No renderable structure data available
BrC1C=C(C=C(C=1)[Si](C)(C)C)BrChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 3,5-DIBROMO-1-TRIMETHYLSILYLBENZENE |
|---|---|
| IUPAC Name | — |
| CAS Number | 17878-23-8 |
| Database ID | 626244 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
3,5-DIBROMO-1-TRIMETHYLSILYLBENZENE (CAS 17878-23-8) product identity, structure identifiers and related reaction data for chemical intermediate research and sourcing review.
Potential Applications
For professional research and industrial use only
Database ID 626244
Safety Notice
For professional research and industrial use only. Review the supplier safety data sheet before handling.
Synthesis data
12 reactions · 12 references
Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-7fd894f7f7e34751a5646de798b3bfc5Conditions: temp:-68.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 17.18 g of 3,5-Dibromo-trimethylsilyl-benzene, 55.8 mmol, was dissolved in 380 ml Et2O. The solution was chilled to -68° C., and 22.3 mL of n-BuLi (2.5 M in hexanes), 55.8 mmol, were added within 18 minutes. The solution changed its color from clear to yellow, and was stirred for 45 minutes at −68° C. 7.5 mL TMSCl, 59 mmol, were added within six minutes. The temperature of solution rose within one hour to −33° C., and after another 30 minutes to −18° C. The solution was stirred overnight at room temperature. 60 mL of 2M HCl were added to the white suspension. Stirring for 30 minutes resulted in two clear phases. Et2O-phase was dried with MgSO4, filtered, and solvent evaporated. Raw product was distilled at a temperature of 70-76° C. and 0.1-0.2 mbar. All pure fractions were combined and gave 15.8 g of product (52.4 mmol, 94%). 1H-NMR (CHCl3=7.24 ppm): δ 7.56 (s, 2H), 7.50 (t, 1H), 0.25 (s, 6×3H). The solution was stirred overnight at room temperature Stirring for 30 minutes resulted in two clear phases Et2O-phase was dried with MgSO4 filtered solvent evaporated Raw product was distilled at a temperature of 70-76° C. and 0.1-0.2 mbar
Source ID: ord-a4839b929c774fdd97a6eeb112dc51f6Conditions: temp:-55.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 42.4 g of Tribromobenzene (134.6 mmol) was dissolved in 600 mL Et2O. The solution was chilled to −55° C., at which temperature starting material precipitated. 54 mL of n-BuLi (2.5 M in hexanes, 135 mmol) were added within 20 minutes. After stirring for 35 minutes at −52° C., 20 ml TMSCl (158 mmol) and 20 mL Et2O were added within 7 minutes. The suspension turned into a solution at −42° C., and a fine precipitate appeared at −30° C. The suspension was stirred overnight at room temperature. 100 mL 2M HCl were used to hydrolyze the mixture. After stirring for 30 minutes, the Et2O-phase was dried with MgSO4, filtered, and solvent evaporated until compound crystallized out of solution. The flask was stored overnight at +4° C. The crystalline compound was filtered, washed with a small amount cold pentane, and dried under vacuo. A second fraction of crystalline compound was obtained from the filtrate. Yield: 31.9 g (103.5 mmol, 77%). 1H-NMR (CHCl3=7.24 ppm): δ 7.62 (t, 1H), 7.49 (d, 2H), 0.25 (s, 3×3H). precipitated turned into a solution at −42° C. appeared at −30° C The suspension was stirred overnight at room temperature After stirring for 30 minutes the Et2O-phase was dried with MgSO4 filtered solvent evaporated until compound crystallized out of solution The flask was stored overnight at +4° C The crystalline compound was filtered washed with a small amount cold pentane dried under vacuo A second fraction of crystalline compound was obtained from the filtrate
