Name: 286438-45-7|2,7-Dibromo-9,9-didodecyl-9H-fluorene|97%
Brand: Ambeed
SKU: A169408
Price: 5.0 USD
Availability: InStock
Rating: 95 (28 reviews)

1
[ 123864-04-0 ]
[ 286438-45-7 ]

Yield	Reaction Conditions	Operation in experiment
80%	With bromine In dichloromethane at 20℃; for 20h;

Reference： [1]Soloducho; Roszak; Chyla; Tajchert [New Journal of Chemistry, 2001, vol. 25, # 9, p. 1175 - 1181]

2
[ 286438-45-7 ]
[ 388602-19-5 ]

Yield	Reaction Conditions	Operation in experiment
70%	In N,N-dimethyl-formamide for 24h; Heating;

Reference： [1]Soloducho; Roszak; Chyla; Tajchert [New Journal of Chemistry, 2001, vol. 25, # 9, p. 1175 - 1181]

3
[ 286438-45-7 ]
[ 873-75-6 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
	With bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; 1,5-cis,cis-cyclooctadiene; 1,1'-bipyridyl In pentane at 85℃; for 48h;

Reference： [1]Kim, Hyun Jung; Kwon, Yong Ku [Molecular Crystals and Liquid Crystals, 2007, vol. 462, # 1, p. 217 - 223]

4
[ 286438-45-7 ]
[ 866889-88-5 ]

Yield	Reaction Conditions	Operation in experiment
53%	With 4-toluenesulfonyl azide; tert.-butyl lithium In tetrahydrofuran; pentane at -78℃;
8%	With n-butyllithium; 4-toluenesulfonyl azide In tetrahydrofuran Inert atmosphere;
	Multi-step reaction with 2 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 80 °C / Inert atmosphere; Schlenk technique 2: sodium azide; copper(l) iodide / methanol / 8 h / 55 °C

Reference： [1]Van Steenis, Dirk Jan V. C.; David, Olivier R. P.; Van Strijdonck, Gino P. F.; Van Maarseveen, Jan H.; Reek, Joost N. H. [Chemical Communications, 2005, # 34, p. 4333 - 4335]
[2]Hwang, Euiyong; Lusker, Kathie L.; Garno, Jayne C.; Losovyj, Yaroslav; Nesterov, Evgueni E. [Chemical Communications, 2011, vol. 47, # 43, p. 11990 - 11992]
[3]Powers, Ian G.; Andjaba, John M.; Luo, Xuyi; Mei, Jianguo; Uyeda, Christopher [Journal of the American Chemical Society, 2018, vol. 140, # 11, p. 4110 - 4118]

5
[ 286438-45-7 ]
[ 388602-21-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 70 percent / dimethylformamide / 24 h / Heating 2: 75 percent / phosphoric acid; H₂O / 24 h / 170 °C 3: 81 percent / thionyl chloride / DMF / 13 h / 20 - 50 °C

Reference： [1]Soloducho; Roszak; Chyla; Tajchert [New Journal of Chemistry, 2001, vol. 25, # 9, p. 1175 - 1181]

6
[ 286438-45-7 ]
[ 388602-23-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: 70 percent / dimethylformamide / 24 h / Heating 2: 75 percent / phosphoric acid; H₂O / 24 h / 170 °C 3: 81 percent / thionyl chloride / DMF / 13 h / 20 - 50 °C 4: 80 percent / triethylamine / benzene / 7 h / 20 - 50 °C 5: phosgene / DMF / toluene / 13 h / 20 - 40 °C 6: potassium tert-butoxide / tetrahydrofuran / 1 h / -10 - 0 °C

Reference： [1]Soloducho; Roszak; Chyla; Tajchert [New Journal of Chemistry, 2001, vol. 25, # 9, p. 1175 - 1181]

7
[ 286438-45-7 ]
[ 388602-22-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 70 percent / dimethylformamide / 24 h / Heating 2: 75 percent / phosphoric acid; H₂O / 24 h / 170 °C 3: 81 percent / thionyl chloride / DMF / 13 h / 20 - 50 °C 4: 80 percent / triethylamine / benzene / 7 h / 20 - 50 °C

Reference： [1]Soloducho; Roszak; Chyla; Tajchert [New Journal of Chemistry, 2001, vol. 25, # 9, p. 1175 - 1181]

8
[ 286438-45-7 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 70 percent / dimethylformamide / 24 h / Heating 2: 75 percent / phosphoric acid; H₂O / 24 h / 170 °C 3: 81 percent / thionyl chloride / DMF / 13 h / 20 - 50 °C 4: 80 percent / triethylamine / benzene / 7 h / 20 - 50 °C 5: phosgene / DMF / toluene / 13 h / 20 - 40 °C

Reference： [1]Soloducho; Roszak; Chyla; Tajchert [New Journal of Chemistry, 2001, vol. 25, # 9, p. 1175 - 1181]

9
[ 286438-45-7 ]
[ 388602-20-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 70 percent / dimethylformamide / 24 h / Heating 2: 75 percent / phosphoric acid; H₂O / 24 h / 170 °C

Reference： [1]Soloducho; Roszak; Chyla; Tajchert [New Journal of Chemistry, 2001, vol. 25, # 9, p. 1175 - 1181]

10
[ 86-73-7 ]
[ 286438-45-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: n-BuLi / hexane; tetrahydrofuran / 1.5 h / -60 °C 1.2: 80 percent / tetrahydrofuran; hexane / 0.5 h / -60 °C 2.1: 80 percent / bromine / I₂ / CH₂Cl₂ / 20 h / 20 °C
	Multi-step reaction with 2 steps 1: bromine; iodine / dichloromethane / 15 h / 20 °C 2: potassium <i>tert</i>-butylate / tetrahydrofuran / 12 h / 0 - 20 °C
	Multi-step reaction with 2 steps 1.1: acetic acid; N-Bromosuccinimide; hydrogen bromide / 3 h / 20 °C 2.1: potassium hydroxide / toluene / 1 h / Inert atmosphere 2.2: 12 h / 60 °C / Inert atmosphere

Multi-step reaction with 2 steps 1: bromine / chloroform / 10 h / 0 °C / Darkness 2: sodium hydroxide; tetrabutylammomium bromide / toluene; water / 24 h / 80 °C / Inert atmosphere

Reference： [1]Soloducho; Roszak; Chyla; Tajchert [New Journal of Chemistry, 2001, vol. 25, # 9, p. 1175 - 1181]
[2]Bleger, David; Ciesielski, Artur; Samori, Paolo; Hecht, Stefan [Chemistry - A European Journal, 2010, vol. 16, # 48, p. 14256 - 14260]
[3]Fong, Darryl; Bodnaryk, William J.; Rice, Nicole A.; Saem, Sokunthearath; Moran-Mirabal, Jose M.; Adronov, Alex [Chemistry - A European Journal, 2016, vol. 22, # 41, p. 14560 - 14566]
[4]Current Patent Assignee: GUILIN UNIVERSITY OF TECHNOLOGY - CN107686448, 2018, A

11
[ 143-15-7 ]
[ 286438-45-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: n-BuLi / hexane; tetrahydrofuran / 1.5 h / -60 °C 1.2: 80 percent / tetrahydrofuran; hexane / 0.5 h / -60 °C 2.1: 80 percent / bromine / I₂ / CH₂Cl₂ / 20 h / 20 °C

Reference： [1]Soloducho; Roszak; Chyla; Tajchert [New Journal of Chemistry, 2001, vol. 25, # 9, p. 1175 - 1181]

12
[ 286438-45-7 ]
[ 61676-62-8 ]
[ 749900-93-4 ]

Yield	Reaction Conditions	Operation in experiment
90%	Stage #1: 2,7-dibromo-9,9-di-n-dodecylfluorene With tert.-butyl lithium In tetrahydrofuran; pentane at -78℃; for 1h; Inert atmosphere; Stage #2: 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In tetrahydrofuran; pentane at -78 - 20℃; Inert atmosphere;
90%	With tert.-butyl lithium In not given 1) t-BuLi, -78°C; 2.) dioxaborolane;
90%	Stage #1: 2,7-dibromo-9,9-di-n-dodecylfluorene With tert.-butyl lithium In tetrahydrofuran; pentane at -78℃; for 0.5h; Inert atmosphere; Stage #2: 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In tetrahydrofuran; pentane at -78 - 20℃; Inert atmosphere;

90%	With tert.-butyl lithium In tetrahydrofuran; pentane at -78 - 20℃;	7 Tert-BuLi (43.9 mL, 74.7 mmol, 1.7 M in pentane) was added over 30 minutes to a solution of 2,7-dibromo-9,9-didodecylfluorene (12.02 g, 18.2 mmol) in dry THF (90.0 mL) under nitrogen at -78°C. The reaction mixture was stirred for 30 minutes at -78°C, and 2-isopropoxy-4,4,5,5-tetramethyl-l,3,2-dioxaborolane (22.2 mL, 108.6 mmol) was added dropwise with stirring at room temperature overnight. The reaction was quenched with water. THF was removed, and the mixture was extracted with diethyl ether. The organic layer was washed with water, dried over MgSO4, filtered, and concentrated to dryness to give 2,7-bis(4,4,5,5- tetramethyl-l,3,2-dioxaborolane)-9,9-didodecylfluorene (7) as a white solid (12.36 g, 90%). 1H NMR (CDCl3): δ 0.55 (t, 4H), 0.88 (m, 6H), 1.01 (m, 6H), 1.15- 1.28 (m, 14H), 1.4 (s, 24 H), 2.0 l(t, 4H), 7.72 (2H, d, J =7.5 Hz), 7.75 (2H, s), 7.82 (2H, d, J =7.5 Hz) ppm.
	With n-butyllithium
	Stage #1: 2,7-dibromo-9,9-di-n-dodecylfluorene With n-butyllithium In diethyl ether at -85℃; Inert atmosphere; Stage #2: 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In diethyl ether at -85 - 25℃; Inert atmosphere;	3.1 preparation of 2, 7- bis (4, 4, 5, 5-tetramethyl-1, 3, 2-dioxaborolan-yl) -9, 9-bis(dodecyl) fluorene General procedure: Anhydrous anaerobic reactor was assembled, under a continuing stirring and N2 protection, white 9.0mmol of2, 7- dibromo-9 , 9- dioctylfluorene were added into a three-necked flask, 150mL of refined tetrahydrofuran solvent wasadded by a syringe, 27.0 mmol of n-BuLi was added by a syringe under a temperature of -78°C, the mixture was stirredfor 2 hours. Then, 30.6mmol of 2- isopropoxy-4, 4, 5, 5-tetramethyl-1, 3, 2- dioxaborolane was added by a syringe undera temperature of -78°C, the temperature was raised to 20°C, and the reaction was carried out for 14 hours.[0051] After the reaction was finished, a saturated aqueous NaCl solution was added, extracted with chloroform, driedby anhydrous sodium sulfate, suction filtered, and the filtrate was collected and solvent was rotary evaporated. The rawproduct was finally refined by a silica gel column chromatography using petroleum ether: ethyl acetate (v/v=15:1) aseluent to obtain powdered solid 2, 7- bis (4, 4, 5, 5-tetramethyl-1 , 3, 2- the dioxaborolan- yl) -9, 9- dioctylfluorene in ayield of 65%. GC-MS (EI-m/z) : 642 (M+). Step one, preparation of 2, 7- bis (4, 4, 5, 5-tetramethyl-1, 3, 2-dioxaborolan-yl) -9, 9-bis(dodecyl) fluorene:[0070] The preparation process was similar to that of Step one in Example 1, and the differences were:[0071] In step S1, the temperature was -85°C, and then was raised to 25°C. The reaction time was 32 hours. Themole ratio of 2, 7-dibromo-9, 9-bis(dodecyl) fluorene to n-BuLi was 1:4; the solvent is ether; the mole amount of 2-isopropoxy-4, 4, 5, 5-tetramethyl-1, 3, 2-dioxaborolane was 2 times of that of 2, 7-dibromo-9, 9-bis (dodecyl) fluorene.

Reference： [1]Usta, Hakan; Facchetti, Antonio; Marks, Tobin J. [Organic Letters, 2008, vol. 10, # 7, p. 1385 - 1388]
[2]Usta, Hakan; Risko, Chad; Wang, Zhiming; Huang, Hui; Deliomeroglu, Murat K.; et al. [Journal of the American Chemical Society, 2009, vol. 131, p. 5586 - 5608]
[3]Usta, Hakan; Risko, Chad; Wang, Zhiming; Huang, Hui; Deliomeroglu, Murat K.; et al. [Journal of the American Chemical Society, 2009, vol. 131, p. 5586 - 5608]
[4]Current Patent Assignee: NORTHWESTERN UNIVERSITY (ILLINOIS) - WO2009/17798, 2009, A1 Location in patent: Page/Page column 63-64
[5]Location in patent: scheme or table Li, Zhongtao; Zhang, Yuan; Holt, Amanda L.; Kolasa, Borys P.; Wehner, Justin G.; Hampp, Andreas; Bazan, Guillermo C.; Nguyen, Thuc-Quyen; Morse, Daniel E. [New Journal of Chemistry, 2011, vol. 35, # 6, p. 1327 - 1334]
[6]Current Patent Assignee: OCEAN'S KING LIGHTING SCIENCE & TECHNOLOGY CO., LTD. - EP2657239, 2013, A1 Location in patent: Paragraph 0049; 0050; 0069-0071

Yield	Reaction Conditions	Operation in experiment
85%	With potassium iodide; potassium hydroxide In dimethyl sulfoxide at 20℃;	7 (1) Synthesis of compound 1 General procedure: 2,7-dibromo-9H-fluorene (15.2g, 45.4mmol, 1eq), bromo-n-hexane (45.4-136.2mmol, 1-3eq), potassium hydroxide (45.4-454mmol, 1-10eq), potassium iodide ( 4.5-45.4mmol, 0.1-1eq) was dissolved in DMSO (80110eq), the system was continuously stirred at 030 for 8-12 hours, then the reaction was followed by a dot plate. After the reaction, the liquid was filtered with suction and used for 300 The mixture was diluted with 500 eq ethyl acetate, the aqueous phase was separated and the aqueous phase was extracted again with 100-300 eq ethyl acetate. The combined organic phase was dried over anhydrous sodium sulfate and concentrated. The residual solid is purified by a silica gel column, and the eluent is petroleum ether and ethyl acetate, and the volume ratio is preferably 100:1 to obtain compound 1 in light green oily form with a yield of 89%.

14
[ 286438-45-7 ]
[ 1269505-28-3 ]
[ 1269505-29-4 ]

Yield	Reaction Conditions	Operation in experiment
33%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetrabutylammomium bromide; potassium carbonate In tetrahydrofuran; water at 90℃; for 12h; Inert atmosphere;

Reference： [1]Bleger, David; Ciesielski, Artur; Samori, Paolo; Hecht, Stefan [Chemistry - A European Journal, 2010, vol. 16, # 48, p. 14256 - 14260]

15
[ 286438-45-7 ]
[ 124-38-9 ]
[ 61676-62-8 ]
[ 1269505-28-3 ]

Yield	Reaction Conditions	Operation in experiment
36%	Stage #1: 2,7-dibromo-9,9-di-n-dodecylfluorene With n-butyllithium In tetrahydrofuran at -78℃; for 0.916667h; Inert atmosphere; Stage #2: 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In tetrahydrofuran at -78 - -50℃; for 1.08333h; Stage #3: carbon dioxide Further stages;

Reference： [1]Bleger, David; Ciesielski, Artur; Samori, Paolo; Hecht, Stefan [Chemistry - A European Journal, 2010, vol. 16, # 48, p. 14256 - 14260]

16
[ 16433-88-8 ]
[ 143-15-7 ]
[ 286438-45-7 ]

Yield	Reaction Conditions	Operation in experiment
92%	With potassium <i>tert</i>-butylate In tetrahydrofuran at 0 - 20℃; for 12h;
87%	With tetrabutylammomium bromide; water; sodium hydroxide In dimethyl sulfoxide at 20℃; for 3h;
86.6%	With tetrabutylammomium bromide; sodium hydroxide In water; toluene at 80℃; for 24h; Inert atmosphere;	1 Synthesis of 2,7-dibromo-9,9-dodecyl-1,6-dinitro-9H-fluorene Dissolve fluorene (5.00 g, 30.08 mmol) in 40 mL of chloroform solution.A solution of Br2 (3.08 mL) dissolved in 15 mL of chloroform was added dropwise to the above solution and stirred at 0°C for 10 hours in the dark.Stop the reaction and pour the mixed solution into aqueous Na2S2O3 solution.Extract with dichloromethane (15 mL × 3), combine the organic layers with deionized water (25 mL × 3) and saturated brine (20 mL), dry the organic layer over anhydrous magnesium sulfate, and remove the solvent using a rotary evaporator.The crude product is recrystallized from absolute ethanol solution.A white solid of 2,7-dibromo-fluorene (7.04 g, 72.2%) was obtained;2,7-Dibromo-fluorene (6.40 g, 19.75 mmol) and tetrabutylammonium bromide (0.10 g, 0.31 mmol) obtained from the previous reactionDissolve 1-bromododecane (10 mL, 41.65 mmol) in 60 mL of toluene and 25 mL of 50 wt% NaOH aqueous solution, and argon at 80 °C for 24 hours under reflux.Stop the reaction and extract the solution with ethyl acetate (25mL x 3). Combine the organic layers with deionized water (25mL x 3)After washing with saturated brine (30 mL), the organic layer was dried over anhydrous magnesium sulfate and the solvent was removed using a rotary evaporator.The crude product was separated by a chromatography column (petroleum ether:dichloromethane=4:1) to give 2,7-dibromo-9,9-didodecyl-fluoreneas a pale yellow solid (11.30 g, 86.6%). );Finally, the resulting 2,7-dibromo-9,9-didodecyl-fluorene (2.00 g, 3.03 mmol) was reacted in the previous step.Dissolve in 60 mL of dichloromethane, add 10 mL of concentrated sulfuric acid, and cool to 0 °C.Ammonium cerium nitrate (4.98 g, 9.08 mmol) was added in portions to the above mixed solution and the reaction was stirred for 1 hour.Stop the reaction by adding 50 mL of deionized water and extract with dichloromethane (15 mL x 3).The organic phase was washed with deionized water (25 mL×3) and saturated brine (20 mL), respectively.Dry the organic layer by adding anhydrous magnesium sulfate,The solvent was removed using a rotary evaporator and the crude product was separated on a chromatography column (petroleum ether: dichloromethane = 4:1).The orange-yellow product 2,7-dibromo-9,9-didoceyl-1,6-dinitrofluorene (1.7 g, 74.56%) was obtained.

84%	With potassium <i>tert</i>-butylate In N,N-dimethyl-formamide at 40℃; for 18h;
82%	With tetrabutylammomium bromide; sodium hydroxide In water; dimethyl sulfoxide at 20℃; for 3h;
80.6%	With sodium hydroxide In dimethyl sulfoxide at 90℃; for 24h;
78%	With tetrabutylammomium bromide; sodium hydroxide In water; dimethyl sulfoxide at 20℃; for 3h;
63%	Stage #1: 2,7-dibromo-9H-fluorene; 1-dodecylbromide With potassium hydroxide In toluene for 1h; Inert atmosphere; Stage #2: With tetrabutylammomium bromide In toluene at 60℃; for 12h; Inert atmosphere;
32%	With tetrabutylammomium bromide; sodium hydroxide In water; toluene Inert atmosphere;
	With N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide at 60℃; for 12h;
	With potassium hydroxide In water; toluene
	With tetrabutylammomium bromide; potassium hydroxide In water; dimethyl sulfoxide

Reference： [1]Bleger, David; Ciesielski, Artur; Samori, Paolo; Hecht, Stefan [Chemistry - A European Journal, 2010, vol. 16, # 48, p. 14256 - 14260]
[2]Moonsin, Preecha; Prachumrak, Narid; Namuangruk, Supawadee; Jungsuttiwong, Siriporn; Keawin, Tinnagon; Sudyoadsuk, Taweesak; Promarak, Vinich [Journal of Materials Chemistry C, 2014, vol. 2, # 28, p. 5540 - 5552]
[3]Current Patent Assignee: GUILIN UNIVERSITY OF TECHNOLOGY - CN107686448, 2018, A Location in patent: Paragraph 0014; 0016; 0017
[4]Rice, Nicole A.; Subrahmanyam, Ayyagari V.; Coleman, Brian R.; Adronov, Alex [Macromolecules, 2015, vol. 48, # 15, p. 5155 - 5161]
[5]Moonsin, Preecha; Prachumrak, Narid; Namuangruk, Supawadee; Jungsuttiwong, Siriporn; Keawin, Tinnagon; Sudyoadsuk, Taweesak; Promarak, Vinich [Chemical Communications, 2013, vol. 49, # 57, p. 6388 - 6390]
[6]Tian, Zhuanzhuan; Yang, Xiaolong; Liu, Boao; Zhao, Jiang; Zhong, Daokun; Wu, Yong; Zhou, Guijiang; Wong, Wai-Yeung [Journal of Materials Chemistry C, 2018, vol. 6, # 22, p. 6023 - 6032] Tian, Zhuanzhuan; Yang, Xiaolong; Liu, Boao; Zhong, Daokun; Zhou, Guijiang; Wong, Wai-Yeung [Journal of Materials Chemistry C, 2018, vol. 6, # 42, p. 11416 - 11426]
[7]Zhao, Gang; Feng, Yan; Guang, Shanyi; Xu, Hongyao; Lin, Naibo; Liu, Xiangyang [RSC Advances, 2017, vol. 7, # 85, p. 53785 - 53796]
[8]Fong, Darryl; Bodnaryk, William J.; Rice, Nicole A.; Saem, Sokunthearath; Moran-Mirabal, Jose M.; Adronov, Alex [Chemistry - A European Journal, 2016, vol. 22, # 41, p. 14560 - 14566]
[9]Hwang, Euiyong; Lusker, Kathie L.; Garno, Jayne C.; Losovyj, Yaroslav; Nesterov, Evgueni E. [Chemical Communications, 2011, vol. 47, # 43, p. 11990 - 11992]
[10]Location in patent: scheme or table Gupta, Jhinuk; Vadukumpully, Sajini; Valiyaveettil, Suresh [Polymer, 2010, vol. 51, # 22, p. 5078 - 5086]
[11]Tao, Feng; Wang, Zheng; Li, Zuojia; Li, Kai; Li, Ying; Peng, Qiang [Asian Journal of Chemistry, 2013, vol. 25, # 13, p. 7499 - 7504]
[12]Zhang, Fang; Zhang, Rong; Liang, Xiaozhong; Guo, Kunpeng; Han, Zhaoxiang; Lu, Xiaoqing; Xie, Jingjuan; Li, Jie; Li, Da; Tian, Xia [Dyes and Pigments, 2018, vol. 155, p. 225 - 232]

17
[ 286438-45-7 ]
[ 3034-86-4 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
	With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine; triphenylphosphine In tetrahydrofuran at 65℃; for 18h; Inert atmosphere;

Reference： [1]Zhang, Xuanjun; Ballem, Mohamed Ali; Hu, Zhang-Jun; Bergman, Peder; Uvdal, Kajsa [Angewandte Chemie - International Edition, 2011, vol. 50, # 25, p. 5729 - 5733]

18
[ 286438-45-7 ]
[ 73183-34-3 ]
[ 749900-93-4 ]

Yield	Reaction Conditions	Operation in experiment
87%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In N,N-dimethyl-formamide at 90℃; for 12h;
76%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 80℃; Inert atmosphere;
74%	Stage #1: 2,7-dibromo-9,9-di-n-dodecylfluorene; bis(pinacol)diborane With potassium acetate In 1,4-dioxane; dimethyl sulfoxide for 1h; Inert atmosphere; Stage #2: With palladium bis[bis(diphenylphosphino)ferrocene] dichloride In 1,4-dioxane; dimethyl sulfoxide at 80℃; for 12h; Inert atmosphere;

68%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 1,4-dioxane at 80℃;
68%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 1,4-dioxane at 80℃; Inert atmosphere; Schlenk technique;
	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 80℃; Inert atmosphere;

Reference： [1]Rice, Nicole A.; Subrahmanyam, Ayyagari V.; Coleman, Brian R.; Adronov, Alex [Macromolecules, 2015, vol. 48, # 15, p. 5155 - 5161]
[2]Location in patent: experimental part Berton, Nicolas; Lemasson, Fabien; Tittmann, Jana; Stuerzl, Ninette; Hennrich, Frank; Kappes, Manfred M.; Mayor, Marcel [Chemistry of Materials, 2011, vol. 23, # 8, p. 2237 - 2249]
[3]Fong, Darryl; Bodnaryk, William J.; Rice, Nicole A.; Saem, Sokunthearath; Moran-Mirabal, Jose M.; Adronov, Alex [Chemistry - A European Journal, 2016, vol. 22, # 41, p. 14560 - 14566]
[4]Location in patent: scheme or table Lemasson, Fabien; Berton, Nicolas; Tittmann, Jana; Hennrich, Frank; Kappes, Manfred M.; Mayor, Marcel [Macromolecules, 2012, vol. 45, # 2, p. 713 - 722]
[5]Powers, Ian G.; Andjaba, John M.; Luo, Xuyi; Mei, Jianguo; Uyeda, Christopher [Journal of the American Chemical Society, 2018, vol. 140, # 11, p. 4110 - 4118]
[6]Lemasson, Fabien; Tittmann, Jana; Hennrich, Frank; Stuerzl, Ninette; Malik, Sharali; Kappes, Manfred M.; Mayor, Marcel [Chemical Communications, 2011, vol. 47, # 26, p. 7428 - 7430]

19
[ 286438-45-7 ]
[ 521947-42-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine / tetrahydrofuran / 20 h / 60 °C / Inert atmosphere 2: sodium hydroxide / toluene / 40 h / Reflux
	Multi-step reaction with 2 steps 1.1: bis-triphenylphosphine-palladium(II) chloride; triphenylphosphine; triethylamine; copper(l) iodide / tetrahydrofuran / 0.1 h / Inert atmosphere; Glovebox; Sealed tube 1.2: 70 °C / Inert atmosphere; Sealed tube; Glovebox 2.1: potassium hydroxide / tetrahydrofuran; methanol / 20 °C / Inert atmosphere
	Multi-step reaction with 2 steps 1: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triphenylphosphine; triethylamine / tetrahydrofuran / 10 h / Reflux; Inert atmosphere 2: potassium hydroxide / toluene / 8 h / 100 °C / Inert atmosphere

	Multi-step reaction with 2 steps 1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride / 20 - 75 °C / Inert atmosphere 2: potassium carbonate / diethyl ether; methanol / 24 h / 20 °C
	Multi-step reaction with 2 steps 1: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide / 12.5 h / 20 - 70 °C / Alkaline conditions 2: tetrabutyl ammonium fluoride / 0.5 h / 20 °C
	Multi-step reaction with 2 steps 1: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine / 12 h / 70 °C 2: tetrabutyl ammonium fluoride / dichloromethane / 0.5 h / 20 °C
	Multi-step reaction with 2 steps 1: copper(l) iodide; N-ethyl-N,N-diisopropylamine; bis-triphenylphosphine-palladium(II) chloride / 20 h / 75 °C / Inert atmosphere; Schlenk technique 2: potassium carbonate; methanol / diethyl ether / 5 h / 20 °C / Inert atmosphere; Schlenk technique

Reference： [1]Juriek, Michal; Felici, Marco; Contreras-Carballada, Pablo; Lauko, Jan; Bou, Sandra Rodriguez; Kouwer, Paul H. J.; Brouwer, Albert M.; Rowan, Alan E. [Journal of Materials Chemistry, 2011, vol. 21, # 7, p. 2104 - 2111]
[2]Jellison, Jessica L.; Lee, Che-Hsiung; Zhu, Xinju; Wood, Jordan D.; Plunkett, Kyle N. [Angewandte Chemie - International Edition, 2012, vol. 51, # 49, p. 12321 - 12324][Angew. Chem., 2012, vol. 124, # 49, p. 12487 - 12490,4]
[3]Tao, Feng; Wang, Zheng; Li, Zuojia; Li, Kai; Li, Ying; Peng, Qiang [Asian Journal of Chemistry, 2013, vol. 25, # 13, p. 7499 - 7504]
[4]Quintiliani, Maurizio; Bassetti, Mauro; Pasquini, Chiara; Battocchio, Chiara; Rossi, Marco; Mura, Francesco; Matassa, Roberto; Fontana, Laura; Russo, Maria Vittoria; Fratoddi, Ilaria [Journal of Materials Chemistry C, 2014, vol. 2, # 14, p. 2517 - 2527]
[5]Tian, Zhuanzhuan; Yang, Xiaolong; Liu, Boao; Zhao, Jiang; Zhong, Daokun; Wu, Yong; Zhou, Guijiang; Wong, Wai-Yeung [Journal of Materials Chemistry C, 2018, vol. 6, # 22, p. 6023 - 6032]
[6]Tian, Zhuanzhuan; Yang, Xiaolong; Liu, Boao; Zhong, Daokun; Zhou, Guijiang; Wong, Wai-Yeung [Journal of Materials Chemistry C, 2018, vol. 6, # 42, p. 11416 - 11426]
[7]Bassetti, Mauro; Battocchio, Chiara; Carlini, Laura; Cerra, Sara; Familiari, Giuseppe; Fontana, Laura; Fratoddi, Ilaria; Matassa, Roberto; Rossi, Enrico; Venditti, Iole [Inorganica Chimica Acta, 2021, vol. 516]

20
[ 286438-45-7 ]
[ 115-19-5 ]
[ 1275593-74-2 ]

Yield	Reaction Conditions	Operation in experiment
87%	With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine In tetrahydrofuran at 60℃; for 20h; Inert atmosphere;
42.8%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; triphenylphosphine In tetrahydrofuran for 10h; Reflux; Inert atmosphere;

Reference： [1]Juriek, Michal; Felici, Marco; Contreras-Carballada, Pablo; Lauko, Jan; Bou, Sandra Rodriguez; Kouwer, Paul H. J.; Brouwer, Albert M.; Rowan, Alan E. [Journal of Materials Chemistry, 2011, vol. 21, # 7, p. 2104 - 2111]
[2]Tao, Feng; Wang, Zheng; Li, Zuojia; Li, Kai; Li, Ying; Peng, Qiang [Asian Journal of Chemistry, 2013, vol. 25, # 13, p. 7499 - 7504]

21
[ 286438-45-7 ]
[ 75927-49-0 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
69%	With palladium diacetate; triethylamine; tris-(o-tolyl)phosphine In N,N-dimethyl-formamide at 110℃; for 7h; Inert atmosphere;

Reference： [1]Location in patent: experimental part Ko, Sangwon; Mondal, Rajib; Risko, Chad; Lee, Jung Kyu; Hong, Sanghyun; McGehee, Michael D.; Bredas, Jean-Luc; Bao, Zhenan [Macromolecules, 2010, vol. 43, # 16, p. 6685 - 6698]

22
[ 286438-45-7 ]
[ 916764-64-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: copper(l) iodide / N,N-dimethyl acetamide / 180 °C 2: hydrazine / ethanol / Reflux

Reference： [1]Wang, Mingfeng; Sun, Yanming; Tong, Minghong; Chesnut, Eneida S.; Seo, Jung Hua; Kumar, Rajeev; Wudl, Fred [Journal of Polymer Science, Part A: Polymer Chemistry, 2011, vol. 49, # 2, p. 441 - 451]

23
[ 286438-45-7 ]
[ 1264735-16-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: copper(l) iodide / N,N-dimethyl acetamide / 180 °C 2: hydrazine / ethanol / Reflux 3: N-sulfinyl-p-toluenesulfonamide / benzene / 22 h / 20 °C / Inert atmosphere

Reference： [1]Wang, Mingfeng; Sun, Yanming; Tong, Minghong; Chesnut, Eneida S.; Seo, Jung Hua; Kumar, Rajeev; Wudl, Fred [Journal of Polymer Science, Part A: Polymer Chemistry, 2011, vol. 49, # 2, p. 441 - 451]

24
[ 286438-45-7 ]
[ CAS Unavailable ]
[ 916764-63-1 ]

Yield	Reaction Conditions	Operation in experiment
	With copper(l) iodide In N,N-dimethyl acetamide at 180℃;

Reference： [1]Location in patent: scheme or table Wang, Mingfeng; Sun, Yanming; Tong, Minghong; Chesnut, Eneida S.; Seo, Jung Hua; Kumar, Rajeev; Wudl, Fred [Journal of Polymer Science, Part A: Polymer Chemistry, 2011, vol. 49, # 2, p. 441 - 451]

25
[ 286438-45-7 ]
[ 1062586-22-4 ]
[ 1269012-52-3 ]

Yield	Reaction Conditions	Operation in experiment
	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In water at 95℃; for 24h; Inert atmosphere;

Reference： [1]Location in patent: experimental part Dikundwar, Amol G.; Dutta, Gitish K.; Row, Tayur N. Guru; Patil, Satish [Crystal Growth and Design, 2011, vol. 11, # 5, p. 1615 - 1622]

26
[ 286438-45-7 ]
[ 1066-54-2 ]
[ 1427465-81-3 ]

Yield	Reaction Conditions	Operation in experiment
89%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide at 20 - 70℃; for 12.5h; Alkaline conditions;
89%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 70℃; for 12h;
73%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide at 20 - 75℃; Inert atmosphere;

54.5%	Stage #1: 2,7-dibromo-9,9-di-n-dodecylfluorene With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; triphenylphosphine In tetrahydrofuran for 0.1h; Inert atmosphere; Glovebox; Sealed tube; Stage #2: trimethylsilylacetylene In tetrahydrofuran at 70℃; Inert atmosphere; Sealed tube; Glovebox;
	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; N-ethyl-N,N-diisopropylamine at 75℃; for 20h; Inert atmosphere; Schlenk technique;

Reference： [1]Tian, Zhuanzhuan; Yang, Xiaolong; Liu, Boao; Zhao, Jiang; Zhong, Daokun; Wu, Yong; Zhou, Guijiang; Wong, Wai-Yeung [Journal of Materials Chemistry C, 2018, vol. 6, # 22, p. 6023 - 6032]
[2]Tian, Zhuanzhuan; Yang, Xiaolong; Liu, Boao; Zhong, Daokun; Zhou, Guijiang; Wong, Wai-Yeung [Journal of Materials Chemistry C, 2018, vol. 6, # 42, p. 11416 - 11426]
[3]Quintiliani, Maurizio; Bassetti, Mauro; Pasquini, Chiara; Battocchio, Chiara; Rossi, Marco; Mura, Francesco; Matassa, Roberto; Fontana, Laura; Russo, Maria Vittoria; Fratoddi, Ilaria [Journal of Materials Chemistry C, 2014, vol. 2, # 14, p. 2517 - 2527]
[4]Jellison, Jessica L.; Lee, Che-Hsiung; Zhu, Xinju; Wood, Jordan D.; Plunkett, Kyle N. [Angewandte Chemie - International Edition, 2012, vol. 51, # 49, p. 12321 - 12324][Angew. Chem., 2012, vol. 124, # 49, p. 12487 - 12490,4]
[5]Bassetti, Mauro; Battocchio, Chiara; Carlini, Laura; Cerra, Sara; Familiari, Giuseppe; Fontana, Laura; Fratoddi, Ilaria; Matassa, Roberto; Rossi, Enrico; Venditti, Iole [Inorganica Chimica Acta, 2021, vol. 516]

27
[ 286438-45-7 ]
[ 86-74-8 ]
[ 2000210-25-1 ]

Yield	Reaction Conditions	Operation in experiment
75%	With potassium phosphate; copper(l) iodide; trans-1,2-Diaminocyclohexane In toluene for 24h; Inert atmosphere; Reflux;
73%	With potassium phosphate; copper(l) iodide; trans-1,2-cyclohexanediamine In toluene for 24h; Reflux; Inert atmosphere;

Reference： [1]Sangchart, Tidaratana; Niroram, Arunroj; Kaewpuang, Teadkait; Prachumrak, Narid; Namuangruk, Supawadee; Sudyoadsuk, Taweesak; Keawin, Tinnagon; Saengsuwan, Sayant; Jungsuttiwong, Siriporn; Maensiri, Santi; Kungwan, Nawee; Promarak, Vinich [RSC Advances, 2015, vol. 5, # 34, p. 26569 - 26579]
[2]Moonsin, Preecha; Prachumrak, Narid; Namuangruk, Supawadee; Jungsuttiwong, Siriporn; Keawin, Tinnagon; Sudyoadsuk, Taweesak; Promarak, Vinich [Chemical Communications, 2013, vol. 49, # 57, p. 6388 - 6390]

28
[ 286438-45-7 ]
[ 606129-90-2 ]
C₇₃H₇₈BrN₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With potassium phosphate; copper(l) iodide; trans-1,2-cyclohexanediamine In toluene for 24h; Reflux; Inert atmosphere;

Reference： [1]Moonsin, Preecha; Prachumrak, Narid; Namuangruk, Supawadee; Jungsuttiwong, Siriporn; Keawin, Tinnagon; Sudyoadsuk, Taweesak; Promarak, Vinich [Chemical Communications, 2013, vol. 49, # 57, p. 6388 - 6390]

29
[ 286438-45-7 ]
[ 1122624-11-6 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
70%	With potassium phosphate; copper(l) iodide; trans-1,2-cyclohexanediamine In toluene for 24h; Reflux; Inert atmosphere;

Reference： [1]Moonsin, Preecha; Prachumrak, Narid; Namuangruk, Supawadee; Jungsuttiwong, Siriporn; Keawin, Tinnagon; Sudyoadsuk, Taweesak; Promarak, Vinich [Chemical Communications, 2013, vol. 49, # 57, p. 6388 - 6390]

30
[ 286438-45-7 ]
[ 108847-76-3 ]
[ 1373485-23-4 ]

Yield	Reaction Conditions	Operation in experiment
47%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In water; toluene; at 90℃; for 24h;Inert atmosphere;	General procedure: The following general Suzuki procedurewas used for the preparation all of the bis(thianthren-1-yl) derivatives. To a three-necked flaskwas added <strong>[108847-76-3]thianthren-1-yl boronic acid</strong> (1.73 g, 6.67 mmol), 9,9-didodecyl-2,7-dibromofluorene(2.00 g, 3.04 mmol), and a mixture of anhydrous toluene (35 ml) and 2 M aqueous potassiumcarbonate solution (21 ml). The flask equipped with a condenser was then evacuated and filledwith nitrogen several times to remove traces of the air. Pd(PPh3)4 (0.45 g, 0.39 mmol) was thenadded under nitrogen atmosphere. The mixture was heated at 90oC for 24h under nitrogen. Theseparated aqueous layer was extracted with chloroform (3x15 ml). The organic phase waswashed thrice with water (15 ml). The combined organic layers were dried over anhydrousmagnesium sulfate, and the solvent was removed by rotary evaporation. The crude product waspurified by silica gel column chromatography with hexane:ethyl acetate (8:1, V/V) as eluent.Product (colourless oil) was obtained with yield 47% (1.33 g). 1H NMR (CDCl3): deltaH 0.85 (6H, t,J=6.8 Hz, 2CH3), 1.05-1.26 (40H, m, 20CH2), 2.05-2.11 (4H, m, 2CH2), 7.14-7.27 (4Harom., m,4CH), 7.29-7.33 (2Harom., dd, J=1.4 Hz, J=7.5 Hz, 2CH), 7.33 (2Harom., d, J=7.5 Hz, 2CH), 7.37(2Harom., d, J=1.3 Hz, 2CH), 7.39 (2Harom., d, J=7.7 Hz, 2CH), 7.46 (2Harom., d, J=1.2 Hz, 2CH),7.50-7.56 (4Harom., m, 4CH), 7.85 (2Harom., d, J=7.7 Hz, 2CH). 13C NMR (CDCl3): deltaC 14.0(2CH3), 22.6 (2CH2), 24.1 (2CH2), 29.2 (2CH2), 29.5 (2CH2), 29.6 (4CH2), 29.7 (2CH2), 30.2(2CH2), 31.8 (2CH2), 40.5 (2CH2), 55.3 (2CH2), 119.6, 124.4, 127.0, 127.5, 127.7, 128.0, 128.1,128.5, 128.7, 129.1, 135.3, 135.3, 136.1, 136.5, 139.0, 140.4, 143.0, 150.9 (C-Ar). Anal. Calcdfor C61H70S4: C, 78.66; H, 7.57; S, 13.77%, Found: C, 78.56; H, 7.59; S, 13.67%

Reference： [1]ARKIVOC,2012,vol. 2012,p. 193 - 209

31
[ 286438-45-7 ]
[ 1586808-78-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride / 20 - 75 °C / Inert atmosphere 2: potassium carbonate / diethyl ether; methanol / 24 h / 20 °C 3: bis(dibenzylideneacetone)-palladium⁽⁰⁾; triphenylphosphine; N-ethyl-N,N-diisopropylamine; copper(l) iodide / tetrahydrofuran / 24 h / 50 °C / Inert atmosphere

Reference： [1]Quintiliani, Maurizio; Bassetti, Mauro; Pasquini, Chiara; Battocchio, Chiara; Rossi, Marco; Mura, Francesco; Matassa, Roberto; Fontana, Laura; Russo, Maria Vittoria; Fratoddi, Ilaria [Journal of Materials Chemistry C, 2014, vol. 2, # 14, p. 2517 - 2527]

32
[ 286438-45-7 ]
[ 75-36-5 ]
[ 1586808-77-6 ]

Yield	Reaction Conditions	Operation in experiment
48%	Stage #1: 2,7-dibromo-9,9-di-n-dodecylfluorene With sodium thiomethoxide at 120℃; for 18h; Inert atmosphere; Stage #2: acetyl chloride at 20℃; for 3h; Inert atmosphere;

Reference： [1]Quintiliani, Maurizio; Bassetti, Mauro; Pasquini, Chiara; Battocchio, Chiara; Rossi, Marco; Mura, Francesco; Matassa, Roberto; Fontana, Laura; Russo, Maria Vittoria; Fratoddi, Ilaria [Journal of Materials Chemistry C, 2014, vol. 2, # 14, p. 2517 - 2527]

33
[ 286438-45-7 ]
[ 1610851-65-4 ]
[ 1610851-62-1 ]

Yield	Reaction Conditions	Operation in experiment
32%	With potassium phosphate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; XPhos In 1,2-dimethoxyethane at 120℃; for 16h; Schlenk technique; Inert atmosphere; Glovebox;

Reference： [1]Jones, Crystalann; Boudinet, Damien; Xia, Yu; Denti, Mitch; Das, Adita; Facchetti, Antonio; Driver, Tom G. [Chemistry - A European Journal, 2014, vol. 20, # 20, p. 5938 - 5945]

34
[ 286438-45-7 ]
[ 551951-04-3 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
76%	With potassium phosphate; copper(l) iodide; trans-1,2-Diaminocyclohexane In toluene for 24h; Inert atmosphere; Reflux;

Reference： [1]Moonsin, