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Chemical Structure| 1307270-15-0 Chemical Structure| 1307270-15-0

Structure of 1307270-15-0

Chemical Structure| 1307270-15-0

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Product Details of [ 1307270-15-0 ]

CAS No. :1307270-15-0
Formula : C55H60Br10O10
M.W : 1680.10
SMILES Code : BrCCOC1=C(CC2=CC(OCCBr)=C(CC3=CC(OCCBr)=C(CC4=C(OCCBr)C=C(CC5=C(OCCBr)C=C(C6)C(OCCBr)=C5)C(OCCBr)=C4)C=C3OCCBr)C=C2OCCBr)C=C(OCCBr)C6=C1

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Application In Synthesis of [ 1307270-15-0 ]

* 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 [ 1307270-15-0 ]

[ 1307270-15-0 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 50-00-0 ]
  • [ 5471-84-1 ]
  • [ 1307270-15-0 ]
YieldReaction ConditionsOperation in experiment
41% With boron trifluoride diethyl etherate; In 1,2-dichloro-ethane; at 20℃; for 3h;Inert atmosphere; Under the protection of nitrogen, product 1 (3.37 g, 11.5mmol) and paraformaldehyde (0.349 g, 11.5mmol) were dissolvedin 200mL of 1,2-dichloroethane. Then, boron trifluorideetherate (BF3¢(OC2H5)2, 1.63 g, 11.5mmol) was added as acatalyst, and the mixture was stirred at room temperature for 3 hto obtain a green solution. After filtration, the solid was placedon silica gel with a mixed solvent of petroleum ether/dichloromethane(1:2 v/v) as the eluent for column chromatographypurification to obtain a white powder product 2 (1.6 g,41%).
40% With boron trifluoride diethyl etherate; In dichloromethane; at 0℃; for 2.5h;Inert atmosphere; Schlenk technique; To a 500 mL Schlenk flask with magnetic stirbar was charged compound 1 (3.0 g 9.2mmol), Paraformaldehyde (0.834 g, 27.8 mmol), CH2Cl2 (200 mL) was then charged, and the solution was cooled to 0 C in an ice bath. Boron trifluorideetherate (3.0 mL, 23.7 mmol) was added to the solution cooling with ice bath under N2 protection. The mixture was stirred for 2.5 hour. The reaction mixture was filtration. Filtrate washed with 2.5 M NaOH (2 ×30 mL) and water (1 × 30 mL) and dried with anhydrous MgSO4. The solvent was evaporated to provide a crude product. Recrystallized from ethyl acetate, and dried under vacuum to afford 2 as white or light yellow powder, 40% (1.2 g, 0.74mmol).
40% With boron trifluoride diethyl etherate; In dichloromethane; at 0℃; for 2.5h;Schlenk technique; Inert atmosphere; To a 500 mL Schlenk flask with magnetic stir bar wascharged compound 1 (3.0 g 9.2 mmol), Paraformaldehyde(0.834 g, 27.8 mmol), CH2Cl2 (200 mL) was then charged,and the solution was cooled to 0 C in an ice bath. Borontrifluoride etherate (3.0 mL, 23.7 mmol) was added to thesolution cooling with ice bath under N2 protection. Themixture was stirred for 2.5 h. The reaction mixture wasfiltration. Filtrate washed with 2.5 M NaOH (2 9 30 mL)and water (1 9 30 mL) and dried with anhydrous MgSO4.The solvent was evaporated to provide a crude product.Recrystallized from ethyl acetate, and dried under vacuumto afford 2 as white or light yellow powder, 40% (1.2 g). 1H NMR (600 MHz, CDCl3): d = 6.91 (s, 10H), 4.22 (t,J = 5.6, 20H), 3.84 (s, 10H), 3.63 (t, J = 5.7, 20H) ppm.13C NMR (150 MHz, CDCl3): d = 149.7, 129.1, 116.0,69.0, 30.7, 29.4 ppm.
38% With boron trifluoride diethyl etherate; In dichloromethane; at 20℃; for 4.16667h; Weigh (1.00g, 3.08mmol) bromo-p-phenylene diethyl ether, (0.14g, 4.67mmol) paraformaldehyde in a 50mL round bottom flask, Dissolve in 10mL of dichloromethane, add 1mL of boron trifluoride ether after stirring for ten minutes; the reaction system is magnetically stirred at room temperature for 4h, TCL detects the progress of the reaction; after the completion of the reaction, the system is concentrated, and the crude product is separated by column chromatography (the volume ratio of petroleum ether: dichloromethane: ethyl acetate is 100:75:1) to obtain brominated column pentaaromatics. White solid, 38%,
35% A mixture of 5 (3.24g, 10mmol) and paraformaldehyde (0.93g, 30mmol) in 1,2-dichloroethane (20mL) was stirred at room temperature for 30min. BF3·Et2O (1.25mL, 10mmol) was added and the reaction mixture was stirred for additional 30min. The reaction mixture was washed with water three times, and the organic phase was concentrated and the product was purified by column chromatography (SiO2; Petroleum ether/CH2Cl2/EA, 2:1:0.03) to give a white solid (1.18g, 35%). 1H NMR (400MHz, CDCl3): δ 6.92 (s, 10H), 4.23 (t, 20H, J=5.6Hz), 3.84 (s, 10H), 3.64 (t, 20H, J=5.6Hz). 13C NMR (101MHz, CDCl3): δ 149.66, 129.06, 116.09, 77.36, 77.05, 76.73, 68.97, 53.43, 30.75, 29.40.
With boron trifluoride diethyl etherate; In 1,2-dichloro-ethane; at 20℃; for 1h;Cooling with ice; (2) Add 3.37g of compound 1, 0.349 g of paraformaldehyde, 50 mL of 1,2-dichloroethane to a round bottom flask, and useIce water bath cooling,Then, 3.26 g of boron trifluoride diethyl ether was added thereto, and the reaction was stirred at room temperature for 1 hour.After the reaction was completed, it was quenched with 50 mL of water and finally extracted with dichloromethane.The organic phase is dried over anhydrous sodium sulfate and concentrated under reduced vacuo.The crude product was purified by silica gel column chromatography eluting with petroleum ether-ethyl acetate (volume ratio: 100:1).The eluate was collected and lyophilized in vacuo to give compound 2,

