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Chemical Structure| 83-53-4 Chemical Structure| 83-53-4
Chemical Structure| 83-53-4

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Product Details of 1,4-Dibromonaphthalene

CAS No. :83-53-4
Formula : C10H6Br2
M.W : 285.96
SMILES Code : C1=CC=CC2=C(C=CC(=C12)Br)Br
MDL No. :MFCD00041823
InChI Key :IBGUDZMIAZLJNY-UHFFFAOYSA-N
Pubchem ID :66521

Safety of 1,4-Dibromonaphthalene

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

Application In Synthesis of 1,4-Dibromonaphthalene

* 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 [ 83-53-4 ]

[ 83-53-4 ] Synthesis Path-Downstream   1~9

  • 3
  • [ 56525-79-2 ]
  • [ 83-53-4 ]
  • [ 1068160-44-0 ]
YieldReaction ConditionsOperation in experiment
6% With potassium phosphate; copper(l) iodide; In 1,4-dioxane; for 15h;Heating / reflux; Preparation of 4'-naphthyl-<strong>[56525-79-2]3,6-diphenylcarbazole</strong> Reaction 6As depicted in Reaction 6, a solution of 1Og (31.3 mmol) of carbazole, 13.5g (31.3 mmol) of 1,4-dibromonaphthalene, CuI, diaminohexane and K3PO4 in dioxane was refluxed for 15 hours. After completion of the reaction, the reaction mixture was <n="32"/>extracted with ethyl acetate. After the solvent was removed under reduced pressure, the residue was purified by column chromatography to give the title compound. The product was collected by filtration under reduced pressure and dried. Yield: 6percent. MS (El) (Calcd. for C34H22BrN: 523.09, Found: 523).
  • 4
  • [ 83-53-4 ]
  • [ 654664-63-8 ]
  • [ 1158227-46-3 ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate;trans-bis(triphenylphosphine)palladium dichloride; In toluene; at 100℃; for 3h; Preparation of Compound (119)Compound (118) (9.2 g, 33.9 mmol), 1,4-dibromonaphthalene (8.8 g 30.8 mmol) and trans-dichlorobistriphenylphosphine palladium (II) (Pd(PPh3)2Cl2 (2.1 g, 3.1 mmol) were dissolved in toluene (300 mL). After adding 2 M sodium carbonate solution (150 mL), the mixture was heated to 100 C., and reacted at the same temperature for 3 hours. The reaction mixture was extracted with dichloromethane (300 mL), and the extract was washed with aqueous sodium chloride solution (300 mL), dried over anhydrous magnesium sulfate, and filtered. After evaporating the organic layer under reduced pressure, the solid obtained was recrystallized from tetrahydrofuran (100 mL) to obtain the desired compound (119) (7.7 g, 17.7 mmol).
  • 5
  • [ 83-53-4 ]
  • [ 97674-02-7 ]
  • [ 46258-62-2 ]
YieldReaction ConditionsOperation in experiment
Example 1, Step aA solution of 1,4-dibromonaphthalene (1.0 g, 3.49 mmol) in toluene (10 niL) was purged with 2 for 10 minutes. Then tributyl(l-ethoxyvinyl)tin (1.38 g, 3.84 mmol) was added followed by Pd(Ph3P)2Cl2 (251 mg, 0.349 mmol). The reaction mixture was purged with 2 for 10 minutes and allowed to reflux at 100 C overnight. The reaction mixture was quenched with saturated KF solution (10 mL) and stirred at room temperature for 2 hrs. The reaction mixture was filtered through a diatomaceous earth (Celite) plug, and the organic layer was separated and concentrated in vacuo. To the resulting residue, 3 N HC1 (20 mL) was added at RT and stirred for 2 hrs. Then the reaction mixture was extracted with EtOAc, washed with brine, dried over Na2S04 and concentrated in vacuo. The crude was purified by flash chromatography (ISCO, EtOAc: petroleum ether, 20:80) to obtain bromide la (600 mg). LC/MS (Condition 8): Rt = 1.99 min. XH NMR (CDCI3, delta = 7.26 ppm, 400 MHz): delta 8.75-8.73 (m, 1H), 8.36-8.34 (m , 1H), 7.85 (d, J = 7.8, 1H), 7.76 (d, J = 7.8, 1H), 7.69-7.65 (m , 2H ), 2.76 (s, 3H ). LC/MS: Anal. Calcd. for [M+H]+ Ci2H10BrO: 248.98; found 249.0.
