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[ CAS No. 258865-48-4 ]

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Chemical Structure| 258865-48-4
Chemical Structure| 258865-48-4
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Product Details of [ 258865-48-4 ]

CAS No. :258865-48-4 MDL No. :MFCD03701608
Formula : C29H44B2O4 Boiling Point : 670.8°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :478.28 g/mol Pubchem ID :-
Synonyms :

Safety of [ 258865-48-4 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 258865-48-4 ]

  • Downstream synthetic route of [ 258865-48-4 ]

[ 258865-48-4 ] Synthesis Path-Downstream   1~15

  • 1
  • [ 198964-46-4 ]
  • [ 258865-48-4 ]
  • poly(9,9-dioctylfluorene), Mn: 7.9, Mw: 13.7, PDI: 1.73, DP: 20.3; Tg: 51 deg C; monomer(s): 2,7-dibromo-9,9-dioctylfluorene; 9,9-dioctylfluorene-2,7-diboronic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate In toluene Heating; Suzuki coupling;
  • 2
  • [ 198964-46-4 ]
  • [ 258865-48-4 ]
YieldReaction ConditionsOperation in experiment
80% Stage #1: 2,7-dibromo-9,9-dioctylfluorene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 4.5h; Inert atmosphere; Stage #2: With Triisopropyl borate In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere;
65% Stage #1: 2,7-dibromo-9,9-dioctylfluorene With n-butyllithium In diethyl ether at -78 - 20℃; Stage #2: With Triisopropyl borate In diethyl ether at 20℃; for 20h; Stage #3: With hydrogenchloride In diethyl ether at 20℃; for 1h;
31% Stage #1: 2,7-dibromo-9,9-dioctylfluorene With iodine; magnesium In tetrahydrofuran Heating; Stage #2: With triethyl borate In tetrahydrofuran at 20℃; for 48h; Further stages.;
Stage #1: 2,7-dibromo-9,9-dioctylfluorene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2h; Stage #2: With Triisopropyl borate In tetrahydrofuran; hexane at -78 - 20℃; Stage #3: With hydrogenchloride In tetrahydrofuran; hexane; water
Multi-step reaction with 2 steps 1.1: Mg; iodine / tetrahydrofuran 1.2: tetrahydrofuran / -78 - 20 °C 2.1: 4.3 g / aq. H2SO4 / cooling
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere 1.2: 1 h / -78 °C 2.1: hydrogenchloride / tetrahydrofuran; hexane

  • 3
  • [ 258865-48-4 ]
  • [ 428865-64-9 ]
  • poly[(9,9-dioctylfluorene-2,7-diyl)3-alt-([1,3,4]oxadiazol-2,5-diyl)], copolymer, Mn: 25.1 kDa, Mw: 62.8 kDa, PDI: 2.50, DP: 20.4; monomer(s): 2,5-bis(9,9-dioctylfluorene-7,7-Br2-2,2ddiyl)-[1,3,4]oxadiazole; 9,9-dioctylfluorene-2,7-di[B(OH)2] [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% With sodium carbonate In toluene Heating; Suzuki coupling;
  • 4
  • [ 258865-48-4 ]
  • [ 428865-65-0 ]
  • poly[(9,9-dioctylfluorene-2,7-diyl)3-co-([1,3,4]oxadiazol-1,5-diyl)-co-(9,9-dioctylfluorene-2,7-diyl)-co-([1,3,4]-oxadiazol-1,5-diyl)], asymmetric copolymer, Mn: 30.4 kDa, Mw: 82.0 kDa, PDI: 2.70, DP: 18.8 [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With sodium carbonate In toluene Heating; Suzuki coupling;
  • 6
  • C33H52B2O4 [ No CAS ]
  • [ 258865-48-4 ]
YieldReaction ConditionsOperation in experiment
4.3 g With sulfuric acid cooling;
  • 7
  • [ 86-73-7 ]
  • [ 258865-48-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: 85 percent / KOH / tetrahydrofuran / 20 °C 2.1: ferric chloride; bromine / CHCl3 / 3 h / 20 °C 3.1: Mg; iodine / tetrahydrofuran 3.2: tetrahydrofuran / -78 - 20 °C 4.1: 4.3 g / aq. H2SO4 / cooling
Multi-step reaction with 3 steps 1.1: n-BuLi / hexane; tetrahydrofuran / 0.75 h / -78 °C 1.2: hexane; tetrahydrofuran / -78 - 20 °C 2.1: Br2; I2 / CH2Cl2 / 20 h / 20 °C 3.1: n-BuLi / diethyl ether / -78 - 20 °C 3.2: triisopropyl boronate / diethyl ether / 20 h / 20 °C 3.3: 65 percent / aq. HCl / diethyl ether / 1 h / 20 °C
  • 8
  • [ 111-83-1 ]
  • [ 258865-48-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: 85 percent / KOH / tetrahydrofuran / 20 °C 2.1: ferric chloride; bromine / CHCl3 / 3 h / 20 °C 3.1: Mg; iodine / tetrahydrofuran 3.2: tetrahydrofuran / -78 - 20 °C 4.1: 4.3 g / aq. H2SO4 / cooling
  • 9
  • [ 123863-99-0 ]
  • [ 258865-48-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: ferric chloride; bromine / CHCl3 / 3 h / 20 °C 2.1: Mg; iodine / tetrahydrofuran 2.2: tetrahydrofuran / -78 - 20 °C 3.1: 4.3 g / aq. H2SO4 / cooling
Multi-step reaction with 2 steps 1.1: Br2; I2 / CH2Cl2 / 20 h / 20 °C 2.1: n-BuLi / diethyl ether / -78 - 20 °C 2.2: triisopropyl boronate / diethyl ether / 20 h / 20 °C 2.3: 65 percent / aq. HCl / diethyl ether / 1 h / 20 °C
  • 10
  • [ 111-83-1 ]
  • [ 258865-48-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: n-BuLi / hexane; tetrahydrofuran / 0.75 h / -78 °C 1.2: hexane; tetrahydrofuran / -78 - 20 °C 2.1: Br2; I2 / CH2Cl2 / 20 h / 20 °C 3.1: n-BuLi / diethyl ether / -78 - 20 °C 3.2: triisopropyl boronate / diethyl ether / 20 h / 20 °C 3.3: 65 percent / aq. HCl / diethyl ether / 1 h / 20 °C
Multi-step reaction with 2 steps 1.1: sodium hydride / tetrahydrofuran / 60 °C 1.2: 75.3 percent / tetrahydrofuran / Heating 2.1: magnesium; iodine / tetrahydrofuran / Heating 2.2: 31 percent / triethyl borate / tetrahydrofuran / 48 h / 20 °C
  • 11
  • [ 16433-88-8 ]
  • [ 258865-48-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium hydride / tetrahydrofuran / 60 °C 1.2: 75.3 percent / tetrahydrofuran / Heating 2.1: magnesium; iodine / tetrahydrofuran / Heating 2.2: 31 percent / triethyl borate / tetrahydrofuran / 48 h / 20 °C
Multi-step reaction with 2 steps 1.1: potassium hydroxide; potassium iodide / dimethyl sulfoxide / 20 °C 2.1: n-butyllithium / tetrahydrofuran / -78 °C 2.3: 1 h
  • 12
  • [ 110046-60-1 ]
  • [ 258865-48-4 ]
  • [ 1446101-17-2 ]
YieldReaction ConditionsOperation in experiment
67.4% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In water; N,N-dimethyl-formamide for 4h; Reflux; Inert atmosphere; 6 Synthesis of Compound (6) EXAMPLE 6 Synthesis of Compound (6) The synthesis of Compound (6) was carried out in accordance with Scheme 6 indicated hereunder: For this purpose, a mixture of 9, 9-dioctylfluorene- 2, 7-diboronic acid (1450 mg, 3.04 mmoles) , Compound (5) (1500 mg, 5.52 mmoles) and palladium (tetrakis ) - triphenylphosphine [Pd(Ph3P)4] (176 mg, 0.152 mmoles), in N, -dimethylformamide (N, -DMF) (140 ml) and sodium carbonate (Na2C03) (10 ml of an aqueous solution 2 M) , was heated to reflux temperature for 4 hours, under a stream of argon. The reaction mixture was left to cool to room temperature (25°C) , 100 ml of distilled water were added and the whole mixture was then filtered, obtaining a solid which was recovered. The solid thus obtained was partially dissolved in ethyl acetate (100 ml), subsequently filtered and the liquid phase obtained was concentrated under vacuum obtaining a reaction raw product. The reaction raw product thus obtained was purified by means of column chromatography [silica gel, gradients from n-heptane 100% to n-heptane/ethyl acetate = 8:2 (v/v) as eluent] obtaining 1060 mg (67.4% in moles) of Compound (6). Said Compound (6) was characterized by means of 1H- NMR (400 MHz, CDC13) obtaining the following spectrum: δ = 9.90 ppm (s, 1H, -CHO) ; 7.75-7.72 ppm (d, 2H, Hm-CH- Th) ; 7.72-7.70 ppm (d, 2H, Th-CH-CH-CHO) ; 7.66-7.62 ppm (q, 2H, Hm-CH-Th) ; 7.59-7.57 ppm (d, 2H, Ho-Th) ; 7.41- 7.39 ppm (d, 2H, CH-CH-Th-CHO) ; 7.38-7.36 ppm (d, 2H, CH-CH-Th-CHO); 2.10-2.03 ppm (m, 4H, C- (CH2) 2- (CH2) 12- CH3), 1.22-1.04 ppm (m, 24H, C- (CH2) 2- (C) 12-CH3) ; 0.84- 0.76 ppm (t, 6H, C- (CH2) 2- (CH2) 12-CH3_) . Said Compound (6) was also characterized by means of IR ( Br) spectrum showing the following bands: v = 1662 cm-1 (aldehyde C-0 stretching) ; 1515 cm"1 (ring mode of the thiophenes), 795 cm-1 (deformation conjugated dithienyls) .
  • 13
  • [ 4701-17-1 ]
  • [ 258865-48-4 ]
  • [ 1445721-14-1 ]
YieldReaction ConditionsOperation in experiment
57.9% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In water; N,N-dimethyl-formamide for 4h; Reflux; Inert atmosphere; 1 Synthesis of Compound (1) Synthesis of Compound (1) The synthesis of Compound (1) was carried out in accordance with Scheme 1 indicated hereunder: Compound (1) heme 1 For this purpose, a mixture of 9, 9-dioctylfluorene- 2 , 7-diboronic acid (730 mg, 1.52 mmoles) , 5-bromo-2- thiophene carbaldehyde (530 mg, 2.76 mmoles), and palladium (tetrakis) triphenylphosphine [Pd(Ph3P)4] (36 mg, 0.03 mmoles), in N, N-dimethylformamide (N,N-DMF) (15 ml) and sodium carbonate (Na2C03) (2 ml of an aqueous solution 2 M) , was heated to reflux temperature for 4 hours, under a stream of argon. The reaction mixture was left to cool to room temperature (25°C), 100 ml of distilled water were added and the whole mixture was then filtered, obtaining a solid which was recovered . The solid thus obtained was partially dissolved in ethyl acetate (100 ml), subsequently filtered and the liquid phase obtained was concentrated under vacuum obtaining a reaction raw product. The reaction raw product thus obtained was purified by means of column chromatography [silica gel, gradients from n-heptane 100% to n- heptane/ethyl acetate = 8:2 (v/v) as eluent] obtaining 537 mg (57.9% in moles) of Compound (1). Said Compound (1) was characterized by means of ""- NMR (400 MHz, CDC13) obtaining the following spectrum: δ = 9.93 ppm (s, 2H, -CHO) ; 7.80-7.75 ppm (m, 4H, H^-CH-Th + Ph-CH-CH-CHO) ; 7.72 - 7.70 ppm (q, 2H, Hm-CH-T.h) ; 7.67 - 7.63 ppm (d, 2H, Ho~Th) ; 7.52-7.49 ppm (d, 2H, Ph-CH- CH-CHO) ; 2.10-2.03 ppm (m, 4H, C- (C) 2- (CH2) 12-CH3) ; 1.22-1.04 ppm (m, 24H, C- (CH2) 2- (CH2) 12-CH3) ; 0.84-0.76 ppm (t, 6H, C- (CH2)2- (CH2) 12-CH3) . Said Compound (1) was also characterized by means of IR (KBr) spectrum showing the following bands: v = 1660 cm"1 (aldehyde C-0 stretching) ; 1527 cm"1 (thienyl stretching) .
  • 14
  • [ 1448344-15-7 ]
  • [ 258865-48-4 ]
  • [ 1448344-16-8 ]
YieldReaction ConditionsOperation in experiment
65% With tris-(dibenzylideneacetone)dipalladium(0); potassium carbonate; tris-(o-tolyl)phosphine In tetrahydrofuran; water at 80℃; for 72h; Inert atmosphere;
  • 15
  • [ 126-30-7 ]
  • [ 258865-48-4 ]
  • 2,7-bis(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-9,9-dioctylfluorene [ No CAS ]
YieldReaction ConditionsOperation in experiment
1.12 g In toluene for 6h; Reflux; Dean-Stark;
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