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[ CAS No. 100516-62-9 ] {[proInfo.proName]}

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Chemical Structure| 100516-62-9
Chemical Structure| 100516-62-9
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Product Details of [ 100516-62-9 ]

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 :

Safety of [ 100516-62-9 ]

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:

Application In Synthesis of [ 100516-62-9 ]

* 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 [ 100516-62-9 ]

[ 100516-62-9 ] Synthesis Path-Downstream   1~11

  • 1
  • [ 100516-62-9 ]
  • [ 100516-61-8 ]
YieldReaction ConditionsOperation 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;

Reference: [1]Diercks, Rainer; Armstrong, James C.; Boese, Roland; Vollhardt, K. Peter C. [Angewandte Chemie, 1986, vol. 98, # 3, p. 270 - 271]
[2]Pan, Chuanqi; Wang, Chenyang; Zhao, Xinya; Xu, Peiyan; Mao, Feihong; Yang, Ji; Zhu, Yuhua; Yu, Ruohan; Xiao, Shiyi; Fang, Yarong; Deng, Hongtao; Luo, Zhu; Wu, Jinsong; Li, Junbo; Liu, Shoujie; Xiao, Shengqiang; Zhang, Lizhi; Guo, Yanbing [Journal of the American Chemical Society, 2022, vol. 144, # 11, p. 4942 - 4951]
[3]Boese, Roland; Matzger, Adam J.; Mohler, Debra L.; Vollhardt, K. Peter C. [Angewandte Chemie, 1995, vol. 107, # 13/14, p. 1630 - 1633]
[4]Holmes, Daniel; Kumaraswamy, Sriram; Matzger, Adam J.; Vollhardt, K. Peter C. [Chemistry - A European Journal, 1999, vol. 5, # 11, p. 3399 - 3412]
[5]Hasegawa, Masashi; Enozawa, Hideo; Kawabata, Youhei; Iyoda, Masahiko [Journal of the American Chemical Society, 2007, vol. 129, # 11, p. 3072 - 3073]
[6]lto, Shunji; Inabe, Haruki; Morita, Noboru; Ohta, Kazuchika; Kitamura, Teruo; Imafuku, Kimiaki [Journal of the American Chemical Society, 2003, vol. 125, # 6, p. 1669 - 1680]
[7]Schmittel, Michael; Mal, Prasenjit [Chemical Communications, 2008, # 8, p. 960 - 962]
[8]Narita, Tomoyuki; Takase, Masayoshi; Nishinaga, Tohru; Iyoda, Masahiko; Kamada, Kenji; Ohta, Koji [Chemistry - A European Journal, 2010, vol. 16, # 40, p. 12108 - 12113]
[9]Qi, Hetong; Yu, Ping; Wang, Yuexiang; Han, Guangchao; Liu, Huibiao; Yi, Yuanping; Li, Yuliang; Mao, Lanqun [Journal of the American Chemical Society, 2015, vol. 137, # 16, p. 5260 - 5263]
[10]Zhou, Jingyuan; Gao, Xin; Liu, Rong; Xie, Ziqian; Yang, Jin; Zhang, Shuqing; Zhang, Gengmin; Liu, Huibiao; Li, Yuliang; Zhang, Jin; Liu, Zhongfan [Journal of the American Chemical Society, 2015, vol. 137, # 24, p. 7596 - 7599]
[11]Yin, Xue-Peng; Wang, Hong-Juan; Tang, Shang-Feng; Lu, Xiu-Li; Shu, Miao; Si, Rui; Lu, Tong-Bu [Angewandte Chemie - International Edition, 2018, vol. 57, # 30, p. 9382 - 9386][Angew. Chem., 2018, vol. 130, p. 9526 - 9530,5]
[12]Ramakrishnan, Vivek; Kim, Hyun; Yang, Beelyong [New Journal of Chemistry, 2019, vol. 43, # 33, p. 12896 - 12899]
[13]Li, Yanbing; Yang, Hao; Wang, Guorong; Ma, Bingzhen; Jin, Zhiliang [ChemCatChem, 2020, vol. 12, # 7, p. 1985 - 1995]
[14]Nobusue, Shunpei; Mukai, Yuichi; Fukumoto, Yo; Umeda, Rui; Tahara, Kazukuni; Sonoda, Motohiro; Tobe, Yoshito [Chemistry - A European Journal, 2012, vol. 18, # 40, p. 12814 - 12824,11]
[15]Current Patent Assignee: EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY - CN111747823, 2020, A Location in patent: Paragraph 0088-0090
[16]Current Patent Assignee: TONGJI UNIVERSITY - CN113336621, 2021, A Location in patent: Paragraph 0042
[17]Su, Peng; Liu, Hai; Jin, Zhiliang [Inorganic Chemistry, 2021, vol. 60, # 24, p. 19402 - 19413] Jin, Zhiliang; Li, Hongying; Li, Junke; Li, Mei [Journal of Materials Chemistry C, 2022, vol. 10, # 6, p. 2181 - 2193]
  • 2
  • [ 87-82-1 ]
  • [ 1066-54-2 ]
  • [ 100516-62-9 ]
YieldReaction ConditionsOperation 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;

  • 3
  • [ 608-74-2 ]
  • [ 1066-54-2 ]
  • [ 113705-23-0 ]
  • [ 100516-62-9 ]
YieldReaction ConditionsOperation 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;
  • 4
  • [ 87-82-1 ]
  • [ 1066-54-2 ]
  • [ 113705-23-0 ]
  • [ 100516-62-9 ]
YieldReaction ConditionsOperation 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.;
  • 5
  • [ 100516-62-9 ]
  • C18(2)H6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium fluoride; 18-crown-6 ether; water-d2 In 1,2-dimethoxyethane at 20℃; for 0.25h;
  • 6
  • [ 87-82-1 ]
  • [ 78389-87-4 ]
  • [ 113705-23-0 ]
  • [ 100516-62-9 ]
YieldReaction ConditionsOperation 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.
  • 7
  • [ 1066-54-2 ]
  • [ 100516-62-9 ]
YieldReaction ConditionsOperation 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
  • 8
  • [ 87-82-1 ]
  • [ 78389-87-4 ]
  • [ 100516-62-9 ]
YieldReaction ConditionsOperation 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;
  • 9
  • [ 100516-62-9 ]
  • [ 604-88-6 ]
YieldReaction ConditionsOperation in experiment
100 mg With tetrabutyl ammonium fluoride In tetrahydrofuran at 0℃; Inert atmosphere;
  • 10
  • [ 100516-62-9 ]
  • 1,2,3,4,5,6-hexa(2-chloroethynyl)benzene [ No CAS ]
YieldReaction ConditionsOperation 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
  • 11
  • [ 100516-62-9 ]
  • hexakis(bromoethynyl)benzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate / tetrahydrofuran; methanol 2: N-Bromosuccinimide; silver nitrate / acetone / 2 h / 20 °C
Same Skeleton Products
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