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Chemical Structure| 1174223-26-7
Chemical Structure| 1174223-26-7
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Product Details of [ 1174223-26-7 ]

CAS No. :1174223-26-7 MDL No. :N/A
Formula : C12H3Br3S3 Boiling Point : -
Linear Structure Formula :- InChI Key :QGROIEURFZUIHM-UHFFFAOYSA-N
M.W : 483.06 Pubchem ID :58400797
Synonyms :

Safety of [ 1174223-26-7 ]

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

Application In Synthesis of [ 1174223-26-7 ]

* 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 [ 1174223-26-7 ]

[ 1174223-26-7 ] Synthesis Path-Downstream   1~37

  • 1
  • [ 1174223-26-7 ]
  • [ 54663-78-4 ]
  • [ 1174223-31-4 ]
YieldReaction ConditionsOperation in experiment
48% With triphenylphosphine; palladium dichloride In N,N-dimethyl-formamide at 130℃; for 24h; Inert atmosphere;
  • 2
  • [ 1174223-26-7 ]
  • [ 175922-79-9 ]
  • [ 1174223-29-0 ]
YieldReaction ConditionsOperation in experiment
69% With triphenylphosphine; palladium dichloride In N,N-dimethyl-formamide at 130℃; for 24h; Inert atmosphere;
  • 3
  • [ 29150-63-8 ]
  • [ 1174223-26-7 ]
YieldReaction ConditionsOperation in experiment
76% With N-Bromosuccinimide; In dichloromethane; acetic acid; at 20℃; for 48h;Inert atmosphere; Darkness; Example 4 Synthesis of 2,5,8-Tribromobenzo[1,2-b:3,4-b':5,6-b"]trithiophene (33) [Show Image] Under a nitrogen atmosphere, in a 50 mL three-neck flask, benzo[1,2-b:4,5-b':5.6-b"]trithiophene (800 mg, 3.25 mmol) obtained in Synthesis Example 3, methylene chloride (22.7 mL) and acetic acid (5.7 mL) were added. Under light exclusion conditions, NBS (1.73 g, 9.74 mmol) was added little by little and stirred at room temperature 48 hours. After completion of the reaction, water (20 mL) was added. A precipitated solid substance was obtained by filtration and washed with ethanol (50 mL) and THF (20 mL) to obtain a light purple solid substance (1.2 g, 76%). 1H-NMR(270MHz,CDCl3)δ7.51(s,3H);M.S.(70eV,EI)m/z=484(M+)
52% With N-Bromosuccinimide; In chloroform; for 12h;Inert atmosphere; Reflux; General procedure: Under a nitrogen gas stream to IC-7-3 (14.5 g, 60.33 mmol) obtained in Step 2 and NBS (11.81 g, 66.36 mmol) in 200 ml of chloroform was refluxed for 12 hours. After the reaction was terminated by using MgSO4 and the organic layer was separated with methylene chloride to remove the water from the organic layer. After removing the solvent in water is removed, the organic layer was purified by column chromatography (Hexane: MC = 15: 1 (v / v)) to obtain the IC-7-2 (11.75 g, yield 61%). Instead of IC-7-3 (14.5 g, 60.33 mmol) and NBS (11.81 g, 66.36 mmol) the IC-12-3 (20 g, 81.18 mmol) and NBS (47.68To g, 267.89 mmol), and performs the same procedure of the Preparation Example 7 step 3 to obtain a IC-15-2 (20.39 g, yield 52%).