Source ID: ord-7838ebdba624441db3f9462acaa75547Conditions: temp:-68.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 17.18 g of 3,5-Dibromo-trimethylsilyl-benzene, 55.8 mmol, was dissolved in 380 ml Et2O. The solution was chilled to −68° C., and 22.3 mL of n-BuLi (2.5 M in hexanes), 55.8 mmol, were added within 18 minutes. The solution changed its color from clear to yellow, and was stirred for 45 minutes at −68° C. 7.5 mL TMSCl, 59 mmol, were added within six minutes. The temperature of solution rose within one hour to −33° C., and after another 30 minutes to −18° C. The solution was stirred overnight at room temperature. 60 mL of 2M HCl were added to the white suspension. Stirring for 30 minutes resulted in two clear phases. Et2O-phase was dried with MgSO4, filtered, and solvent evaporated. Raw product was distilled at a temperature of 70-76° C. and 0.1-0.2 mbar. All pure fractions were combined and gave 15.8 g of product (52.4 mmol, 94%). 1H-NMR (CHCl3=7.24 ppm): δ 7.56 (s, 2H), 7.50 (t, 1H), 0.25 (s, 6×3H). The solution was stirred overnight at room temperature Stirring for 30 minutes resulted in two clear phases Et2O-phase was dried with MgSO4 filtered solvent evaporated Raw product was distilled at a temperature of 70-76° C. and 0.1-0.2 mbar
Source ID: ord-f169457b93bc485ab0197fba1f194878Conditions: temp:-55.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 42.4 g of Tribromobenzene (134.6 mmol) was dissolved in 600 mL Et2O. The solution was chilled to −55° C., at which temperature starting material precipitated. 54 mL of n-BuLi (2.5 M in hexanes, 135 mmol) were added within 20 minutes. After stirring for 35 minutes at −52° C., 20 ml TMSCl (158 mmol) and 20 mL Et2O were added within 7 minutes. The suspension turned into a solution at −42° C., and a fine precipitate appeared at −30° C. The suspension was stirred overnight at room temperature. 100 mL 2M HCl were used to hydrolyze the mixture. After stirring for 30 minutes, the Et2O-phase was dried with MgSO4, filtered, and solvent evaporated until compound crystallized out of solution. The flask was stored overnight at +4° C. The crystalline compound was filtered, washed with a small amount cold pentane, and dried under vacuo. A second fraction of crystalline compound was obtained from the filtrate. Yield: 31.9 g (103.5 mmol, 77%). 1H-NMR (CHCl3=7.24ppm): δ 7.62 (t, 1H), 7.49 (d, 2H), 0.25 (s, 3×3H). precipitated turned into a solution at −42° C. appeared at −30° C The suspension was stirred overnight at room temperature After stirring for 30 minutes the Et2O-phase was dried with MgSO4 filtered solvent evaporated until compound crystallized out of solution The flask was stored overnight at +4° C The crystalline compound was filtered washed with a small amount cold pentane dried under vacuo A second fraction of crystalline compound was obtained from the filtrate
Source ID: ord-df1087661be14b3ab9860e40947b06d7Conditions: temp:-55.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 42.4 g of Tribromobenzene (134.6 mmol) was dissolved in 600 mL Et2O. The solution was chilled to −55° C., at which temperature starting material precipitated. 54 mL of n-BuLi (2.5 M in hexanes, 135 mmol) were added within 20 minutes. After stirring for 35 minutes at −52° C., 20 ml TMSCl (158 mmol) and 20 mL Et2O were added within 7 minutes. The suspension turned into a solution at −42° C., and a fine precipitate appeared at −30° C. The suspension was stirred overnight at room temperature. 100 mL 2M HCl were used to hydrolyze the mixture. After stirring for 30 minutes, the Et2O-phase was dried with MgSO4, filtered, and solvent evaporated until compound crystallized out of solution. The flask was stored overnight at +4° C. The crystalline compound was filtered, washed with a small amount cold pentane, and dried under vacuo. A second fraction of crystalline compound was obtained from the filtrate. Yield: 31.9 g (103.5 mmol, 77%). 1H-NMR (CHCl3=7.24ppm): δ 7.62 (t, 1H), 7.49 (d, 2H), 0.25 (s, 3×3H). precipitated turned into a solution at −42° C. appeared at −30° C The suspension was stirred overnight at room temperature After stirring for 30 minutes the Et2O-phase was dried with MgSO4 filtered solvent evaporated until compound crystallized out of solution The flask was stored overnight at +4° C The crystalline compound was filtered washed with a small amount cold pentane dried under vacuo A second fraction of crystalline compound was obtained from the filtrate
Source ID: ord-df1087661be14b3ab9860e40947b06d7Conditions: temp:-68.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 17.18 g of 3,5-Dibromo-trimethylsilyl-benzene, 55.8 mmol, was dissolved in 380 ml Et2O. The solution was chilled to −68° C., and 22.3 mL of n-BuLi (2.5 M in hexanes), 55.8 mmol, were added within 18 minutes. The solution changed its color from clear to yellow, and was stirred for 45 minutes at −68° C. 7.5 mL TMSCl, 59 mmol, were added within six minutes. The temperature of solution rose within one hour to −33° C., and after another 30 minutes to −18° C. The solution was stirred overnight at room temperature. 60 mL of 2M HCl were added to the white suspension. Stirring for 30 minutes resulted in two clear phases. Et2O-phase was dried with MgSO4, filtered, and solvent evaporated. Raw product was distilled at a temperature of 70-76° C. and 0.1-0.2 mbar. All pure fractions were combined and gave 15.8 g of product (52.4 mmol, 94%). 1H-NMR (CHCl3=7.24 ppm): δ 7.56 (s, 2H), 7.50 (t, 1H), 0.25 (s, 6×3H). The solution was stirred overnight at room temperature Stirring for 30 minutes resulted in two clear phases Et2O-phase was dried with MgSO4 filtered solvent evaporated Raw product was distilled at a temperature of 70-76° C. and 0.1-0.2 mbar
Source ID: ord-c5fb19d3a85e4978918ac6e36d28fd23Conditions: temp:-55.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 42.4 g of Tribromobenzene (134.6 mmol) was dissolved in 600 mL Et2O. The solution was chilled to −55° C., at which temperature starting material precipitated. 54 mL of n-BuLi (2.5 M in hexanes, 135 mmol) were added within 20 minutes. After stirring for 35 minutes at −52° C., 20 ml TMSCl (158 mmol) and 20 mL Et2O were added within 7 minutes. The suspension turned into a solution at −42° C., and a fine precipitate appeared at −30° C. The suspension was stirred overnight at room temperature. 100 mL 2M HCl were used to hydrolyze the mixture. After stirring for 30 minutes, the Et2O-phase was dried with MgSO4, filtered, and solvent evaporated until compound crystallized out of solution. The flask was stored overnight at +4° C. The crystalline compound was filtered, washed with a small amount cold pentane, and dried under vacuo. A second fraction of crystalline compound was obtained from the filtrate. Yield: 31.9 g (103.5 mmol, 77%). 1H-NMR (CHCl3=7.24 ppm): δ 7.62 (t, 1H), 7.49 (d, 2H), 0.25 (s, 3×3H). precipitated turned into a solution at −42° C. appeared at −30° C The suspension was stirred overnight at room temperature After stirring for 30 minutes the Et2O-phase was dried with MgSO4 filtered solvent evaporated until compound crystallized out of solution The flask was stored overnight at +4° C The crystalline compound was filtered washed with a small amount cold pentane dried under vacuo A second fraction of crystalline compound was obtained from the filtrate
Source ID: ord-55c4b0a1e502418c9d54fc5857498bcfConditions: temp:-55.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 42.4 g of Tribromobenzene (134.6 mmol) was dissolved in 600 mL Et2O. The solution was chilled to −55° C., at which temperature starting material precipitated. 54 mL of n-BuLi (2.5 M in hexanes, 135 mmol) were added within 20 minutes. After stirring for 35 minutes at −52° C., 20 ml TMSCl (158 mmol) and 20 mL Et2O were added within 7 minutes. The suspension turned into a solution at −42° C., and a fine precipitate appeared at −30° C. The suspension was stirred overnight at room temperature. 100 mL 2M HCl were used to hydrolyze the mixture. After stirring for 30 minutes, the Et2O-phase was dried with MgSO4, filtered, and solvent evaporated until compound crystallized out of solution. The flask was stored overnight at +4° C. The crystalline compound was filtered, washed with a small amount cold pentane, and dried under vacuo. A second fraction of crystalline compound was obtained from the filtrate. Yield: 31.9 g (103.5 mmol, 77%). 1H-NMR (CHCl3=7.24 ppm): δ 7.62 (t, 1H), 7.49 (d, 2H), 0.25 (s, 3×3H). precipitated turned into a solution at −42° C. appeared at −30° C The suspension was stirred overnight at room temperature After stirring for 30 minutes the Et2O-phase was dried with MgSO4 filtered solvent evaporated until compound crystallized out of solution The flask was stored overnight at +4° C The crystalline compound was filtered washed with a small amount cold pentane dried under vacuo A second fraction of crystalline compound was obtained from the filtrate
Source ID: ord-55c4b0a1e502418c9d54fc5857498bcfConditions: temp:-68.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 17.18 g of 3,5-Dibromo-trimethylsilyl-benzene, 55.8 mmol, was dissolved in 380 ml Et2O. The solution was chilled to −68° C., and 22.3 mL of n-BuLi (2.5M in hexanes), 55.8 mmol, were added within 18 minutes. The solution changed its color from clear to yellow, and was stirred for 45 minutes at −68° C. 7.5 mL TMSCl, 59 mmol, were added within six minutes. The temperature of solution rose within one hour to −33° C., and after another 30 minutes to −18° C. The solution was stirred overnight at room temperature. 60 mL of 2M HCl were added to the white suspension. Stirring for 30 minutes resulted in two clear phases. Et2O-phase was dried with MgSO4, filtered, and solvent evaporated. Raw product was distilled at a temperature of 70-76° C. and 0.1-0.2 mbar. All pure fractions were combined and gave 15.8 g of product (52.4 mmol, 94%). 1H-NMR (CHCl3=7.24 ppm): δ 7.56 (s, 2H), 7.50 (t, 1H), 0.25 (s, 6×3H). The solution was stirred overnight at room temperature Stirring for 30 minutes resulted in two clear phases Et2O-phase was dried with MgSO4 filtered solvent evaporated Raw product was distilled at a temperature of 70-76° C. and 0.1-0.2 mbar
Source ID: ord-36a991319d644be48b4185fcf2687995Conditions: temp:-55.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 42.4 g of Tribromobenzene (134.6 mmol) was dissolved in 600 mL Et2O. The solution was chilled to −55° C., at which temperature starting material precipitated. 54 mL of n-BuLi (2.5 M in hexanes, 135 mmol) were added within minutes. After stirring for 35 minutes at −52° C., 20 ml TMSCl (158 mmol) and 20 mL Et2O were added within 7 minutes. The suspension turned into a solution at −42° C., and a fine precipitate appeared at −30° C. The suspension was stirred overnight at room temperature. 100 mL 2M HCl were used to hydrolyze the mixture. After stirring for 30 minutes, the Et2O-phase was dried with MgSO4, filtered, and solvent evaporated until compound crystallized out of solution. The flask was stored overnight at +4° C. The crystalline compound was filtered, washed with a small amount cold pentane, and dried under vacuo. A second fraction of crystalline compound was obtained from the filtrate. Yield: 31.9 g (103.5 mmol, 77%). 1H-NMR (CHCl3=7.24 ppm): δ 7.62 (t, 1H), 7.49 (d, 2H), 0.25(s, 3×3H). precipitated turned into a solution at −42° C. appeared at −30° C The suspension was stirred overnight at room temperature After stirring for 30 minutes the Et2O-phase was dried with MgSO4 filtered solvent evaporated until compound crystallized out of solution The flask was stored overnight at +4° C The crystalline compound was filtered washed with a small amount cold pentane dried under vacuo A second fraction of crystalline compound was obtained from the filtrate
Source ID: ord-6b3f45060903460997e70495c9b5988eConditions: temp:-68.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 17.18 g of 3,5-Dibromo-trimethylsilyl-benzene, 55.8 mmol, was dissolved in 380 ml Et2O. The solution was chilled to −68° C., and 22.3 mL of n-BuLi (2.5 M in hexanes), 55.8 mmol, were added within 18 minutes. The solution changed its color from clear to yellow, and was stirred for 45 minutes at −68° C. 7.5 mL TMSCl, 59 mmol, were added within six minutes. The temperature of solution rose within one hour to −33° C., and after another 30 minutes to −18° C. The solution was stirred overnight at room temperature. 60 mL of 2M HCl were added to the white suspension. Stirring for 30 minutes resulted in two clear phases. Et2O-phase was dried with MgSO4, filtered, and solvent evaporated. Raw product was distilled at a temperature of 70-76° C. and 0.1-0.2 mbar. All pure fractions were combined and gave 15.8 g of product (52.4 mmol, 94%). 1H-NMR (CHCl3=7.24 ppm): δ7.56 (s, 2H), 7.50 (t, 1H), 0.25 (s, 6×3H). The solution was stirred overnight at room temperature Stirring for 30 minutes resulted in two clear phases Et2O-phase was dried with MgSO4 filtered solvent evaporated Raw product was distilled at a temperature of 70-76° C. and 0.1-0.2 mbar
Source ID: ord-a12c7991851749efb7c068052a5b83cfPubChem References
These sources are listed in the compound's public database record.
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