAYAS, Jensen; LI, Sheng; MOCHIZUKI, Amane; CHAF, Hyunsik; HARDING, Brett, T.; WO2011/8560; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 2620-76-0, 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. 2620-76-0, name is 2-(4-Bromophenyl)-1-phenyl-1H-benzoimidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

In a 50 mL three-neck flask were put 1.4 g (5.2 mmol) of 2-(4-bromophenyl)-1,3-benzoxazole, 0.8 g (2.5 mmol) of N,N’-diphenylbenzidine, 1.0 g (10 mmol) of sodium tert-butoxide, and 28 mg (50 mumol) of bis(dibenzylideneacetone)palladium(0), and the air in the flask was replaced with nitrogen. Then, 20 mL of dehydrated xylene was added to this mixture. After the mixture was deaerated while being stirred under reduced pressure, 0.3 mL (0.2 mmol) of tri(tert-butyl)phosphine (10 wt percent hexane solution) was added thereto. This mixture was stirred under a nitrogen atmosphere at 130° C. for 4.5 hours to be reacted.After the reaction, 200 mL of ethyl acetate was added to this reaction mixture, and this suspension was filtered through Florisil and Celite. The obtained filtrate was concentrated and purified by silica gel column chromatography (developing solvent, toluene:ethyl acetate=9:1). The obtained fraction was concentrated, and acetone and methanol were added thereto. The mixture was irradiated with supersonic and then recrystallized, so that the object of the synthesis was obtained as 1.7 g of a yellow powder in a yield of 96percent.A reaction scheme of the above synthesis method is illustrated in the following scheme (B-1). The Rf values of the object of the synthesis, 2-(4-bromophenyl)-1,3-benzoxazole, and N,N’-diphenylbenzidine were respectively 0.35, 0.67, and 0.30 which were found by silica gel thin layer chromatography (TLC) (developing solvent, ethyl acetate_hexane=1:5).Results of nuclear magnetic resonance spectrometry (1H-NMR), by which the compound obtained by the above synthesis method was analyzed, are shown below. In addition, the 1H-NMR charts are shown in FIGS. 10A and 10B. FIG. 10B illustrates an enlarged view within a range of 6 ppm to 9 ppm in FIG. 10A. The results reveal that N,N’-diphenyl-N,N’-di-{4-(1,3-benzoxazol-2-yl)-phenyl}benzidine (abbreviation: BOxABP), which is the triarylamine compound of one embodiment of the present invention represented by the structural formula (135) shown above, was obtained.1H NMR (CDCl3, 300 MHz): delta (ppm)=7.11-7.24 (m, 14H), 7.28-7.35 (m, 8H), 7.51-7.55 (m, 6H), 7.70-7.73 (m, 2H), 8.90 (d, J=8.7 Hz, 4H).Next, ultraviolet-visible absorption spectra (hereinafter, simply referred to as “absorption spectra”) and emission spectra of BOxABP were measured. The absorption spectra were measured using an ultraviolet-visible light spectrophotometer (V550 type manufactured by Japan Spectroscopy Corporation). The emission spectra were measured using a fluorescence spectrophotometer (FS920 manufactured by Hamamatsu Photonics Corporation). The absorption spectra and the emission spectra of a toluene solution of BOxABP and a thin film of BOxABP were measured. Put in a quartz cell, the toluene solution (0.120 mmol/L) was subjected to the measurements at room temperature. As for the measurements of the absorption spectrum of the thin film, the thin film which was evaporated over a quartz substrate was used and a value obtained by subtraction of an absorption spectrum of quartz from absorption spectra of the thin film and quartz is shown.FIGS. 11A and 11B show measurement results of the absorption spectra and emission spectra. FIG. 11A shows the measurement results of the toluene solution of BOxABP. FIG. 11B shows the measurement results of the thin film of BOxABP. In each of FIGS. 11A and 11B, the horizontal axis represents wavelength (nm) and the vertical axis represents absorption intensity (arbitrary unit) or emission intensity (arbitrary unit). In each of FIGS. 11A and 11B, the two solid lines are shown, and the thin line represents absorption spectrum while the thick line represents emission spectrum.In the case of the toluene solution of BOxABP, an absorption peak is observed at around 381 nm as shown in FIG. 11A. In the case of the thin film of BOxABP, an absorption peak is observed at around 384 nm as shown in FIG. 11B.Further, in the case of the toluene solution of BOxABP, the maximum emission wavelength is 435 nm (excitation wavelength: 380 nm) as shown in FIG. 11A. In the case of the thin film of BOxABP, the maximum emission wavelength is 472 nm (excitation wavelength: 400 nm) as shown in FIG. 11B.As described above, BOxABP was found to emit blue light and accordingly can be used for a blue light-emitting material.Further, the HOMO level and the LUMO level of BOxABP were obtained by cyclic voltammetry (CV) measurements. An electrochemical analyzer (ALS model 600A or 600C, manufactured by BAS Inc.) was used for the CV measurements.Further, as for a solution used for the CV measurements, dehydrated dimethylformamide (DMF, manufactured by Sigma-Aldrich Inc., 99.8percent, Catalog No. 22705-6) was used as a solvent, and tetra-n-butylammonium perchlorate (n-Bu4NClO4, manufactured by Tokyo Chemical Industry Co., Ltd., Catalog No. T0836), which was a supporting electrolyte, was dissolved in the solvent such that the concentration of tetra-n-butylammonium perchlorat…