  • 6
  • [ 83-53-4 ]
  • [ 128733-85-7 ]
  • 1-bromo-4-(5-tert-butyl-2-methoxyphenyl)naphthalene [ No CAS ]
  • 7
  • [ 83-53-4 ]
  • [ 952514-79-3 ]
  • C48H32N4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
47.33% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; water; toluene; at 80℃; for 16h; 1,4-Dibromonaphthalene (10 g, 34.69 mmol),4- (1-Phenyl-1H-benzimidazol-2-yl) phenylboronic acid (23.17 g, 76.91 mmol)Potassium carbonate (24.16 g, 157.96 mmol) andPd (PPh3) 4 (4.04 g) was placed in a reaction flask,Then add 150 ml of toluene,Ethanol 30 ml and deionized water 60 ml,Stir and reflux at 80 C for 16 hours.After the reaction was added 100 ml of deionized water and stirred to room temperature, the solid was filtered off, and then added to 250 ml of tetrahydrofuran was heated with stirringTo the solid solution, through a silica gel column, concentrated by distillation, ethyl acetate was added and the solid was filtered off,Drying of compound A1 (11 g, 47.33% yield) as a white solid.
  • 8
  • [ 83-53-4 ]
  • [ 626-13-1 ]
  • C38H34N2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
3 g With tri-tert-butyl phosphine; palladium diacetate; sodium t-butanolate; In toluene; at 50 - 60℃; 1,4-dibromonaphthalene (2 g, 6.99 mmol) and di-m-tolylamine (2.89 g, 14.687 mmol) were added in a reaction flask. After the toluene was sufficiently dry, dry toluene (30 mL) was added thereto, and then the mixture was heated and stirred. Sodium t-butoxide (1.74 g, 18.18 mmol) was added when the mixture was heated to 50 C., and the mixture was heated and stirred again. Pd(OAc)2 (0.047 g, 0.21 mmol) and tri-tert-butylphosphine (0.12 g, 0.56 mmol) were added when the temperature reached 60 C., and the reaction underwent overnight. After the reaction completed, deionized water (50 mL) was added, and the mixture was stirred for 30 minutes. Solid was filtered, and the organic layer was collected after removing the aqueous layer from the filtrate. The organic layer was purified through silicon chromatography, and the purified organic layer and the solid filtered were combined and concentrated via distillation. Methanol (100 mL) was added for precipitation, and the precipitate was filtered to obtain Compound A3 (3 g) as a pale-yellow solid. 1H NMR (400 MHz, CDCl3, delta):delta 8.03-7.965 (dd, 3H); 7.345-7.24 (m, 7H); 7.12-7.06 (t, 6H); 6.91-6.86 (s, 6H); 6.85-6.8 (d, 6H); 6.85-6.74 (d, 6H).
  • 9
  • [ 83-53-4 ]
  • [ 1036378-83-2 ]
  • C28H19Br [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water;Reflux; In a 2L round flask, terphenylpinacolborane 55g (154.38mmol, 1eq) and 1,4-dibromobenzene 66.2g (231.57mmol, 1.5eq), Pd(pph3)48.9g (7.72mmol, 0.05eq), K2CO364g( 463.13mmol, 3eq), and THF/H2O was added at 1500ml/300ml, respectively, and stirred under reflux.After the reaction was completed, the mixturewas extracted withCH2Cl2/H2O, and the CH2Cl2layerwas dried withMgSO4.Silica-gel column purification gave 43.4 g of compound 2-1 in 65% yield.
 

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