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CAS No. : | 100516-62-9 | MDL No. : | MFCD32701954 |
Formula : | C36H54Si6 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | STTDQWBKXQKNIK-UHFFFAOYSA-N |
M.W : | 655.33 | Pubchem ID : | 11262312 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With potassium fluoride In 1,2-dimethoxyethane at 0℃; for 2.5h; | |
62% | With N,N,N-tributylbutan-1-aminium fluoride In tetrahydrofuran at 0℃; for 0.166667h; | |
With potassium fluoride; 18-crown-6 ether In 1,2-dimethoxyethane at 23℃; |
With potassium fluoride; 18-crown-6 ether In 1,2-dimethoxyethane at 23℃; for 0.5h; | ||
With methanol; potassium carbonate In tetrahydrofuran at 20℃; for 0.5h; | ||
With potassium carbonate In tetrahydrofuran; methanol at 20℃; for 1.66667h; | ||
With potassium carbonate In tetrahydrofuran; methanol at 20℃; for 2h; | ||
With methanol; potassium carbonate In tetrahydrofuran at 20℃; for 0.5h; | ||
With N,N,N-tributylbutan-1-aminium fluoride In tetrahydrofuran at 8℃; for 0.166667h; | ||
With N,N,N-tributylbutan-1-aminium fluoride | ||
With N,N,N-tributylbutan-1-aminium fluoride | ||
With N,N,N-tributylbutan-1-aminium fluoride In tetrahydrofuran at 8℃; for 0.166667h; | ||
With N,N,N-tributylbutan-1-aminium fluoride In tetrahydrofuran at 8℃; for 0.166667h; | ||
With N,N,N-tributylbutan-1-aminium fluoride In tetrahydrofuran at 20℃; for 0.25h; Inert atmosphere; | ||
With potassium fluoride; 18-crown-6 ether In 1,2-dimethoxyethane at 20℃; for 3h; | 3 Dissolve 1,2,3,4,5,6-hexatrimethylsilylethynylbenzene (100mg, 0.15mmol) in 20mL of ethylene glycol dimethyl ether, add potassium fluoride (350mg, 6.02mmol) and 18 -Crown ether-6 (20mg, 0.0757mmol) mixed uniformly, detrimethylsilane reaction at room temperature for 3h, after the reaction is completed, washed with saturated brine (30mL×3) and extracted with dichloromethane 3 times in sequence (30mL×3), dry with anhydrous magnesium sulfate, filter to remove magnesium sulfate and concentrate to obtain 1,2,3,4,5,6-hexaethynylbenzene | |
With potassium carbonate In tetrahydrofuran; methanol | ||
With N,N,N-tributylbutan-1-aminium fluoride In tetrahydrofuran at 8℃; for 0.166667h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
28% | With triethylamine | |
20% | With triethylamine at 120℃; for 72h; | |
Stage #1: trimethylsilylacetylene With n-butyllithium In tetrahydrofuran at -78.16℃; for 0.5h; Inert atmosphere; Stage #2: With zinc(II) chloride In tetrahydrofuran for 2h; Inert atmosphere; Stage #3: hexabromobenzene With tetrakis(triphenylphosphine) palladium(0) In toluene at 80℃; for 336h; Inert atmosphere; |
Stage #1: trimethylsilylacetylene With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h; Stage #2: With zinc(II) chloride In tetrahydrofuran for 0.5h; Stage #3: hexabromobenzene With tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran; toluene at 80℃; for 72h; Inert atmosphere; | ||
Stage #1: trimethylsilylacetylene With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h; Inert atmosphere; Stage #2: With zinc(II) chloride In tetrahydrofuran for 0.5h; Inert atmosphere; Stage #3: hexabromobenzene With tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran; toluene at 80℃; for 72h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 1% 2: 14% | With piperidine; copper(l) iodide; bis(benzonitrile)palladium(II) dichloride; triphenylphosphine In various solvent(s) at 0℃; for 27h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 64% 2: 10% | Stage #1: trimethylsilylacetylene With n-butyllithium; zinc(II) chloride In tetrahydrofuran at -78℃; Stage #2: hexabromobenzene With tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran; toluene at 80℃; for 72h; Further stages.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium fluoride; 18-crown-6 ether; water-d2 In 1,2-dimethoxyethane at 20℃; for 0.25h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 64% 2: 9% | Stage #1: hexabromobenzene In toluene at 20℃; Stage #2: ((trimethylsilyl)ethynyl)zinc(II) chloride In tetrahydrofuran; toluene at 80℃; for 67h; | 1.2 (2) Preparation of Hexakis[(trimethylsilyl)ethynyl]benzene A rotator was placed in a 30 mL two neck flask, and the flask was equipped with a condenser and a blowing tube. The whole of the apparatus was dried, and thereafter allowed to cool to room temperature under a nitrogen atmosphere. The flask was charged with 550 mg (1.0 mmol) of hexabromobenzene, 210 mg (0.19 mmol) of Pd(PPh3)4 and 7 mL of toluene, and the mixture was stirred at room temperature. Subsequently, the previously prepared suspension of 10 mmol of the [(trimethylsilyl)ethynyl]zinc reagent in 10 mL of tetrahydrofuran was added thereto. The flask was immersed in an oil bath at 80°C, and the contents were reacted for 67 hours. The reaction progress was monitored by high-performance liquid chromatography using a reversed phase column. After the termination of the reaction, 50 mL of diethyl ether was added to the resulting reaction mixture, and the mixture was washed with 50 mL of a 0.5 N hydrochloric acid and 100 mL of saturated brine. Anhydrous magnesium sulfate was added as a desiccant to a separated organic layer, and the organic layer was dried for 1 hour. After the desiccant was removed by filtration, the solvent was distilled off under reduced pressure, to give 1.20 g of a brown sticky solid. The product was isolated and purified by silica gel column chromatography, to give 418 mg of hexakis[(trimethylsilyl)ethynyl]benzene, a pale yellow solid in 64% isolated yield. In addition, 54 mg of pentakis[(trimethylsilyl)ethynyl]benzene, a pale yellow solid, was obtained as a by-product, in 9% isolated yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: tert.-butyl lithium / tetrahydrofuran; pentane / 0.67 h / -78 °C / Inert atmosphere 1.2: 3 h / 0 °C / Inert atmosphere 2.1: tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran; pentane; toluene / 72 h / 80 °C / Inert atmosphere | ||
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C 1.2: 0.5 h / -78 °C 2.1: tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran; toluene / 72 h / 80 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40% | With tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran; toluene; pentane at 80℃; for 72h; Inert atmosphere; | |
With tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran; toluene at 80℃; for 72h; Inert atmosphere; | ||
With tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran; toluene at 80℃; for 72h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100 mg | With tetrabutyl ammonium fluoride In tetrahydrofuran at 0℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: potassium fluoride; 18-crown-6 ether / 1,2-dimethoxyethane / 3 h / 20 °C 2: tetrabutyl-ammonium chloride; silver carbonate; N-chloro-succinimide / acetonitrile / 12 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: potassium carbonate / tetrahydrofuran; methanol 2: N-Bromosuccinimide; silver nitrate / acetone / 2 h / 20 °C |