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[ CAS No. 476360-83-5 ] {[proInfo.proName]}

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Chemical Structure| 476360-83-5
Chemical Structure| 476360-83-5
Structure of 476360-83-5 * Storage: {[proInfo.prStorage]}
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Product Details of [ 476360-83-5 ]

CAS No. :476360-83-5 MDL No. :MFCD23703117
Formula : C32H47B2NO4 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 531.34 Pubchem ID :-
Synonyms :

Safety of [ 476360-83-5 ]

Signal Word:Warning Class:
Precautionary Statements:P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330 UN#:
Hazard Statements:H302-H315-H319 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 476360-83-5 ]

* 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 [ 476360-83-5 ]

[ 476360-83-5 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 476360-83-5 ]
  • [ 60404-24-2 ]
  • [ 1374294-86-6 ]
  • 2
  • [ 476360-83-5 ]
  • [ 1193092-32-8 ]
  • 2,7-di((N-(2-ethylhexyl)-1,8-naphthalimide)-4-yl)-9-(2-ethylhexyl)-9H-carbazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
62% With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate In tetrahydrofuran; water at 80℃; for 16h; Schlenk technique; Inert atmosphere; 4 2,7-Di((N-(2-ethylhexyl)-1,8-naphthalimide)-4-yl)-9-(2-ethylhexyl)-9H-carbazole (DENC) 4-Bromo-N-(2-ethylhexyl)-1,8-naphthalimide (1a) (0.47 g, 1.21 mmol) and 9-(2-ethylhexyl)-2,7-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-diyl)-9H-carbazole (2a) (0.30 g, 0.55 mmol) were taken in a 100 mL Schlenk flask to which a solvent mixture of 20 mL of tetrahydrofuran (THF) and 2 mL of water was added. Powdered potassium carbonate (1.13 g, 8.19 mmol) was added and the reaction mixture was purged with nitrogen for 5 min. The reaction flask was degassed and then, again purged with nitrogen for 2 min. Bis(triphenylphosphine) palladium(II) dichloride (Pd(Ph3)2Cl2) (0.02 g, 0.03 mmol) was added into it and stirred for 16 h at 80 °C under nitrogen. The reaction mixture was allowed to cool down to the room temperature, diluted with water and extracted with ethyl acetate. The organic layers were dried over sodium sulphate and evaporated at reduced pressure. The product was purified by silica gel column chromatography using using an eluent mixture of hexane and ethyl acetate in a volume ratio of 10:1 to obtain DENC as yellow crystals. Yield = 62% (0.12 g); (FW = 910.26 g/mol); M.p. = 124-125 °C. 1H NMR spectrum (300 MHz, CDCl3, δ, ppm): 8.75 (d, 2H, J = 7.5 Hz, -HNaphthalimide), 8.71 (dd, 2H, J1 = 7.5 Hz, J2 = 1.2 Hz, -HNaphthalimide), 8.65 (dd, 1H, J1 = 1.2 Hz, J2 = 7.2 Hz, -HNaphthalimide), 8.46 (d, 1H, J = 1.2 Hz, -HNaphthalimide), 8.43 (d, 1H, J = 1.1 Hz, -HNaphthalimide), 8.36 (d, 2H, J = 7.9 Hz, -HNaphthalimide), 8.26 (dd, 1H, J1 = 1.1 Hz, J2 = 8.28 Hz, -HNaphthalimide) 7.90 (d, 1H, J = 7.9 Hz, -HCarbazole), 7.80-7.73 (q, 3H, -HCarbazole), 7.60 (s, 1H, -HCarbazole), 7.48 (dd, 1H, J1 = 1.2 Hz, J2 = 7.9 Hz, -HCarbazole), 4.28-4.18 (m, 4H, -NCH2Naphthalimide), 2.06-1.99 (m, 3H, -CHNaphthalimide, -CHCarbazole), 1.45-1.19 (m, 24H, -CH2Naphthalimide, -CH2Carbazole), 1.02-0.89 (m, 18H, -CH3Naphthalimide, CH3Carbazole). 13C NMR spectrum (75.4 MHz, CDCl3, δ, ppm): 162.6, 160.7, 148.6, 143.5, 142.4, 141.9, 138.6, 136.4, 135.4, 134.3, 133.2, 132.5, 131.2, 130.7, 130.2, 129.6, 128.2, 127.4, 126.6, 125.3, 124.6, 123.2, 122.5, 122.1, 121.5, 120.7, 118.4, 116.6, 115.1, 109.6, 106.8, 103.2, 64.4, 45.3, 38.4, 37.7, 36.3, 33.2, 28.3, 26.1, 25.2, 23.2, 18.3, 13.3, 10.7. IR, (in KBr), cm-1: (arene C-H) 3055; (aliphatic C-H) 2942, 2914; (imide C=Osymmetric) 1698; (imide C=Oasymmetric) 1664; (Ar C=C) 1577, 1518; (imide C-N) 1353, 1268; (Ar C-H) 786, 753, 612. MS (APCI+, 20 V), m/z: 911 ([M + H]+). Anal. Calcd. for C61H71N3O4: C, 80.49; H, 7.86, N, 4.62; O, 7.03%; found C 80.52, H 7.81, N 4.67%.
