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Product Details of [ 1741-50-0 ]

CAS No. :1741-50-0 MDL No. :MFCD09033221
Formula : C13H9BrN2 Boiling Point : -
Linear Structure Formula :- InChI Key :GVFCYTFUNNARML-UHFFFAOYSA-N
M.W : 273.13 Pubchem ID :12948775
Synonyms :

Safety of [ 1741-50-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1741-50-0 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 1741-50-0 ]

[ 1741-50-0 ] Synthesis Path-Downstream   1~35

  • 1
  • [ 202328-05-0 ]
  • [ 1741-50-0 ]
YieldReaction ConditionsOperation in experiment
99% In 1-methyl-pyrrolidin-2-one; water; at 445℃; under 187519.0 Torr; for 0.00277778h;Supercritical conditions; General procedure: Under the same conditions as in Example 1-5 except that N-methyl-1,2-phenylenediamine (manufactured by Sigma-Aldrich) and benzoic acid hydride (manufactured by Tokyo Chemical Industry Co., Ltd.) were used at a pressure of 25 MPa, (13) was carried out in supercritical water. As a result, the reaction time was 10 seconds, and the yield was 99%
88% With acetic acid; at 20℃; for 0.166667h; General procedure: Add 1 ml of catalytic amount of glacial acetic acid to the mortar.O-phenylenediamine 1 mmol,1.2 mmol of benzaldehyde was rapidly ground at room temperature for 10 minutes.The product was extracted with ethyl acetate and water.Concentrated under reduced pressure,The product was purified by column chromatography to give a white solid.The yield was 93%.
32% With [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]bis{3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-κN]phenyl-κC}iridium(III) hexafluorophosphate; In tert-butyl methyl ether; at 20℃; for 36.0h;Schlenk technique; Sealed tube; General procedure: In a 25mL Schlenk tube, add 0.2mmol of intermediate 5, 1% of the photocatalyst Ir [dF (CF3) ppy] 2 (dtbbpy) PF6, seal, insert an argon balloon, replace the gas three to four times, and then inject 1mL Methyl tert-butyl ether was placed in a photoreactor and allowed to react at room temperature for 36 hours. After the reaction was completed, 15 mL of ethyl acetate was added to dilute the reaction solution, poured into a separating funnel, 10 mL of saturated sodium carbonate solution was added, extraction was performed, and the liquid phase was extracted with ethyl acetate (20 mL × 2). The organic layers were combined, It was washed with saturated sodium chloride, dried over anhydrous sodium sulfate, and dissolved under reduced pressure. The crude product was separated by column chromatography to obtain 16 mg of the target product I, a white solid, a yield of 40%, and a melting point of 297-298 C. 1H NMR (400MHz, DMSO-d6) δ 12.97 (s, 1H), 9.34 (d, J = 1.8Hz, 1H), 8.45 (d, J = 1.8Hz, 1H), 7.66 (d, J = 7.2Hz 1H), 7.52 (d, J = 7.2Hz, 1H), 7.27-7.16 (m, 2H). 13C NMR (100MHz, DMSO-d6) δ 156.1, 147.6, 147.5, 144.2, 134.8, 123.1, 122.2, 119.9, 119.2, 112.2. HR-MS (ESI): Calcd for C10H8N3S [M + H] +202.0433, found 202.0434.
  • 4
  • [ 7647-01-0 ]
  • [ 202328-05-0 ]
  • Sn [ No CAS ]
  • [ 1741-50-0 ]
  • 5
  • [ 100-52-7 ]
  • [ 1575-37-7 ]
  • [ 1741-50-0 ]
YieldReaction ConditionsOperation in experiment
78% In 1,4-dioxane; at 100℃; Add S1 (1 mmol),Benzaldehyde (1mmol), 8ml 1,4-dioxane, heat to 100C,After the reaction was completed, the solvent was distilled off under reduced pressure,The crude product was purified by column chromatography (dichloromethane/n-hexane/methanol (volume ratio 20:10:1)) to obtain Intermediate 1-1 (yield 78%).
