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[ CAS No. 628336-95-8 ]

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2D
Chemical Structure| 628336-95-8
Chemical Structure| 628336-95-8
Structure of 628336-95-8 *Storage: {[proInfo.prStorage]}

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Product Details of [ 628336-95-8 ]

CAS No. :628336-95-8MDL No. :MFCD20528097
Formula : C30H43B2NO4 Boiling Point : -
Linear Structure Formula :-InChI Key :N/A
M.W :503.29Pubchem ID :-
Synonyms :

Computed Properties of [ 628336-95-8 ]

TPSA : - H-Bond Acceptor Count : -
XLogP3 : - H-Bond Donor Count : -
SP3 : - Rotatable Bond Count : -

Safety of [ 628336-95-8 ]

Signal Word:WarningClass:N/A
Precautionary Statements:P261-P305+P351+P338UN#:N/A
Hazard Statements:H302-H315-H319-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 628336-95-8 ]

  • Downstream synthetic route of [ 628336-95-8 ]

[ 628336-95-8 ] Synthesis Path-Downstream   1~8

  • 1
  • [ 150623-72-6 ]
  • [ 61676-62-8 ]
  • [ 628336-95-8 ]
YieldReaction ConditionsOperation in experiment
64% Stage #1: 3,6-dibromo-9-hexyl-9H-carbazole With n-butyllithium In tetrahydrofuran at -78℃; for 2h; Stage #2: 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In tetrahydrofuran at -78 - 20℃;
  • 2
  • [ 25015-63-8 ]
  • [ 156972-66-6 ]
  • [ 628336-95-8 ]
YieldReaction ConditionsOperation in experiment
44% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; triethylamine In 1,4-dioxane at 90℃; Inert atmosphere;
  • 3
  • [ 628336-95-8 ]
  • [ 1519104-49-4 ]
  • [ 1519104-41-6 ]
YieldReaction ConditionsOperation in experiment
23% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,2-dimethoxyethane; water for 18h; Inert atmosphere; Reflux;
  • 4
  • [ 150623-72-6 ]
  • [ 73183-34-3 ]
  • [ 628336-95-8 ]
YieldReaction ConditionsOperation in experiment
94% With palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; anhydrous potassium acetate In 1,4-dioxane at 90℃; for 16h; 5.1; 6.1 (1) Compound 3,6-dibromo-9-hexyl-9H-carbazole (0.82g, 2mmol), pinacol biboronate (1.53g, 6mmol), Pd(dppf) were added to a 50mL Schlenk reaction tube Cl2 (42 mg, 0.06 mmol), potassium acetate (1.18 g, 12 mmol) and anhydrous 1,4-dioxane (15 mL), followed by three pumpings, and reacted at 90° C. for 16 hours under nitrogen atmosphere. After the reaction was completed, the reaction solution was cooled to room temperature, then 50 mL of water was added to the reaction solution, and the aqueous phase was extracted three times with dichloromethane. After the organic phase was dried over anhydrous Na2SO4, the solvent was removed by distillation under reduced pressure. The crude product was purified by column chromatography (petroleum ether:ethyl acetate=25:1 as eluent) to give 9-hexyl-3,6-bis(4,4,5,5-tetramethyl- 1,3,2-Dioxaboran-2-yl)-9H-carbazole (0.95 g, 94% yield).
72% With anhydrous potassium acetate; palladium (II) chloride In N,N-dimethyl-formamide at 110℃; for 24h;
60% With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); anhydrous potassium acetate In dimethyl sulfoxide at 85℃; for 12h; Inert atmosphere; 3 Synthesis of compound 11 Under the protection of an inert gas, in a 50 mL Shrek bottle which has been cooled by high temperature baking,Compound 10 (1.2 g, 2.9 mmol) and B2Pin2 (1.4 g, 5.6 mmol (1.9-fold amount)) were added in this order,Pd (PPh3) 2Cl2 (0.06 times the amount) and KOAc (6 times the amount),And DMSO (20 mL) was added as a solvent. The mixture was heated to 85 ° C. and reacted for 12 h.After the reaction is completed, the reaction system is cooled to room temperature, filtered to remove insoluble matters, and washed with chloroform.The reaction mixture was then washed with deionized water (3 x 50 mL), the organic layer was collected and dried over anhydrous sodium sulfate, and filtered with suction.After removing the solvent in vacuo, the crude product was purified by column separation (eluent: hexane to hexane / dichloromethane = 2/1 to 1/1 as eluent),870 mg of a white solid were obtained with a yield of 60%.
59.6% With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); anhydrous potassium acetate In dimethyl sulfoxide at 85℃; for 12h;
With palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; anhydrous potassium acetate In N,N-dimethyl-formamide at 60℃; Inert atmosphere; 2 Will M3 (7mmol, 2.856g),Bornazolium diborate (15mmol, 3.8g),Potassium acetate (2g) and 50mLThe N,N-dimethylformamide solvent was added to a 250 mL two-necked flask.Stir slowly at room temperature, vacuum through nitrogen,Under a nitrogen atmosphere,Add 1,1'-bis(di-phenylphosphino)ferrocene palladium dichloride (Pd(dppf)Cl2) (548 mg),Continue to vacuum and pass nitrogen, slowly warming to 60 ° C,After the reaction was completed, the reaction was stopped and cooled to room temperature.Extract with water and dichloromethane,The organic layer was collected, and an appropriate amount of anhydrous magnesium sulfate was added to remove excess water and filtered.After the liquid is concentrated by spin drying,Purification by column chromatography gave product M4.
With anhydrous potassium acetate; Pd(II)(dppf) In N,N-dimethyl-formamide for 12h; Inert atmosphere; Reflux; Sealed tube; 2.3. 9-Hexyl-3, 6-bis(4,4,5,5 tetramethyl-1,3,2-dioxoborolan-2-yl) -2-yl)-9H-carbazole (HCOB) (3) Compound 3 was synthesized by following the Miyauraboryla- tion reaction [26] . The reaction was accomplished in a round bot- tom flask fitted with a condenser and closed with a septum. The set-up was evacuated and nitrogen purged. A nitrogen atmosphere was maintained until the completion of the reaction. 3, 6-dibromo- 9-hexyl-9H-carbazole (100 mg, 0.246 mM), bis(pinacoloto)diboron (16.17 mg, 2.5 eq), potassium acetate (72.6 mg, 3 eq) were charged to the reaction chamber. Pd(II)(dppf) (0.05 eq.) was used as the catalyst. Dimethylformamide was used as the solvent. The reaction was allowed to reflux in a nitrogen atmosphere for 12 h. Then, the reaction was monitored with TLC. Finally, the crude product was extracted with DCM and further purified with column chromatog- raphy. FT-IR (KBr, cm -1 ): 3424, 2974 (aromatic CH), 2846 (m, aliphatic CH), 1621 (aromatic C = C), 1447 (m, C-H bend, alkane), 1378 (B-C), 1330 (B-O), 1123 (C-O), 807, 836 (aromatic C-H bend- ing). 1 H NMR (500 MHz, CDCl 3, ppm) 8.66 (s, 2H), 7.90 (d, J = 8.2 Hz, 2H), 7.39 (d, J = 8.2 Hz, 2H), 4.30 (t, J = 7.2 Hz, 2H), 1.88 -1.81 (m, 2H), 1.39 (s, 24H), 1.30 -1.23 (m, 6H), 0.84 (t, J = 6.9 Hz, 3H). 13 C NMR (126 MHz, CDCl 3, ppm) 139.13, 129.35, 123.44, 123.25, 112.06, 110.17, 71.21, 43.53, 32.82, 30.97, 29.35, 28.79, 26.87, 26.23, 22.74, 13.9. (See supporting information, Figure S1, S4, S5). Cross peaks of the coupling are marked in the COSY spectrum (S13).