  • 2
  • [ 50-00-0 ]
  • [ 5471-84-1 ]
  • [ 1307270-15-0 ]
  • C66H72Br12O12 [ No CAS ]
  • 3
  • [ 50-00-0 ]
  • [ 5471-84-1 ]
  • [ 1307270-15-0 ]
  • [ 1446394-07-5 ]
  • 5
  • [ 110-88-3 ]
  • [ 5471-84-1 ]
  • [ 1307270-15-0 ]
YieldReaction ConditionsOperation in experiment
79.4% With boron trifluoride diethyl etherate; In dichloromethane; at 20℃; for 36h; <strong>[5471-84-1]1,4-bis(2-bromoethoxy)benzene</strong> and 1,3,5-trioxane are added to dichloromethane (or chloroform) in a molar ratio of 1:1.1, At 0 C, add the catalyst boron trifluoride ether, the molar ratio of boron trifluoride ether to <strong>[5471-84-1]1,4-bis(2-bromoethoxy)benzene</strong> is 1:1; after reacting at room temperature for 36 hours, Add deionized water for quenching, separation and extraction, drying, column chromatography purification, white powdery solid bis(2-bromoethoxy) column [5] aromatic hydrocarbon (compound 1a).
50% (Fig. 5) 1,4- dibromoethylbenzene(2.0 g, 6.0 mmol) and trioxymethylene (0.55 g, 6.0 mmol)were dissolved in dichloromethane (200 mL) and stirredat 25 for 30 min. Then Boron trifluoride etherate (0.9 g,6.0 mmol) was added, and the mixture was stirred at 25for 72 h. Hydrochloric acid solution (1.0 mol/L, 20 mL)was added to quenching the reaction, then the mixture waswashed with water (2 × 50 mL) and dried over Na2SO4.Concentrationprovided a crude product, purification by columnchromatography, using petroleum ether/dichloromethane(1:1, v/v) as eluent afforded 1a (1.0 g, 50%). 1H NMR(400 MHz, CDCl3-d) δ = 6.90 (s, 10H), 4.22 (t, J = 5.6 Hz,20H), 3.84 (s, 10H), 3.62 (t, J = 5.6 Hz, 20H).
 

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