Name: 17878-23-8|(3,5-Dibromophenyl)trimethylsilane|97%
Brand: Ambeed
SKU: A868665
Price: 17.0 USD
Availability: InStock
Rating: 93 (29 reviews)

1
[ 75-77-4 ]
[ 626-39-1 ]
[ 17878-23-8 ]

Yield	Reaction Conditions	Operation in experiment
95%	Stage #1: 1,3,5-trisbromobenzene With n-butyllithium In diethyl ether at -78℃; Stage #2: chloro-trimethyl-silane In diethyl ether	1 5,10,15,20-tetrakis (3-carboxy-5-trimethylsilyl phenyl) porphyrin sodium salt (hereinafter, SiC 4 may be called) was synthesized by the following procedure. The 1,3,5-bromo benzene in dry diethyl ether, and lithiation with an equal volume of n- butyl lithium at -78 , then was allowed to react with chlorotrimethylsilane, in a yield of 95% 3,5 dibromo trimethylsilyl benzene was obtained. Then in dry diethyl ether this, lithiation with an equal volume of n- butyl lithium at -78 , then was allowed to react with DMF, 3-bromo-5-trimethylsilyl benzaldehyde in 45% yield was obtained . This was dissolved in dry toluene, p- toluenesulfonic acid present of at reacted with ethylene glycol, to give the 3-bromo-5-trimethylsilyl benzaldehyde ethylene acetal in 90% yield. Then after the reaction with magnesium it in dry THF, it is reacted with carbon dioxide at 0 ° C., to obtain a 3-carboxy-5-trimethylsilyl benzaldehyde ethylene acetal in 40% yield. This by treatment with hydrochloric acid, to give 3-carboxy-5-trimethylsilyl benzaldehyde. This was then reacted with ethyl iodide under potassium carbonate present in a DMF, to give the 3-carboxy-5-trimethylsilyl benzaldehyde ethyl ester. Pyrrole this in chloroform is reacted with boron fluoride ether complex, by treatment with subsequent DDQ, 5,10,15,20-tetrakis (3-carboxy-5-trimethylsilyl-phenyl) to give a porphyrin ethyl ester. Finally, by treating it with sodium hydroxide to obtain a 5,10,15,20-tetrakis (3-carboxy-5-trimethylsilyl phenyl) porphyrin sodium salt.
94%	Stage #1: 1,3,5-trisbromobenzene With n-butyllithium In diethyl ether; hexane at -78℃; for 3h; Inert atmosphere; Stage #2: chloro-trimethyl-silane In diethyl ether; hexane at 20℃; Inert atmosphere;	1,3-Dibromo-5-trimethylsilylbenzene (1). Commercial 1,3,5-tribromobenzene (5.00 g, 15.9 mmol) was dissolved in diethyl ether (100 ml). Thesolution was put under N2 atmosphere and then cooled to -78 °C. 1.6 M n-butyllithium in hexane solution(7.0 ml, 17.5 mmol) was added dropwise, and the suspension was stirred at -78 °C for 3 hours prior toadding trimethylsilyl chloride in dropwise fashion. The reaction mixture was stirred at room temperatureovernight, and then H2O (100 ml) was added. After extraction with diethyl ether, the combined organicphases were dried over anhydrous Na2SO4. After solvent removal on a rotary evaporator, the crudeproduct was purified by chromatography on silica gel column, using diethyl ether as the eluent. The pureproduct was obtained as a pale-yellow liquid (4.34 g, 14.1 mmol, 94%). 1H NMR (400 MHz, CDCl3): δ 7.48(t, J=2 Hz, 1H), 7.38 (d, J=2 Hz, 2 H), 0.15 ppm (s, 9H).
90%	Stage #1: 1,3,5-trisbromobenzene With n-butyllithium In diethyl ether; hexane at -80 - -30℃; for 1h; Stage #2: chloro-trimethyl-silane In diethyl ether; hexane at -30 - 20℃;

89%	With n-butyllithium In diethyl ether; hexane at -78 - 20℃; for 3h; Inert atmosphere;
87%	In diethyl ether; hexane at 20℃; for 1h;
85%	Stage #1: 1,3,5-trisbromobenzene With n-butyllithium In diethyl ether at -78℃; for 0.666667h; Inert atmosphere; Glovebox; Sealed tube; Stage #2: chloro-trimethyl-silane In diethyl ether at 20℃; for 1h; Inert atmosphere; Glovebox; Sealed tube;
79%	Stage #1: 1,3,5-trisbromobenzene With n-butyllithium Stage #2: chloro-trimethyl-silane
79%	Stage #1: 1,3,5-trisbromobenzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Stage #2: chloro-trimethyl-silane In tetrahydrofuran; hexane at -78 - 20℃; Further stages.;
78%	Stage #1: 1,3,5-trisbromobenzene With n-butyllithium In diethyl ether at -78℃; for 0.5h; Stage #2: chloro-trimethyl-silane In diethyl ether at 0℃; for 0.333333h;
	With n-butyllithium 1.) Et₂O, hexane, -78 deg C, 30 min, 2.) Et₂O, hexane, -25 deg C, 1 h; Yield given. Multistep reaction;
	Stage #1: 1,3,5-trisbromobenzene With n-butyllithium In diethyl ether Stage #2: chloro-trimethyl-silane In diethyl ether Further stages.;
	Stage #1: 1,3,5-trisbromobenzene With n-butyllithium In diethyl ether; hexane at -78℃; for 3h; Stage #2: chloro-trimethyl-silane In diethyl ether; hexane at -78 - 20℃; Further stages.;
	Stage #1: 1,3,5-trisbromobenzene With n-butyllithium In tetrahydrofuran at -78℃; for 2h; Stage #2: chloro-trimethyl-silane In tetrahydrofuran at 20℃;	5 Synthesis of Intermediate 1 g of 1,3,5-tribromobenzene was added to 20 mL of tetrahydrofuran and the temperature was adjusted to -78°C.Subsequently, 1.65 mL of butyllithium was slowly added dropwise. The mixture was stirred for 2 hr while maintainingits temperature, and 0.45 g of chlorotrimethylsilane was slowly added dropwise, after which the temperature of themixture was raised to room temperature. After completion of the reaction, triethylamine and methanol were added,and the reaction mixture was stirred and extracted, followed by drying the solvent. The resulting solid was filtered andpurified, yielding (3,5-dibromophenyl)trimethylsilane as an intermediate.
	Stage #1: 1,3,5-trisbromobenzene With n-butyllithium In diethyl ether; hexane at -78℃; for 0.5h; Inert atmosphere; Stage #2: chloro-trimethyl-silane In diethyl ether; hexane at -78 - 20℃; for 2h; Inert atmosphere;
	With n-butyllithium

Reference： [1]Current Patent Assignee: GUNMA UNIVERSITY - JP5843113, 2016, B2 Location in patent: Paragraph 0025
[2]Arshad, Ifzan; Channar, Pervaiz Ali; Irfan, Rana Muhammad; Saeed, Aamer; Shehzadi, Syeda Aaliya [Synlett, 2019, vol. 30, # 16, p. 1886 - 1890]
[3]Horiuchi, Hiroaki; Hosaka, Masahiro; Mashio, Hiroyuki; Terata, Motoki; Ishida, Shintaro; Kyushin, Soichiro; Okutsu, Tetsuo; Takeuchi, Toshiyuki; Hiratsuka, Hiroshi [Chemistry - A European Journal, 2014, vol. 20, # 20, p. 6054 - 6060]
[4]Bonn, Annabell G.; Yushchenko, Oleksandr; Vauthey, Eric; Wenger, Oliver S. [Inorganic Chemistry, 2016, vol. 55, # 6, p. 2894 - 2899]
[5]Rehm, J. D. Daniel; Ziemer, Burghard; Szeimies, Guenter [European Journal of Organic Chemistry, 1999, # 9, p. 2079 - 2085]
[6]Sevov, Christo S.; Hartwig, John F. [Journal of the American Chemical Society, 2014, vol. 136, # 30, p. 10625 - 10631]
[7]Klotz, Eric J. F.; Claridge, Tim D. W.; Anderson, Harry L. [Journal of the American Chemical Society, 2006, vol. 128, # 48, p. 15374 - 15375]
[8]Gong; Hu; Pu [Journal of Organic Chemistry, 2001, vol. 66, # 7, p. 2358 - 2367]
[9]Droege, Daniel G.; Johnstone, Timothy C. [Chemical Communications, 2022, vol. 58, # 16, p. 2722 - 2725]
[10]Chen, Grace J.; Tamborski, Christ [Journal of Organometallic Chemistry, 1983, vol. 251, # 2, p. 149 - 158]
[11]Bo, Zhishan; Schlueter, A. Dieter [Journal of Organic Chemistry, 2002, vol. 67, # 15, p. 5327 - 5332]
[12]Lin, Chih-Hsiu; Tour, James [Journal of Organic Chemistry, 2002, vol. 67, # 22, p. 7761 - 7768]
[13]Current Patent Assignee: SK CHEMICALS CO LTD - JP5856161, 2016, B2 Location in patent: Paragraph 0056
[14]Chen, Xiao-Yang; Shen, Dengke; Cai, Kang; Jiao, Yang; Wu, Huang; Song, Bo; Zhang, Long; Tan, Yu; Wang, Yu; Feng, Yuanning; Stern, Charlotte L.; Stoddart, J. Fraser [Journal of the American Chemical Society, 2020, vol. 142, # 47, p. 20152 - 20160]
[15]Yin, Zhibo; Fan, Luoyi; Lin, Chaojun; Shi, Haonan; Xiong, Bangyuan; Gu, Jiajian; Zhu, Yanpeng; Wang, Jiaobing [Chinese Chemical Letters, 2022, vol. 33, # 1, p. 280 - 282]

2
[ 75-77-4 ]
[ 626-39-1 ]
[ 17878-23-8 ]
[ 81500-92-7 ]

Reference： [1]Journal of Organometallic Chemistry,1982,vol. 225,p. 203 - 210
[2]Journal of Organometallic Chemistry,1982,vol. 225,p. 203 - 210

3
[ 344-04-7 ]
[ 17878-23-8 ]
[ 137897-05-3 ]

Yield	Reaction Conditions	Operation in experiment
83%	With copper at 200℃; for 120h;

Reference： [1]Miller, Timothy M.; Neenan, Thomas X.; Zayas, Roberto; Bair, Harvey E. [Journal of the American Chemical Society, 1992, vol. 114, # 3, p. 1018 - 1025]

4
[ 17878-23-8 ]
[ 128388-54-5 ]
[ 128388-55-6 ]

Yield	Reaction Conditions	Operation in experiment
90%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In tetrahydrofuran for 48h; Heating;
81%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate In tetrahydrofuran; ethanol; toluene for 48h; Heating;

Reference： [1]Gong; Hu; Pu [Journal of Organic Chemistry, 2001, vol. 66, # 7, p. 2358 - 2367]
[2]Miller, Timothy M.; Neenan, Thomas X.; Zayas, Roberto; Bair, Harvey E. [Journal of the American Chemical Society, 1992, vol. 114, # 3, p. 1018 - 1025]

5
[ 17878-23-8 ]
[ 128388-56-7 ]
C₉₃H₇₀Si [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
67%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate In tetrahydrofuran for 72h; Heating;

Reference： [1]Miller, Timothy M.; Neenan, Thomas X.; Zayas, Roberto; Bair, Harvey E. [Journal of the American Chemical Society, 1992, vol. 114, # 3, p. 1018 - 1025]

6
[ 17878-23-8 ]
[ 137915-47-0 ]
C₄₅H₁₈F₂₀Si [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate In tetrahydrofuran; ethanol; toluene for 48h; Heating;

Reference： [1]Miller, Timothy M.; Neenan, Thomas X.; Zayas, Roberto; Bair, Harvey E. [Journal of the American Chemical Society, 1992, vol. 114, # 3, p. 1018 - 1025]

7
[ 17878-23-8 ]
[ 17878-47-6 ]

Yield	Reaction Conditions	Operation in experiment
75%	With n-butyllithium In diethyl ether; hexane at -78℃; for 0.5h;

Reference： [1]Chen, Grace J.; Tamborski, Christ [Journal of Organometallic Chemistry, 1983, vol. 251, # 2, p. 149 - 158]

8
[ 17878-23-8 ]
[ 98-80-6 ]
[ 128388-53-4 ]

Yield	Reaction Conditions	Operation in experiment
86%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate In ethanol; toluene for 6h; Heating;
80%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In tetrahydrofuran for 24h; Heating;

Reference： [1]Miller, Timothy M.; Neenan, Thomas X.; Zayas, Roberto; Bair, Harvey E. [Journal of the American Chemical Society, 1992, vol. 114, # 3, p. 1018 - 1025]
[2]Gong; Hu; Pu [Journal of Organic Chemistry, 2001, vol. 66, # 7, p. 2358 - 2367]

9
[ 17878-23-8 ]
[ 245507-96-4 ]
1,3-bis(3-tert-butylbicyclo[1.1.1]pent-1-yl)-5-(trimethylsilyl)benzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%	In 1,4-dioxane at 20℃; for 48h;

Reference： [1]Rehm, J. D. Daniel; Ziemer, Burghard; Szeimies, Guenter [European Journal of Organic Chemistry, 1999, # 9, p. 2079 - 2085]

10
[ 17878-23-8 ]
[ 245507-97-5 ]
1,3-bis(3-cyclohexylbicyclo[1.1.1]pent-1-yl)-5-(trimethylsilyl)benzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	In 1,4-dioxane at 20℃; for 48h;

Reference： [1]Rehm, J. D. Daniel; Ziemer, Burghard; Szeimies, Guenter [European Journal of Organic Chemistry, 1999, # 9, p. 2079 - 2085]

11
[ 17878-23-8 ]
[ 123324-71-0 ]
(4,4''-di-<i>tert</i>-butyl-[1,1';3',1'']terphenyl-5'-yl)-trimethyl-silane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾
42%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate In water; toluene Inert atmosphere; Glovebox; Reflux;

Reference： [1]Kimura; Shiba; Yamazaki; Hanabusa; Shirai; Kobayashi [Journal of the American Chemical Society, 2001, vol. 123, # 24, p. 5636 - 5642]
[2]Sevov, Christo S.; Hartwig, John F. [Journal of the American Chemical Society, 2014, vol. 136, # 30, p. 10625 - 10631]

12
[ 17878-23-8 ]
3,5-di(4-tertiarybutylphenyl)phenylboronic acid [ No CAS ]
C₆₁H₇₀Si [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾

Reference： [1]Kimura; Shiba; Yamazaki; Hanabusa; Shirai; Kobayashi [Journal of the American Chemical Society, 2001, vol. 123, # 24, p. 5636 - 5642]

13
[ 17878-23-8 ]
[ 873297-68-8 ]
[ 453538-44-8 ]

Yield	Reaction Conditions	Operation in experiment
79.2%	With sodium hydroxide In tetrahydrofuran for 48h; Heating;

Reference： [1]Bo, Zhishan; Schlueter, A. Dieter [Journal of Organic Chemistry, 2002, vol. 67, # 15, p. 5327 - 5332]

14
[ 17878-23-8 ]
[ 19752-57-9 ]

Yield	Reaction Conditions	Operation in experiment
85%	With Iodine monochloride In dichloromethane at 0℃; for 2.16667h;

Reference： [1]Bo, Zhishan; Schlueter, A. Dieter [Journal of Organic Chemistry, 2002, vol. 67, # 15, p. 5327 - 5332]

15
[ 17878-23-8 ]
[(S)-2,2'-dibutoxy-4'-hexyl-1,1'-binaphthalen-4-yl]boronic acid [ No CAS ]
1,3-bis(2,2'-dibutoxy-4'-hexyl-1,1'-binaphthalen-4-yl)-5-(trimethylsilyl)benzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
52%	With sodium carbonate In ethanol; water; toluene for 24h; Heating;

Reference： [1]Chow, Hak-Fun; Wan, Chi-Wai [Helvetica Chimica Acta, 2002, vol. 85, # 10, p. 3444 - 3454]

16
[ 17878-23-8 ]
[ 73183-34-3 ]
[ 383175-93-7 ]

Yield	Reaction Conditions	Operation in experiment
90%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In N,N-dimethyl-formamide at 90℃;	(3,5-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)trimethylsilane (2) To a degassed solution of 1,3-Dibromo-5-trimethylsilylbenzene 1 (1 g, 3.24 mmol, 1 eq.),bis(pinacolato)diboron (1.73 g, 6.81 mmol, 2.1 eq.) and KOAc (1.11 g, 11.36 mmol, 3.5 eq.) in dry DMF (20mL), was added Pd(dppf)Cl2 (92 mg, 3.5 %). The reaction mixture was stirred at 90 °C for 24 hours. Afterevaporation of the solvents, the crude product was purified by column chromatography (SiO2, PetroleumEther/DCM - 9:1), affording the desired product as a white solid which crystallizes in 90 % yield (1.2 g). 1HNMR (400 MHz, CDCl3): (ppm) = 8.30 (t, J = 1.2 Hz, 1H), 8.07 (d, 2H), 1.31 (s, 24H), 0.31 (s, 9H).
76%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In dimethyl sulfoxide at 80℃; for 4h;
76%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In dimethyl sulfoxide heating of 5-trimethyl-1,3-dibromobenzene, diborane pinacol ester, PdCl2(dppf), KOAc and DMSO at 80°C for 4 h; cooling, addn. of H2O, extn. with CH2Cl2, washing of org. layer with brine, drying over Na2SO4, evapn. of solvent, passing through alumina column, purification by GPC;

17.3 g	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate In 1,4-dioxane at 80℃; for 18h; Inert atmosphere;
	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate

Reference： [1]Arshad, Ifzan; Channar, Pervaiz Ali; Irfan, Rana Muhammad; Saeed, Aamer; Shehzadi, Syeda Aaliya [Synlett, 2019, vol. 30, # 16, p. 1886 - 1890]
[2]Itoh, Tetsuji; Hirai, Katsuyuki; Tomioka, Hideo [Journal of the American Chemical Society, 2004, vol. 126, # 4, p. 1130 - 1140]
[3]Itoh, Tetsuji; Hirai, Katsuyuki; Tomioka, Hideo [Journal of the American Chemical Society, 2004, vol. 126, # 4, p. 1130 - 1140]
[4]Chen, Xiao-Yang; Shen, Dengke; Cai, Kang; Jiao, Yang; Wu, Huang; Song, Bo; Zhang, Long; Tan, Yu; Wang, Yu; Feng, Yuanning; Stern, Charlotte L.; Stoddart, J. Fraser [Journal of the American Chemical Society, 2020, vol. 142, # 47, p. 20152 - 20160]
[5]Yin, Zhibo; Fan, Luoyi; Lin, Chaojun; Shi, Haonan; Xiong, Bangyuan; Gu, Jiajian; Zhu, Yanpeng; Wang, Jiaobing [Chinese Chemical Letters, 2022, vol. 33, # 1, p. 280 - 282]

17
[ 14047-29-1 ]
[ 17878-23-8 ]
[ 918410-60-3 ]

Yield	Reaction Conditions	Operation in experiment
80%	With potassium carbonate In N,N-dimethyl-formamide at 80℃;
79%	With 5%-palladium/activated carbon; sodium carbonate In ethanol at 70℃; for 30h; Inert atmosphere;

Reference： [1]Klotz, Eric J. F.; Claridge, Tim D. W.; Anderson, Harry L. [Journal of the American Chemical Society, 2006, vol. 128, # 48, p. 15374 - 15375]
[2]Alezi, Dalal; Belmabkhout, Youssef; Suyetin, Mikhail; Bhatt, Prashant M.; Weseliński, Lukasz J.; Solovyeva, Vera; Adil, Karim; Spanopoulos, Ioannis; Trikalitis, Pantelis N.; Emwas, Abdul-Hamid; Eddaoudi, Mohamed [Journal of the American Chemical Society, 2015, vol. 137, # 41, p. 13308 - 13318]

18
[ 17878-23-8 ]
[ 156642-03-4 ]
[ 943024-31-5 ]

Yield	Reaction Conditions	Operation in experiment
51%	With sodium carbonate In tetrahydrofuran; water for 48h; Heating;

Reference： [1]Hong, Dong-Je; Lee, Eunji; Lee, Myongsoo [Chemical Communications, 2007, # 18, p. 1801 - 1803]

19
[ 17878-23-8 ]
[ 73852-19-4 ]
[ 625122-27-2 ]

Yield	Reaction Conditions	Operation in experiment
92%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate In water; toluene for 12h; Inert atmosphere; Glovebox; Reflux;
	With potassium phosphate; triphenylphosphine In N,N-dimethyl-formamide at 100℃;

Reference： [1]Sevov, Christo S.; Hartwig, John F. [Journal of the American Chemical Society, 2014, vol. 136, # 30, p. 10625 - 10631]
[2]Kano, Taichi; Lan, Quan; Wang, Xisheng; Maruoka, Keiji [Advanced Synthesis and Catalysis, 2007, vol. 349, # 4-5, p. 556 - 560]

20
[ 17878-23-8 ]
[ 625122-29-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: PPh₃; K₃PO₄*nH₂O / Pd(OAc)2 / dimethylformamide / 100 °C 2.1: NCS; NaI / acetic acid; CH₂Cl₂ / 80 °C 3.1: i-PrMgBr / tetrahydrofuran / -78 - 0 °C 3.2: B(OMe)3 / tetrahydrofuran / -78 - 20 °C 3.3: aq. HCl / tetrahydrofuran / 20 °C

Reference： [1]Kano, Taichi; Lan, Quan; Wang, Xisheng; Maruoka, Keiji [Advanced Synthesis and Catalysis, 2007, vol. 349, # 4-5, p. 556 - 560]

21
[ 17878-23-8 ]
C₄₄H₂₆F₁₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: PPh₃; K₃PO₄nH₂O / Pd(OAc)2 / dimethylformamide / 100 °C 2.1: NCS; NaI / acetic acid; CH₂Cl₂ / 80 °C 3.1: i-PrMgBr / tetrahydrofuran / -78 - 0 °C 3.2: B(OMe)3 / tetrahydrofuran / -78 - 20 °C 3.3: aq. HCl / tetrahydrofuran / 20 °C 4.1: PPh₃; K₃PO₄nH₂O / Pd(OAc)2 / dimethylformamide / 110 °C

Reference： [1]Kano, Taichi; Lan, Quan; Wang, Xisheng; Maruoka, Keiji [Advanced Synthesis and Catalysis, 2007, vol. 349, # 4-5, p. 556 - 560]

22
[ 17878-23-8 ]
C₄₄H₂₄Br₂F₁₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: PPh₃; K₃PO₄nH₂O / Pd(OAc)2 / dimethylformamide / 100 °C 2.1: NCS; NaI / acetic acid; CH₂Cl₂ / 80 °C 3.1: i-PrMgBr / tetrahydrofuran / -78 - 0 °C 3.2: B(OMe)3 / tetrahydrofuran / -78 - 20 °C 3.3: aq. HCl / tetrahydrofuran / 20 °C 4.1: PPh₃; K₃PO₄nH₂O / Pd(OAc)2 / dimethylformamide / 110 °C 5.1: NBS; AIBN / benzene / Heating

Reference： [1]Kano, Taichi; Lan, Quan; Wang, Xisheng; Maruoka, Keiji [Advanced Synthesis and Catalysis, 2007, vol. 349, # 4-5, p. 556 - 560]

23
[ 17878-23-8 ]
[ 625122-28-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: PPh₃; K₃PO₄*nH₂O / Pd(OAc)2 / dimethylformamide / 100 °C 2: NCS; NaI / acetic acid; CH₂Cl₂ / 80 °C

Reference： [1]Kano, Taichi; Lan, Quan; Wang, Xisheng; Maruoka, Keiji [Advanced Synthesis and Catalysis, 2007, vol. 349, # 4-5, p. 556 - 560]

24
[ 17878-23-8 ]
[ 943024-36-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 51 percent / Na₂CO₃ / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / H₂O; tetrahydrofuran / 48 h / Heating 2: 68.2 percent / ICl / CH₂Cl₂ / 0.5 h / -78 °C 3: 89.7 percent / BBr₃ / CH₂Cl₂ / 6 h / 20 °C 4: 53 percent / K₂CO₃ / acetone; ethanol / 2 h / Heating

Reference： [1]Hong, Dong-Je; Lee, Eunji; Lee, Myongsoo [Chemical Communications, 2007, # 18, p. 1801 - 1803]

25
[ 17878-23-8 ]
[ 943024-37-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 51 percent / Na₂CO₃ / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / H₂O; tetrahydrofuran / 48 h / Heating 2: 68.2 percent / ICl / CH₂Cl₂ / 0.5 h / -78 °C 3: 89.7 percent / BBr₃ / CH₂Cl₂ / 6 h / 20 °C 4: 53 percent / K₂CO₃ / acetone; ethanol / 2 h / Heating 5: 73 percent / K₂CO₃ / acetonitrile / 12 h / Heating

Reference： [1]Hong, Dong-Je; Lee, Eunji; Lee, Myongsoo [Chemical Communications, 2007, # 18, p. 1801 - 1803]

26
[ 17878-23-8 ]
[ 943024-32-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 51 percent / Na₂CO₃ / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / H₂O; tetrahydrofuran / 48 h / Heating 2: 68.2 percent / ICl / CH₂Cl₂ / 0.5 h / -78 °C

Reference： [1]Hong, Dong-Je; Lee, Eunji; Lee, Myongsoo [Chemical Communications, 2007, # 18, p. 1801 - 1803]

27
[ 17878-23-8 ]
[ 943024-33-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 51 percent / Na₂CO₃ / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / H₂O; tetrahydrofuran / 48 h / Heating 2: 68.2 percent / ICl / CH₂Cl₂ / 0.5 h / -78 °C 3: 89.7 percent / BBr₃ / CH₂Cl₂ / 6 h / 20 °C

Reference： [1]Hong, Dong-Je; Lee, Eunji; Lee, Myongsoo [Chemical Communications, 2007, # 18, p. 1801 - 1803]

28
[ 17878-23-8 ]
[ 943024-34-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 51 percent / Na₂CO₃ / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / H₂O; tetrahydrofuran / 48 h / Heating 2: 68.2 percent / ICl / CH₂Cl₂ / 0.5 h / -78 °C 3: 89.7 percent / BBr₃ / CH₂Cl₂ / 6 h / 20 °C 4: 56 percent / K₂CO₃ / acetonitrile / 12 h / Heating

Reference： [1]Hong, Dong-Je; Lee, Eunji; Lee, Myongsoo [Chemical Communications, 2007, # 18, p. 1801 - 1803]

29
[ 17878-23-8 ]
[ 918410-53-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 80 percent / potassium carbonate / tetrakis(triphenylphosphine)palladium⁽⁰⁾ / dimethylformamide / 80 °C 2: 82 percent / iodine monochloride / dimethylformamide / 64 h / 20 °C
	Multi-step reaction with 2 steps 1: sodium carbonate; 5%-palladium/activated carbon / ethanol / 30 h / 70 °C / Inert atmosphere 2: Iodine monochloride / N,N-dimethyl-formamide

Reference： [1]Klotz, Eric J. F.; Claridge, Tim D. W.; Anderson, Harry L. [Journal of the American Chemical Society, 2006, vol. 128, # 48, p. 15374 - 15375]
[2]Alezi, Dalal; Belmabkhout, Youssef; Suyetin, Mikhail; Bhatt, Prashant M.; Weseliński, Lukasz J.; Solovyeva, Vera; Adil, Karim; Spanopoulos, Ioannis; Trikalitis, Pantelis N.; Emwas, Abdul-Hamid; Eddaoudi, Mohamed [Journal of the American Chemical Society, 2015, vol. 137, # 41, p. 13308 - 13318]

30
[ 121-43-7 ]
[ 17878-23-8 ]
[ 950603-55-1 ]

Yield	Reaction Conditions	Operation in experiment
86%	Stage #1: 3,5-dibromo-1-trimethylsilylbenzene With n-butyllithium In tetrahydrofuran; diethyl ether at -75℃; for 0.5h; Inert atmosphere; Stage #2: Trimethyl borate In tetrahydrofuran; diethyl ether at -75℃; for 0.5h; Inert atmosphere; Stage #3: With sulfuric acid In tetrahydrofuran; diethyl ether; water

Reference： [1]Location in patent: experimental part Durka; Górka; Kurach; Luliński; Serwatowski [Journal of Organometallic Chemistry, 2010, vol. 695, # 24, p. 2635 - 2643]

31
[ 4334-88-7 ]
[ 17878-23-8 ]
[ 1417799-37-1 ]

Yield	Reaction Conditions	Operation in experiment
97%	With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate; 18-crown-6 ether In tetrahydrofuran; ethanol at 90℃; for 24h; Inert atmosphere;

Reference： [1]Luebke, Ryan; Cairns, Amy J.; Alkordi, Mohamed; Eddaoudi, Mohamed; Eubank, Jarrod F.; Nouar, Farid; Wojtas, Lukasz; Bousquet, Till; Hight, Matthew R.; Eckert, Juergen; Embs, Jan P.; Georgiev, Peter A. [Angewandte Chemie - International Edition, 2012, vol. 51, # 40, p. 10099 - 10103,5][Angewandte Chemie, 2012, vol. 124, # 40, p. 10246 - 10250,5]

32
[ 626-39-1 ]
[ 17878-23-8 ]

Yield	Reaction Conditions	Operation in experiment
	With n-butyllithium; chloro-trimethyl-silane; triethylamine In tetrahydrofuran; methanol	P.5 Synthesis of Intermediate Preparation Example 5 Synthesis of Intermediate 1 g of 1,3,5-tribromobenzene was added to 20 mL of tetrahydrofuran and the temperature was adjusted to -78° C. Subsequently, 1.65 mL of butyllithium was slowly added dropwise. The mixture was stirred for 2 hr while maintaining its temperature, and 0.45 g of chlorotrimethylsilane was slowly added dropwise, after which the temperature of the mixture was raised to room temperature. After completion of the reaction, triethylamine and methanol were added, and the reaction mixture was stirred and extracted, followed by drying the solvent. The resulting solid was filtered and purified, yielding (3,5-dibromophenyl)trimethylsilane as an intermediate.

Reference： [1]Current Patent Assignee: SK CHEMICALS CO LTD - US2013/119367, 2013, A1 Location in patent: Page/Page column

33
[ 17878-23-8 ]
[ 86-74-8 ]
[ 1353645-90-5 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate In 1,2-dichloro-benzene	P.6 Synthesis of Intermediate Preparation Example 6 Synthesis of Intermediate 1.19 g of 9H-carbazole, 1 g of (3,5-dibromophenyl)trimethylsilane, 3.57 g of potassium carbonate, 0.82 g of copper powder and 0.17 g of dibenzo-18-crown-6 were dissolved in 20 mL of o-dichlorobenzene, and the resulting solution was refluxed at a steady 100° C. After completion of the reaction, the reaction mixture was extracted with dichloromethane and distilled water, and the solvent was dried. The resulting solid was filtered and purified, yielding 9,9'-(5-(trimethylsilyl)-1,3-phenylene)bis(9H-carbazole) as an intermediate.
	With dibenzo-18-crown-6; copper; potassium carbonate In 1,2-dichloro-benzene at 100℃;	6 Synthesis of Intermediate 1.19 g of 9H-carbazole, 1 g of (3,5-dibromophenyl)trimethylsilane, 3.57 g of potassium carbonate, 0.82 g of copperpowder and 0.17 g of dibenzo-18-crown-6 were dissolved in 20 mL of o-dichlorobenzene, and the resulting solutionwas refluxed at a steady 100°C. After completion of the reaction, the reaction mixture was extracted withdichloromethane and distilled water, and the solvent was dried. The resulting solid was filtered and purified, yielding9,9'-(5-(trimethylsilyl)-1,3-phenylene)bis(9H-carbazole) as an intermediate.

Reference： [1]Current Patent Assignee: SK CHEMICALS CO LTD - US2013/119367, 2013, A1 Location in patent: Page/Page column
[2]Current Patent Assignee: SK CHEMICALS CO LTD - JP5856161, 2016, B2 Location in patent: Paragraph 0056

34
[ 75-76-3 ]
[ 626-39-1 ]
[ 17878-23-8 ]

Yield	Reaction Conditions	Operation in experiment
92%	Stage #1: 1,3,5-trisbromobenzene With n-butyllithium In tetrahydrofuran; hexane; toluene at -78℃; for 0.25h; Inert atmosphere; Stage #2: tetramethylsilane In tetrahydrofuran; hexane; toluene at -78 - 20℃; Inert atmosphere;

Reference： [1]Graff, Julien; Debande, Thibaut; Praz, Jezabel; Guenee, Laure; Alexakis, Alexandre [Organic Letters, 2013, vol. 15, # 16, p. 4270 - 4273]

35
[ 17878-23-8 ]
[ 1449204-16-3 ]

Yield	Reaction Conditions	Operation in experiment
22%	Stage #1: 3,5-dibromo-1-trimethylsilylbenzene With lithium diisopropyl amide In tetrahydrofuran; hexane at -78℃; for 2h; Inert atmosphere; Stage #2: With copper(l) cyanide; lithium chloride In tetrahydrofuran; hexane at -78℃; for 2h; Inert atmosphere; Stage #3: With p-benzoquinone In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere;

Reference： [1]Graff, Julien; Debande, Thibaut; Praz, Jezabel; Guenee, Laure; Alexakis, Alexandre [Organic Letters, 2013, vol. 15, # 16, p. 4270 - 4273]

36
[ 17878-23-8 ]
[ 33513-42-7 ]
[ 1006708-27-5 ]

Yield	Reaction Conditions	Operation in experiment
85%	Stage #1: 3,5-dibromo-1-trimethylsilylbenzene With lithium dipropan-2-ylazanide In tetrahydrofuran at -70℃; for 1h; Inert atmosphere; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran at -70℃; for 0.5h; Inert atmosphere;
1.072 g	With lithium dipropan-2-ylazanide In tetrahydrofuran; n-heptane; ethylbenzene at -75℃; for 3h;

Reference： [1]Guillerm, Vincent; Weselinski, Ukasz J.; Alkordi, Mohamed; Mohideen, M. Infas H.; Belmabkhout, Youssef; Cairns, Amy J.; Eddaoudi, Mohamed [Chemical Communications, 2014, vol. 50, # 16, p. 1937 - 1940]
[2]Droege, Daniel G.; Johnstone, Timothy C. [Chemical Communications, 2022, vol. 58, # 16, p. 2722 - 2725]

37
[ 17878-23-8 ]
[ 33513-42-7 ]
[ 1361964-14-8 ]

Yield	Reaction Conditions	Operation in experiment
74%	Stage #1: 3,5-dibromo-1-trimethylsilylbenzene With n-butyllithium In diethyl ether; hexane at -80 - -30℃; for 3.5h; Stage #2: N,N-dimethyl-formamide In diethyl ether; hexane at -30 - 20℃;
45%	Stage #1: 3,5-dibromo-1-trimethylsilylbenzene With n-butyllithium In diethyl ether at -78℃; Stage #2: N,N-dimethyl-formamide In diethyl ether	1 5,10,15,20-tetrakis (3-carboxy-5-trimethylsilyl phenyl) porphyrin sodium salt (hereinafter, SiC 4 may be called) was synthesized by the following procedure. The 1,3,5-bromo benzene in dry diethyl ether, and lithiation with an equal volume of n- butyl lithium at -78 , then was allowed to react with chlorotrimethylsilane, in a yield of 95% 3,5 dibromo trimethylsilyl benzene was obtained. Then in dry diethyl ether this, lithiation with an equal volume of n- butyl lithium at -78 , then was allowed to react with DMF, 3-bromo-5-trimethylsilyl benzaldehyde in 45% yield was obtained . This was dissolved in dry toluene, p- toluenesulfonic acid present of at reacted with ethylene glycol, to give the 3-bromo-5-trimethylsilyl benzaldehyde ethylene acetal in 90% yield. Then after the reaction with magnesium it in dry THF, it is reacted with carbon dioxide at 0 ° C., to obtain a 3-carboxy-5-trimethylsilyl benzaldehyde ethylene acetal in 40% yield. This by treatment with hydrochloric acid, to give 3-carboxy-5-trimethylsilyl benzaldehyde. This was then reacted with ethyl iodide under potassium carbonate present in a DMF, to give the 3-carboxy-5-trimethylsilyl benzaldehyde ethyl ester. Pyrrole this in chloroform is reacted with boron fluoride ether complex, by treatment with subsequent DDQ, 5,10,15,20-tetrakis (3-carboxy-5-trimethylsilyl-phenyl) to give a porphyrin ethyl ester. Finally, by treating it with sodium hydroxide to obtain a 5,10,15,20-tetrakis (3-carboxy-5-trimethylsilyl phenyl) porphyrin sodium salt.

Reference： [1]Horiuchi, Hiroaki; Hosaka, Masahiro; Mashio, Hiroyuki; Terata, Motoki; Ishida, Shintaro; Kyushin, Soichiro; Okutsu, Tetsuo; Takeuchi, Toshiyuki; Hiratsuka, Hiroshi [Chemistry - A European Journal, 2014, vol. 20, # 20, p. 6054 - 6060]
[2]Current Patent Assignee: GUNMA UNIVERSITY - JP5843113, 2016, B2 Location in patent: Paragraph 0025

38
[ 629-74-3 ]
[ 17878-23-8 ]
[3-bromo-5-(hexadec-1-ynyl)phenyl]trimethylsilane [ No CAS ]
[3,5-di(hexadec-1-ynyl)phenyl]trimethylsilane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 70% 2: 8.6%	With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine In tetrahydrofuran at 60℃; for 4h; Inert atmosphere;

Reference： [1]Sekiguchi, Ryuta; Takahashi, Kei; Kawakami, Jun; Sakai, Atsushi; Ikeda, Hiroshi; Ishikawa, Aya; Ohta, Kazuchika; Ito, Shunji [Journal of Organic Chemistry, 2015, vol. 80, # 10, p. 5092 - 5110]

39
[ 17878-23-8 ]
[ 1816997-25-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: sodium carbonate; 5%-palladium/activated carbon / ethanol / 30 h / 70 °C / Inert atmosphere 2: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate / N,N-dimethyl-formamide; water / 20 h / 80 °C / Inert atmosphere

Reference： [1]Alezi, Dalal; Belmabkhout, Youssef; Suyetin, Mikhail; Bhatt, Prashant M.; Weseliński, Lukasz J.; Solovyeva, Vera; Adil, Karim; Spanopoulos, Ioannis; Trikalitis, Pantelis N.; Emwas, Abdul-Hamid; Eddaoudi, Mohamed [Journal of the American Chemical Society, 2015, vol. 137, # 41, p. 13308 - 13318]

40
[ 17878-23-8 ]
[ 1816997-26-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: sodium carbonate; 5%-palladium/activated carbon / ethanol / 30 h / 70 °C / Inert atmosphere 2: Iodine monochloride / N,N-dimethyl-formamide 3: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate / water; d<SUB>7</SUB>-N,N-dimethylformamide / 32 h / 80 °C / Inert atmosphere

Reference： [1]Alezi, Dalal; Belmabkhout, Youssef; Suyetin, Mikhail; Bhatt, Prashant M.; Weseliński, Lukasz J.; Solovyeva, Vera; Adil, Karim; Spanopoulos, Ioannis; Trikalitis, Pantelis N.; Emwas, Abdul-Hamid; Eddaoudi, Mohamed [Journal of the American Chemical Society, 2015, vol. 137, # 41, p. 13308 - 13318]

41
[ 5765-44-6 ]
[ 17878-23-8 ]
4-(3,5-dibromo)-5-methylisoxazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
13%	With 1-hydroxy-1,2-benzodioxol-3-(1H)-one; camphor-10-sulfonic acid; [gold(I)Cl(1-(2,4,6-Me3C6H2)-3,5-di(2,6-Me2C6H3) 2-pyridylidene)]; In methanol; chloroform; at 65℃; for 48h;Inert atmosphere; Sealed tube;	General procedure: Triarylpyridylidene-gold complex AuCl(PyC) (6.4 mg, 10 mumol, 5 mol %), heteroarene (0.20 mmol), and aryl(trimethyl)silane (0.20 mmol), 2-iodosobenzoic acids (IBA) (53 mg, 0.20 mmol), (+)-10-camphorsulfonic acid (CSA) (47 mg, 0.20 mmol) and a stirring bar were placed in a screw test tube, and dry chloroform/methanol (1.0 mL/0.10 mL) was added under N2 atmosphere. The tube was sealed with a cap equipped with a Teflon-coated silicon rubber septum, and the mixture was stirred at 65 C for 18-48 h. The reaction was quenched by addition of excess saturated NaHCO3 aq, the aqueous layer was extracted with dichloromethane and the combined organic layers were dried over Na2SO4, filtrated, and concentrated under reduced pressure. The residue was purified by flash chromatography (FC) to afford the coupling product.

Reference： [1]Beilstein Journal of Organic Chemistry,2015,vol. 11,p. 2737 - 2746

42
[ 100-43-6 ]
[ 17878-23-8 ]
C₂₃H₂₄N₂Si [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
0.89 g	With palladium diacetate; triethylamine; tris-(o-tolyl)phosphine In acetonitrile at 80℃; for 12h;	3A Synthesis of Intermediate 11 of the structural formula 11 To the reaction flask was replaced by nitrogen 4-vinylpyridine 0.84 g,3,5-dibromo-trimethylsilyl benzene 1.2 g, palladium acetate 0.07 g, tri -o-tolyl phosphine 0.19 g, triethylamine 0.89 g, and acetonitrile were charged 20ml, the mixture was stirred for 12 hours at 80 ° C. After cooling, the reactionmixture was diluted with chloroform, was filtered off the insoluble material,washed with water The chloroform solution was evaporated and chloroform wasdried over anhydrous sodium sulfate. The resulting solid in toluene / acetone(volume ratio; 1/1) was purified by silica gel column chromatography elutingwith to give the intermediate. 11 0.89 g. Measurement of the GC / MS of thisproduct, the molecular ion peak was M = 356.

Reference： [1]Current Patent Assignee: RICOH CO LTD; YAMADA CHEMICAL CO LTD - JP5900813, 2016, B2 Location in patent: Paragraph 0129

43
3-chloro-5-t-butyl-phenylboronic acid pinacol ester [ No CAS ]
[ 17878-23-8 ]
C₂₉H₃₆Cl₂Si [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In tetrahydrofuran at 75℃; for 24h; Inert atmosphere;

Reference： [1]Ikemoto, Koki; Kobayashi, Ryo; Sato, Sota; Isobe, Hiroyuki [Angewandte Chemie - International Edition, 2017, vol. 56, # 23, p. 6511 - 6514][Angew. Chem., 2017, vol. 129, p. 6611 - 6614]

44
[ 1402929-36-5 ]
[ 17878-23-8 ]
C₃₃H₁₈F₂₈Si [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; caesium carbonate; bis(dibenzylideneacetone)-palladium⁽⁰⁾ In toluene at 100℃; for 12h; Schlenk technique; Inert atmosphere;

Reference： [1]Arlt, Alexander; Toyama, Hideaki; Takada, Koji; Hashimoto, Takuya; Maruoka, Keiji [Chemical Communications, 2017, vol. 53, # 35, p. 4779 - 4782]

45
[ 17878-23-8 ]
[ 16400-50-3 ]

Yield	Reaction Conditions	Operation in experiment
24.7 mg	With tetrakis(acetonitrile)palladium(II) bis(tetrafluoroborate); o-tetrachloroquinone; In chloroform; at 60℃; for 10h;Inert atmosphere;	General procedure: To a screw-capped glass tube containing a magnetic stirrer bar were addedaryltrimethylsilane 1 (0.30 mmol, 1.0 equiv), Pd(CH3CN)4(BF4)2 (3.3 mg, 0.075 mmol, 2.5mol%), CHCl3 (1.5 mL) or CHCl3/1,2-dichloroethane (1:4, 1.5 mL) and o-chloranil (55.9 mg, 0.225 mmol, 0.75 equiv) under a stream of nitrogen. After stirring at 60 C for 10 hours, thereaction mixture was cooled to room temperature, and then passed through a short pad of silicagel (eluent: CHCl3). After the organic solvent was removed under reduced pressure, the residuewas purified by flash column chromatography on silica gel to yield biaryl 2. The reactions wereconducted in 0.50 mmol scale for 1a in 2.5 mL of CHCl3, 0.30 mmol scale for 1b-1t in 1.5 mLof the indicated solvent, and 0.20 mmol scale for 1w in the indicated solvent, respectively.

Reference： [1]Chemistry Letters,2017,vol. 46,p. 1701 - 1704

46
[ 1598370-75-2 ]
[ 17878-23-8 ]
3,5-di(1-adamantyl)-1-trimethylsilylbenzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
59%	With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate In tetrahydrofuran at 50℃; for 3h; Inert atmosphere; Schlenk technique;

Reference： [1]Rösel, Sören; Becker, Jonathan; Allen, Wesley D.; Schreiner, Peter R. [Journal of the American Chemical Society, 2018, vol. 140, # 43, p. 14421 - 14432]

47
[ 17878-23-8 ]
C₅₄H₇₂Si₆ [ No CAS ]
C₄₅H₆₀Si₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 0.43 g 2: 1.50 g	With [2,2]bipyridinyl; bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; cyclo-octa-1,5-diene In N,N-dimethyl-formamide; toluene at 80℃; for 3h; Inert atmosphere;

Reference： [1]Ikemoto, Koki; Isobe, Hiroyuki; Mio, Tatsuru; Sato, Sota [Angewandte Chemie - International Edition, 2020, vol. 59, # 16, p. 6567 - 6571][Angew. Chem., 2020, vol. 132, # 16, p. 6629 - 6633,5]

48
[ 17878-23-8 ]
[ 196212-27-8 ]
C₂₄H₂₈Br₂Si₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In water; N,N-dimethyl-formamide at 80℃; for 18h; Inert atmosphere;

Reference： [1]Ikemoto, Koki; Isobe, Hiroyuki; Mio, Tatsuru; Sato, Sota [Angewandte Chemie - International Edition, 2020, vol. 59, # 16, p. 6567 - 6571][Angew. Chem., 2020, vol. 132, # 16, p. 6629 - 6633,5]

49
[ 5720-07-0 ]
[ 17878-23-8 ]
[ 7509-20-8 ]

Yield	Reaction Conditions	Operation in experiment
70%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾ In tetrahydrofuran; water for 48h; Inert atmosphere; Reflux;

Reference： [1]Che, Chi-Ming; Guan, Xiangguo; Huang, Jie-Sheng; Qin, Lin; Yang, Chen [Chemistry - A European Journal, 2018, vol. 24, # 54, p. 14400 - 14408]

50
[ 17878-23-8 ]
[ 994-28-5 ]
(3-bromo-5-(triethylgermyl)phenyl)trimethylsilane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	Stage #1: 3,5-dibromo-1-trimethylsilylbenzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Schlenk technique; Stage #2: triethylgermanium chloride In tetrahydrofuran; hexane Schlenk technique;
82%	Stage #1: 3,5-dibromo-1-trimethylsilylbenzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere; Stage #2: triethylgermanium chloride In tetrahydrofuran; hexane at 20℃; Inert atmosphere;

Reference： [1]Deckers, Kristina; Fricke, Christoph; Hupperich, Daniel; Kreisel, Tatjana; Mendel, Marvin; Queen, Adele E.; Riegger, Julian; Schoenebeck, Franziska [Angewandte Chemie - International Edition, 2022, vol. 61, # 20][Angew. Chem., 2022, vol. 134, # 20]
[2]Dahiya, Amit; Fricke, Christoph; Funes-Ardoiz, Ignacio; Gevondian, Avetik G.; Schoenebeck, Franziska; Sherborne, Grant J. [Angewandte Chemie - International Edition, 2020, vol. 59, # 36, p. 15543 - 15548][Angew. Chem., 2020, vol. 132, # 36, p. 15673 - 15678,6]

51
[ 17878-23-8 ]
C₉H₁₃BrOSi [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	Stage #1: 3,5-dibromo-1-trimethylsilylbenzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere; Schlenk technique; Stage #2: With Trimethyl borate In tetrahydrofuran; hexane at -78 - 20℃; for 1h; Inert atmosphere; Schlenk technique; Stage #3: With dihydrogen peroxide; sodium hydroxide In tetrahydrofuran; hexane; water at 20℃; for 1h;

Reference： [1]Zuo, Ziqing; Kim, Raphael S.; Watson, Donald A. [Journal of the American Chemical Society, 2021, vol. 143, # 3, p. 1328 - 1333]

52
[ 17878-23-8 ]
[ 17049-49-9 ]
C₂₅H₄₆Si [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
41%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In tetrahydrofuran; diethyl ether at 55℃; for 16h;	27 Intermediate 52 To octylmagnesium bromide solution (183 cm3, 365 mmol, 2.0 M in ether) and tetrahydrofuran (450 cm3) is added (3,5-dibromophenyl)trimethylsilane (45.0 g, 146 mmol) and [1,1′-bis(diphenylphosphino)ferrocene]dichloro-palladium (II) (1.60 g, 2.19 mmol). The reaction mixture is heated at 55° C. for 16 hours before it is cooled to 0° C. and water (250 cm3) added. The organics extracted with dichloromethane (2×250 cm3). The combined organics are washed with brine (100 cm3), dried over anhydrous magnesium sulfate, filtered and the solvent removed in vacuo. The crude is purified by column chromatography (heptane) to give intermediate 52 (22.2 g, 41%) as a colourless oil. 1H NMR (400 MHz, CDCl3) 7.15 (2H, d, J 1.6), 7.00 (1H, s), 2.52-2.64 (4H, m), 1.55-1.68 (24H, m), 0.84-0.89-5 (6H, m), 0.22-0.31 (9H, m).

Reference： [1]Current Patent Assignee: MERCK KGAA; RAYNERGY TEK INCORPORATION - US2021/70770, 2021, A1 Location in patent: Paragraph 0702; 0703

53
[ 196083-18-8 ]
[ 17878-23-8 ]
C₂₅H₁₈F₁₂Si [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	With tetrakis(triphenylphosphine) palladium(0); barium hydroxide octahydrate; In 1,4-dioxane; water; at 100.0℃; for 24h;	3,5-Dibromophenyltrimethylsilane (0.85 g, 2.75 mmol), Ba(OH)28H2O(3.0 g, 9.60 mmol), <strong>[196083-18-8]2,5-bis(trifluoromethyl)phenylboronic acid</strong> (2.86 g, 11.0mmol),5 and Pd(PPh3)4 (0.26 g, 0.22 mmol) were mixed in dioxane/H2O (5/1)(48 mL). The mixture was stirred at 100 C. After 24 h, the reaction mixturewas quenched with 1N HCl, extracted with CH2Cl2. The combined organiclayer was washed with H2O and brine, dried over Na2SO4, and evaporated.The crude product was purified by column chromatography (hexane) to giveS1’ (1.4 g, 89 %). white solid; m.p. 98-108 C; 1H NMR (400 MHz, CDCl3) δ 7.91 (d, J = 8.3 Hz, 2H), 7.78 (d, J = 8.3 Hz, 2H), 7.62 (s, 2H), 7.56 (d, J = 1.4Hz, 2H), 7.24 (s, 1H), 1.53 (s, 9H); 13C NMR (101 MHz, CDCl3) δ 140.0, 139.7,133.8 (q, J = 33.2 Hz), 132.0 (q, J = 30.8 Hz), 131.8, 128.7 (q, J = 3.9 Hz),128.2, 127.1 (q, J = 4.6 Hz), 125.2 (q, J = 3.7 Hz), 123.1 (q, J = 274.1 Hz), 0.0;19F NMR (376 MHz, CDCl3) δ 57.5, 63.19; HRMS (FD+) m/z calcd forC25H18F12Si [M]+ 574.09861, found 574.09898,.

Reference： [1]Chemistry Letters,2021,vol. 50,p. 1781 - 1783

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CAS No. :	17878-23-8	MDL No. :	MFCD03844787
Formula :	C₉H₁₂Br₂Si	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	SZQQTWLBYAKIOT-UHFFFAOYSA-N
M.W :	308.09	Pubchem ID :	626244
Synonyms :

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 17878-23-8 ] {[proInfo.proName]}

Quality Control of [ 17878-23-8 ]

Related Doc. of [ 17878-23-8 ]

Product Details of [ 17878-23-8 ]

Safety of [ 17878-23-8 ]

Application In Synthesis of [ 17878-23-8 ]

[ 17878-23-8 ] Synthesis Path-Upstream 1~2

[ 17878-23-8 ] Synthesis Path-Downstream 1~53

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry