Name: 18733-98-7|Tetrakis(4-bromophenyl)silane|97%
Brand: Ambeed
SKU: A770831
Price: 36.0 USD
Availability: InStock
Rating: 98 (28 reviews)

1
[ 124-38-9 ]
[ 18733-98-7 ]
[ 10256-84-5 ]

Yield	Reaction Conditions	Operation in experiment
50%	Stage #1: tetrakis(4-bromophenyl)silane With n-butyllithium In tetrahydrofuran at -78 - 20℃; for 1h; Inert atmosphere; Stage #2: carbon dioxide In tetrahydrofuran at 20℃; Inert atmosphere;
	With n-butyllithium; N,N,N,N,-tetramethylethylenediamine 1.) hexane, 0 deg C 2.) THF; Yield given. Multistep reaction;

Reference： [1]Bassanetti, Irene; Bracco, Silvia; Comotti, Angiolina; Negroni, Mattia; Bezuidenhout, Charl; Canossa, Stefano; Mazzeo, Paolo Pio; Marchió, Luciano; Sozzani, Piero [Journal of Materials Chemistry A, 2018, vol. 6, # 29, p. 14231 - 14239]
[2]Kirste, Burkhard; Harrer, Wolfgang; Kurreck, Harry [Angewandte Chemie, 1981, vol. 93, # 10, p. 912 - 913]

2
[ 106-37-6 ]
[ 18733-98-7 ]

Yield	Reaction Conditions	Operation in experiment
93%	Stage #1: 1.4-dibromobenzene With n-butyllithium In diethyl ether; hexane at -50 - -10℃; Inert atmosphere; Stage #2: With tetrachlorosilane In diethyl ether; hexane at -10 - 25℃; Inert atmosphere;
90%	With n-butyllithium; tetrachlorosilane In hexane	Tetrakis(4-bromophenyl)silane (16b) Tetrakis(4-bromophenyl)silane (16b) was synthesized as described in [25] using 36.18 g (0.1563 mol) of p-dibromobenzene, 60 mL (0.15 mol) of 2.5 M n-BuLi in hexane, and 4,32 mL (0.0376 mol) of trichloro( methyl)silane. Yield 22.5 g (90%), purity 97% (GPC). The product was used in further synthesis without additional purification. 1H NMR spectrum (CDCl3), δ, ppm (J, Hz): 7.36 m (8H, J = 8.5), 7.54 m (8H, J = 8.5).
85%	Stage #1: 1.4-dibromobenzene With n-butyllithium In diethyl ether; hexane at -10℃; for 0.25h; Inert atmosphere; Stage #2: With tetrachlorosilane at -10 - 25℃; for 12.5h;

82.3%	Stage #1: 1.4-dibromobenzene With n-butyllithium In tetrahydrofuran at -78℃; for 2h; Schlenk technique; Stage #2: With tetrachlorosilane In tetrahydrofuran at -78 - 20℃; Schlenk technique;
78.9%	Stage #1: 1.4-dibromobenzene With n-butyllithium In tetrahydrofuran at -78℃; for 2h; Schlenk technique; Stage #2: With tetrachlorosilane In tetrahydrofuran at -78 - 20℃; Schlenk technique;
75%	Stage #1: 1.4-dibromobenzene With n-butyllithium In diethyl ether; hexane at -78 - 0℃; for 1.25h; Inert atmosphere; Stage #2: With tetrachlorosilane In diethyl ether; hexane for 1h; Inert atmosphere; Stage #3: With water; acetic acid In diethyl ether; hexane for 0.5h;
74.3%	Stage #1: 1.4-dibromobenzene With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Inert atmosphere; Stage #2: With tetrachlorosilane In tetrahydrofuran at 20℃; for 13h; Inert atmosphere;	1 4.00 g of 1,4-dibromobenzene was dissolved in 50 mL of tetrahydrofuran under the protection of nitrogen, cooled to -78°C, and 7.41 mL of 2.4 M n-butyllithium was slowly added to the solution through a syringe. Reaction 1 hour. 0.65 g of silicon tetrachloride was then dissolved in 5 mL of tetrahydrofuran under nitrogen and added dropwise to the reaction solution. After 1 hour of low temperature reaction,The temperature was gradually raised to room temperature. After reacting for 12 hours, 5 mL of water was added to the reaction solution, and the solvent was evaporated to dryness under reduced pressure. MixtureThe organic layer was washed three times with 50 mL of water in 80 mL of dichloromethane. Then, the organic layer was dried over anhydrous magnesium sulfate and filtered to obtain a filtrate.The filtrate was evaporated to dryness under reduced pressure, and the resulting crude product was subjected to column chromatography using petroleum ether as an eluent to obtain 1.84 g of a white solid 1 which was four pairs of bromophenylsilane in a yield of 74.3%.
69%	Stage #1: 1.4-dibromobenzene With n-butyllithium In diethyl ether; hexane at -70℃; Stage #2: With tetrachlorosilane In hexane Stage #3: In hexane Acidic conditions;
67%	Stage #1: 1.4-dibromobenzene With n-butyllithium In diethyl ether at -78.16℃; for 2h; Stage #2: With tetrachlorosilane In diethyl ether at 20℃; for 10h;
62%	Stage #1: 1.4-dibromobenzene With magnesium In tetrahydrofuran at 20 - 65℃; Stage #2: With tetraethoxy orthosilicate In tetrahydrofuran for 20h; Heating;
61%	Stage #1: 1.4-dibromobenzene With n-butyllithium In diethyl ether at -20℃; for 3.5h; Inert atmosphere; Stage #2: With tetrachlorosilane In diethyl ether Inert atmosphere;
58%	Stage #1: 1.4-dibromobenzene With n-butyllithium In diethyl ether; hexane for 0.5h; Inert atmosphere; Cooling; Stage #2: With tetrachlorosilane In diethyl ether; hexane at 20℃; Inert atmosphere; Cooling;
54.1%	Stage #1: 1.4-dibromobenzene With n-butyllithium In diethyl ether; hexane at -15℃; Inert atmosphere; Stage #2: With tetrachlorosilane In diethyl ether; hexane at -15 - 20℃; Inert atmosphere;
52.6%	Stage #1: 1.4-dibromobenzene With n-butyllithium In hexanes; diethyl ether at -78℃; Inert atmosphere; Stage #2: With tetrachlorosilane In hexanes; diethyl ether at -78 - 20℃;
17%	Stage #1: 1.4-dibromobenzene With n-butyllithium In diethyl ether at -78℃; for 0.5h; Inert atmosphere; Stage #2: With tetrachlorosilane In diethyl ether at -10℃; for 0.25h; Inert atmosphere;	Tetrakis-(4-bromophenyl)silane (2) Tetrakis-(4-bromophenyl)silane (2) n-BuLi (89 ml, 0.22 mol, 2.5M) was added dropwise to a solution of 1,4-dibromobenzene (50 g, 0.21 mol) in anhydrous diethyl ether (500 ml) at -78° C. under nitrogen. After stirring for 30 min, the reaction mixture was warmed to -10° C. and SiCl4 (9.0 g, 0.05 mol) was added dropwise. After a further 15 min, the reaction mixture was quenched with HCl (250 ml, 1.5M) and ethyl acetate (500 ml) was added. The organic phase was separated, washed with NaCl (750 ml), dried over sodium sulphate, filtered and concentrated. The crude oil was purified by column chromatography (silca-gel 230-400 mesh, hexane) and recrystalization (EtOAc) to give silane (2) as a while solid (24 g, 17% yield). 1H-NMR 400 MHz, CDCl3: δ 7.36 (d, J=8.2 Hz, 8H), 7.56 (d, J=8.2 Hz, 8H). 13C NMR 75 MHz, CDCl3: 125.38, 131.37, 131.41, 137.54.
	With n-butyllithium; tetrachlorosilane 1.) ether, hexane, 30 min, 20 deg C 2.) hexane; Yield given. Multistep reaction;
	Stage #1: 1.4-dibromobenzene With n-butyllithium In hexane Stage #2: With tetrachlorosilane Further stages.;
	Stage #1: 1.4-dibromobenzene With n-butyllithium In diethyl ether at -10℃; for 4h; Stage #2: With trichlorosilane at -10 - 20℃;