  • 3
  • [ 476360-83-5 ]
  • [ 344-04-7 ]
  • 4,7-bis(2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)benzo-[c][1,2,5]thiadiazole [ No CAS ]
  • C70H56F10N4O4S3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% Stage #1: N-(2-ethylhexyl)-2,7-bis(4′,4′,5′,5′-tetramethyl-1′,3′,2′-dioxaboralan-2′-yl)-9H-carbazole; 4,7-bis(2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)benzo-[c][1,2,5]thiadiazole With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In water; toluene for 48h; Inert atmosphere; Reflux; Stage #2: bromopentafluorobenzene In water; toluene for 24h; Inert atmosphere; Reflux; via Suzuki coupling: General procedure: Di-Br-di-thien-BTZ (50.00mg, 0.11mmol, 1 eq) and di-boronic ester-EH-carbazole (462.00mg, 0.09mmol, 8 eq) were dissolved in 10mL of degassed toluene, in a round bottom flask equipped with a stir bar and a reflux condenser, under inert atmosphere, followed by the addition of 0.4mL Na2CO3 (aq. solution, 0.87mmol, 8 eq) and 7.6mgPd(PPh3)4 (6.00 μmol, 0.06 eq). The mixture was refluxed for 48h, cooled at RT and bromopentafluorobenzene (76 μL, 0.61mmol, 5.6 eq) was then added and stirred for another 24h under reflux. The mixture was cooled at RT, filtered and extracted using CHCl3 and H2O. The organic layer was dried over MgSO4, filtered and the solvent was removed in a rotary evaporator. The final product thus obtained, was dried under vacuum at 45°C for 18h. Yield 82%.
  • 4
  • [ 476360-83-5 ]
  • [ 344-04-7 ]
  • [ 288071-87-4 ]
  • C66H52F10N4S3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% Stage #1: N-(2-ethylhexyl)-2,7-bis(4′,4′,5′,5′-tetramethyl-1′,3′,2′-dioxaboralan-2′-yl)-9H-carbazole; 4,7-bis(5-bromothiophen-2-yl)benzo-2,1,3-thiadiazole With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In water; toluene for 48h; Inert atmosphere; Reflux; Stage #2: bromopentafluorobenzene In water; toluene for 24h; Inert atmosphere; Reflux; via Suzuki coupling: Di-Br-di-thien-BTZ (50.00mg, 0.11mmol, 1 eq) and di-boronic ester-EH-carbazole (462.00mg, 0.09mmol, 8 eq) were dissolved in 10mL of degassed toluene, in a round bottom flask equipped with a stir bar and a reflux condenser, under inert atmosphere, followed by the addition of 0.4mL Na2CO3 (aq. solution, 0.87mmol, 8 eq) and 7.6mgPd(PPh3)4 (6.00 μmol, 0.06 eq). The mixture was refluxed for 48h, cooled at RT and bromopentafluorobenzene (76 μL, 0.61mmol, 5.6 eq) was then added and stirred for another 24h under reflux. The mixture was cooled at RT, filtered and extracted using CHCl3 and H2O. The organic layer was dried over MgSO4, filtered and the solvent was removed in a rotary evaporator. The final product thus obtained, was dried under vacuum at 45°C for 18h. Yield 82%. 1H NMR (CDCl3, δ ppm): 0.83-1.03 (two t, 12H), 1.04-1.5 (three broad, 16H), 2.12 (m, 2H), 4.20 (m, 4H), 7.35 (d, 2H), 7.51 (d, 4H), 7.69 (s, 4H), 7.94 (s, 2H), 8.08 (d, 4H), 8.21 (d, 2H). 19F NMR (CDCl3, δ ppm):-142.82 to-143.02 (two m, 4F),-156.09 to-156.24 (m, 2F),-162.16 to-162.52 (m, 4F).
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