  • 4
  • [ 1174223-26-7 ]
  • [ 1260140-91-7 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
33% With tetrakis(triphenylphosphine) palladium(0) In toluene for 16h; Inert atmosphere; Reflux;
  • 5
  • [ 1174223-26-7 ]
  • [ 1260140-92-8 ]
  • [ 1260140-89-3 ]
YieldReaction ConditionsOperation in experiment
81% With tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide for 12h; Inert atmosphere; Reflux;
  • 6
  • [ 1174223-26-7 ]
  • [ 1260140-92-8 ]
  • [ 1260140-93-9 ]
YieldReaction ConditionsOperation in experiment
42% With tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide at 80℃; for 12h; Inert atmosphere;
  • 7
  • [ 108-70-3 ]
  • [ 1174223-26-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: iodine; sulfuric acid / 72 h / 140 °C 2: diisopropylamine / tetrakis(triphenylphosphine) palladium(0); copper(l) iodide / tetrahydrofuran / 63 h / Inert atmosphere; Reflux 3: sodiumsulfide nonahydrate / 1-methyl-pyrrolidin-2-one / 38 h / 180 - 190 °C 4: N-Bromosuccinimide / dichloromethane; acetic acid / 48 h / 20 °C / Inert atmosphere; Darkness
Multi-step reaction with 4 steps 1: iodine; sulfuric acid / 72 h / 140 °C 2: diisopropylamine / tetrakis(triphenylphosphine) palladium(0); copper(l) iodide / tetrahydrofuran / 63 h / Inert atmosphere; Reflux 3: sodiumsulfide nonahydrate / 1-methyl-pyrrolidin-2-one / 38 h / 180 - 190 °C 4: N-Bromosuccinimide / dichloromethane; acetic acid / 24 h / 20 °C / Inert atmosphere; Darkness
Multi-step reaction with 4 steps 1: periodic acid; iodine; sulfuric acid / 20 °C / Inert atmosphere 2: diisopropylamine; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / Inert atmosphere; Reflux 3: sodium sulfide / 1-methyl-pyrrolidin-2-one / 185 °C / Inert atmosphere 4: N-Bromosuccinimide; acetic acid / chloroform / 60 °C / Inert atmosphere
Multi-step reaction with 4 steps 1: iodine; sulfuric acid; periodic acid / 20 °C 2: tetrakis(triphenylphosphine) palladium(0); copper(l) iodide; diisopropylamine / tetrahydrofuran / Reflux 3: sodium sulfide / 1-methyl-pyrrolidin-2-one / 185 °C 4: acetic acid; N-Bromosuccinimide / chloroform / 60 °C
Multi-step reaction with 4 steps 1: periodic acid; sulfuric acid; iodine / 48 h / 20 °C / Cooling with ice 2: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine / tetrahydrofuran / 48 h / Inert atmosphere; Reflux 3: sodium sulfide / 1-methyl-pyrrolidin-2-one / 24 h / 185 - 195 °C 4: N-Bromosuccinimide; acetic acid / chloroform / 20 °C / Inert atmosphere

  • 8
  • [ 1174223-26-7 ]
  • [ 86-74-8 ]
  • [ 1227939-44-7 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate In nitrobenzene at 210℃; for 3h; Inert atmosphere; 20 synthesis of 2,5,8-tris(N-carbazolylamino)benzo[1,2-b:3,4-b':5,6-b']trithiophene Example 20 Synthesis of 2, 5, 8-Tris(N-carbazolylamino)benzo[1,2-b:3,4-b':5,6-b"]trithiophene (1021) [Show Image] Under a nitrogen atmosphere, 2,5,8-tribromobenzo[1,2-b:3,4-b':5,6-b"]trithiophene (33) (500 mg, 1.04 mmol) obtained in Example 4, carbazole (0.78 g, 4.68 mmol), potassium carbonate (1.29 g, 9.36 mmol) and CuI (29.7 mg, 0.156 mmol) were suspended in nitrobenzene (3.5 mL) and reacted with heating at 210°C for 3 hours. After completion of the reaction, methanol was added. A precipitated solid substance was obtained by filtration, washed with water and methanol and dried under reduced pressure. The resultant solid substance was subjected to column chromatography (silica gel, dichloromethane) and reprecipitated from dichloromethane and acetonitrile to obtain a solid substance (640 mg), which was further subjected to vacuum sublimation purification to obtain a light yellow substance. H-NNM(400MHz,CDCl3)6=7.36(dd,J=7.2,7.6Hz,6H), 7.50(dd,J=8.0,6.0Hz,6H), 7.69(d,J=9.2Hz,6H), 7.78(s,3H), 8,15(d,J=J=6.8Hz,6H), ;MS(EI,70eV)m/z=741(M+); m.p.204.5-206.2°C