Reference： [1]Zhang, Bufeng; Wang, Zhonggang [Chemical Communications, 2009, # 33, p. 5027 - 5029]
[2]Skorotetcky; Borshchev; Cherkaev; Ponomarenko [Russian Journal of Organic Chemistry, 2019, vol. 55, # 1, p. 25 - 41][Zh. Org. Khim., 2019, vol. 55, # 1, p. 40 - 59,20]
[3]Liu, Shi-Yong; Jung, Jae Woong; Li, Chang-Zhi; Huang, Jiang; Zhang, Jianyuan; Chen, Hongzheng; Jen, Alex K.-Y. [Journal of Materials Chemistry A, 2015, vol. 3, # 44, p. 22162 - 22169]
[4]Xue, Rongming; Zhang, Moyao; Xu, Guiying; Zhang, Jingwen; Chen, Weijie; Chen, Haiyang; Yang, Ming; Cui, Chaohua; Li, Yaowen; Li, Yongfang [Journal of Materials Chemistry A, 2018, vol. 6, # 2, p. 404 - 413]
[5]Yang, Jianzhong; He, Wenhan; Denman, Kimberly; Jiang, Ying-Bing; Qin, Yang [Journal of Materials Chemistry A, 2015, vol. 3, # 5, p. 2108 - 2119]
[6]Location in patent: experimental part Yu, Hao; Shen, Changjiang; Tian, Mengzhe; Qu, Jing; Wang, Zhonggang [Macromolecules, 2012, vol. 45, # 12, p. 5140 - 5150]
[7]Current Patent Assignee: SOOCHOW UNIVERSITY (SUZHOU) - CN108117568, 2018, A Location in patent: Paragraph 0022-0023
[8]Gontarczyk, Krzysztof; Durka, Krzysztof; Klimkowski, Piotr; Luliński, Sergiusz; Serwatowski, Janusz; Woźniak, Krzysztof [Journal of Organometallic Chemistry, 2015, vol. 783, p. 1 - 9]
[9]Location in patent: experimental part Kim, Seul-Ong; Zhao, Qinghua; Thangaraju; Kim, Jang Joo; Kim, Yun-Hi; Kwon, Soon-Ki [Dyes and Pigments, 2011, vol. 90, # 2, p. 139 - 145]
[10]Liu, Xue-Ming; He, Chaobin; Hao, Xiao-Tao; Tan, Li-Wei; Li, Yanqing; Ong [Macromolecules, 2004, vol. 37, # 16, p. 5965 - 5970]
[11]Morandi, Bill; Rivero-Crespo, Miguel A.; Toupalas, Georgios [Journal of the American Chemical Society, 2021, vol. 143, # 50, p. 21331 - 21339]
[12]Uptmoor, Andrea C.; Geyer, Florian L.; Rominger, Frank; Freudenberg, Jan; Bunz, Uwe H. F. [ChemPlusChem, 2018, vol. 83, # 5, p. 448 - 454]
[13]Beele, Bjoern; Guenther, Johannes; Perera, Melanie; Stach, Michaela; Oeser, Thomas; Bluemel, Janet [New Journal of Chemistry, 2010, vol. 34, # 12, p. 2729 - 2731]
[14]Location in patent: experimental part Wang, Dengxu; Niu, Yuzhong; Wang, Yike; Han, Jianjun; Feng, Shengyu [Journal of Organometallic Chemistry, 2010, vol. 695, # 21, p. 2329 - 2337]
[15]Current Patent Assignee: SUMITOMO CHEMICAL COMPANY LIMITED; Sumitomo Chemical (w/o Dongwoo Fine-Chem) - US2017/40556, 2017, A1 Location in patent: Paragraph 0305-0310
[16]Kirste, Burkhard; Harrer, Wolfgang; Kurreck, Harry [Angewandte Chemie, 1981, vol. 93, # 10, p. 912 - 913]
[17]Rose, Marcus; Boehlmann, Winfried; Sabo, Michal; Kaskel, Stefan [Chemical Communications, 2008, # 21, p. 2462 - 2464]
[18]Dong, Jinqiao; Liu, Yan; Cui, Yong [Chemical Communications, 2014, vol. 50, # 95, p. 14949 - 14952]

