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Chemical Structure| 51044-13-4 Chemical Structure| 51044-13-4

Structure of 51044-13-4

Chemical Structure| 51044-13-4

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Product Details of [ 51044-13-4 ]

CAS No. :51044-13-4
Formula : C25H21Br2P
M.W : 512.22
SMILES Code : BrC1=CC=C(C=C1)C[P+](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC=C4.[Br-]
MDL No. :MFCD00051922
InChI Key :FQJYKXVQABPCRA-UHFFFAOYSA-M
Pubchem ID :2724858

Safety of [ 51044-13-4 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of [ 51044-13-4 ]

* 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 [ 51044-13-4 ]

[ 51044-13-4 ] Synthesis Path-Downstream   1~6

  • 2
  • [ 51044-13-4 ]
  • [ 110677-45-7 ]
  • [ 916060-59-8 ]
  • [ 1019779-50-0 ]
YieldReaction ConditionsOperation in experiment
With potassium tert-butylate; In tetrahydrofuran; at 20℃;Inert atmosphere; [Step 2; Synthesis of (E)-4-bromo-4'-(9H-carbazol-9-yl)stilbene] Next, 9.44 g (18.4 mmol) of 4-bromobenzyl triphenylphosphonium bromide obtained in Step 1 and 5.00 g (18.4 mmol) of <strong>[110677-45-7]4-(9H-carbazol-9-yl)benzaldehyde</strong> were placed into a 300 mL three-neck flask, and nitrogen substitution was carried out in the three-neck flask. Then, 50 mL of tetrahydrofuran (THF) was added thereto. A suspension in which 2.07 g (18.4 mmol) of potassium tert-butoxide was mixed in 50 mL of THF was dropped into this mixture. After the completion of the dropping, the reaction mixture was stirred at room temperature for 24 hours. After the completion of the reaction, water was added to the reaction mixture, and the precipitate was collected by suction filtration. 4.41 g of a yellow powdered solid, (E)-4-bromo-4'-(9H-carbazol-9-yl)stilbene, which was the target substance, was obtained in a yield of 56.4%. It was confirmed that (Z)-4-bromo-4'-(9H-carbazol-9-yl)stilbene which is an isomer of the target substance was included in the obtained filtrate. A synthetic scheme (a-2) of (E)-4-bromo-4'-(9H-carbazol-9-yl)stilbene is shown below.
  • 3
  • [ 100-43-6 ]
  • [ 51044-13-4 ]
  • [ 7310-97-6 ]
  • 4,4'-((1E,1'E)-(((1E,1'E)-(2,5-dimethoxy-1,4-phenylene)bis(ethene-2,1-diyl))bis(4,1-phenylene))bis(ethene-2,1-diyl))dipyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
79.4% With 1,3-bis-(diphenylphosphino)propane; tetrabutylammomium bromide; palladium diacetate; potassium carbonate; In N,N-dimethyl acetamide; at 140℃; for 24h;Inert atmosphere; A two neck round bottom flask was charged with <strong>[7310-97-6]2,5-dimethoxyterephthalaldehyde</strong>(0.150 g, 0.773 mmol), 4-bromobenzyltriphenylphosphine bromide (0.792 g, 1.546 mmol), 4-vinyl pyridine (0.178 g, 1.546 mmol), K2CO3 (0.854 g,6.180 mmol), palladium acetate (0.0034 g, 0.0154 mmol), dppp (0.0095 g,0.023 mmol), TBAB (0.049 g, 0.154 mmol) in N,N-dimethylacetamide (10 mL) and was stirred at 140oC under N2 atmosphere for 24 h. The cooled mixture was then poured in water (100 mL) and extracted with ethyl acetate(3 50 mL). The organic layer was washed with water (2 20 mL) and dried over anhydrous sodium sulfate. The solution was concentrated under reduced pressure to obtain a viscous liquid, which was purified by column chromatography on silica gel and petroleum ether-ethyl acetate mixture as eluent to give pure product as orange solid (0.336 g, 79.40%).
  • 4
  • [ 51044-13-4 ]
  • [ 54117-37-2 ]
