Structure of 3894-25-5
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CAS No. : | 3894-25-5 |
Formula : | C15H10BrN |
M.W : | 284.15 |
SMILES Code : | BrC1=CC=C2N=C(C3=CC=CC=C3)C=CC2=C1 |
MDL No. : | MFCD17392928 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-P305+P351+P338 |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
42% | With Ag(I) exchanged montmorillonite K10; In neat (no solvent); at 120℃; for 3h;Green chemistry; | General procedure: Amine (1.50 mmol) and aldehyde (1.00 mmol) were dissolved in 1.5 mL of Et2O in a reaction vial equipped with a magnetic stirrer bar, followed by the addition of Ag(I)-exchanged Montmorillonite K10 (0.50 g). After 5 min stirring, the solvent was removed in vacuo to obtain a dry powder. The reaction mixture was heated at a temperature of 120 oC for 3 h. After cooling to room temperature, the reaction mixture was filtered through a short silica plug and the solid residues washed well with CH2Cl2. The solvent was removed in vacuo and the crude product purified by column chromatography over silica gel eluting with a mixture of Hexane EtOAc to produce the title compounds (3a-3k). NOTE. For the recycle/reuse study, the crude product was gravity filtered and the clay material washed several times with CH2Cl2, air dried and weighed. This process was repeated for consecutive recycle/reuse reactions. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With palladium diacetate; caesium carbonate; triethylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In 1,4-dioxane; at 100℃; | EXAMPLE 47CN-(diphenylmethylene)-2-phenylquinolin-6-amineIn a 20 mL microwave tube was charged cesium carbonate (0.440 mL, 5.50 mmol), palladium(II) acetate (0.018 g, 0.079 mmol), and 9,9-dimethyl-4,5- bis(diphenylphosphino)xanthene (0.068 g, 0.118 mmol) in dioxane (6.0 mL) to give a yellow suspension. The mixture was stirred for 10 minutes and then triethylamine (0.016 mL, 0.118 mmol) was added. The solution was stirred for another 10 minutes; and then8489667 1 <strong>[3894-25-5]6-bromo-2-phenylquinoline</strong> (1.1168 g, 3.93 mmol) and benzophenone imine (0.791 niL, 4.72 mmol) were added as a solution in dioxane (6.0 mL). The mixture was heated at 100 0C overnight. The mixture was cooled to room temperature and dilute with ethyl acetate. The organics were washed 2 x 100 mL with water, dried over magnesium sulfate, filtered, and concentrated onto silica gel. The reaction was purified by flash chromatography using an Argonaut Flashmaster Solo, 20g column (10% ethyl acetate:hexanes for 30 min) to afford a yellow oil. (ES I(+)) m/e 385.0 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With potassium tert-butylate; cobalt(II) diacetate tetrahydrate; In toluene; at 110℃; for 12h;Inert atmosphere; | The reaction vessel was charged with 2-amino-5-bromobenzyl alcohol 1s (202.0 mg, 1.0 mmol), acetophenone 2a (120.2 mg, 1.0 mmol), Co(OAc)2 4H2O (19.9 mg, 0.08 mmol) and KOtBu (112.0 mg, 1.0 mmol).Under an argon atmosphere, 2 mL of toluene was added and heated at 110 C for 12 h.After cooling to room temperature, 10 mL of water was added, and the mixture was extracted with EtOAc (3 x 10 mL).The combined organic phases were concentrated under reduced pressure.The residue was then purified by flash column chromatography (petroleum ether:ethyl acetate 100:1, v/v) to give 3s as a white solid (234.9 mg, 83% yield). |
80% | With C22H24N6O2Ru(1+)*Cl(1-); potassium hexamethylsilazane; In toluene; at 110℃; for 12h;Inert atmosphere; | Add 2-amino-5-bromobenzyl alcohol 2q (201.0mg, 1.0mmol), acetophenone 3a (120.2mg, 1.0 mmol), complex 1a (10.8mg, 0.02mmol) and KHMDS (1mL, 1.0mmol). Under a nitrogen atmosphere, 2 mL of toluene was added and heated at 110 C. for 12 h. After cooling to room temperature, 10 mL of water was added, and the mixture was extracted with EtOAc (3×10 mL). The combined organic phase was concentrated under reduced pressure. The residue was then purified by flash column chromatography (petroleum ether: ethyl acetate 100:1, v/v) to obtain 4q (226 mg, 80%) as a white solid. |
With C22H24N6O2Ru(1+)*Cl(1-); potassium hexamethylsilazane; In tetrahydrofuran; toluene; at 110℃; for 12h;Inert atmosphere; | General procedure: A mixture of 2-aminophenylmethanol (2a) (123.2 mg, 1.0 mmol),acetophenone (3a) (120.2 mg, 1.0 mmol), complex 1a (10.8 mg,0.02 mmol), and KHMDS (1.0 mL, 1.0 M in THF) in 2 mL of toluene wasstirred at 110 C for 12 h under a nitrogen atmosphere. After cooling toambient temperature, 10 mL water was added and the mixture wasextracted with EtOAc (3 × 10 mL). The combined organic layer wasdried over anhydrous Na2SO4 and concentrated under reduced pressure.The resulting residue was subjected to purification by flash columnchromatography on alumina (petroleum ether: ethyl acetate 100: 1, v/v)to afford 4a as a white solid (190.9 mg, 93% yield), which was identifiedby NMR analysis. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With trifluorormethanesulfonic acid; copper(l) chloride; at 90℃; for 12h;Sealed tube; | In a Schlenk tube with a screw cap, washed added benzaldehyde (0.2mmol, 21.2mg), bromine aniline (0.4mmol, 68.0mg), copper (0.04mmol, 2.69mg) chloride, 4.0mL 1,4 dioxane, trifluoromethanesulfonate (0.1mmol, 15.0mg), and finally under air conditions, the sealed reactor tube placed in an oil bath at 90 pot heated with stirring for about 12 hours.Distillation under reduced pressure, to remove unreacted 1,4-dioxane, the final product was purified by column chromatography, and then dried to give a white solid solid powder 36.9 mg, 65% yield |
65% | With trifluorormethanesulfonic acid; copper dichloride; at 90℃; for 0.12h;Schlenk technique; Sealed tube; | In a Schlenk tube with a screw cap, add benzaldehyde (0.2mmol, 21.2mg), p-bromoaniline (0.4mmol, 68.0mg), copper chloride (0.04mmol, 2.69mg), 4.0mL of 1,4- Dioxane, trifluoromethanesulfonic acid (0.1mmol, 15.0mg), and finally under air conditions, place the sealed reaction tube in an oil bath at 90C and heat and stir for about 12 hours.Under reduced pressure distillation, the unreacted 1,4-dioxane was removed, and finally the product was separated and purified by column chromatography, and then dried to obtain 36.9 mg of white solid powder with a yield of 65%.Melting point: 112-113C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
35 mg; 45 mg | With ammonium peroxodisulfate; zinc trifluoromethanesulfonate; silver nitrate; In dichloromethane; water; at 20℃; for 4h; | General procedure: Ammonium persulfate (3 equiv, 342 mg), phenylboronic acid (1.5 equiv, 91 mg), silver nitrate (0.2 equiv, 17 mg), and zinc trifluoromethanesulfonate (0.2 equiv, 36 mg) were combined ina 10 mL round bottom flask. A heterocycle (1 equiv, 0.5 mmol) was then added to the same flask and solvated with water (0.4 mL) and CH2Cl2 (1.6 mL). The resulting mixture was sonicated for 10 sec and placed on a stir plate to stir vigorously at room temperature for 4 h. The reaction was quenched with 28% ammonium hydroxide (2 mL), diluted with water (10 mL), and extracted with CH2Cl2 (3 x 10 mL). The organic layer was dried over sodium sulfate, filtered through cotton, and evaporated en vacuo. The products were purified by column chromatography (SiO2, 5-20% EtOAc/hexanes). Products 3b, 3c, and 3d required further purification by crystallization as the trifluoromethanesulfonic acid salts and recrystallization from THF/hexanes. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | General procedure: Iron powder (0.4 eq.) was added to a solution of o-nitrobenzaldehyde (11a-11g, 1.0 eq.) in EtOH(2.0 mL) followed by HCl (0.05 eq.) [19]. The reaction mixture was refluxed for 40 min followedby cooling to room temperature. The corresponding aldehyde or ketone (1.2 eq.) was added to thereaction mixture followed by KOH (1.2 eq.). The reaction mixture was stirred at RT for 30 min andrefluxed for an additional 3 h. The reaction mixture was filtered, the filtrate was neutralized (HCl),extracted with EtOAc, and the combined extracts were dried and concentrated to dryness. The residuewas subjected to FCC (EtOAc-hexane, 3:7) to afford substituted quinolines 5a-7g. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | With sodium persulfate; silver nitrate; trifluoroacetic acid; In dichloromethane; water; at 25℃; for 0.5h; | General procedure: A dried glass reaction tube equipped with a magnetic stir bar was charged with 1a (1.5 mmol, 3.0 equiv), Na2S2O8 (0.5 mmol, 1.0 equiv) and AgNO3 (0.15 mmol, 0.3 equiv), 2a (0.5 mmol, 1.0 equiv), DCM:H2O = 1:1 (4.0 mL). The resulting mixture was then stirred at 25C for 0.5 h. The crude production was diluted with EA and Na2CO3 aqueous solution (1 mol/L) and then the resulting mixture was filtered through a pad of Celite. The filtrate was extracted with Na2CO3 aqueous solution (1 mol/L, 20 mL), and the aqueous layer was extracted with EA (3 × 10 mL). The combined organic layers dried over anhydrous Na2SO4, concentrated in vacuo, and purified by flash column chromatograph to give the pure products. The products were characterized by 1H NMR, 13C NMR, LC-MS. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In ethanol; water; toluene; for 3h;Reflux; | General procedure: 9-(naphthalen-2-yl)anthracen-10-yl-10-boronic acid(1.7 mmol) and the corresponding aryl bromides(1.4 mmol), Pd(PPh34 (0.06 mmol), aqueous 2.0 M Na2CO3 (7 mL), ethanol, and toluene were mixed in aflask. The mixture was refluxed for 3 h. After the reactionwas completed, water was added to quench the reaction.After being cooled, the solutions were extracted twice withethyl acetate. The combined organic solution layers werewashed with brine and MgSO4. After filtration and concentrationthe solvents, the crude solutions were purified bycolumn chromatography (silica gel, hexane: ethyl acetate)and recrystallization with ethanol and dichloromethane. |
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