3
[ 100-42-5 ]
[ 18733-98-7 ]
tetrastilbenylsilane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
52%	With palladium diacetate; tetrabutylammomium bromide; potassium carbonate In N,N-dimethyl acetamide at 80℃; for 48h;

Reference： [1]Wang, Shujun; Oldham Jr., Warren J.; Hudack Jr., Raymond A.; Bazan, Guillermo C. [Journal of the American Chemical Society, 2000, vol. 122, # 24, p. 5695 - 5709]

4
[ 18733-98-7 ]
[ 183051-50-5 ]
tetrakis(4-tert-butylstyrylstilbenyl)silane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
40%	With palladium diacetate; tetrabutylammomium bromide; potassium carbonate In N,N-dimethyl acetamide at 80℃; for 72h;

Reference： [1]Wang, Shujun; Oldham Jr., Warren J.; Hudack Jr., Raymond A.; Bazan, Guillermo C. [Journal of the American Chemical Society, 2000, vol. 122, # 24, p. 5695 - 5709]

5
[ 5419-55-6 ]
[ 18733-98-7 ]
C₄₈H₇₂B₄O₈Si [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: tetrakis(4-bromophenyl)silane With n-butyllithium In tetrahydrofuran; hexane at -78℃; Stage #2: Triisopropyl borate In tetrahydrofuran; hexane at -78 - 25℃; Further stages.;

Reference： [1]Fournier, Jean-Hugues; Maris, Thierry; Wuest, James D.; Guo, Wenzhuo; Galoppini, Elena [Journal of the American Chemical Society, 2003, vol. 125, # 4, p. 1002 - 1006]

6
[ 18733-98-7 ]
[ 203927-98-4 ]
polymer, M_w = 7640, M_w/M_n = 1.15; monomer(s): 9,9-dihexylfluorene-2,7-diboronic acid; tetra(4-bromophenyl)silane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
52%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In tetrahydrofuran for 4h; Heating;

Reference： [1]Liu, Xue-Ming; He, Chaobin; Hao, Xiao-Tao; Tan, Li-Wei; Li, Yanqing; Ong [Macromolecules, 2004, vol. 37, # 16, p. 5965 - 5970]

7
[ 18733-98-7 ]
[ 51-79-6 ]
C₃₆H₄₀N₄O₈Si [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
18%	With caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene for 48h; Heating;

Reference： [1]Laliberte, Dominic; Maris, Thierry; Wuest [Canadian Journal of Chemistry, 2004, vol. 82, # 2, p. 386 - 398]

8
[ 90-30-2 ]
[ 18733-98-7 ]
C₅₆H₄₀Br₂N₂Si [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
25%	With potassium phosphate at 230℃; for 48h;

Reference： [1]Bai, Dong-Ren; Liu, Xiang-Yang; Wang, Suning [Chemistry - A European Journal, 2007, vol. 13, # 20, p. 5713 - 5723]

9
[ 18733-98-7 ]
di(p-1-naphthylphenylamino)di(p-dimesitylboronylphenyl)silane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: 25 percent / potassium phosphate / cupric sulfate hydrate / 48 h / 230 °C 2.1: nBuLi / hexane; diethyl ether / 1 h / 20 °C 2.2: 70 percent / hexane; diethyl ether / 20 °C

Reference： [1]Bai, Dong-Ren; Liu, Xiang-Yang; Wang, Suning [Chemistry - A European Journal, 2007, vol. 13, # 20, p. 5713 - 5723]

10
[ 18733-98-7 ]
(silanetetrayltetra-4,1-phenylene)tetrakisboronic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	Stage #1: tetrakis(4-bromophenyl)silane With n-butyllithium In tetrahydrofuran; hexane at -78℃; Stage #2: With Triisopropyl borate In tetrahydrofuran; hexane Stage #3: With sulfuric acid In tetrahydrofuran; hexane
	Multi-step reaction with 2 steps 1.1: butyllithium / tetrahydrofuran; hexane / -78 °C 1.2: tetrahydrofuran; hexane / -78 - 25 °C 2.1: 0.860 g / 1 M aq. NaOH
	Stage #1: tetrakis(4-bromophenyl)silane With n-butyllithium In tetrahydrofuran; hexane at -78℃; Inert atmosphere; Stage #2: With Triisopropyl borate In tetrahydrofuran; hexane at -78 - 25℃; Inert atmosphere;

Reference： [1]Gontarczyk, Krzysztof; Durka, Krzysztof; Klimkowski, Piotr; Luliński, Sergiusz; Serwatowski, Janusz; Woźniak, Krzysztof [Journal of Organometallic Chemistry, 2015, vol. 783, p. 1 - 9]
[2]Fournier, Jean-Hugues; Maris, Thierry; Wuest, James D.; Guo, Wenzhuo; Galoppini, Elena [Journal of the American Chemical Society, 2003, vol. 125, # 4, p. 1002 - 1006]
[3]Zhang, Bufeng; Wang, Zhonggang [Chemical Communications, 2009, # 33, p. 5027 - 5029]

11
[ 18733-98-7 ]
[ 31825-72-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 1.) n-BuLi, N,N,N',N'-tetramethylethylenediamin / 1.) hexane, 0 deg C 2.) THF 2: 80 percent

Reference： [1]Kirste, Burkhard; Harrer, Wolfgang; Kurreck, Harry [Angewandte Chemie, 1981, vol. 93, # 10, p. 912 - 913]

12
[ 686-69-1 ]
[ 18733-98-7 ]
[ 1013692-79-9 ]

Yield	Reaction Conditions	Operation in experiment
71 mg	Stage #1: tetrakis(4-bromophenyl)silane With n-butyllithium In diethyl ether; hexane at -78 - 20℃; for 2.5h; Stage #2: diethylchlorophosphine In diethyl ether; hexane at -78 - 20℃; Further stages.;

Reference： [1]Yang, Yuan; Beele, Bjoern; Bluemel, Janet [Journal of the American Chemical Society, 2008, vol. 130, # 12, p. 3771 - 3773]

13
[ 13716-10-4 ]
[ 18733-98-7 ]
[ 1013692-81-3 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: tetrakis(4-bromophenyl)silane With n-butyllithium In diethyl ether; hexane at -78 - 20℃; Stage #2: di(tert-butyl)chlorophosphine In diethyl ether; hexane at -78 - 20℃; Further stages.;

Reference： [1]Yang, Yuan; Beele, Bjoern; Bluemel, Janet [Journal of the American Chemical Society, 2008, vol. 130, # 12, p. 3771 - 3773]

14
[ 18733-98-7 ]
[ 130914-24-8 ]
C₆₄H₈₈P₄Si [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: tetrakis(4-bromophenyl)silane With n-butyllithium In diethyl ether; hexane at -78 - 20℃; Stage #2: chlorodicyclopentylphosphine In diethyl ether; hexane at -78 - 20℃; Further stages.;

Reference： [1]Yang, Yuan; Beele, Bjoern; Bluemel, Janet [Journal of the American Chemical Society, 2008, vol. 130, # 12, p. 3771 - 3773]

15
[ 18733-98-7 ]
[ 1079-66-9 ]
[ 1013692-78-8 ]

Yield	Reaction Conditions	Operation in experiment
55%	Stage #1: tetrakis(4-bromophenyl)silane With n-butyllithium In diethyl ether; hexane at -78 - 20℃; Inert atmosphere; Stage #2: chloro-diphenylphosphine In diethyl ether; hexane at -78 - 20℃; Inert atmosphere;
	Stage #1: tetrakis(4-bromophenyl)silane With n-butyllithium In diethyl ether; hexane at -78 - 20℃; Stage #2: chloro-diphenylphosphine In diethyl ether; hexane at -78 - 20℃; Further stages.;

Reference： [1]Beele, Bjoern; Guenther, Johannes; Perera, Melanie; Stach, Michaela; Oeser, Thomas; Bluemel, Janet [New Journal of Chemistry, 2010, vol. 34, # 12, p. 2729 - 2731]
[2]Yang, Yuan; Beele, Bjoern; Bluemel, Janet [Journal of the American Chemical Society, 2008, vol. 130, # 12, p. 3771 - 3773]

16
[ 18733-98-7 ]
[ 16523-54-9 ]
[ 1013692-80-2 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: tetrakis(4-bromophenyl)silane With n-butyllithium In diethyl ether; hexane at -78 - 20℃; Stage #2: chlorodicyclohexylphosphane In diethyl ether; hexane at -78 - 20℃; Further stages.;

Reference： [1]Yang, Yuan; Beele, Bjoern; Bluemel, Janet [Journal of the American Chemical Society, 2008, vol. 130, # 12, p. 3771 - 3773]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: p-Br-C₆H₄-X, X = I or X = Br With n-butyllithium In diethyl ether; hexane at -15℃; Stage #2: With tetrachlorosilane In diethyl ether; hexane at -78 - 20℃; Further stages.;

18
[ 5419-55-6 ]
[ 18733-98-7 ]
[ 7732-18-5 ]
[ 499142-70-0 ]

Yield	Reaction Conditions	Operation in experiment
84%	With n-butyl lithium In tetrahydrofuran byproducts: LiBr; (BrC6H4)4C in THF was stirred at -78°C under N2, treated dropwisewith BuLi in hexane, the mixt. was kept at -78°C for 30 min, B(O C3H7)3 was added dropwsie, stirred at -78°C for 20 min, at 25°C for 1 h, aq. HCl was added; concd., treated with aq. 1M NaOH, filtered, acidified with aq. HCl, ppt.was filtered, dried in air; elem. anal.;

