1,2-Bis(dimethylsilyl)benzene
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1,2-Bis(dimethylsilyl)benzene
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CAS No:
17985-72-7
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Formula:
C10H18Si2
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Chemical Name:
1,2-Bis(dimethylsilyl)benzene
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Synonyms:
1,2-Bis(dimethylsilyl)benzene,98%;1,2-Bis(dimethylsily)benzene;O-PHENYLEN-BIS-(DIMETHYLSILAN);1,2-BIS(DIMETHYLSILYL)BENZENE;1,2-PHENYLENEBIS(DIMETHYLSILANE);Silane, 1,2-phenylenebisdimethyl-;o-phenylenebis(dimethylsilane);1,2-BIS(DIMETHYLSILYL)BENZENE 98%
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CAS No:
Characteristics
0
Liquid
0.898 g/mL at 25 °C(lit.)
<25°C
101 °C13 mm Hg(lit.)
158 °F
n 20/D 1.51(lit.)
insoluble
1,2-Bis(dimethylsilyl)benzene Use and Manufacturing
General procedure: Into a dried two-necked flask (50 mL) equipped with a condenser were placed a stirrer bar, Mg powder (99.9percent, 24 mmol), LiCl (24mmol), DMI (20 mL), and chlorodimethylsilane (48 mmol). After stirring the mixture at rt for 15 min, 1, 2-dibromoarene (3 mmol) was added and the mixture was stirred for 4 h. The mixture was quenched with sat. NaHCO3 and the resulting precipitates were filtered off. The filtrate was extracted with hexane (3 ×) and the combined organic extract was washed with brine, dried (anhyd Na2SO4), and concentrated by a rotary evaporator. The crude product was purified by column chromatography (silica gel, hexane or hexane/CH2Cl2).A solution of 1, 2-dibromobenzene (16.5 g, 70 mmol) in 70 ml of THF was added slowly to a stirred mixture of magnesium powder (3.7 g, 147 mmol) and chlorodimethylsilane (14.0 g, 147 mmol) in 15 ml of THF. The mixture was refluxed for 3 h. After cooling, the solution was decanted from solid magnesium salts and the solvent was removed under vacuum. The residual oil was extracted and washed with a large amount of n-hexane. After removal of the solvent, the residue was purified by distillation under reduced pressure to afford 1, 2-bis(dimethylsilyl)benzene (1) in 60percent yield. Compound 1 (20 mmol) was mixed with 40 ml of dry carbon tetrachloride and 0.2 g of palladium dichloride in a 100 ml two necked flask equipped with a reflux condenser. The mixture was refluxed for 3 h and excess carbon tetrachloride and chloroform were removed by evacuation. the residual oil was distilled at 85 °C (1 mbar) to obtain compound 2 in 90percent yield.
Computed Properties
Molecular Weight:192.40
Rotatable Bond Count:2
Exact Mass:192.07905358
Monoisotopic Mass:192.07905358
Heavy Atom Count:12
Complexity:116
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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