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Chemical Structure| 856422-44-1 Chemical Structure| 856422-44-1

Structure of 856422-44-1

Chemical Structure| 856422-44-1

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Product Details of [ 856422-44-1 ]

CAS No. :856422-44-1
Formula : C23H29BO2
M.W : 348.29
SMILES Code : CC1(C)C(C)(C)OB(C2=CC(C(CC)(CC)C3=C4C=CC=C3)=C4C=C2)O1
English Name :2-(9,9-Diethyl-9H-fluoren-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
MDL No. :MFCD35125807

Safety of [ 856422-44-1 ]

Application In Synthesis of [ 856422-44-1 ]

* 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 [ 856422-44-1 ]

[ 856422-44-1 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 61676-62-8 ]
  • [ 287493-15-6 ]
  • [ 856422-44-1 ]
YieldReaction ConditionsOperation in experiment
61% Stage #1: 2-bromo-9,9-diethyl-9H-fluorene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2h; Inert atmosphere; Stage #2: 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere;
With n-butyllithium at -78℃;
With n-butyllithium In tetrahydrofuran at -78 - 20℃; Inert atmosphere;
  • 2
  • [ 856422-44-1 ]
  • [ 128406-10-0 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
70% With tetrakis(triphenylphosphine) palladium(0); tetrabutylammomium bromide; sodium hydroxide In tetrahydrofuran at 80 - 90℃; Inert atmosphere; Darkness;
  • 3
  • [ 856422-44-1 ]
  • [ 30363-03-2 ]
  • [ 1261082-35-2 ]
YieldReaction ConditionsOperation in experiment
35% With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate In tetrahydrofuran; water at 80℃; Inert atmosphere; 1 2.1.1. General procedure for Suzuki-Miyaura reactions General procedure: 2,4,6-Tris(4-bromophenyl)-1,3,5-triazine (300 mg, 0.55 mmol) and the respective mono boronic acid pinacol esters (3.2 molar eq.) were dissolved in a solvent mixture of THF (20 mL) and water (2 mL). Powdered potassium carbonate (5 molar eq.) was added and the reaction mixture was purged with nitrogen for 5 min. The reaction mixture was degassed and then, again purged with nitrogen. Bis (triphenylphosphine) palladium (II) dichloride (0.06 molar eq.) was added and stirred for 10-12 h at 80 °C under nitrogen. The reaction mixture was cooled, diluted with water and extracted using ethyl acetate. The organic layer was dried over sodium sulphate and evaporated under reduced pressure. The crude product was purified by column chromatography using silicagel as stationary phase. The solvent mixture of hexane and ethyl acetate in a volume ratio of 96:4 for 1; 1:1 for 2 and chloroform for 3 were used as eluents. Compound 1 was further purified by recrystallization from methanol after column chromatography. 2.1.1.1 2,4,6-Tris(4-(9,9-diethyl-9H-fluoren-2-yl)phenyl)-1,3,5-triazine (1) Yield = 35% (186 mg); White crystals (FW = 970.33 g/mol). Mp: 253-254 °C. 1H NMR (300 MHz, CDCl3, δ ppm): 8.93 (d, J = 2.8 Hz, 6H), 7.93 (d, J = 2.8 Hz, 6H), 7.85 (d, J = 2.7 Hz, 3H), 7.79-7.69 (m, 10H), 7.40-7.34 (m, 8H), 2.16-2.08 (m, 12H, CH2), 0.41 (t, J = 4.9 Hz, 18H, CH3). IR (KBr, υ cm-1): (arene C-H) 3061; (aliphatic C-H) 2961, 2919, 2874; (Ar C=C) 1606, 1580. Anal. Calc. for C72H63N3: C, 89.13; H, 6.54; N, 4.33%. Found: C, 88.94; H, 6.78; N, 4.43%. MS (MALDI-TOF) m/z = 969.41 (exact mass = 969.5).
 

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