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Chemical Structure| 856422-41-8 Chemical Structure| 856422-41-8

Structure of 856422-41-8

Chemical Structure| 856422-41-8

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Product Details of [ 856422-41-8 ]

CAS No. :856422-41-8
Formula : C26H36BNO2
M.W : 405.38
SMILES Code : CC1(C)C(C)(C)OB(C2=CC3=C(C=C2)N(CC(CC)CCCC)C4=C3C=CC=C4)O1
English Name :9-(2-Ethylhexyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole
MDL No. :MFCD31618140

Safety of [ 856422-41-8 ]

Application In Synthesis of [ 856422-41-8 ]

* 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 [ 856422-41-8 ]

[ 856422-41-8 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 15155-41-6 ]
  • [ 856422-41-8 ]
  • [ 1505514-93-1 ]
YieldReaction ConditionsOperation in experiment
30% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran at 70 - 80℃; for 24h; Inert atmosphere; 3.4. General synthesis of the precursors 1a, 2a, 3a, 4a, 5a and 6a General procedure: Compounds 1a, 2a, 3a, 4a, 5a were synthesized from 4,7-dibromobenzo[c][1,2,5]thiadiazole reaction with N-phenylcarbazoleboronic ester using Suzuki coupling reaction. Method described for 1a was used for rest of the compounds. A stirred mixture of 4,7-dibromobenzo[c][1,2,5]thiadiazole (0.293 g, 1 mmol), 1 (0.368 g, 1 mmol), Pd(PPh3)4 (60 mg, 0.05 mmol), K2CO3 (2 M, 5 mL) in THF (20 mL) was heated at 70-80 °C under N2 atmosphere for 24 h. When the reaction was complete, water was added to quench the reaction. The product was extracted with dichloromethane. The organic layer was collected, dried over anhydrous Na2SO4 and concentrated to dryness. The solid was adsorbed on silica and purified by column chromatography using a mixture of dichloromethane-hexane (1:4) as eluent to give 1a, yellow solid (186mg, 40% yield).
  • 2
  • [ 856422-41-8 ]
  • [ CAS Unavailable ]
  • [ 1367370-96-4 ]
YieldReaction ConditionsOperation in experiment
85.2% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; toluene for 24h; Inert atmosphere; Reflux; 2.2.4 Synthesis of L1 General procedure: Up to 0.909g (1.5mmol) 7, 1.12g (3.0mmol) 4, and 3mL of 2M sodium carbonate solution were added to the solvent containing 30mL toluene and 15mL ethanol. After degassing with argon, 0.069g Pd(PPh3)4 was added. The mixture was refluxed for 24h under argon, and then 10mL water was added after the solution cooled. The aqueous layer was extracted with dichloromethane three times and dried with anhydrous magnesium sulfate. The product was purified by silica-gel column chromatography using dichloromethane/petroleum ether (1/9) as the eluent and dried in vacuum to yield a white powder (1.03g, 73.9%).
  • 3
  • [ 61676-62-8 ]
  • [ 628336-85-6 ]
  • [ 856422-41-8 ]
YieldReaction ConditionsOperation in experiment
89% Stage #1: 3-bromo-9-(2-ethylhexyl)-9H-carbazole With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 2h; Inert atmosphere; Stage #2: 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In tetrahydrofuran; hexane at 20℃; Inert atmosphere;
With n-butyllithium In tetrahydrofuran
With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 24h;
Stage #1: 3-bromo-9-(2-ethylhexyl)-9H-carbazole With n-butyllithium In tetrahydrofuran; hexane at -80 - 20℃; for 2h; Inert atmosphere; Stage #2: 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In tetrahydrofuran; hexane at -80 - 20℃; for 12h; Inert atmosphere; 2.3.9 Boronic acid pinacol ester derivatives (9) General procedure: Solvents and glasswares used in this experiment are dried thoroughly prior to use. The typical experimental procedure is given below: The THF (100mL) solution of compounds 4, 6 or 8 is degassed, cooled to -80°C followed by the dropwise addition of n-BuLi in n-hexane (2.5M, 1.2eq.) under stirring within 1h. Then, the liquid nitrogen/ethyl acetate bath is removed to continue the reaction at room temperature for another 1h. Afterwards, being cooled down to -80°C again, 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1eq.) is added dropwise by syringe to this anhydrous and anaerobic system. The reaction temperature is allowed to return to room temperature under stirring for 12h and subsequently terminated by distilled water. Ethyl ether is used to extract the product from water layer, followed by being dried over anhydrous MgSO4. After the solvent is removed, the residual is purified by column chromatography (silica-gel, the ratio of elution will be respectively shown as below).

  • 4
  • [ 1193092-32-8 ]
  • [ 856422-41-8 ]
  • [ 1641586-76-6 ]
YieldReaction ConditionsOperation in experiment
71% With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate In tetrahydrofuran; water at 80℃; for 24h; Inert atmosphere; 2.3.1 3,6-((Di(N-(2-ethylhexyl)-1,8-naphthalimide)-4-yl)-9-metyl-9H-carbazole (5) General procedure: 4-Bromo-N-(2-ethylhexyl)-1,8-naphthalimide (4) (0.5 g, 1.29 mmol) and 15 mL of dry THF and aqueous K2CO3 solution (0.81 g, 5.85 mmol) in 2 mL H2O were added via a syringe under nitrogen to a three-necked round-bottomed flask (50 mL) equipped with a magnetic stirrer, a reflux condenser and a nitrogen input tube. 9-Methyl-3,6-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)-9H-carbazole (3a) (0.25 g, 0.59 mmol) and Pd(PPh3)2Cl2 (0.02 g, 0.02 mmol) were successively added and the reaction mixture was refluxed at 80 °C for 24 h under nitrogen atmosphere. After cooling down to the room temperature methylene chloride (200 mL) was added to the reaction mixture. Then it was washed three times with distilled water, and dried with anhydrous magnesium sulfate. The solution was filtered and concentrated. The crude product was purified by column chromatography on silica gel with ethyl acetate and hexane (1:9, V:V) as eluent and crystallized from the eluent mixture of solvents to give 5 as yellow crystals.
  • 5
  • [ 628336-85-6 ]
  • [ 73183-34-3 ]
  • [ 856422-41-8 ]
YieldReaction ConditionsOperation in experiment
87.24% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 60℃; for 12h; 1 7.7 g of compound (b) (21.48 mmol) and 8.18 g of bis (pinacolato) diboron,32.23 mmol) were dissolved in 1,4-dioxane,4.21 g of potassium acetate (42.97 mmol),0.3 g of pd (dppf) Cl2 was added.After heating for 12 hours at 60 ° C, the reaction was allowed to cool to room temperature,And extracted three times with water and ether.The water in the organic layer was removed using MgSO4 (magnesium sulfate), and the purified compound (c) was obtained using a silica column. (Yield: 87.24%).
65% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In N,N-dimethyl-formamide at 80℃; Inert atmosphere;
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,4-dioxane at 80℃; for 18h;
 

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