  • 9
  • [ 1174223-26-7 ]
  • [ 122-39-4 ]
  • [ 1227938-41-1 ]
YieldReaction ConditionsOperation in experiment
39% With sodium t-butanolate In xylene for 34h; Reflux; Inert atmosphere; 13 synthesis of 2,5,8-tris(diphenylamino)benzo[1,2-b:3,4-b':5,6-b']trithiophene Example 13 Synthesis of 2,5,8-Tris(diphenylamino)benzo[1,2-b:3,4-b':5,6-b"]trithiophene (67) [Show Image] Under a nitrogen atmosphere, 2,5,8-tribromobenzo[1,2-b:3,4-b':5,6-b"]trithiophene (33) (500 mg, 1.04 mmol) obtained in Example 4, diphenyl amine (0.78 g, 4.66 mmol) and tertiary butoxy sodium (0.39 g, 4.0 mmol) were suspended in xylene (10 mL) and degassed by Ar bubbling for 30 minutes. Pd(OAc)2 (2.3 mg, 0.01 mmol) and tri(tert-butyl) phosphine (10 mg) were added and heated at a reflux temperature for 34 hours. After completion of the reaction, water (1.0 mL) was added. The mixture was extracted with chloroform, washed and dried over anhydrous magnesium sulfate, and a solvent was distilled away under reduced pressure. The residue was dissolved in methylene chloride, reprecipitated from acetonitrile. The precipitated solid substance was obtained by filtration, washed with water (50 mL) and dried under reduced pressure. Vacuum sublimation purification was performed to obtain a light yellow substance (300 mg, 39%). H-NMR(400NMz,CDCl3)δ=6.87(s,3H), 7.08(t,J=8.4Hz,6H), 7.21(d,J=7.6Hz,12H), 7.28(dd,J=7.2Hz,J=8.8Hz,12H), ;MS(EI,70eV)m/z=747(M+); m.p.130.6-132.2 Abs.λmax340nm(ε=60800); Emis.λmax410nm
  • 10
  • [ 151721-79-8 ]
  • [ 1174223-26-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: diisopropylamine / tetrakis(triphenylphosphine) palladium(0); copper(l) iodide / tetrahydrofuran / 63 h / Inert atmosphere; Reflux 2: sodiumsulfide nonahydrate / 1-methyl-pyrrolidin-2-one / 38 h / 180 - 190 °C 3: N-Bromosuccinimide / dichloromethane; acetic acid / 48 h / 20 °C / Inert atmosphere; Darkness
Multi-step reaction with 3 steps 1: diisopropylamine / tetrakis(triphenylphosphine) palladium(0); copper(l) iodide / tetrahydrofuran / 63 h / Inert atmosphere; Reflux 2: sodiumsulfide nonahydrate / 1-methyl-pyrrolidin-2-one / 38 h / 180 - 190 °C 3: N-Bromosuccinimide / dichloromethane; acetic acid / 24 h / 20 °C / Inert atmosphere; Darkness
Multi-step reaction with 3 steps 1: diisopropylamine; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / Inert atmosphere; Reflux 2: sodium sulfide / 1-methyl-pyrrolidin-2-one / 185 °C / Inert atmosphere 3: N-Bromosuccinimide; acetic acid / chloroform / 60 °C / Inert atmosphere
Multi-step reaction with 3 steps 1: tetrakis(triphenylphosphine) palladium(0); copper(l) iodide; diisopropylamine / tetrahydrofuran / Reflux 2: sodium sulfide / 1-methyl-pyrrolidin-2-one / 185 °C 3: acetic acid; N-Bromosuccinimide / chloroform / 60 °C
Multi-step reaction with 3 steps 1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine / tetrahydrofuran / 48 h / Inert atmosphere; Reflux 2: sodium sulfide / 1-methyl-pyrrolidin-2-one / 24 h / 185 - 195 °C 3: N-Bromosuccinimide; acetic acid / chloroform / 20 °C / Inert atmosphere

  • 11
  • [ 351014-15-8 ]