Reference： [1]Fournier, Jean-Hugues; Maris, Thierry; Wuest, James D.; Guo, Wenzhuo; Galoppini, Elena [Journal of the American Chemical Society, 2003, vol. 125, # 4, p. 1002 - 1006]

19
1,4-diethynyl-2,5-bis-dodecylbenzene [ No CAS ]
[ 18733-98-7 ]
(4-bromophenyl)silane]-co-(1,4-didodecyl-2,5-diethynylbenzene)}, synthesized by Sonogashira coupling reaction; monomer(s): tetra(4-bromophenyl)silane; 1,4-didodecyl-2,5-diethynylbenzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
366 mg	With triethylamine In tetrahydrofuran at 65℃; for 48h;

Reference： [1]Kobayashi, Norifumi; Kijima, Masashi [Journal of Materials Chemistry, 2007, vol. 17, # 40, p. 4289 - 4296]

20
[ 935-14-8 ]
[ 18733-98-7 ]
(4-bromophenyl)silane]-co-(1,4-diethynylbenzene)}, synthesized by Sonogashira coupling reaction; monomer(s): tetra(4-bromophenyl)silane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
347 mg	With triethylamine In tetrahydrofuran at 65℃; for 48h;

Reference： [1]Kobayashi, Norifumi; Kijima, Masashi [Journal of Materials Chemistry, 2007, vol. 17, # 40, p. 4289 - 4296]

21
[ 18733-98-7 ]
[ 128834-29-7 ]
(4-bromophenyl)silane]-co-(1,4-dibutoxy-2,5-diethynylbenzene)}, synthesized by Sonogashira coupling reaction; monomer(s): tetra(4-bromophenyl)silane; 1,4-dibutoxy-2,5-diethynylbenzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
480 mg	With triethylamine In tetrahydrofuran at 65℃; for 48h;

Reference： [1]Kobayashi, Norifumi; Kijima, Masashi [Journal of Materials Chemistry, 2007, vol. 17, # 40, p. 4289 - 4296]

22
[ 18733-98-7 ]
poly(1,4-phenylene)silane; monomer(s): tetrakis(4-bromophenyl)silane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: tetrakis(4-bromophenyl)silane With n-butyllithium In tetrahydrofuran; hexane at -10.16℃; for 0.166667h; Stage #2: With tetraethoxy orthosilicate In tetrahydrofuran; hexane Further stages.;

Reference： [1]Rose, Marcus; Boehlmann, Winfried; Sabo, Michal; Kaskel, Stefan [Chemical Communications, 2008, # 21, p. 2462 - 2464]

23
[ 288-32-4 ]
[ 18733-98-7 ]
[ 1251826-66-0 ]

Yield	Reaction Conditions	Operation in experiment
10.5%	With potassium carbonate; copper(II) sulfate at 180℃; for 24h; Inert atmosphere; Autoclave;
	With potassium carbonate; copper(II) sulfate at 180℃; for 24h; Inert atmosphere; Autoclave;	Synthesis of imidazole functional silanes (1a-i) General procedure: (Imidazole functionalized silanes were synthesized as our previous report [44]. The typical synthetic procedure is mentioned below. Bromophenylsilane (1 equiv), imidazole (1.2 equiv calculated as molar percent of bromophenyl), K2CO3 (2 equiv calculated as molar percent of bromophenyl) and CuSO4 (0.01 equiv calculated as molar percent of bromophenyl) were mixed and heated at 180 °C for 24 h in a Teflon autoclave under argon. After cooling to ambient temperature, the mixture was dissolved in CH2Cl2/H2O (1:1) mixture. The water layer was separated and extracted with CH2Cl2 three times. The combined organic layers were washed with water, dried over anhydrous MgSO4 and filtered. The solvents were evaporated under reduced pressure and the pure products were obtained by column chromatography (CH2Cl2/MeOH as eluent). The characterization of imidazole functional silanes, including bis(4-(imidazol-1- yl)phenyl)dimethylsilane (1a), tri(4-(imidazol-1-yl)phenyl)methylsilane (1b), bis(4-(imidazol-1-yl)phenyl)diphenylsilane (1c), tri(4-(imidazol-1-yl)phenyl)phenylsilane (1d) and [tri(4-(imidazol- 1-yl)phenyl)] (4-bromophenyl)silane (1e) were shown in our previous report [44]

Reference： [1]Location in patent: experimental part Wang, Dengxu; Niu, Yuzhong; Wang, Yike; Han, Jianjun; Feng, Shengyu [Journal of Organometallic Chemistry, 2010, vol. 695, # 21, p. 2329 - 2337]
[2]Wang, Dengxu; Wang, Linlin; Xue, Lei; Zhou, Debo; Feng, Shengyu; Zhao, Xian [Journal of Organometallic Chemistry, 2013, vol. 735, p. 58 - 64]

24
[ 2227-29-4 ]
[ 18733-98-7 ]
[ 1238618-96-6 ]

Yield	Reaction Conditions	Operation in experiment
66.7%	Stage #1: tetrakis(4-bromophenyl)silane With tert.-butyl lithium In tetrahydrofuran; pentane at -78℃; for 1h; Stage #2: chlorodiisopropylsilane In tetrahydrofuran; hexane at -78 - 20℃;

Reference： [1]Location in patent: experimental part Kawakami, Yoshiteru; Sakuma, Yoshinobu; Wakuda, Takashi; Nakai, Tatsuya; Shirasaka, Masayoshi; Kabe, Yoshio [Organometallics, 2010, vol. 29, # 15, p. 3281 - 3288]

25
[ 453530-49-9 ]
[ 18733-98-7 ]
[ 1283748-32-2 ]

Yield	Reaction Conditions	Operation in experiment
45%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In tetrahydrofuran for 24h; Reflux;

Reference： [1]Location in patent: experimental part Kim, Seul-Ong; Zhao, Qinghua; Thangaraju; Kim, Jang Joo; Kim, Yun-Hi; Kwon, Soon-Ki [Dyes and Pigments, 2011, vol. 90, # 2, p. 139 - 145]

26
[ 453530-49-9 ]
[ 18733-98-7 ]
[ 1283748-33-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate / tetrahydrofuran / 24 h / Reflux 2: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate / tetrahydrofuran / 24 h / Reflux

Reference： [1]Kim, Seul-Ong; Zhao, Qinghua; Thangaraju; Kim, Jang Joo; Kim, Yun-Hi; Kwon, Soon-Ki [Dyes and Pigments, 2011, vol. 90, # 2, p. 139 - 145]

27
[ 5720-07-0 ]
[ 18733-98-7 ]
[ 950191-42-1 ]

Yield	Reaction Conditions	Operation in experiment
89%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In 1,4-dioxane; water for 48h; Inert atmosphere; Reflux;

Reference： [1]Location in patent: experimental part Yu, Hao; Shen, Changjiang; Tian, Mengzhe; Qu, Jing; Wang, Zhonggang [Macromolecules, 2012, vol. 45, # 12, p. 5140 - 5150]

28
[ 18733-98-7 ]
[ 930598-99-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate / 1,4-dioxane; water / 48 h / Inert atmosphere; Reflux 2.1: boron tribromide / dichloromethane 2.2: 0.5 h

Reference： [1]Yu, Hao; Shen, Changjiang; Tian, Mengzhe; Qu, Jing; Wang, Zhonggang [Macromolecules, 2012, vol. 45, # 12, p. 5140 - 5150]

29
[ 18733-98-7 ]
[ 1380235-93-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate / 1,4-dioxane; water / 48 h / Inert atmosphere; Reflux 2.1: boron tribromide / dichloromethane 2.2: 0.5 h 3.1: triethylamine / acetone / 2 h / -10 - 10 °C

Reference： [1]Yu, Hao; Shen, Changjiang; Tian, Mengzhe; Qu, Jing; Wang, Zhonggang [Macromolecules, 2012, vol. 45, # 12, p. 5140 - 5150]

30
tetrachlorosilane [ No CAS ]
[ 106-37-6 ]
[ 18733-98-7 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 1.4-dibromobenzene With n-butyllithium In diethyl ether at -78℃; for 1h; Inert atmosphere; Stage #2: tetrachlorosilane In diethyl ether at -78 - 20℃; Inert atmosphere;	Synthesis of (4-bromophenyl)silane (4a-f) and (3-bromophenyl)silane (5a-c) General procedure: (4-Bromophenyl)silane (4a-f) and (3-bromophenyl)silane (5a-c) were synthesized as our previous reports [44]. The typical synthetic procedure for the bromophenylsilanes is mentioned below. 1,4-Dibromobenzene or 1,3-dibromobenzene (1 equiv) was dissolved in dry Et2O and cooled to 78 °C under argon. n-BuLi (1.05 equiv) was added into this solution dropwise and stirred for another 1 h at 78 °C. Chlorosilane (chlorotrimethylsilane: 1 equiv; dichlorodimethylsilane or dichlorodiphenylsilane: 0.5 equiv; trichloromethylsilane or trichlorophenylsilane: 0.33 equiv; tetrachlorosilane: 0.25 equiv) was then added dropwise at this temperature. After the end of the addition, the reaction mixture was slowly raised to room temperature and stirred overnight. Then the reaction was quenched by H2O and the organic layer was separated. The water layer was washed twice by Et2O. The organic layers were combined, washed by brine, dried over anhydrous MgSO4 and then filtered. Removal of the solvents under vacuum gave the crude product and the pure products were obtained by column chromatography or recrystallization. The physical and spectroscopic data of 4aef were shown in our previous report [44].
	Stage #1: 1.4-dibromobenzene With n-butyllithium Stage #2: tetrachlorosilane

Reference： [1]Wang, Dengxu; Wang, Linlin; Xue, Lei; Zhou, Debo; Feng, Shengyu; Zhao, Xian [Journal of Organometallic Chemistry, 2013, vol. 735, p. 58 - 64]
[2]Wang, Linlin; Wang, Dengxu; Wang, Hua; Feng, Shengyu [Journal of Organometallic Chemistry, 2014, vol. 767, p. 40 - 45]

31
[ 18733-98-7 ]
[ 126747-14-6 ]
tetra-(4-cyanodiphenyl)silane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68.7%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In ethanol; toluene for 12h; Reflux; Inert atmosphere;	Synthesis of bis (4-cyandiphenyl) dimethylsilane (1) General procedure: Synthesis of bis (4-cyandiphenyl) dimethylsilane (1) Bis(4-bromophenyl)dimethylsilane (98 mg, 0.15 mmol), 4-cyanphenylboronic acid (155 mg, 0.9 mmol), K2CO3 (248 mg, 1.8 mmol), and Pd(PPh3)4 (5 mg, 0.004 mmol) in 30 mL of degassed toluene/ethanol (10/1) were mixed and refluxed for 12 h under Ar, then filtrated. The dark filtrate was evaporated under reduced pressure. The crude products were purified by column chromatography (silica gel) from n-hexane/ethyl acetate as eluent to give the product as a white solid in 95.5% yield (0.045 g).

Reference： [1]Wang, Linlin; Wang, Dengxu; Wang, Hua; Feng, Shengyu [Journal of Organometallic Chemistry, 2014, vol. 767, p. 40 - 45]

32
[ 18733-98-7 ]
[ 73183-34-3 ]
tetrakis[4-(4′,4′,5′,5′-tetramethyl-1′,3′,2′-dioxaborolanephenyl)]silane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In dimethyl sulfoxide
	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate In 1,4-dioxane at 80℃; for 48h; Inert atmosphere; Schlenk technique;

Reference： [1]Dong, Jinqiao; Liu, Yan; Cui, Yong [Chemical Communications, 2014, vol. 50, # 95, p. 14949 - 14952]
[2]Liu, Yuhang; Lai, Joshua Yuk Lin; Chen, Shangshang; Li, Yunke; Jiang, Kui; Zhao, Jingbo; Li, Zhengke; Hu, Huawei; Ma, Tingxuan; Lin, Haoran; Liu, Jing; Zhang, Jie; Huang, Fei; Yu, Demei; Yan, He [Journal of Materials Chemistry A, 2015, vol. 3, # 26, p. 13632 - 13636]

33
C₂₄H₃₂O₂S₃Sn [ No CAS ]
[ 18733-98-7 ]
C₁₀₀H₉₂O₄S₁₂Si [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
43.3%	Stage #1: C₂₄H₃₂O₂S₃Sn; tetrakis(4-bromophenyl)silane With tetrakis(triphenylphosphine) palladium⁽⁰⁾ In N,N-dimethyl-formamide at 90℃; for 24h; Inert atmosphere; Sealed tube; Stage #2: With hydrogenchloride In water; N,N-dimethyl-formamide

Reference： [1]Yang, Jianzhong; He, Wenhan; Denman, Kimberly; Jiang, Ying-Bing; Qin, Yang [Journal of Materials Chemistry A, 2015, vol. 3, # 5, p. 2108 - 2119]

34
[ 116-17-6 ]
[ 18733-98-7 ]
tetraphenylsilane tetrakis(4-diisopropyl phosphonate) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
35%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾

Reference： [1]Schütrumpf, Alexandra; Kirpi, Erdoʇan; Bulut, Aysun; Morel, Flavien L.; Ranocchiari, Marco; Lork, Enno; Zorlu, Yunus; Grabowsky, Simon; Yücesan, Gündoʇ; Beckmann, Jens [Crystal Growth and Design, 2015, vol. 15, # 10, p. 4925 - 4931]

35
[ 1421711-94-5 ]
[ 18733-98-7 ]
C₁₆₈H₁₈₈N₈O₈S₈Si [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%	With palladium diacetate; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 105 - 110℃; for 24h; Inert atmosphere; Schlenk technique;

Reference： [1]Liu, Shi-Yong; Jung, Jae Woong; Li, Chang-Zhi; Huang, Jiang; Zhang, Jianyuan; Chen, Hongzheng; Jen, Alex K.-Y. [Journal of Materials Chemistry A, 2015, vol. 3, # 44, p. 22162 - 22169]

36
6,13-dimethoxy-13-(triisopropylsilyl)ethynyl-6-ethynyl-6,13-dihydropentacene [ No CAS ]
[ 18733-98-7 ]
tetrakis(4-((6,13-dimethoxy-13-((triisopropylsilyl)ethynyl)-6,13-dihydropentacen-6-yl)ethynyl)phenyl)silane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	With copper(l) iodide; diisopropylamine; bis(dibenzylideneacetone)-palladium⁽⁰⁾; tri tert-butylphosphoniumtetrafluoroborate In tetrahydrofuran at 20℃; for 72h;

Reference： [1]Geyer; Schmid; Brosius; Bojanowski; Bollmann; Brödner; Bunz [Chemical Communications, 2016, vol. 52, # 33, p. 5702 - 5705]

37
C₄₇H₃₆N₂ [ No CAS ]
[ 18733-98-7 ]
C₂₁₂H₁₅₆N₈Si [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
20%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; triphenylphosphine; sodium t-butanolate In toluene at 100℃; for 24h;	III.2 Synthesis of 1-10 Sub 1(3) in a round bottom flask (13.0g, 20mmol), Sub 2 (9) (50.3g, 80mmol), Pd2(dba) 3 (3.6g, 4mmol), PPh3 (2.0g, 8mmol), NaOt- after addition of Bu (22.0g,240mmol), each of the toluene (840mL), stirred and refluxed for 24 hours at 100 ° C.The organic layer was dried over MgSO4, and extracted with water and ether andrecrystallized silicagel column and the resulting organics concentrated and then 11.4g ofwater to the final crisp 1-10 (yield: 20%) was obtained.

