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Chemical Structure| 1228595-79-6 Chemical Structure| 1228595-79-6

Structure of 1228595-79-6

Chemical Structure| 1228595-79-6

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Product Details of [ 1228595-79-6 ]

CAS No. :1228595-79-6
Formula : C14H12Br2Si
M.W : 368.14
SMILES Code : C[Si]1(C)C2=CC(Br)=CC=C2C3=CC=C(Br)C=C31
MDL No. :MFCD28963502
InChI Key :FAJDSWHVALMLLF-UHFFFAOYSA-N
Pubchem ID :68562959

Safety of [ 1228595-79-6 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of [ 1228595-79-6 ]

* 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 [ 1228595-79-6 ]

[ 1228595-79-6 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 852138-89-7 ]
  • [ 75-78-5 ]
  • [ 1228595-79-6 ]
YieldReaction ConditionsOperation in experiment
76% comprising the compound B-4 (4g, 7. Lmmol) A round bottom flask filled with argon, and to this 30mL of THF was added . The mixture was cooled to -78C. Was slowly added n-BuLi (in hexane 2. 5M, 6. 2mL, 15. 6mmol) and stirred for 1 hour. to this dichlorodimethylsilane (2. 0g, 15. 6mmol) was added , and slowly heated to reflux for 12 hours at room temperature. After extraction with EA and washed with water, drying the resulting organic layer to give Compound B-5 (2g, 76%) was purified by column chromatography on silica
76% A round bottom flask containing 4 g (7.1 mmol) of compound B-4 was charged with argon gas, 30 mL of THF was added, and the solution was cooled to -78 C. 6.2 mL (15.6 mmol) of n-BuLi (2.5 M in hexane) was added slowly and stirred for 1 hour. 2.0 g (15.6 mmol) of dichlorodimethylsilane was added and the temperature was slowly raised to room temperature while stirring for 12 hours, followed by extraction with EA and washing with water. The obtained organic layer was dried and purified by silica column to obtain 2 g (76%) of Compound B-5.
76% A round-bottom flask containing 4 g (7.1 mmol) of Intermediate 4-3 was filled with argon gas and 30 mL of tetrahydrofuran (THF). The resulting mixture was then cooled to a temperature of about -78 C. 6.2 mL (15.6 mmol) of n-BuLi (2.5 molar (M) in hexane) was slowly added thereto, and the resulting solution was stirred for about 1 hour. 2.0 g (15.6 mmol) of dichlorodimethyl silane was added thereto. The resulting solution was stirred for about 12 hours and the temperature was allowed to slowly come to room temperature. An organic layer was extracted using ethyl acetate and washed with water. The obtained organic layer was dried and purified through silica gel chromatography, thereby producing 2 g (yield: 76%) of Intermediate 4-4.
56.36% To a solution of <strong>[852138-89-7]4,4'-dibromo-2,2'-diiodo-1,1'-biphenyl</strong> (10.0 g, 17.74 mmol, 1.00 eq) in 70 ml of tetrahydrofuranAfter dissolution, 2.5 M n-Butyl lithium in hexane (35.47 ml, 56.76 mmol, 3.2 eq) was slowly added at 100 C.After 5 hours of reaction, dichlorodimethylsilane (2.4 g, 18.62 mmol, 1.05 eq) was slowly added.After 24 hours of reaction, the reaction mixture was distilled under reduced pressure to remove the solvent. Distilled water (100 ml × 3) and dichloromethane were added to the reaction mixture to remove water with MgSO 4. After filtering and drying, 3.68 g of the target compound (yield: 56.36%) was obtained.
50% Under nitrogen protection, in a 500mL three-necked bottle containing magnets,Adding 4,4-dibromo-2,2-diiodobiphenyl as raw material(52g, 92.8mmol, 1eq), dissolved in 300mL of tetrahydrofuran,The reaction solution was cooled to a low temperature of -78 C, then 2.5 M n-butyllithium / n-hexane solution (142 mL, 185.6 mmol, 2 eq) was added dropwise, and stirred at a constant temperature for 1 h.Then dichlorodimethylsilane (35 g, 185.6 mmol, 2 eq) was added dropwise, and stirred at constant temperature for 1 h.Then it was stirred at room temperature for 12 h.After the end of the reaction, it was extracted three times with EA/H 2 O.The crude product was purified by silica column chromatography.White solid17 g, yield 50%.
50% Under the protection of nitrogen, in a 500mL three-necked bottle with magnets,Add the starting material 4,4-dibromo-2,2-diiodobiphenyl (52g, 92.8mmol, 1eq) and add 300mL tetrahydrofuran to dissolve,Lower the reaction temperature to -78 C, then dropwise add a 2.5M n-butyllithium / n-hexane solution (142 mL, 185.6 mmol, 2 eq), and stir at constant temperature for 1 h.Dichlorodimethylsilane (35 g, 185.6 mmol, 2 eq) was then added dropwise, stir at constant temperature for 1 h, then return to room temperature and stir for 12 h.After the reaction, it was extracted three times with EA / H2O.The combined organic phases were concentrated to give a crude product.The crude product was purified by silica column chromatography to obtain 17 g of a white solid with a yield of 50%.
45% Step B - Preparation of Compound Int-43cTo a stirred solution of compound Int-43b (2.8 g, 4.9 mmol) in THF (90 mL) at -78 C was added n-BuLi (2.5 M in hexanes, 7.8 mL, 19.5 mmol) dropwise over in -2.5 h. Once the addition was complete, the mixture was allowed to stir for one hour at -78 C whereupon Me2SiCl2 (0.65 mL, 5.4 mmol) was added rapidly. The mixture was allowed to stir for an additional 35 minutes at -78 C, the cooling bath was removed, and the mixture was stirred overnight at rt. Water (10 mL) was added followed by dilution with hexanes (100 mL) and the layers were separated. The organic layer was washed with brine (1 x 25 mL), dried (Na2S04), filtered, and concentrated in vacuo. The crude product was purified using flash chromatography eluting with hexanes to provide 0.82 g (45%) of compound Int- 43c as a white solid
30.1% n-BuLi (2.5 M, 17 mL) was slowly added to the solution of 4,4?-dibromo-2,2?-diiodo-biphenyl (6 g, 10.64 mmol) and THF(100 mL) at 90 C. The solution was kept for 1 h. Afterdichlorodimethylsilane(5.70 g, 44.16 mL) was slowly added to thesolution at the 90 C, the temperature was slowly increased toroom temperature, and stirred for 12 h. The reaction wasterminated by water, and organic layer was extracted by ether.The crude product was purified by n-hexane, and recrystallizedin methanol. Yield: 1.12 g (30.1%) 1H NMR (300 MHz, CD2Cl2):delta 7.68 (d, 2H), 7.63 (d, 2H), 7,5 (s, 2H), 0.43 (s, 6H) 13C NMR(500 MHz, CDCl3): delta 145.7, 141.6, 135.7, 133.4, 122.7, 122.6, 3.25.
under the protection of nitrogen, 5.64 g of 4,4?-dibromo-2,2?-diiodo biphenyl was dissolved in 40 mL of THF, cooled to -25 C., to the solution was added dropwise 20.00 mL of n-butyl lithium solution (n-butyl lithium/n-hexane in 1.0 mol/L). After 2 hours of reaction, 1.29 g of dimethyl dichlorosilane was added, and the reaction was continued for another 24 hours. After the completion of the reaction, a deionized water was added and the resulting mixture was extracted with diethyl ether, then dried over anhydrous magnesium sulfate, rotary evaporated, and column chromatographed to give the product. MALDI-TOF-MS (m/z): 368.1 (M+);
under the protection of nitrogen, 5.64 g of 4, 4'-dibromo-2, 2'-diiodo biphenyl was dissolved in 40 mL of THF, cooled to -25 C, to the solution was added dropwise 20.00 mL of n-butyl lithium solution (n-butyl lithium/n-hexane in 1.0 mol / L). After 2 hours of reaction, 1.29 g of dimethyl dichlorosilane was added, and the reaction was continued for another 24 hours. After the completion of the reaction, a deionized water was added and the resulting mixture was extracted with diethyl ether, then dried over anhydrous magnesium sulfate, rotary evaporated, and column chromatographed to give the product. MALDI-TOF-MS (m / z): 368.1 (M+);

 

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[ 1228595-79-6 ]

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