  • [ 1174223-26-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodiumsulfide nonahydrate / 1-methyl-pyrrolidin-2-one / 38 h / 180 - 190 °C 2: N-Bromosuccinimide / dichloromethane; acetic acid / 48 h / 20 °C / Inert atmosphere; Darkness
Multi-step reaction with 2 steps 1: sodiumsulfide nonahydrate / 1-methyl-pyrrolidin-2-one / 38 h / 180 - 190 °C 2: N-Bromosuccinimide / dichloromethane; acetic acid / 24 h / 20 °C / Inert atmosphere; Darkness
Multi-step reaction with 2 steps 1: sodium sulfide / 1-methyl-pyrrolidin-2-one / 185 °C / Inert atmosphere 2: N-Bromosuccinimide; acetic acid / chloroform / 60 °C / Inert atmosphere
  • 12
  • [ 419536-33-7 ]
  • [ 1174223-26-7 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
5% In N,N-dimethyl-formamide at 90 - 100℃; for 18h; 12 synthesis of 2,5,8-tris(4-(N-carbazolyl)phenyl)benzo[1,2-b:3,4-b':5,6-b']trithiophene Example 12 Synthesis of 2,5,8-Tris(4-(N-carbazolyl)phenyl)benzo[1,2-b:3,4-b':5,6-b"]trithiophene (1013) [Show Image] Under a nitrogen atmosphere, 2,5,8-tribromobenzo[1,2-b:3,4-b':5,6-b"]trithiophene (33) (500 mg, 1.04 mmol) obtained in Example 4, 4-(N-carbazolyl)phenyl boronic acid (1.34 g, 4.66 mmol) and tripotassium phosphate hydrate (3.96 g, 18.6 mmol) were suspended in DMF (40 mL) and degassed by Ar bubbling for 30 minutes. Pd(PPh3)4 (179 mg, 0.155 mmol) was added and heated at 90-100°C for 18 hours. After completion of the reaction, water (30 mL) was added. A precipitated solid substance was obtained by filtration, washed with water (50 mL) and acetone (10 mL) and dried under reduced pressure. Vacuum sublimation purification was performed to obtain a light yellow substance (47.7 mg, 5%). MS(MALDI-TOF,1,8,9-trihydroxyanthracene matrix)m/z=966.34
  • 13
  • [ 717888-41-0 ]
  • [ 1174223-26-7 ]
  • 2,5,8-tris(4-(N-(1-naphthyl)-N-phenyl-amino)phenyl)benzo[1,2-b:3,4-b':5,6-b"]trithiophene [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% In N,N-dimethyl-formamide at 90 - 100℃; for 18h; Inert atmosphere; 6 Example 6 Synthesis of 2,5,8-Tris(4-(N-(1-naphthyl)-N-phenyl-amino)phenyl)benzo[1,2-b:3,4-b':5,6-b"]trithiophene (1029): Ndpa-BTT [Show Image] Under a nitrogen atmosphere, 2,5,8-tribromobenzo[1,2-b:3,4-b':5,6-b"]trithiophene (450 mg, 0.93 mmol) obtained in Example 4,4-(1-naphthylphenylamino)phenyl boronic acid (1.42 g, 4.19 mmol) and tripotassium phosphate hydrate (4.74 g, 22.4 mmol) were suspended in DMF (18.9 mL) and degassed by Ar bubbling for 30 minutes. Pd(PPh3)4 (161 mg, 0.14 mmol) was added and heated at 90-100°C for 18 hours. After completion of the reaction, water (20 mL) was added. A precipitated solid substance was obtained by filtration, washed with water (50 mL) and acetone (10 mL) and dried under reduced pressure. Extraction was continuously performed with chloroform by means of Soxhlet. The extract was dissolved in hot chloroform and reprecipitated from acetonitrile to obtain a light yellow substance (969 mg, 92%). H-NMR(400MHz,CDCl3)δ=6.99(d,J=8.0Hz,3H), 7.03(d,J=8.8Hz,6H), 7.13(d,J=8.0Hz,6H), 7.24(d,J=8.0Hz,6H), 7.39(t,J=8.8Hz,6H), 7.47(t,J=8,8Hz,3H),7.52(d,J=8.0Hz,3H), 7.58(d,J=8.8Hz,6.H), 7.61(s,3H),7,81(d,J=7.6Hz,3H),7.91(d,J=8.4Hz,3H), 7.95(d,J=8.4Hz,3H), MS(MALDI-TOF,1,8,9-trihydroxyanthracene matrix)m/z=1127.27
  • 14
  • [ 1174223-26-7 ]
  • [ 201802-67-7 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
86% In N,N-dimethyl-formamide at 90 - 100℃; for 16.5h; Inert atmosphere; 5 Example 5 Synthesis of 2,5,8-Tris(4-(N,N-Diphenylamino)phenyl)benzo[1,2-b:3,4-b':5,6-b"]trithiophene (1010): Tpa-BTT [Show Image] Under a nitrogen atmosphere, 2,5,8-tribromobenzo[1,2-b:3,4-b':5,6-b"]trithiophene (450 mg, 0.93 mmol) obtained in Example 4, 4-(diphenylamino)phenyl boronic acid (1.2 g, 4.19 mmol) and tripotassium phosphate hydrate (4.74 g, 22.4 mmol) were suspended in DMF (18.9 mL) and degassed by Ar bubbling for 40 minutes. Pd(PPh3)4 (161 mg, 0.14 mmol) was added and heated at 90-100°C for 16.5 hours. After completion of the reaction, water (10 mL) was added. A precipitated solid substance was obtained by filtration, washed with water (50 mL) and acetone (10 mL) and dried under reduced pressure. Extraction was continuously performed with chloroform by means of Soxhlet. The extract was dissolved in hot chloroform and reprecipitated from acetonitrile to obtain a light yellow substance (780 mg, 86%). 1H-NMR(400MHz,CDCl3)δ7.07(t,J=6.0Hz,6H), 7.14(dd,J=9.6Hz, 12H), 7.16(d,J=8.8Hz,6H), 7.30(dd,J=7.6Hz,12H), 7.65(dt,J=6.0,3.6Hz,6H).7.69(s,3H); M.S.(70eVEI)m/z=484(M+); mp>300°C; Anal.Calcd for C66H4sN3S3:C,81.20; H,4.65; N,4.30%.Found:C,80.96; H,4.34; N,4.31%.
  • 15
  • [ 29150-63-8 ]
  • [ 1174223-26-7 ]
  • [ 1227938-08-0 ]
YieldReaction ConditionsOperation in experiment
With N-Bromosuccinimide; In dichloromethane; acetic acid; at 20℃; for 24h;Inert atmosphere; Darkness; Example 16 Dibromination reaction of <strong>[29150-63-8]BTT</strong> by NBS bromination reaction [Show Image] Under a nitrogen atmosphere, in a 50 mL three-neck flash, benzo[1,2-b:4,5-b':5,6-b"]trithiophene (Scheme 1-(2)) (800 mg, 3.25 mmol) obtained in Synthesis Example 3, methylene chloride (22.7 mL) and acetic acid (5.7 mL) were added. Under light exclusion conditions, NBS (1.16 g, 6.5 mmol) was added little by little and stirred at room temperature for 24 hours. After completion of the reaction, water (20 mL) was added. A precipitated solid substance was obtained by filtration and washed with ethanol (50 mL) and water (20 mL) to obtain a light purple solid substance. The resultant solid substance was analyzed by HPLC. As a result, it was found that a production ratio of 34:35:33 is 0.01:1:0.17.
  • 16
  • [ 1174223-26-7 ]
  • [ 1620392-75-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium carbonate; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran; water / 24 h / Inert atmosphere; Reflux 2: dihydrogen peroxide; acetic acid / 20 °C
  • 17
  • [ 1174223-26-7 ]
  • [ 1637378-05-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium carbonate; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran; water / 24 h / Inert atmosphere; Reflux 2.1: dihydrogen peroxide; acetic acid / 20 °C 3.1: trifluoroacetic acid / 24 h / 20 °C 3.2: 12 h / Reflux
  • 18
  • [ 1174223-26-7 ]
  • [ 168618-42-6 ]
  • [ 1620392-74-6 ]
YieldReaction ConditionsOperation in experiment
88% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In tetrahydrofuran; water for 24h; Inert atmosphere; Reflux;
  • 19
  • [ 108-73-6 ]
  • [ 1174223-26-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: trifluorormethanesulfonic acid / chlorobenzene / Reflux 2: chloranil / toluene / Reflux 3: acetic acid; N-Bromosuccinimide / dichloromethane / 60 h / 20 °C
Multi-step reaction with 3 steps 1: trifluorormethanesulfonic acid / chlorobenzene / 6 h / 20 °C / Reflux; Inert atmosphere 2: chloranil / toluene / 48 h / 100 °C / Inert atmosphere 3: N-Bromosuccinimide / chloroform / 12 h / Inert atmosphere; Reflux
  • 20
  • [ 1174223-26-7 ]
  • [ 1066-54-2 ]
  • [ 1698057-66-7 ]
YieldReaction ConditionsOperation in experiment
86% With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine In tetrahydrofuran Inert atmosphere; Reflux;
56% With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine In tetrahydrofuran Reflux; Inert atmosphere;
  • 21
  • [ 1174223-26-7 ]
  • [ 101-70-2 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
60% With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; XPhos In toluene for 3.5h; Inert atmosphere; Reflux;
  • 22
  • [ 1174223-26-7 ]
  • [ CAS Unavailable ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
64% With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; XPhos In toluene for 4h; Inert atmosphere; Reflux;
  • 23
  • [ 875667-84-8 ]
  • [ 1174223-26-7 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
54% With potassium phosphate; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide at 80℃; for 18h; Inert atmosphere;
  • 24
  • [ 1174223-26-7 ]
  • [ 5570-19-4 ]
  • [ 1689518-97-5 ]
YieldReaction ConditionsOperation in experiment
35% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at 40 - 80℃; for 12h; Inert atmosphere; 16.1 Step 1: Synthesis of IC-16-1 General procedure: A stream of nitrogen 2-nitrophenylboronic acid (3.84 g, 22.99 mmol) obtained in the above 2-bromophenanthro[9,10-b]thiophene (6 g, 19.16 mmol), K2CO3 (7.94 g, 57.47 mmol) and THF / H2O (100 ml / 50 ml) the mixture, and then insert the Pd (PPh3) 4 (1.11 g, 5 mol%) at 40 °C was stirred at 80 °C for 12 hours. After completion of the reaction was extracted with methylene chloride, filtered, put MgSO4. After removal of the solvent from the organic layer thus obtained was columnChromatography (Hexane: MC = 5: 1 (v / v)) to give 2-(2-nitrophenyl)phenanthro[9,10-b]thiophene (4.29 g as,With a yield of 63%). Instead of 2-bromophenanthro [9,10-b] thiophene (6 g, 19.16 mmol) and IC-15-2 (20 g, 41.40 mmol) and 2-nitrophenylboronic acid (16.59 g, 99.37 mmol)Was obtained by the procedure is the same as of the IC-16-1 Preparation Example 1 step 2(8.22 g, yield 35%).
  • 25
  • [ 1174223-26-7 ]
  • [ 5570-19-4 ]
  • [ 1689518-99-7 ]
YieldReaction ConditionsOperation in experiment
39% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at 40 - 80℃; for 12h; Inert atmosphere; 17.1 Step 1: Synthesis of IC-17-1 General procedure: A stream of nitrogen 2-nitrophenylboronic acid (3.84 g, 22.99 mmol) obtained in the above 2-bromophenanthro[9,10-b]thiophene (6 g, 19.16 mmol), K2CO3 (7.94 g, 57.47 mmol) and THF / H2O (100 ml / 50 ml) the mixture, and then insert the Pd (PPh3) 4 (1.11 g, 5 mol%) at 40 °C was stirred at 80 °C for 12 hours. After completion of the reaction was extracted with methylene chloride, filtered, put MgSO4. After removal of the solvent from the organic layer thus obtained was columnChromatography (Hexane: MC = 5: 1 (v / v)) to give 2-(2-nitrophenyl)phenanthro[9,10-b]thiophene (4.29 g as,With a yield of 63%). Instead of 2-bromophenanthro [9,10-b]thiophene (6 g, 19.16 mmol) for the using of IC-15-2 (20 g, 41.40 mmol) and 2-nitrophenylboronic acid (24.88 g, 149.05 mmol) Was obtained by following the same procedure as in The preparation of Example 1 step 2 the IC-17-1 (9.84 g, yield 39%)
  • 26
  • [ 35991-61-8 ]
  • [ 1174223-26-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: chloranil / toluene / 48 h / 100 °C / Inert atmosphere 2: N-Bromosuccinimide / chloroform / 12 h / Inert atmosphere; Reflux
  • 27
  • [ 1174223-26-7 ]
