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Chemical Structure| 517-51-1 Chemical Structure| 517-51-1

Structure of Rubrene
CAS No.: 517-51-1

Chemical Structure| 517-51-1

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Product Details of [ 517-51-1 ]

CAS No. :517-51-1
Formula : C42H28
M.W : 532.67
SMILES Code : C12=C(C3=CC=CC=C3)C4=C(C5=CC=CC=C5)C6=CC=CC=C6C(C7=CC=CC=C7)=C4C(C8=CC=CC=C8)=C1C=CC=C2
English Name :5,6,11,12-Tetraphenyltetracene
MDL No. :MFCD00003703
InChI Key :YYMBJDOZVAITBP-UHFFFAOYSA-N
Pubchem ID :68203

Safety of [ 517-51-1 ]

Application In Synthesis of [ 517-51-1 ]

* 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 [ 517-51-1 ]

[ 517-51-1 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 517-51-1 ]
  • [ 32287-37-9 ]
YieldReaction ConditionsOperation in experiment
99% With 1,4,8,11,15,18,22,25-octakis(phenylsulfanyl)phthalocyaninato zinc(II); oxygen In toluene at 20℃; for 20h; Irradiation;
98% With sodium molybdate; dihydrogen peroxide; sodium dodecyl-sulfate In dichloromethane; water; butan-1-ol at 25℃; for 0.5h;
98% With bis(dimethyl-di-n-octylammonium) molybdate; dihydrogen peroxide In water; benzene at 25℃; for 0.5h;
97% With air In chloroform for 24h; Irradiation;
92% With dihydrogen peroxide In 1,4-dioxane at 30℃; for 2.5h;
82% With CaO2*2H2O2 In tetrahydrofuran at 50℃; for 3h;
67% With 9,10-bis(4-tertbutylphenylethynyl)-9,10-dihydro-9,10-epidioxidoanthracene In chloroform at 25℃;
With benzene Irradiation.beim Belichten an der Luft;
With triphenyl phosphite ozonide In dichloromethane
With trishomobullvalene; oxygen; ozone 1.) CH2Cl2, -30 deg C, 0.5 min, 2.) CH2Cl2, -100 deg C to 0 deg C, 30 min; Multistep reaction;
With P(OPh)3(-O-O-O-) In dichloromethane -80 deg C to RT;
With oxygen for 0.283333h; Irradiation; var. times and pressures; effect of irradiation; testing with X-ray photoelectron spectroscopy;
With oxygen In chloroform-d1 Irradiation;
With air In 1,1,2,2-tetrachloroethane Irradiation;

