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Chemical Structure| 324750-99-4
Chemical Structure| 324750-99-4
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Product Details of [ 324750-99-4 ]

CAS No. :324750-99-4 MDL No. :MFCD18968034
Formula : C28H18O2 Boiling Point : -
Linear Structure Formula :- InChI Key :LBPGUWKCPYZVIE-UHFFFAOYSA-N
M.W : 386.44 Pubchem ID :11451989
Synonyms :

Safety of [ 324750-99-4 ]

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 [ 324750-99-4 ]

* 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 [ 324750-99-4 ]

[ 324750-99-4 ] Synthesis Path-Downstream   1~20

  • 1
  • [ 523-27-3 ]
  • [ 87199-17-5 ]
  • [ 324750-99-4 ]
YieldReaction ConditionsOperation in experiment
98.1% With dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II); triethylamine In water at 20℃; for 0.166667h; Inert atmosphere;
95% With dichloro[1,1′-bis[bis(1,1-dimethylethyl)phosphino]ferrocene-P,P′]palladium; triethylamine In water at 20℃; for 12h; Green chemistry;
83% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene
78% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; benzene for 48h; Heating;
70% With sodium carbonate In tetrahydrofuran; toluene Heating;
70% With sodium carbonate In tetrahydrofuran; toluene at 85℃; for 8h;
64.3% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene for 48h; Reflux; Inert atmosphere; 4 Example 4 Add in a 150mL three-necked flask 4-formylbenzeneboronic acid (2.82 g, 2.5 equiv, 18.8 mmol), 9,10-Dibromoindole (2.53 g, 1 equiv, 7.5 mmol) was dissolved in 60 mL of toluene and 12 mL of ethanol, and K2CO3 (5.92 g, 34.5 mmol) was dissolved in 23 mL of distilled water and mixed into the above solution. Then argon was bubbled through the mixed solution for 15 minutes, followed by four (triphenylphosphine) palladium (0) (0.25 g, 0.82 mmol), and then argon was bubbled in for 5 minutes, and then heated under reflux in an argon atmosphere. During the reaction, the progress of the reaction was followed by a dot plate. The developing solvent was dichloromethane. 1: petroleum ether 1, the reaction proceeds to 48h, the raw material 9,10-two The point of bromine disappeared almost and the reaction was stopped. After the reaction is completed, the reaction solution is distilled under reduced pressure to obtain a black solid mixture. The organic phase is separated and extracted by using dichloromethane and saturated brine, and the product is separated by column chromatography after adding anhydrous Na 2 SO 4 to remove water. Dichloromethane 3: petroleum ether 4, which was re-crystallized twice by solvent evaporation to give 9,10-(4-formyl)phenylhydrazine (hereinafter referred to as p-FDPA) as a pale yellow powder. Yield 64.3%.
64.3% Stage #1: 9,10-Dibromoanthracene; 4-formylphenylboronic acid, With potassium carbonate In ethanol; water; toluene for 0.25h; Inert atmosphere; Stage #2: With tetrakis(triphenylphosphine) palladium(0) In ethanol; water; toluene for 48h; Reflux; Inert atmosphere; 1 Example 1: 4-formylphenylboronic acid (2.82 g, 2.5 equiv, 18.8 mmol) was added to a 150 mL three-necked flask.9,10-dibromo anthracene(2.53 g, 1 equiv, 7.5 mmol) was dissolved in 60 mL of toluene and 12 mL of ethanol, and K2CO3 (5.92 g, 34.5 mmol) was dissolved in 23 mL of distilled water.Mix in the above solution. Then argon was bubbled through the mixed solution for 15 minutes.Subsequently, tetrakis(triphenylphosphine)palladium(0) (0.25 g, 0.82 mmol) was added.Then argon was bubbled in for 5 minutes, and then heated to reflux under an argon atmosphere.The progress of the reaction is tracked through the point plate during the reaction.The developing solvent was dichloromethane 1: petroleum ether 1, and the reaction proceeded to 48 h.The point of the raw material 9,10-dibromofluorene almost disappeared and the reaction was stopped.The reaction solution was distilled under reduced pressure to give a black solid mixture.The organic phase is separated and extracted by using dichloromethane and saturated brine.After adding anhydrous Na2SO4 to remove water, the product was separated by column chromatography.The developing solvent used was dichloromethane/petroleum ether (3/4, v/v),Further recrystallization by solvent evaporation to purify twice to obtain the reaction intermediate 9,10-(4-formylphenyl)anthracene (p-FDPA) as a yellow powder.The weight is 1.84g (4.0 mmol)The yield was 64.3%.
61% Stage #1: 9,10-Dibromoanthracene; 4-formylphenylboronic acid, With tetrabutylammomium bromide; potassium carbonate In water; toluene at 20℃; for 0.5h; Inert atmosphere; Stage #2: With tetrakis(triphenylphosphine) palladium(0) In water; toluene at 90℃; for 24h; Inert atmosphere;
48% With sodium carbonate In methanol; toluene
27.7% With bis-triphenylphosphine-palladium(II) chloride In tetrahydrofuran; toluene at 90℃; Inert atmosphere; 8.A Example 8: A.Compound 9,10-dibromoanthracene (500 mg, 1.49 mmol)4-formylphenylboronic acid (490.85 mg, 3.27 mmol)Bis (triphenylphosphine) palladium dichloride Pd (PPh3) 2Cl2 (104.58 mg, 0.15 mmol)Was dissolved in 40 mL of a mixed solvent of toluene and tetrahydrofuran (Vtoluene: VTHF = 1: 1)The reaction was refluxed at 90 ° C under nitrogen,Thin layer chromatography to the reaction is complete.After the resulting solution was spin off the organic solvent,Extracted with ethyl acetate,Organic layer washed three times,Saturated NaCl solution once,Dried over anhydrous sodium sulfate,The solvent is evaporated under reduced pressure;The crude product was passed through a column of petroleum ether and ethyl acetate mixed solvent (20: 1)4,4 '- (anthracene-9,10-diyl) benzaldehyde (white solid, 159.5 mg, yield 27.7%).
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; benzene
With sodium carbonate In ethanol; water; toluene 2 The bisaldehyde derivative of anthracene is formed in a first step by Suzuki coupling between 9,10-dibromoanthracene and 4-formylphenylboronic acid in the presence of a source of palladium and of a base in two-phase medium. Next, it reacts with two equivalents of DCDHF in ortho-dichlorobenzene in the presence of a base and a catalyst, titanium tetrachloride. The product is obtained in the form of a red solid. Deposition by drop casting of a solution of this compound in benzonitrile onto a transistor, irrespective of its geometry, results in the formation of crystals.
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; toluene for 48h; Reflux;

Reference: [1]Sanzone, Alessandro; Mattiello, Sara; Garavaglia, Giulia Maria; Calascibetta, Adiel Mauro; Ceriani, Chiara; Sassi, Mauro; Beverina, Luca [Green Chemistry, 2019, vol. 21, # 16, p. 4400 - 4405]
[2]Mattiello, Sara; Rooney, Myles; Sanzone, Alessandro; Brazzo, Paolo; Sassi, Mauro; Beverina, Luca [Organic Letters, 2017, vol. 19, # 3, p. 654 - 657]
[3]Grajewski, Jakub; Zgorzelak, Mikołaj; Janiak, Agnieszka; Taras-Goślińska, Katarzyna [ChemPlusChem, 2022, vol. 87, # 3]
[4]Teki; Miyamoto; Nakatsuji; Miura [Journal of the American Chemical Society, 2001, vol. 123, # 2, p. 294 - 305]
[5]Kotha, Sambasivarao; Ghosh, Arun Kumar [Synlett, 2002, # 3, p. 451 - 452]
[6]Kotha, Sambasivarao; Ghosh, Arun Kumar; Deodhar, Kodand Dinkar [Synthesis, 2004, # 4, p. 549 - 557]
[7]Current Patent Assignee: SUZHOU UNIVERSITY OF SCIENCE AND TECHNOLOGY - CN108997101, 2018, A Location in patent: Paragraph 0035-0038
[8]Current Patent Assignee: SUZHOU UNIVERSITY OF SCIENCE AND TECHNOLOGY - CN110229055, 2019, A Location in patent: Paragraph 0023
[9]Akkaya, Engin U.; Aydonat, Simay; Baytekin, Bilge; Beduk, Tutku; Canyurt, Merve; Turksoy, Abdurrahman; Yildiz, Deniz [RSC Advances, 2020, vol. 10, # 16, p. 9182 - 9186]
[10]Kuhnert, Nikolai; Patel, Chirag; Jami, Fatemeh [Tetrahedron Letters, 2005, vol. 46, # 44, p. 7575 - 7579]
[11]Current Patent Assignee: SHANGHAI UNIVERSITY - CN106883182, 2017, A Location in patent: Paragraph 13
[12]Location in patent: scheme or table Yang, Wenbin; Greenaway, Alex; Lin, Xiang; Matsuda, Ryotaro; Blake, Alexander J.; Wilson, Claire; Lewis, William; Hubberstey, Peter; Kitagawa, Susumu; Champness, Neil R.; Schroeder, Martin [Journal of the American Chemical Society, 2010, vol. 132, # 41, p. 14457 - 14469]
[13]Current Patent Assignee: COMMISSARIAT A L'ENERGIE ATOMIQUE ET AUX ENERGIES ALTERNATIVES - US2012/116084, 2012, A1 Location in patent: Page/Page column 11-12
[14]Chen, Shuoran; Li, Lin; Song, Yanlin; Wang, Xiaomei; Xu, Lei; Ye, Changqing; Zhang, Chun [Angewandte Chemie - International Edition, 2021, vol. 60, # 51, p. 26725 - 26733][Angew. Chem., 2021, vol. 133, # 51, p. 26929 - 26937]
  • 2
  • [ 14384-45-3 ]
  • [ 324750-99-4 ]
  • [ 324751-03-3 ]
YieldReaction ConditionsOperation in experiment
44% With 2,3-bis(hydroxyamino)-2,3-dimethylbutane monosulfate In methanol; chloroform for 72h; Heating;
  • 3
  • [ 20439-47-8 ]
  • [ 324750-99-4 ]
  • C102H84N6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% In dichloromethane at 20℃; for 12h;
  • 5
  • [ 171082-32-9 ]
  • [ 324750-99-4 ]
  • [ 1256572-76-5 ]
YieldReaction ConditionsOperation in experiment
With 1,8-diazabicyclo[5.4.0]undec-7-ene In 1,2-dichloro-benzene 2 The bisaldehyde derivative of anthracene is formed in a first step by Suzuki coupling between 9,10-dibromoanthracene and 4-formylphenylboronic acid in the presence of a source of palladium and of a base in two-phase medium. Next, it reacts with two equivalents of DCDHF in ortho-dichlorobenzene in the presence of a base and a catalyst, titanium tetrachloride. The product is obtained in the form of a red solid. Deposition by drop casting of a solution of this compound in benzonitrile onto a transistor, irrespective of its geometry, results in the formation of crystals.
  • 6
  • [ 861072-30-2 ]
  • [ 324750-99-4 ]
  • C60H38N4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% With sodium metabisulfite In N,N-dimethyl-formamide at 110℃; for 18h; Inert atmosphere; 8 example 8 preparation of a naphthalene [1,2] benzimidazole of the n-type compound 8 Specific preparation steps are as follows: in the 250 ml flask in three, will N-benzene -1,2-diamine naphthalin from (12mmol, 2 . 8g), 9,10-bis (4- formacyl benzene ) anthracene (5mmol, 1 . 9g) is added to 100 ml of N, N '-dimethyl formamide (DMF) is dissolved in, then adding sodium metabisulfite (20mmol, 3 . 6g). In the argon atmosphere is heated to 110 °C, reaction 18 hours. Then the mixed solution is poured into 300 ml water, and products is extracted with methylene chloride. Drying by anhydrous magnesium sulphate the organic phase, removing the solvent after the separation, column separation and purification by silica gel chromatography to obtain strawcoloured solid, dried after sublimation under vacuum to obtain high-purity product (2.45g, yield 60%).
  • 7
  • [ 38369-74-3 ]
  • [ 324750-99-4 ]
  • C60H38N4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
51% With sodium metabisulfite In N,N-dimethyl-formamide at 110℃; for 18h; Inert atmosphere; 7 example 7 preparation of a naphthalene [1,2] benzimidazole of the n-type compound 7 Specific preparation steps are as follows: in the 250 ml flask in three, will N '-benzene -1,2-diamine naphthalin from (12mmol, 2 . 8g), 9,10-bis (4- formacyl benzene ) anthracene (5mmol, 1 . 9g) is added to 100 ml of N, N' -dimethyl formamide (DMF) is dissolved in, then adding sodium metabisulfite (20mmol, 3 . 6g). In the argon atmosphere is heated to 110 °C, reaction 18 hours. Then the mixed solution is poured into 300 ml water, and products is extracted with methylene chloride. Drying by anhydrous magnesium sulphate the organic phase, removing the solvent after the separation, column separation and purification by silica gel chromatography to obtain strawcoloured solid, dried after sublimation under vacuum to obtain high-purity product (2.08g, yield 51%).
  • 8
  • [ 863992-56-7 ]
  • [ 1122-91-4 ]
  • [ 324750-99-4 ]
YieldReaction ConditionsOperation in experiment
53% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; at 78℃;Inert atmosphere; General procedure: The optimized procedure is based on similar reports.S8,S9 To a solution of <strong>[863992-56-7]9,10-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)anthracene</strong> (1) (0.930 mmol), brominated aromatic aldehyde (2.800 mmol) and Pd(PPh3)4 ( 0.140 mmol) in THF (30 mL), was added drop-wise an aqueous solution of K2CO3 (2.6 mL, 2M) at room temperature under argon atmosphere. After refluxing at 78 C for 12 hours, the reaction mixture was cooled to room temperature. The solvent was evaporated under reduced pressure. The solid residue was dissolved in DCM and washed with water. The organic layers were dried over MgSO4 and concentrated. Further purification was carried out by silica column chromatography.
  • 9
  • [ 109-77-3 ]
  • [ 324750-99-4 ]
  • C34H18N4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
63% With triethylamine In chloroform Reflux; 2.4. General procedure for the synthesis of DCV-end capped chromophores. The dicyanovinyl derivatives were synthesized via a Knoevenagel condensation reaction of the previously prepared carboxyaldehyde (2-6). Bisaldehydes (0.251 mmol), malononitrile (0.627 mmol) and 0.5 mL of TEA were stirred in chloroform (30 mL) at reflux temperature until aldehyde was digested. Solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel to obtain the desired product.
  • 10
  • N<SUP>2</SUP>-phenyl-9,9-diethyl-9H-fluorene-2,3-diamine [ No CAS ]
  • [ 324750-99-4 ]
  • C74H58N4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
19% With Oxone In water; N,N-dimethyl-formamide at 20℃; 8.B Example 8: B.The compound (159.5 mg, 0.41 mmol) obtained in Step A,The compound 2- (N-phenyl) -3-amino-9,9'-diethylfluorene (298.48 mg, 0.91 mmol) was dissolved in 20 mL of a mixed solvent of DMF and H2O (VDMF: VH2O = 30:Oxidator oxone (332 mg, 0.54 mmol) was then added,Stir at room temperature,Thin layer chromatography to the reaction is complete.The resulting solution was extracted with ethyl acetate,Organic layer washed three times,]Saturated NaCl solution once,Dried over anhydrous sodium sulfate,The solvent is evaporated under reduced pressure;The crude product was passed through a pure dichloromethane column,Compound 8 (white solid, 78 mg, yield 19%) was obtained.
  • 11
  • [ 324750-99-4 ]
  • [ 534-85-0 ]
  • C52H34N4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
25 mmol In water; N,N-dimethyl-formamide at 80℃; for 6h; Inert atmosphere; 3.3 Step3.5-2, 50mmol,1-1,100mmol,Dissolved in DMF and water at 9:1 (v/v)In a mixed solvent,Heated to 80 ° C,Passing oxygen,Stir the reaction for 6 hours,After the reaction is completed,The organic phase is dried,Column chromatography,The product was obtained in 5,25 mmol.
  • 12
  • [ 95952-57-1 ]
  • [ 33513-42-7 ]
  • [ 324750-99-4 ]
YieldReaction ConditionsOperation in experiment
50 mmol Stage #1: 9,10-bis-(4-chloro-phenyl)-anthracene With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran at 0℃; 3.2 Step2. Will 5-3,85mmol was dissolved in anhydrous THF.Cool to -78 ° C,Add n-butyl lithium 100mmol,React at this temperature for 1 hour,Add 2 equivalents of DMF,Gradually warm up to 0 ° C,Reacted overnight,Join after the reaction is completedDeionized water 200mmol,After the reaction is completed,Add DCM extraction,The organic phase is dried,Column chromatography,The product obtained was 5-2, 50 mmol.
  • 13
  • [ 1679-18-1 ]
  • [ 324750-99-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / water; toluene; ethanol / 6 h / Inert atmosphere; Sonication; Reflux 2.1: n-butyllithium / tetrahydrofuran / 1 h / -78 °C 2.2: 0 °C
  • 14
  • [ 523-27-3 ]
  • [ 324750-99-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / water; toluene; ethanol / 6 h / Inert atmosphere; Sonication; Reflux 2.1: n-butyllithium / tetrahydrofuran / 1 h / -78 °C 2.2: 0 °C
  • 15
  • [ 324750-99-4 ]
  • 9,10-bis(4-hydroxymethylphenyl)anthracene [ No CAS ]
YieldReaction ConditionsOperation in experiment
99% With sodium tetrahydroborate; ethanol at 20℃; for 0.5h;
72.8% With potassium borohydride In ethanol at 20℃; for 24h; 8 Example 8 20 mL of ethanol, 9,10-(3-formyl)phenylhydrazine (1.16 g, 3 mmol) and KBH4 (432 mg, 8 mmol) were added to a 50 mL one-neck flask, and the reaction was stirred at room temperature for 24 h. After the reaction is completed, the reaction solution is poured into a large amount of distilled water, and charged. After stirring, suction filtration, repeated washing with distilled water, drying in a vacuum oven at 60 ° C, and recrystallization after CHCl 3 A white powder of 9,10-(3-hydroxymethyl)phenylhydrazine (hereinafter referred to as p-HDPA) was obtained in a yield of 72.8%.
With potassium borohydride; ethanol at 20℃; for 24h;
  • 16
  • [ 324750-99-4 ]
  • C28H18O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
40% With potassium permanganate In ethanol at 20℃; for 24h; 2 Example 2: The intermediate 9,10-bis(4-formylphenyl)indole (p-FDPA, 1 g, 2.6 mmol) and KMnO4 (4.5 g, 28.5 mmol) in Example 1 were added to 20 mL of ethanol at room temperature. The reaction was stirred for 24 h. After the reaction is over,The reaction solution was cooled to room temperature, suction filtered and washed with 40 ml of dichloromethane.The filtrate is poured into a large amount of distilled water to precipitate a precipitate, which is then suction filtered.After the obtained crude product is vacuum dried,Column chromatography (purification of ethyl acetate / methylene chloride = 1/4, v / v) afforded 0.4 g of pale yellow powder product p-FCA (yield: 40%).
  • 17
  • [ 324750-99-4 ]
  • C28H20O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
43.1% With potassium borohydride; water In ethanol at 20℃; for 24h; 1 An aqueous solution of p-FDPA (1.16 g, 3 mmol) and KBH4 (0.35 g, 6.5 mmol) was added to 20 mL of ethanol, and the reaction was stirred at room temperature for 24 h.After the reaction is completed, the reaction solution is cooled to room temperature, poured into a large amount of distilled water to precipitate a precipitate, and suction-filtered, and the obtained crude product is dried in vacuo and purified by column chromatography (eluent ethyl acetate / petroleum ether = 1 / 2, v/v),0.5 g of a bright yellow powder product p-HFA was obtained (yield: 43.1%).
  • 18
  • [ 27318-90-7 ]
  • [ 324750-99-4 ]
  • 9,10-bis(4-(1H-imidazo[4,5-f][1,10]phenanthrolin-2-yl)phenyl)anthracene [ No CAS ]
YieldReaction ConditionsOperation in experiment
23% With ammonium acetate; acetic acid for 8h; Reflux; Inert atmosphere; 2.3. Synthesis 1,10-Phenanthroline-5,6-dione (353 mg), 4,4’-(anthracene-9,10-diyl)dibenzaldehyde(216 mg), and ammonium acetate were added to glacial acetic acid, which wasrefluxed under N2 for 8 h. Upon cooling to room temperature, the reaction mixturewas added to 100 mL water, and was neutralized with ammonia. The yellow solid wascollected by filtration, washed with methanol and vacuum dried. The crude productwas recrystallization with chloroform/methanol (v/v=4:1). Yield: 23.0%.M.P: 273-274 °C.1H NMR (δH, ppm, 400 MHz, DMSO-d6): 14.67 (s, 2H), 9.44 (d, J8 Hz, 4H), 9.24 (d,J4 Hz, 4H), 8.69 (d, J8 Hz, 4H), 8.27 (t, 4H), 7.81 (d, J8 Hz, 4H), 7.76 (dd, J1 8 Hz, J2 4 Hz, 4H), 7.53 (dd, J1 8 Hz, J2 4 Hz, 4H). ESI-MS: m/z=383.76([M+2H+]2+), m/z766.77 ([M+H+]+). Theoretical exact mass: m/z=384.13([M+2H+]2+), m/z=767.26 ([M+H+]+). Anal. Calcd for C52H30N8: C, 81.44; H, 3.94; N,14.61. Found: C, 81.26; H, 3.97; N, 14.52.
  • 19
  • [ 3291-00-7 ]
  • [ 324750-99-4 ]
  • C42H30N4O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% In ethanol; dichloromethane for 24h; Reflux;
  • 20
  • [ 20439-47-8 ]
  • [ 324750-99-4 ]
  • C102H84N6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% With toluene-4-sulfonic acid In toluene Dean-Stark; Darkness;
Same Skeleton Products
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