  • 5
  • [ 4701-17-1 ]
  • [ 628336-95-8 ]
  • [ 1383124-67-1 ]
YieldReaction ConditionsOperation in experiment
77% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,2-dimethoxyethane; water at 100℃; for 24h;
  • 6
  • [ 6825-20-3 ]
  • [ 628336-95-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tetrabutylammomium bromide; potassium hydroxide / toluene; water 2: palladium dichloride; potassium acetate / N,N-dimethyl-formamide / 24 h / 110 °C
  • 7
  • [ 111-25-1 ]
  • [ 628336-95-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tetrabutylammomium bromide; potassium hydroxide / toluene; water 2: palladium dichloride; potassium acetate / N,N-dimethyl-formamide / 24 h / 110 °C
Multi-step reaction with 3 steps 1.1: potassium hydroxide / N,N-dimethyl-formamide / 1 h / 20 °C 1.2: 48 h / 20 °C 2.1: N-Bromosuccinimide / chloroform / 40 °C 3.1: potassium acetate; bis-triphenylphosphine-palladium(II) chloride / dimethyl sulfoxide / 12 h / 85 °C
Multi-step reaction with 3 steps 1.1: potassium hydroxide / N,N-dimethyl-formamide / 1 h / 20 °C 1.2: 48 h / 20 °C 2.1: N-Bromosuccinimide / chloroform / 12 h / 40 °C 3.1: bis-triphenylphosphine-palladium(II) chloride; potassium acetate / dimethyl sulfoxide / 12 h / 85 °C / Inert atmosphere
  • 8
  • [ 628336-95-8 ]
  • [ 1261172-47-7 ]
  • C90H107N3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; toluene at 110℃; Inert atmosphere; 2 M1 (2 mmol, 1, 141 g), M4 (1 mmol, 409 mg),2M potassium carbonate aqueous solution (10 mL) and 50 mL of toluene solvent were added to a 250 mL two-necked flask.Stir slowly at room temperature, vacuum through nitrogen,Under a nitrogen atmosphere,Add tetrakis(triphenylphosphine)palladium (Pd(pph3)4) (115mg),Continue to vacuum and pass nitrogen gas, and slowly heat up to 110 ° C reflux.After the reaction was completed, the reaction was stopped and cooled to room temperature.Extract with water and dichloromethane and collect the organic layer.Add an appropriate amount of anhydrous magnesium sulfate to remove excess water and filter.After the liquid was concentrated by spin-drying, it was separated and purified by a chromatography column to obtain a final product.
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