References: [1]Katsurayama, Yoshino; Ikabata, Yasuhiro; Maeda, Hajime; Segi, Masahito; Nakai, Hiromi; Furuyama, Taniyuki [Chemistry - A European Journal, 2022, vol. 28, # 2].
[2]Aubry, Jean-Marie; Bouttemy, Sabine [Journal of the American Chemical Society, 1997, vol. 119, # 23, p. 5286 - 5294].
[3]Nardello-Rataj, Veronique; Caron, Laurent; Borde, Cedric; Aubry, Jean-Marie [Journal of the American Chemical Society, 2008, vol. 130, # 45, p. 14914 - 14915].
[4]Ly, Jack T.; Lopez, Steven A.; Lin, Janice B.; Kim, Jae Joon; Lee, Hyunbok; Burnett, Edmund K.; Zhang, Lei; Aspuru-Guzik, Alán; Houk; Briseno, Alejandro L. [Journal of Materials Chemistry C, 2018, vol. 6, # 14, p. 3757 - 3761].
[5]Sels, Bert F.; De Vos, Dirk E.; Jacobs, Pierre A. [Journal of the American Chemical Society, 2007, vol. 129, # 21, p. 6916 - 6926].
[6]Pierlot, Christel; Nardello, Veronique; Schrive, Jordane; Mabille, Caroline; Barbillat, Jacques; Sombret, Bernard; Aubry, Jean-Marie [Journal of Organic Chemistry, 2002, vol. 67, # 8, p. 2418 - 2423].
[7]Fudickar, Werner; Linker, Torsten [Chemistry - A European Journal, 2011, vol. 17, # 49, p. 13661 - 13664].
[8]Moureu; Dufraisse [Zeitschrift fur Physikalische Chemie, Stoechiometrie und Verwandtschaftslehre, 1927, vol. 130, p. 473] Moureu; Dufraisse; Butler [Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1926, vol. 183, p. 101] Moureu; Dufraisse; Dean [Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1926, vol. 182, p. 1442,1585].
[9]Khatib, F. el; Caminade, A. M.; Koenig, M. [Phosphorus and Sulfur and the Related Elements, 1984, vol. 20, p. 55 - 66].
[10]Zarth, Martin; Meijere, Armin de [Chemische Berichte, 1985, vol. 118, # 6, p. 2429 - 2449].
[11]Caminade, Anne Marie; Khatib, Fayez El; Koenig, Max; Aubry, Jean Marie [Canadian Journal of Chemistry, 1985, vol. 63, p. 3203 - 3209].
[12]Yamada, Masamichi; Ikemoto, Isao; Kuroda, Haruo [Bulletin of the Chemical Society of Japan, 1988, vol. 61, # 4, p. 1057 - 1062].
[13]Koylu, Damla; Sarrafpour, Syena; Zhang, Jingjing; Ramjattan, Sanya; Panzer, Matthew J.; Thomas, Samuel W. [Chemical Communications, 2012, vol. 48, # 76, p. 9489 - 9491].
[14]Uttiya; Miozzo; Fumagalli; Bergantin; Ruffo; Parravicini; Papagni; Moret; Sassella [Journal of Materials Chemistry C, 2014, vol. 2, # 21, p. 4147 - 4155].
  • 2
  • [ 127257-80-1 ]
  • [ 517-51-1 ]
YieldReaction ConditionsOperation in experiment
88% With aluminum tri-bromide; cesium iodide In chloroform -78 deg C -> room temp.;
  • 3
  • [ 517-51-1 ]
  • [ 1943664-64-9 ]
YieldReaction ConditionsOperation in experiment
63% With trifluoroacetic acid In dichloromethane at 20℃; for 3h;
  • 4
  • [ 1522-13-0 ]
  • [ 517-51-1 ]
YieldReaction ConditionsOperation in experiment
With methanesulfonyl chloride; triethylamine In toluene at 0 - 110℃; for 4.5h; Heating / reflux; 1 Propargyl alcohol PA-1, (10.0 g, 35 mMole) was dissolved in toluene (70 mL), with slight heating to get complete dissolution, cooled and stirred at 0° C. under a nitrogen atmosphere. To this solution was added triethylamine (NEt3), (4.95 g, 6.3 mL, 49 mMole) and then treated drop-by-drop with methanesulfonyl chloride (CH3SO2Cl), (6.29 g, 4.24 mL 49 mMole), keeping the temperature of the reaction below 10° C. After the addition, the solution was stirred at 0° C. for 15 minutes, at room temperature for 15 minutes and then heated to 110° C. for 4 hours. After this period, the reaction was cooled, diluted with ethyl acetate (100 mL) and washed with 2N-HCl. The organic layer was collected, dried (MgSO4), filtered and concentrated under reduced pressure to an oil. This oil was dissolved in the minimum amount of ether (approx. 40 mL) and treated with the same volume of methanol. The product YD-1, crystallized out. It was filtered off, washed well with methanol and dried.
  • 5
  • [ 517-51-1 ]
  • [ 98453-04-4 ]
YieldReaction ConditionsOperation in experiment
88% With hydrogenchloride In chloroform for 120h; Irradiation;
  • 6
  • [ 62409-66-9 ]
  • [ 98-80-6 ]
  • [ 517-51-1 ]
YieldReaction ConditionsOperation in experiment
70 % With tris-(dibenzylideneacetone)dipalladium(0); sodium carbonate; XPhos In tetrahydrofuran; water; toluene at 95℃; Inert atmosphere; Method B. General procedure: Tetrahaloacenes, aryl boronic acids (5.0 eq), Pd2(dba)3 (0.05 eq), XPhos (0.2 eq),and Na2CO3 (5.0 eq.) were added to an argon-purged mixture of THF/toluene/water (3:2:1).The resulting reaction mixture was heated to 95°C for 13 h. After cooling to room temperature,an excess of water was added; the organic layer was separated, and the aqueous layer was extracted with chloroform. The organic and aqueous layers were washed, dried over MgSO4,and evaporated. The resulting residue was purified by Silica gel chromatography using ethyl acetate/hexane (1:4) as the eluent to afford a series of tetraaryl-substituted acenes (70-72%).
 

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