  • [ 1689518-59-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran; water / 12 h / 40 - 80 °C / Inert atmosphere 2: triphenylphosphine / 1,2-dichloro-benzene / 12 h / Inert atmosphere 3: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran; water / 12 h / 40 - 80 °C / Inert atmosphere 4: potassium carbonate; sodium sulfate; copper / nitrobenzene / 24 h / 200 °C 5: palladium diacetate; sodium t-butanolate; tri-tert-butyl phosphine / toluene / 12 h / 110 °C
  • 28
  • [ 1174223-26-7 ]
  • [ 1689518-61-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran; water / 12 h / 40 - 80 °C / Inert atmosphere 2: triphenylphosphine / 1,2-dichloro-benzene / 12 h / Inert atmosphere 3: potassium carbonate; sodium sulfate; copper / nitrobenzene / 24 h / 200 °C / Inert atmosphere 4: palladium diacetate; sodium t-butanolate; tri-tert-butyl phosphine / toluene / 12 h / 110 °C
  • 29
  • [ 1174223-26-7 ]
  • [ 1689519-14-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran; water / 12 h / 40 - 80 °C / Inert atmosphere 2: triphenylphosphine / 1,2-dichloro-benzene / 12 h / Inert atmosphere 3: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran; water / 12 h / 40 - 80 °C / Inert atmosphere
  • 30
  • [ 1174223-26-7 ]
  • [ 1689519-15-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran; water / 12 h / 40 - 80 °C / Inert atmosphere 2: triphenylphosphine / 1,2-dichloro-benzene / 12 h / Inert atmosphere 3: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran; water / 12 h / 40 - 80 °C / Inert atmosphere 4: potassium carbonate; sodium sulfate; copper / nitrobenzene / 24 h / 200 °C
  • 31
  • [ 1174223-26-7 ]
  • [ 1689519-17-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran; water / 12 h / 40 - 80 °C / Inert atmosphere 2: triphenylphosphine / 1,2-dichloro-benzene / 12 h / Inert atmosphere 3: potassium carbonate; sodium sulfate; copper / nitrobenzene / 24 h / 200 °C / Inert atmosphere
  • 32
  • [ 1174223-26-7 ]
  • [ 1689518-98-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran; water / 12 h / 40 - 80 °C / Inert atmosphere 2: triphenylphosphine / 1,2-dichloro-benzene / 12 h / Inert atmosphere
  • 33
  • [ 1174223-26-7 ]
  • [ 1689519-00-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran; water / 12 h / 40 - 80 °C / Inert atmosphere 2: triphenylphosphine / 1,2-dichloro-benzene / 12 h / Inert atmosphere
  • 34
  • [ 875667-84-8 ]
  • [ 1174223-26-7 ]
  • [ 1908506-93-3 ]
YieldReaction ConditionsOperation in experiment
54% With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide at 80℃; for 18h; Inert atmosphere; Reflux; 1 Synthesis of compound of formula (31) or BTT-3 A solution of tribromo-BTT (300 mg, 0.62 mmol), 4-(4,4,5,5-Tetramethyl-l ,3,2- dioxaborolan-2-yl)-N,N-bis(4-methoxyphenyl)aniline (1.07 gr, 2.48 mmol), 3P04 (3.16 gr, 14.90 mmol) and Pd(PPh3)4 (179.4 mg, 0.15 mmol) in DMF (22 ml) was degassed for 1 hour under nitrogen. The reaction was heated at 80 °C for 18 hours. The mixture was cooled to room temperature and washed with NH4C1. The combined organic extracts (CH2C12) were dried over Na2S04. After removal the solvent under reduced pressure the crude product was purified by flash column chromatography (silica gel, CH2C12 and then CH2Cl2:AcOEt (120: 1)) to afford BTT-3 (Figure 1C) as a yellow solid (382 mg, 0.33 mmol), yield 54 %. NMR (400 MHz, THF-d8) δ 7.82 (s, 3H), 7.68 (d, J = 8.7 Hz, 6H), 7.12 (d, J = 8.7 Hz, 12H), 6.98 (d, J = 8.7 Hz, 6H), 6.91 (d, J = 8.7 Hz, 12H), 3.81 (s, 18H); 13C NMR (101 MHz, CDC13) 6 156.1 , 148.8, 143.6, 140.5, 132.5, 129.7, 126.9, 126.8, 126.0, 120.2, 1 16.0, 1 14.8, 55.5; FTIR (neat): 3035, 2945, 2832, 1499, 1239, 1034, 821 cm"1 ; HRMS calcd for C72H57N306S3 [M+], 1 155.3404; found 1 155.3374. Example 2: Optoelectronic and/or electrochemical devices of the invention
  • 35
  • [ 1174223-26-7 ]
  • [ 101-70-2 ]
  • [ 1908506-91-1 ]
YieldReaction ConditionsOperation in experiment
60% With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; XPhos In toluene for 3.5h; Inert atmosphere; Reflux; 1 Synthesis of compound of formula (29) or BTT-1 Tribromo-BTT (150 mg, 0.31 mmol), bis(4-methoxyphenyl)amine (250 mg, 1.08 mmol), Pd2(dba)3 (20 mg, 0.02 mmol) and Xphos (15 mg, 0.03 mmol) were disolved in 21 mL of Toluene. The mixture was degassed for 30 minutes at room temperature. After that, sodium ter-butoxide (180 mg, 1.86 mmol) was added and the reaction was heated at reflux for 3.5 hours under nitrogen atmosphere. After cooling to room temperature, the mixture was quenched by adding water and extracted with toluene. The combined organic extracts were dried over Na2S04. After removal the solvent under reduced pressure the crude product was purified by flash column chromatography (silica gel, CH2C12) to afford BTT-1 (Figure IB) as a yellow solid (174 mg, 0.19 mmol), yield 60 %. NMR (400 MHz, CDC13) δ 7.16 (d, J = 8.9 Hz, 12H), 6.83 (d, J = 8.9 Hz, 12H), 6.53 (s, 3H), 3.79 (s, 18); 13C NMR (101 MHz, CDCI3) δ 156.4, 153.0, 140.9, 130.6, 125.5, 121.6, 114.6, 107.6, 55.5; FTIR (neat): 3039, 2905, 2833, 1502, 1239, 1033, 866 cm"1; HRMS calcd for C54H45N306S3 [M+], 927.2465; found 927.2446. Synthesis of compound of formula (30) or BTT-2
  • 36
  • [ 1174223-26-7 ]
  • [ 1630723-98-6 ]
  • [ 1908506-92-2 ]
YieldReaction ConditionsOperation in experiment
64% With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; XPhos In toluene for 4h; Inert atmosphere; Reflux; 1 Synthesis of compound of formula (30) or BTT-2 Tribromo-BTT (300 mg, 0.62 mmol), N3,N3,N6,N6-tetrakis(4-methoxyphenyl)-9H- carbazole-3,6-diamine (1.27 g, 2.04 mmol), Pd2(dba)3 (39 mg, 0.04 mmol) and Xphos (29 mg, 0.06 mmol) were disolved in toluene (41 ml). The mixture was purged with nitrogen for 30 minutes at room temperature. After that, sodium ter-butoxide (358 mg, 3.72 mmol) was added. The reaction was heated at reflux for 4 hours under nitrogen atmosphere. The mixture was quenched by adding water and extracted with toluene. The combined organic extracts were dried over Na2S04. After removal the solvent under reduced pressure the crude product was purified by flash column chromatography (silica gel, CH2C12 and then CH2Cl2:AcOEt (120: 1)) to afford BTT-2 (Figure 1 C) as a yellow solid (842 mg, 0.40 mmol), yield 64 %.1H NMR (400 MHz, THF-dg) δ 7.99 (s, 3H), 7.69 (d, J = 2.1 Hz, 6H), 7.55 (d, J = 8.8 Hz, 6H), 7.15 (dd, J = 8.8, J = 2.1 Hz, 6H), 6.95 (d, J = 8.8 Hz, 24H), 6.76 (d, J = 8.8 Hz, 24H), 3.71 (s, 36H); 13C NMR (101 MHz, CDC13) δ 154.9, 142.3, 139.2, 138.1 , 129.8, 129.4, 124.7, 124.6, 124.3, 1 18.6, 1 16.0, 1 14.6, 1 1 1.0, 55.5; FTIR (neat): 3040, 2939, 2831 , 1501 , 1452, 1234, 1033, 819 cm"1 ; HRMS calcd for Ci32Hio5N9Oi2S3 [M+], 2103.7039; found 2103.7085.
  • 37
  • [ 1174223-26-7 ]
  • [ 1384897-25-9 ]
  • [ 2415431-42-2 ]
YieldReaction ConditionsOperation in experiment
61% With palladium diacetate; potassium carbonate; tris-(o-tolyl)phosphine; Trimethylacetic acid In N,N-dimethyl-formamide at 150℃; for 30h; Inert atmosphere;
Same Skeleton Products
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