The synthetic route of 2-(4-Bromophenyl)-1-phenyl-1H-benzoimidazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Semiconductor Energy Laboratory Co., Ltd.; US2012/330025; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 2620-76-0, name is 2-(4-Bromophenyl)-1-phenyl-1H-benzoimidazole, belongs to imidazoles-derivatives 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 2620-76-0, HPLC of Formula: C19H13BrN2

A mixture of compound 1a (1.745 g, 5.0 mmol),(1.91 g, 7.5 mmol) and KOAc (1.47 g, 15.0)Was dissolved in anhydrous 1,4-dioxane (40 mL)After nitrogen replacement,Pd (dppf) Cl2 (0.18 g, 0.25 mmol) was added,Heated to reflux for 3h.After completion of the reaction, the mixture was cooled to room temperature, the mixture was poured into water and extracted with dichloromethane. The organic layer was dried over anhydrous MgSO4 and the solvent was removed by steaming.The final crude product was purified using n-hexane / ethyl acetate (v / v = 1: 3) SiO2 column,A white powdery solid was obtained.Yield: 1.88 g, 95%.

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-(4-Bromophenyl)-1-phenyl-1H-benzoimidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; China University of Mining and Technology; Ni Zhonghai; Zhang Ran; Zhang Lifang; Zhao Yun; (20 pag.)CN106905242; (2017); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 2620-76-0, name is 2-(4-Bromophenyl)-1-phenyl-1H-benzoimidazole, belongs to imidazoles-derivatives 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 2620-76-0, HPLC of Formula: C19H13BrN2

The solution of n-BuLi in 2.5Mn-hexane (2.64 mL,6.6 mmol)was added dropwise to a solution of 2-(4-bromophenyl)-1-phenyl-1H-benzo[d] imidazole (2.09 g, 6 mmol) in dry THF(30 mL) at 78 C. At temperature of 78 C, the resulting reactionmixture was stirred continuously. Thereafter, we slowly added trimethylchlorosilane(0.76 mL, 6 mmol) to the mixture. Then, thereaction temperature was allowed to warm at room temperatureand stirred overnight. The reaction was quenched by adding water, and the crude product was extracted twice using 100 mL ofdichloromethane. Finally, the crude productwaswashed with brine.The combined organic layer was dried over MgSO4 and subjected tofiltration. The filtrates were dried under reduced pressure, and theresidue was subjected to column chromatography using ethyl acetate/n-hexane (v:v 1:10) as an eluent. Compound 1 was obtainedas a white solid with yield of 78%. We could not perform train sublimationof compound 1 due to its poor thermal stability.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-(4-Bromophenyl)-1-phenyl-1H-benzoimidazole, and friends who are interested can also refer to it.

Reference:
Article; Yi, Seungjun; Kim, Jin-Hyoung; Bae, Woo-Ri; Lee, Jiwon; Han, Won-Sik; Son, Ho-Jin; Kang, Sang Ook; Organic electronics; vol. 27; (2015); p. 126 – 132;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 2620-76-0,Some common heterocyclic compound, 2620-76-0, name is 2-(4-Bromophenyl)-1-phenyl-1H-benzoimidazole, molecular formula is C19H13BrN2, 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 1.3.3; 10; [0087] l-phenyl-2-(4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)phenyl)- lH-benzo[d] imidazole (10): A mixture of Compound 9 (0.70 g, 2 mmol), bis(pinacolate)diborane (0.533 g, 2.1 mmol), l,l’-Bis(diphenylphosphino)ferrocene] dichloropalladium (Pd(dppf)Cl2) (0.060 g, 0.08 mmol) and anhydrous potassium acetate (0.393 g, 4mmol) in 1,4-dioxane (20 mL) was heated at 800C under argon overnight. After cooling to r.t., the whole mixture was diluted with ethyl acetate (80 mL) then filtered. The solution was absorbed on silica gel, then purified by column chromatography (hexanes/ethyl acetate 5:1 to 3:1) to give a white solid (Compound 10) (0.64 g, in 81% yield).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(4-Bromophenyl)-1-phenyl-1H-benzoimidazole, its application will become more common.

Reference:
Patent; NITTO DENKO CORPORATION; ZHENG, Shijun; CAYAS, Jensen; LI, Sheng; MOCHIZUKI, Amane; CHAF, Hyunsik; HARDING, Brett, T.; WO2011/8560; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 2620-76-0, A common heterocyclic compound, 2620-76-0, name is 2-(4-Bromophenyl)-1-phenyl-1H-benzoimidazole, molecular formula is C19H13BrN2, 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.