  • (E)-9-benzyl-3-(4-bromostyryl)-9H-carbazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% With sodium hydride; In tetrahydrofuran;Reflux; To a suspension of <strong>[54117-37-2]9-benzyl-9H-carbazole-3-carbaldehyde</strong> (650 mg, 2.28 mmol) and 4-bromobenzyltriphenylphosphonium bromide 8 (1.17 g, 2.28 mmol) in 100 mL dry THF was addedsodium hydride (1 g, 41.67 mmol). The solution was refluxed overnight. During reflux, the colorchanged from white to light yellow. The residue was quenched with water. The organic phaseswere combined, dried over magnesium sulfate and the solvent removed under reduced pressure.The residue was purified by column chromatography (SiO2) using DCM:pentane 1:1 as the eluent(678 mg, 68% yield).
  • 5
  • [ 51044-13-4 ]
  • [ 110677-45-7 ]
  • 9-(4-(4-bromostyryl)phenyl)-9H-carbazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% Previously reported procedures were employed for the synthesis ofCz9SBr [9]. Under nitrogen atmosphere and at -20 C, a solution of 4-bromobenzyltriphenylphosphonium bromide (3.07 g, 10 mmol) in anhydrousTHF (20 mL) was added in portions over a period of 10 min to amixture of sodium hydride (0.36 g, 15 mmol) in anhydrous THF(80 mL). After 10 min, a mixture of Cz9PhCHO (2.71 g, 10 mmol) anddry THF (50 mL) was added to the reaction mixture and stirred foranother 8 h at room temperature under nitrogen atmosphere. The resultingproduct was poured into water, neutralized with dilute hydrochloricacid, and extracted with dichloromethane. Then, the obtainedorganic layer was dried over magnesium sulfate. After the organicsolvent was removed by distillation under reduced pressure, the residuewas purified by column chromatography on silica gel to yield Cz9SBr asa green-yellow solid (2.92 g, 70%). 1H NMR (400 MHz, CDCl3, δ/ppm):8.12 (d, J=7.5 Hz, 2H), 7.69 (d, J=9.0 Hz, 2H), 7.54 (d, J=8.4 Hz,2H), 7.49 (d, J=8.4 Hz, 2H), 7.37-7.45 (m, 6H), 7.25 (t, J=8.1 Hz,2H), 7.16 (d, J=16.5 Hz, 1H), 7.07 (d, J=16.5 Hz, 1H); 13C NMR(100 MHz, CDCl3) δ 140.74, 137.14, 136.10, 136.06, 131.90, 128.39,128.27, 128.08, 127.88, 127.25, 125.99, 123.46, 121.65, 120.35, 120.05, 109.81. HRMS (m/z): calcd for C26H18BrN: 423.0623. Found:423.0624.
  • 6
  • [ 108-86-1 ]
  • [ 51044-13-4 ]
  • [ 31736-73-9 ]
YieldReaction ConditionsOperation in experiment
AlCl3 (15.0 g, 1 12.5 mmol) was added to a 250 ml Schlenk containing a stirring bar. Dried and degassed dichloromethane (100 ml) was added. A solution of 3-chloropropionyl chloride (12.14 ml, 127 mmol) in 20 ml of dichloromethane was added dropwise to the yellow slurry and stirred 15 min to obtain a dark brown solution. A solution of bromobenzene (10.92 ml, 104 mmol) in 20 ml of dichloromethane was added dropwise to the brown solution and the mixture was stirred 24 h at room temperature until no HCI overpressure was observed. The brown mixture was poured onto ice and extracted with dichloromethane (3 x 120 ml). The organic phase was washed with aqueous NaHCC>3 and brine and dried over Na2S04. Volatiles were pumped off to give 3-chloro-1 -(4-bromo)propanone as a light brown solid. This solid was used without further purification. 1H NMR for 3-chloro-1 -(4-bromo)propanone (400 MHz, Chloroform-d) delta 7.79 (dt, J = 8.7, 2.3 Hz, 2H, 3'a, 3'b), 7.64 - 7.55 (m, 2H, 2'a, 2'b), 3.89 (td, J = 6.8, 2.0 Hz, 2H, 2a, 2b), 3.40 (td, J = 6.8, 1.9 Hz, 2H, 3a, 3b).
 

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