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Chemical Structure| 51339-30-1 Chemical Structure| 51339-30-1

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Chemical Structure| 51339-30-1

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Product Details of [ 51339-30-1 ]

CAS No. :51339-30-1
Formula : C13H10Br2O
M.W : 342.03
SMILES Code : OC(C1=CC=CC(Br)=C1)C2=CC=CC(Br)=C2

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Application In Synthesis of [ 51339-30-1 ]

* 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 [ 51339-30-1 ]

[ 51339-30-1 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 25032-74-0 ]
  • [ 51339-30-1 ]
YieldReaction ConditionsOperation in experiment
88% With pyridinium chlorochromate; In dichloromethane; for 1.5h;Molecular sieve; Next, 200 mL Erlenmeyer flask was charged with Celite8.5 g,3.4 g of active molecular sieves 3A, 60 ml of dichloromethane,2.72 g (12.6 mmol) of pyridinium chlorochromate was added and stirred.Compound h 1.44 g (4.21 mmol) of dichloromethane 10 mlAfter adding the solution, the mixture was stirred for 1.5 hours. For the reaction mixture,The insoluble portion was removed with an alumina short column. After concentration of the filtrate,The obtained viscous substance was purified by silica gel column chromatography (hexane: ethyl acetate = 9: 1) to obtain 1.26 g (3.71 mmol) of the target compound i,Obtained in 88% yield.
  • 2
  • [ 51339-30-1 ]
  • [ 25032-74-0 ]
YieldReaction ConditionsOperation in experiment
88% With pyridinium chlorochromate; In dichloromethane; at 20℃; for 1.5h; A mixture of pyridiniumchlofochromate (2.72 g, 12.6 mmol) in dichloromethane (60 mL) was added a solution of 3,3'-Dibromophenylmethanol in dichloromethane (10 mL). The resulting mixture was stirred 1.5 h at room temperature. The organic layer was concentrated under reduced pressure and the crude product purified by silica gel column chromatography (hexane:ethylacetate = 9:1) to give 2 as a pale yellow solid. (1.26 g, 88%).
85% With pyridinium chlorochromate; In dichloromethane; at 0 - 20℃; for 5.66667h; Bis(3-bromophenyl) ketone. 30 mL of anhydrous CH2Cl2 were poured into a flask containing PCC (1.92 g, 8.73 mmol) and celite (1.9 g). The suspension was stirred at 0 C. under nitrogen for 10 minutes, at which point, 10 mL of a CH2Cl2 solution of the appropriate alcohol (1.99 g, 5.82 mmol) were added. After the reaction was stirred at room temperature for 5.5 h, 15 mL of Et2O were added and the reaction mixture was filtered through fluorisil-silica gel and rinsed with extra Et2O (10 mL). The organic phase was dried under Na2SO4 and the solvent was evaporated to afford 1.673 g (4.92 mmol) of pure product in a 85% yield.1H NMR (300 MHz, CDCl3, δ): 7.92 (t, J=1.8, ArH, 2H), 7.73 (ddd, J=8.0, 2.0, 1.1, ArH, 2H), 7.68 (ddd, J=7.7, 1.6, 1.2, ArH, 2H), 7.37 (t, J=7.8, ArH, 2H).13C NMR (75 MHz, CDCl3): δ 193.7, 138.8, 135.7, 132.7, 130.0, 128.5, 122.8.
76.8% With pyridinium chlorochromate; In dichloromethane; at 20℃; for 12h; In a 5 L round bottom flask, 150 mL of methylene chloride was added to 10 g (0.05 mol) of the compound represented by the formula [1-b] obtained from the scheme 2, and pyridinium chlorochromate25.7 g was dissolved in 200 mL of methylene chloride and added to the reaction.The mixture was stirred at room temperature for 12 hours. After completion of the reaction, 900 mL of ethanol was added and stirred, followed by filtration. The organic layer was concentrated under reduced pressure and then dried to obtain 7.6 g (76.8%) of a compound represented by the formula 1-c
72% With dipyridinium dichromate; In dichloromethane; at 0 - 25℃; for 3h; The product obtained in step (1) was added to dry dichloromethane (DCM) (75mL), dissolved at room temperature with stirring, then cooled to 0C, and pyridinium dichromate (PDC) (12.4g, 32.96) was slowly added. mmol), the reaction mixture was stirred at room temperature for 3 hours.At the end of the reaction, H2O and ethyl acetate (EA) (the mass ratio ofH2O: EA is 1:1) are added for extraction, the organic phases are combined, dried with anhydrous Na2SO4,and then removed by a rotary evaporator. The solvent was removed to obtain the crude product.The crude product was purified by column chromatography (silica gel column, eluent PE:EA=50:1, volume ratio) to obtain a white powder as the product with a yield of 72%.
With manganese(IV) oxide; In dichloromethane; at 20℃; for 1h; Under a nitrogen atomosphere, a tetrahydrofuran solution (10 mL) of 1,3-dibromobenzene (1.9 mL, 16.1 mmol) was cooled to -70 C. and then n-butyllithium (10.0 mL, 1.60 N, 16.1 mmol) was added dropwise thereto over a period of 15 minutes. After the mixture was stirred at -70 C. additionally for 20 minutes, a tetrahydrofuran (10 mL) solution of 3-bromobenzaldehyde (1.7 mL, 14.6 mmol) was added dropwise over a period of 15 minutes, and the mixture after the dropwise addition was allowed to warm to room temperature. The reaction solution was poured into aqueous ammonium chloride-saturated solution, and the mixture was extracted with toluene. The organic phases obtained were combined and concentrated to give 1,1-bis(3-bromophenyl)methanol as a colorless oily substance. The substance was used in the next reaction without further purification. Manganese dioxide (14.2 g, 146.0 mmol) was added to a methylene chloride (70 mL) solution of 1,1-bis(3-bromophenyl)methanol (14.6 mmol) and the mixture was stirred at room temperature in air for 1 hour. The reaction solution was filtered. The filtrate was concentrated and the residue obtained was purified by silica gel column chromatography and recrystallization to give 3,3'-dibromobenzophenone as white powder (3.5 g). Yield: 70.5%. 1H-NMR (200 MHz, CDCl3) δ: 7.38 (t, J=8.0 Hz, 2H), 7.65-7.79 (m, 4H), and 7.93 (dd, J=1.6, 2.0 Hz, 2H).

 

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