Reference： [1]Current Patent Assignee: DUK SAN NEOLUX CO., LTD. - KR2015/93995, 2015, A Location in patent: Paragraph 0220; 0225-0227

38
bis-4-(4'-n-octyl)biphenylamine [ No CAS ]
[ 18733-98-7 ]
C₁₈₄H₂₁₆N₄Si [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
40%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; sodium t-butanolate; tri tert-butylphosphoniumtetrafluoroborate In toluene at 90℃; for 16h; Inert atmosphere;	A solution of tetrakis-(4-bromophenyl)-silane (2) (25 g, 0.04 mol), bis-4-(4’-n-octyl)biphenylamine (5) (93.3 g, 0.17 mol), tl3uONa (21.9 g, 0.23 mol) in toluene (2.25 L) was degassed by purging with nitrogen for 30 mi Pd2 (dba)3 (1.8 g, 0.002 mol) and Bu3PHBF; (0.8 g, 0.003 mol) were added and the reaction mixture was heated at 90° C. 16 h. The resulting dark mixture was filtered through celite and washed with methyl tbutyl ether (2 L). The filtrate was washed with water (2 L), NaC1 (2 L), dried over sodium sulphate, filtered and concentrated. The crude material was purified by column chromatography (silca 230-400 mesh, 1% EtOAc:hexane) and recrystalization (EtOAc, 850 ml) togive (le) as a white solid (38 g, 40% yield). 1H NMR 400 MHz, CDC13: ö 0.89 (t, J=6.6 Hz, 24H), 1.25-1.45 (m, 80H), 1.62-1.68 (m, 16H), 2.64 (t, J=7.6 Hz, 16H), 7.17 (d, J=8.4 Hz, 8H), 7.21-7.25 (m, 32H), 7.49-7.53 (m, 40H).13C NMR 100 MHz, CDC13: 14.10, 22.67, 29.27,29.39, 29.49, 31.48, 31.89, 35.61, 122.23, 125.02, 126.55,127.71, 128.80, 135.96, 137.32, 137.92, 141.73, 146.37,148.681 HRMS: 2511M HPLC: 99.71%.

Reference： [1]Current Patent Assignee: SUMITOMO CHEMICAL COMPANY LIMITED; Sumitomo Chemical (w/o Dongwoo Fine-Chem) - US2017/40556, 2017, A1 Location in patent: Paragraph 0305; 0136-0319

39
[ 18733-98-7 ]
[ 86-74-8 ]
9,9',9''-(((4-bromophenyl)silanetriyl)tris(benzene-4,1-diyl))tris(9H-carbazole) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
31%	With potassium phosphate; copper(l) iodide; trans-1,2-Diaminocyclohexane In toluene Inert atmosphere; Reflux;

Reference： [1]Choi, Suna; Godumala, Mallesham; Lee, Ji Hyung; Kim, Gyeong Heon; Moon, Ji Su; Kim, Jun Yun; Yoon, Dae-Wi; Yang, Joong Hwan; Kim, Jinook; Cho, Min Ju; Kwon, Jang Hyuk; Choi, Dong Hoon [Journal of Materials Chemistry C, 2017, vol. 5, # 26, p. 6570 - 6577]

40
[ 18733-98-7 ]
[ 86-74-8 ]
bis(4-(9H-carbazol-9-yl)phenyl)bis(4-bromophenyl)silane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
35%	With potassium phosphate; copper(l) iodide; trans-1,2-Diaminocyclohexane In toluene Inert atmosphere; Reflux;

Reference： [1]Choi, Suna; Godumala, Mallesham; Lee, Ji Hyung; Kim, Gyeong Heon; Moon, Ji Su; Kim, Jun Yun; Yoon, Dae-Wi; Yang, Joong Hwan; Kim, Jinook; Cho, Min Ju; Kwon, Jang Hyuk; Choi, Dong Hoon [Journal of Materials Chemistry C, 2017, vol. 5, # 26, p. 6570 - 6577]

41
[ 18733-98-7 ]
[ 86-74-8 ]
9-(4-(tris(4-bromophenyl)silyl)phenyl)-9H-carbazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
29%	With potassium phosphate; copper(l) iodide; trans-1,2-Diaminocyclohexane In toluene Inert atmosphere; Reflux;

Reference： [1]Choi, Suna; Godumala, Mallesham; Lee, Ji Hyung; Kim, Gyeong Heon; Moon, Ji Su; Kim, Jun Yun; Yoon, Dae-Wi; Yang, Joong Hwan; Kim, Jinook; Cho, Min Ju; Kwon, Jang Hyuk; Choi, Dong Hoon [Journal of Materials Chemistry C, 2017, vol. 5, # 26, p. 6570 - 6577]

42
[ 18733-98-7 ]
[ 86-74-8 ]
bis(4-(9H-carbazol-9-yl)phenyl)bis(4-(pyridin-3-yl)phenyl)silane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: trans-1,2-Diaminocyclohexane; potassium phosphate; copper(l) iodide / toluene / Inert atmosphere; Reflux 2: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tris-(o-tolyl)phosphine; potassium carbonate / toluene; water; methanol / 6 h / Inert atmosphere; Reflux

Reference： [1]Choi, Suna; Godumala, Mallesham; Lee, Ji Hyung; Kim, Gyeong Heon; Moon, Ji Su; Kim, Jun Yun; Yoon, Dae-Wi; Yang, Joong Hwan; Kim, Jinook; Cho, Min Ju; Kwon, Jang Hyuk; Choi, Dong Hoon [Journal of Materials Chemistry C, 2017, vol. 5, # 26, p. 6570 - 6577]

43
[ 18733-98-7 ]
C₃₆H₃₈Br₂O₄Si [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: n-butyllithium / tetrahydrofuran / -78 °C 2: toluene-4-sulfonic acid / benzene / 80 °C