70% With H2SO4 in hydrothermal carbon(II); In ethanol; at 80℃; for 1.5h; General procedure: In an oven-dried 25mL round-bottomed flask equipped with a magnetic stir bar,o-phenylenediamine (1 mmol), benzaldehyde (1 mmol) and 100 mg of H2SO4HTC (II) were mixed and diluted with 5ml of ethanol. The mixture was stirred at reflux for1.5 hr. At the end of the reaction, the catalyst was recovered by filtration and the filtratewas extracted with ethyl acetate (310 mL). The combined organic layers were washedwith 10 ml of water, dried over anhydrous Na2SO4 and filtered. The solvent was evaporated.Pure product was obtained using flash chromatography on silica gel using 20%ethyl acetate in hexane.
To a mixture of 4-bromobenzene-1,2-diamine (0.2 g) in DMF/water (2 mL/50 μL) was added oxone (0.4 g) and benzaldehyde (0.12 g) in DMF (2 mL). After 1 hour, the mixture was diluted with water, treated with K2CO3 and filtered. The filtrate was dissolved in dichloromethane, and this mixture was dried (Na2SO4), filtered and concentrated. The concentrate was chromatographed on silica with an Intelliflash-280 purification system with ethyl acetate/hexanes.
  • 6
  • [ 728-90-5 ]
  • [ 1741-50-0 ]
  • 7
  • [ 1741-50-0 ]
  • [ 73183-34-3 ]
  • [ 1257250-52-4 ]
YieldReaction ConditionsOperation in experiment
With potassium acetate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In N,N-dimethyl-formamide; at 160 - 180℃; for 0.583333h;microwave irradiation; A mixture of EXAMPLE 1A (0.095 g), bis(pinacolato)diboron (0.17 g), potassium acetate (0.10 g) and dichloro(1,1'-bis(diphenylphosphino)ferrocene)-palladium(II).dichloromethane (0.007 g) in DMF (2.5 mL) was stirred at 160 C. for 15 minutes in a microwave reactor. Fresh bis(pinacolato)diboron (2 equivalents), potassium acetate (3 equivalents), and dichloro(1,1'-bis(diphenylphosphino)ferrocene) palladium(II).dichloromethane (0.03 equivalents) were added, and the mixture was stirred at 180 C. for another 20 minutes, cooled, filtered through diatomaceous earth (Celite) and concentrated. The concentrate was purified on silica gel with an Intelliflash-280 purification system with ethyl acetate/hexanes. To the product was added cis-4-(4-(4-amino-3-iodopyrazolo[3,4-d]pyrimidin-1-yl)cyclohexyl)-1-methylpiperazin-2-one, prepared as described in WO 05/074603, (0.11 g), 2M Na2CO3 (0.23 mL) and dichlorobis(triphenyl-phosphine)palladium(II) (8 mg) in ethanol/water (2 mL/1 mL). The mixture was stirred at 120 C. for 20 minutes in a microwave reactor, cooled, filtered through diatomaceous earth (Celite) and dried (Na2SO4) filtered and concentrated. The concentrate was purified by reverse phase HPLC with CH3CN/water/0.1% TFA. 1H NMR (300 MHz, DMSO-d6) δ 13.09 (d, 1H), 8.25-8.20 (m, 3H), 7.89-7.68 (m, 2H), 7.61-7.50 (m, 4H), 4.88-4.78 (m, 1H), 3.07 (bs, 2H), 2.83 (s, 3H), 2.74-2.71 (m, 2H), 2.36-2.22 (m, 3H), 2.16-2.04 (m, 2H), 1.76-1.60 (m, 4H).
  • 8
  • [ 875-51-4 ]
  • [ 707-07-3 ]
  • [ 1741-50-0 ]
  • [ 716-79-0 ]
YieldReaction ConditionsOperation in experiment
80% With indium; acetic acid; In ethyl acetate; for 1.5h;Reflux; Inert atmosphere; General procedure: 2-Nitroaniline derivative (1 mmol) was added to a mixture of indium powder (574 mg, 5.0 mmol for 2-nitroaniline, 918 mg 8.0 mmol for 1,2-dinitroarene), and acetic acid (0.572 mL, 10 mmol) in ethyl acetate (2 mL), followed by the addition of trimethyl orthoester (2.0 mmol) in ethyl acetate (3 mL for 2-nitroaniline; 8 mL for 1,2-dinitroarene). The reaction mixture was stirred at reflux under a nitrogen atmosphere. After the reaction was completed, the reaction mixture was diluted with ethyl acetate (30 mL), filtered through Celite, poured into 10% NaHCO3 (30 mL), and then extracted with ethyl acetate (30 mL×3). The combined organic extracts were dried over MgSO4, filtered, and concentrated. The residue was eluted with ethyl acetate/hexane (v/v=10/90) for 2-phenylbenzimidazole derivatives or methanol/dichloromethane (v/v=1/99) for 2-methylbenzimidazole derivatives through a silica gel column to give the corresponding benzimidazoles. The structures of the benzimidazoles were characterized by 1H NMR, 13C NMR, FTIR, and GC-MS, and were mostly known compounds. HRMS data were reported in addition for unknown compounds.
  • 9
  • [ 100-47-0 ]
  • [ 106-40-1 ]
  • [ 1741-50-0 ]
  • 10
  • [ 1418298-88-0 ]
  • [ 1741-50-0 ]
  • 11
  • [ 1242182-79-1 ]
  • [ 1741-50-0 ]
  • 12
  • [ 100-47-0 ]
  • [ 591-19-5 ]
  • [ 1741-50-0 ]
  • 13
  • [ 66416-72-6 ]
  • [ 100-47-0 ]
  • [ 1741-50-0 ]
  • 14
  • [ 100-47-0 ]
  • [ 64085-52-5 ]
  • [ 1741-50-0 ]
  • 15
  • [ 1741-50-0 ]
  • [ 832114-00-8 ]
  • [ 1613695-61-6 ]
  • 16
  • [ 875-51-4 ]
  • [ 100-51-6 ]
  • [ 1741-50-0 ]
YieldReaction ConditionsOperation in experiment
81% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In toluene; at 160℃; for 24.0h;Schlenk technique; Inert atmosphere; Sealed tube; General procedure: GeneralProcedure for the preparation of 2-Phenyl-1H-benzoimidazole (3aa): A 25mL over-dried Schlenk tube was charged with 2-nitroaniline (41.4 mg, 0.3 mmol),benzyl alcohol (97.2 mg, 0.90 mmol) and Pd(dppf)Cl2 (12.2 mg, 0.015mmol). The tube was purged with nitrogen three times. Toluene (1 mL) was addedto the sealed reaction vessel by syringe. The reaction mixture was stirred in apreheated oil bath at 160 oC for 24 h. After cooling to roomtemperature, the reaction mixture was then concentrated in vacuo, and theresidue was purified by column chromatography (silica gel, petroleumether/ ethyl acetate = 4:1) to give 3aa as a pale yellow solid (56.5 mg, 97%).
73% With sodium sulfide hydrate; iron(III) chloride hexahydrate; at 140℃; for 24.0h;Inert atmosphere; General procedure: A 20-mL test-tube equipped with a magnetic stirring bar was charged with o-nitroaniline 1 (2.5 mmol, 1 equiv), alcohol 2 or 5 (3 mmol, 1.2equiv), Na2S·nH2O (≥60%, 130 mg, 1 mmol, 40 mol%) and FeCl3·6H2O(7 mg, 0.025 mmol, 1 mol%). The resulting mixture was stirred for 24h under an argon atmosphere at the indicated temperature (see Schemes 2 and 3 and Table 2). After cooling to r.t., the mixture was purified in different ways. (i) For NH benzimidazole products, the mixture was washed with CH2Cl2 (3 × 2 mL) then dissolved in MeOH.The MeOH solution was filtered through a short pad of silica gel. The filtrate was concentrated in vacuo to afford the NH benzimidazole product. Further purification by column or recrystallization was carried out if necessary. (ii) For N-methyl-2-phenylbenzimidazole 3ha and quinoxalines 5, the crude mixture was dissolved in a minimum volume of CH2Cl2 and purified by column chromatography (silica gel or alumina, heptane-EtOAc, EtOAc, EtOAc-MeOH, hexane-Et2O). We noted that some 13C NMR signals of NH-benzimidazoles are missing or difficult to observe.
73% With 1,1'-bis-(diphenylphosphino)ferrocene; In toluene; at 150℃; for 24.0h;Inert atmosphere; Sealed tube; General procedure: The preparation of 2-phenyl-1H-benzoimidazole (3a): A 15 mL capped tube was charged with 2-nitroaniline (0.36 mmol), benzyl alcohol (0.094 mL, 0.90 mmol) and dppf (0.018 mmol). The tube was flushed with argon for 10 min. Then the degassed toluene (3 mL) was added. The tube was flushed with argon, capped, and heated at 150 C for 24 h. After cooling to room temperature, the reaction mixture was then concentrated in vacuo, and the residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate = 4:1) to afford the pure 3a as a white solid. The product was identified by NMR and MS and the data are identical to the reported values.
  • 19
  • [ 93-97-0 ]
  • [ 1575-37-7 ]
  • [ 1741-50-0 ]
  • 20
  • [ 611-73-4 ]
  • [ 1575-37-7 ]
  • [ 1741-50-0 ]
  • 21
  • [ 1741-50-0 ]
  • [ 501-65-5 ]
  • 10-bromo-5,6-diphenylbenzo[4,5]imidazo[2,1-a]isoquinoline [ No CAS ]
  • 22
  • [ 615-57-6 ]
  • [ 100-52-7 ]
  • [ 1741-50-0 ]
YieldReaction ConditionsOperation in experiment
76% With ammonium hydroxide; 8-quinolinol; caesium carbonate; nickel dichloride; at 100℃; for 0.216667h;Sealed tube; Microwave irradiation; General procedure: A 10 mL glass tube was charged with the appropriate 2-haloaniline(0.5 mmol), 25-28% aq NH3 (2 mL), the appropriate aldehyde(0.6 mmol), NiCl2 (11.88 mg, 0.05 mmol), quinolin-8-ol(7.258 mg, 0.05 mmol), and Cs2CO3 (325.82 mg, 1.0 mmol). Thevessel was then sealed with a septum and placed in the cavity ofa Discover microwave synthesizer (CEM Corp., Buckingham,UK), and irradiated at 130 W. The temperature was rampedfrom r.t. to the desired temperature of 100 C, then held at thistemperature for 13 min. The mixture was stirred continuouslyduring the reaction. The mixture was then allowed to cool to r.t.and the solvent was removed under reduced pressure. Theresidue was purified by column chromatography (silica gel) toafford the corresponding product. The structures of the productswere confirmed by NMR and MS spectroscopic analyses.2-Phenyl-1H-benzo[d]imidazole (2a)Light-yellow solid; yield: 89.24 mg (92%).
  • 23
  • [ 66416-72-6 ]
  • [ 100-52-7 ]
  • [ 1741-50-0 ]
YieldReaction ConditionsOperation in experiment
84% With ammonium hydroxide; 8-quinolinol; caesium carbonate; nickel dichloride; at 100℃; for 0.216667h;Sealed tube; Microwave irradiation; General procedure: A 10 mL glass tube was charged with the appropriate 2-haloaniline(0.5 mmol), 25-28% aq NH3 (2 mL), the appropriate aldehyde(0.6 mmol), NiCl2 (11.88 mg, 0.05 mmol), quinolin-8-ol(7.258 mg, 0.05 mmol), and Cs2CO3 (325.82 mg, 1.0 mmol). Thevessel was then sealed with a septum and placed in the cavity ofa Discover microwave synthesizer (CEM Corp., Buckingham,UK), and irradiated at 130 W. The temperature was rampedfrom r.t. to the desired temperature of 100 C, then held at thistemperature for 13 min. The mixture was stirred continuouslyduring the reaction. The mixture was then allowed to cool to r.t.and the solvent was removed under reduced pressure. Theresidue was purified by column chromatography (silica gel) toafford the corresponding product. The structures of the productswere confirmed by NMR and MS spectroscopic analyses.2-Phenyl-1H-benzo[d]imidazole (2a)Light-yellow solid; yield: 89.24 mg (92%).
  • 24
  • [ 1741-50-0 ]
  • [ 100-42-5 ]
  • 5-bromo-2-(2-styrylphenyl)-1H-benzo[d]imidazole [ No CAS ]
  • 25
  • [ 1741-50-0 ]
  • [ 100-42-5 ]
  • 9-bromo-6-phenyl-5,6-dihydrobenzo[4,5]imidazo[2,1-a]isoquinoline [ No CAS ]
  • 10-bromo-6-phenyl-5,6-dihydrobenzo[4,5]imidazo[2,1-a]isoquinoline [ No CAS ]
  • 9-bromo-6-phenyl-1-styryl-5,6-dihydrobenzo[4,5]imidazo[2,1-a]isoquinoline [ No CAS ]
  • 10-bromo-6-phenyl-1-styryl-5,6-dihydrobenzo[4,5]imidazo[2,1-a]isoquinoline [ No CAS ]
  • 26
  • [ 698-16-8 ]
  • [ 1741-50-0 ]
  • 27
  • [ 106-40-1 ]
  • [ 1741-50-0 ]
  • 28
  • (E)-N-(4-bromophenyl)-N′-hydroxybenzimidamide [ No CAS ]
  • [ 1741-50-0 ]
  • 29
  • (E)-N-(4-bromophenyl)-N′-((4-(trifluoromethyl)benzoyl)oxy)benzimidamide [ No CAS ]
  • [ 1741-50-0 ]
  • 30
  • [ 721-04-0 ]
  • [ 1575-37-7 ]
  • [ 1741-50-0 ]
  • [ 4887-88-1 ]
  • [ 108-95-2 ]
YieldReaction ConditionsOperation in experiment
With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In 2-methoxy-ethanol; at 120℃; for 24.0h;Sealed tube; Put 0.1mmol oxidized lignin model substrate 1 in a 10mL pressure tube, add 0.01mmol HNO3, 1mL DMSO and 0.2mmol o-phenylenediamine 2,After tightening the cap, heat the resulting reaction solution (the concentration of oxidized lignin in the reaction solution is 0.1 mmol/mL) in an oil bath at 100C for 12 hours,The decomposition reaction is carried out. After the reaction is completed, the obtained product is taken out and the solvent is drained and separated by a column to obtain two nitrogen-containing heterocyclic products.
  • 31
  • [ 1741-50-0 ]
  • C45H31N5 [ No CAS ]
  • 32
  • [ 1741-50-0 ]
  • [ 201802-67-7 ]
  • C31H23N3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In toluene; at 100℃;Inert atmosphere; In a 25 ml round bottom two-necked flask,Add Intermediate 1-1 (1mmol), compound S2 (1mmol), potassium carbonate (1.2mmol), toluene (8ml), water (1ml), tetrakis(triphenylphosphine)palladium (0.05mmol), nitrogen protection After the reaction is completed, it is heated to 100C, quenched by adding water, extracted with dichloromethane, and the organic layer is dried with anhydrous magnesium sulfate, filtered, and spin-dried.The crude product was purified by column chromatography (dichloromethane/n-hexane/methanol (volume ratio 20:10:1)) to obtain Intermediate 2-1 (yield 88%).
  • 33
  • 1-phenyl-3-hydroxy-2-phenoxy propan-1-one [ No CAS ]
  • [ 1575-37-7 ]
  • [ 1741-50-0 ]
  • [ 4887-88-1 ]
  • [ 108-95-2 ]
  • 34
  • [ 721-04-0 ]
  • [ 1741-50-0 ]
  • 35
  • [ 70-11-1 ]
  • [ 1741-50-0 ]
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