In a glovebox, three oven-dried reaction jars were each charged with 2-(4- bromophenyl)-l -phenyl- lH-benzimidazole 12 (4.20 g, 12.0 mmol), bis(pinacolato)- diboron (Bpin) (3.05 g, 12 mmol, 1 eq.), potassium acetate (2.95 g, 30 mmol, 2.5 eq.), and Pd(dppf)Cl2 (300 mg, 0.36 mmol, 3 mol%). The solvent (1,4-dio-xane, 80 mL) was added to each jar and the reactions were stirred at 80 C overnight. After complete conversion (-95%) as determined by LC-MS, the contents of the reaction jars were mixed and the solvent removed under reduced pressure. Water (200 mL) was added the product was extracted into chloroform (3×200 mL), the product was passed through a silica plug and recrystallized from acetonitrile. The reaction was successfully scaled up to 12 g in 90% yield after recrystallization to give the desired boronic ester 8 at -98% purity as judged by LC-MS and NMR. *H NMR (500 MHz, cdcl3) delta 7.90 (dt, J = 8.1, 0.9 Hz, 1H), 7.76 – 7.71 (m, 2H), 7.60 – 7.55 (m, 2H), 7.49 – 7.41 (m, 3H), 7.35 – 7.21 (m, 6H), 1.32 (s, 12H); 13C NMR (126 MHz, CDC13) delta 172.37, 157.10, 152.56, 135.25,133.58, 133.11, 131.25, 130.46, 128.49, 128.13, 128.03, 127.96, 127.73, 127.11, 126.47, 125.24, 124.99, 123.30

The synthetic route of 2620-76-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DOW GLOBAL TECHNOLOGIES LLC; ROHM AND HAAS ELECTRONIC MATERIALS KOREA LTD.; ONDARI, Mark E.; WELSH, Dean M.; FROESE, Robert DJ; NA, Hong-Yeop; (38 pag.)WO2016/209895; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 2620-76-0, 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 2620-76-0 as follows.

A four-neck, 500 mL round bottom flask equipped with a top stirrer, nitrogen inlet, 125 mL addition funnel, and thermocouple was rinsed with dry nitrogen for 10 minutes. The flask was charged with 2-(4-bromophenyl)-1-phenyl-1H-benzo[d]imidazole (25.0 g, 71.59 mmol) and THF (250 mL), and the reaction was cooled to an internal temperature of -71V. 1.6 ME butyllithium (67 mL, 107.2 mmol) in hexane was added dropwise via an addition funnel over 30 minutes, and an additional 30 min was stirred at -72 °C. Add 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-di|1B boron boron by adding funnel (out 0 parent 31301>013116) (32 1111 ^, 171.99 mmol) to a deep red solution for 30 minutes, keeping the temperature below -70t. Remove the cold bath and allow the yellow slurry to warm to room temperature and mix for 16 h. The reaction was concentrated by rotary evaporation, then dissolved in dichloromethane (350 mL) and washed with water (200 mL) to form a cloudy mixture. The aqueous layer was extracted with dichloromethane (2 chi 150 mL) and the combined organic layers dried over EtOAc EtOAc EtOAc The resulting yellow solid was washed with hexanes (100 mL) which removed most of the color to afford 22.2 g of light brown solid. The solid was separated into two portions and recrystallized from EtOAc (EtOAc: EtOAc: EtOAc: EtOAc:

According to the analysis of related databases, 2620-76-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; DOW GLOBAL TECHNOLOGIES LLC; ROHM AND HAAS ELECTRONIC MATERIALS KOREA LTD.; WELSH, DEAN M.; ONDARI, MARK E.; GRAY, KAITLYN; KIM, BONG-OK; CHEE, MOO-KEUN; FROESE, ROBERT D.; (60 pag.)TWI631109; (2018); B;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 2620-76-0, name is 2-(4-Bromophenyl)-1-phenyl-1H-benzoimidazole, belongs to imidazoles-derivatives 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 2620-76-0, Computed Properties of C19H13BrN2

(4-7) Synthesis of Compound (4); Into a 300 ml three-necked flask, 1.1 g (2.1 mmole) of Intermediate 14, 1.6 g (4.6 mmole) of 2-(4-bromophenyl)-1-phenylbenzimidazole, 0.10 g (0.09 mmole) of tetrakis(triphenylphosphine)palladium(0), 20 ml of 1,2-dimethoxyethane and 6.5 ml (13 mmole) of a 2 M aqueous solution of sodium carbonate were placed under the stream of argon, and the resultant mixture was heated under the refluxing condition for 8 hours. When the reaction was completed, the organic layer was washed with water and dried with magnesium sulfate, and the solvent was removed by distillation using a rotary evaporator. The obtained crude crystals were washed with 50 ml of toluene and 100 ml of methanol, and 1.6 g of a light yellow powder substance was obtained. The obtained substance was identified to be Compound (4) by the measurement of the field desorption mass spectrum (FD-MS) (the yield: 78percent).

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-(4-Bromophenyl)-1-phenyl-1H-benzoimidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Idemitsu Kosan Co., Ltd.; US8058450; (2011); B2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem