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[ CAS No. 776-76-1 ]

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2D
Chemical Structure| 776-76-1
Chemical Structure| 776-76-1
Structure of 776-76-1 *Storage: {[proInfo.prStorage]}

Quality Control of [ 776-76-1 ]

Purity: {[proInfo.showProBatch.pb_purity]}

Related Doc. of [ 776-76-1 ]

SDS

Product Details of [ 776-76-1 ]

CAS No. :776-76-1MDL No. :MFCD00008255
Formula :C13H14SiBoiling Point :266.8°C at 760 mmHg
Linear Structure Formula :(C6H5)2SiHCH3InChI Key :OKHRRIGNGQFVEE-UHFFFAOYSA-N
M.W :198.34Pubchem ID :6327660
Synonyms :

Computed Properties of [ 776-76-1 ]

TPSA : - H-Bond Acceptor Count : -
XLogP3 : - H-Bond Donor Count : -
SP3 : - Rotatable Bond Count : -

Safety of [ 776-76-1 ]

Signal Word:WarningClassN/A
Precautionary Statements:P305+P351+P338UN#:N/A
Hazard Statements:H315-H319Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 776-76-1 ]

  • Downstream synthetic route of [ 776-76-1 ]

[ 776-76-1 ] Synthesis Path-Downstream   1~10

  • 1
  • [ 101268-55-7 ]
  • [ 776-76-1 ]
  • 4,4-bis(carbethoxy)-1-(Z)-methyldiphenylsilylmethylidene-2-methylcyclopentane [ No CAS ]
  • 2
  • [ 592-41-6 ]
  • [ 776-76-1 ]
  • [ 23812-96-6 ]
YieldReaction ConditionsOperation in experiment
74% With tris(pentafluorophenyl)borate; In dichloromethane; at 20℃; for 16h;Inert atmosphere; Schlenk technique; Sealed tube; PhMe2SiH (0.21g, 1.1mmol) and B(C6F5)3 (0.025g, 0.049mmol) were combined with 1-hexene (1.0mL, 4.0mmol) and CH2Cl2 (0.5mL) in a Schlenk flask. The mixture was stirred under N2 with the flask closed for 16h. The volatiles were removed under vacuum, and the resulting oily residue was dissolved in pentane (1mL) and filtered through a Florisil column to remove residual B(C6F5)3 (a faint brown color was retained on the column). The column was washed with pentane (3×1mL), and the volatiles were removed under vacuum from the combined filtrates to give a clear and colorless oil (0.22g, 74%, trace impurities were observed by 1H NMR). 1H NMR (300MHz, C6D6) delta 0.51 (s, 3H, Si-CH3), 0.86 (t, 3JHH=7Hz, 3H, (CH2)5CH3), 1.00-1.46 (overlapping m, 10H, Si-CH2CH2CH2CH2CH2), 7.18-7.23 (overlapping m, 6H, Hm/p-SiPh2), 7.53 (d, 3JHH=4Hz, 4H, Ho-SiPh2); 13C NMR (75MHz, C6D6) delta-4.2 (SiCH3), 14.3 (Si(CH2)5CH3), 14.6 (SiCH2), 23.0 (Si(CH2)4CH2), 24.2 (Si(CH2)3CH2), 31.8 (Si(CH2)2CH2), 33.7 (SiCH2CH2) 128.2 (Cm-SiPh2), 129.4 (Cp-SiPh2), 134.9 (Co-SiPh2). DEPT30 29Si NMR (99MHz, C6D6) delta-7.1. Anal. (calcd for C19H26Si): C 80.68 (80.78) H 9.53 (9.28).
  • 3
  • [ 5192-03-0 ]
  • [ 776-76-1 ]
  • 1-(methyldiphenylsilyl)-1H-indol-5-amine [ No CAS ]
  • 4
  • [ 776-76-1 ]
  • [ 17422-32-1 ]
  • 5-chloro-1-(methyldiphenylsilyl)-1H-indole [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% With dodecacarbonyl-triangulo-triruthenium; In toluene; at 120℃; for 16h;Schlenk technique; Inert atmosphere; General procedure: Condition B: A mixture of 33 indole (1) (0.2mmol, 1equiv), hydrosilanes (2) (0.3mmol, 1.5 equiv), 16 Ru3(CO)12 (3.8mg, 0.006mmol, 3.0mol %), were weighted in a Schlenk tube equipped with a stir bar. Dry 11 toluene (2.0mL) was added and the mixture was stirred at 120C for 12-24h under Ar atmosphere. Afterwards, it was diluted with CH2Cl2 and transferred to a 50mL round bottom flask. Silica was added to the flask and solvents were evaporated under reduced pressure. Flash column chromatography on silica gel with EtOAc:petroleum ether=1:100 as eluent afforded the 47 N-silylated indole.
  • 5
  • [ 399-52-0 ]
  • [ 776-76-1 ]
  • 5-fluoro-1-(methyldiphenylsilyl)-1H-indole [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% With dodecacarbonyl-triangulo-triruthenium; In toluene; at 120℃; for 12h;Schlenk technique; Inert atmosphere; General procedure: Condition B: A mixture of 33 indole (1) (0.2mmol, 1equiv), hydrosilanes (2) (0.3mmol, 1.5 equiv), 16 Ru3(CO)12 (3.8mg, 0.006mmol, 3.0mol %), were weighted in a Schlenk tube equipped with a stir bar. Dry 11 toluene (2.0mL) was added and the mixture was stirred at 120C for 12-24h under Ar atmosphere. Afterwards, it was diluted with CH2Cl2 and transferred to a 50mL round bottom flask. Silica was added to the flask and solvents were evaporated under reduced pressure. Flash column chromatography on silica gel with EtOAc:petroleum ether=1:100 as eluent afforded the 47 N-silylated indole.
  • 6
  • [ 776-76-1 ]
  • [ 108-95-2 ]
  • [ 42073-30-3 ]
YieldReaction ConditionsOperation in experiment
79% With tert.-butylhydroperoxide; ammonium iodide; In water; at 80℃; for 24h; General procedure: 70% aq TBHP (4.0 mmol) was added dropwise over 10 min to asolution of the appropriate silane (1.0 mmol) and NH4I (0.20mmol) in the appropriate alcohol (1 mL), and the mixture wasstirred at r.t. until the reaction was complete (TLC). The reactionwas then quenched with sat. aq Na2S2O3, and the mixture waswashed with brine, extracted with EtOAc, dried (Na2SO4), andconcentrated under vacuum. The crude product was purified bycolumn chromatography (silica gel, PE).Ethoxy(triphenyl)silane (3aa)Colorless liquid; yield: 280 mg (92%).
  • 7
  • [ 776-76-1 ]
  • [ 67-63-0 ]
  • [ 58657-48-0 ]
YieldReaction ConditionsOperation in experiment
83% With tert.-butylhydroperoxide; ammonium iodide; In water; at 20℃; for 24h; General procedure: 70% aq TBHP (4.0 mmol) was added dropwise over 10 min to asolution of the appropriate silane (1.0 mmol) and NH4I (0.20mmol) in the appropriate alcohol (1 mL), and the mixture wasstirred at r.t. until the reaction was complete (TLC). The reactionwas then quenched with sat. aq Na2S2O3, and the mixture waswashed with brine, extracted with EtOAc, dried (Na2SO4), andconcentrated under vacuum. The crude product was purified bycolumn chromatography (silica gel, PE).Ethoxy(triphenyl)silane (3aa)Colorless liquid; yield: 280 mg (92%).
  • 8
  • [ 144-79-6 ]
  • [ 776-76-1 ]
  • [ 1172-76-5 ]
YieldReaction ConditionsOperation in experiment
91%; 5% To 0.5 ml of THF, 0.5 mmol of methyldiphenylsilyl chloride, which is a silyl halide compound, and 2.0 molar equivalents of SD were added and reacted at 30 C. for 10 hours to synthesize methyldiphenylsilylsodium that was a silyl sodium compound. At this time, the reaction was carried out without adding additives other than the above.The yield of sodium methyldiphenylsilyl was determined by reacting the obtained sodium methyldiphenylsilyl with hydrogen chloride in a 1,4-dioxane solution in which hydrogen chloride was dissolved to synthesize [776-76-1]methyldiphenylsilane. It was calculated indirectly by calculating the ratio by NMR. The yield of sodium methyldiphenylsilyl is the ratio (%) of sodium methyldiphenylsilyl actually obtained to sodium methyldiphenylsilyl theoretically produced from methyldiphenylsilyl chloride added to the reaction system.FIG. 1 summarizes the reaction scheme, reaction conditions, and yield. As a result, it was revealed that methyldiphenylsilylsodium could be synthesized in a high yield of 91%.
  • 9
  • [ 776-76-1 ]
  • [ 538-51-2 ]
  • N-benzyl-N-methyldiphenylsilylaniline [ No CAS ]
YieldReaction ConditionsOperation in experiment
97% With tris(pentafluorophenyl)borate; triphenylphosphine; In benzene; at 60℃;Inert atmosphere; Sealed tube; Schlenk technique; General procedure: Substrate was added with stirring to a toluene or benzene solution of Ph2MeSiH and B(C6F5)3 in a Schlenk flask. The mixture was left stirring under N2, either is a sealed flask or open to a Nujol bubbler. PPh3 was added to quench the catalyst and the volatiles were removed under vacuum. Addition of hexanes or pentane to the resulting oily residue caused precipitation of the borane-phosphine adduct, which was removed by filtration through a Celite filter stick. Additional solvent was added to ensure elution of the product(s) from the filter stick, and volatiles were removed under vacuum from the combined washings to give the final isolated product(s). (0020) Ph2MeSiOCH2CH2CH3 (1). Ph2MeSiH (0.10g, 0.52mmol), B(C6F5)3 (0.009g, 0.02mmol), toluene (1mL), propionaldehyde (0.10mL, 1.4mmol); stirred under N2 (closed flask) for 16h PPh3 (0.005g, 0.02mmol), hexanes (4×1mL). Dried under vacuum at RT for 16h. Clear, colorless oil (0.13g, in 76% purity. The remaining 24% was the over-reduction product, (Ph2MeSi)2O).
  • 10
  • [ 104-93-8 ]
  • [ 776-76-1 ]
  • [ 42073-31-4 ]
YieldReaction ConditionsOperation in experiment
99% With tris(pentafluorophenyl)borate; triphenylphosphine; In toluene; at 20℃; for 1h;Inert atmosphere; Schlenk technique; General procedure: Substrate was added with stirring to a toluene or benzene solution of Ph2MeSiH and B(C6F5)3 in a Schlenk flask. The mixture was left stirring under N2, either is a sealed flask or open to a Nujol bubbler. PPh3 was added to quench the catalyst and the volatiles were removed under vacuum. Addition of hexanes or pentane to the resulting oily residue caused precipitation of the borane-phosphine adduct, which was removed by filtration through a Celite filter stick. Additional solvent was added to ensure elution of the product(s) from the filter stick, and volatiles were removed under vacuum from the combined washings to give the final isolated product(s). (0020) Ph2MeSiOCH2CH2CH3 (1). Ph2MeSiH (0.10g, 0.52mmol), B(C6F5)3 (0.009g, 0.02mmol), toluene (1mL), propionaldehyde (0.10mL, 1.4mmol); stirred under N2 (closed flask) for 16h PPh3 (0.005g, 0.02mmol), hexanes (4×1mL). Dried under vacuum at RT for 16h. Clear, colorless oil (0.13g, in 76% purity. The remaining 24% was the over-reduction product, (Ph2MeSi)2O).
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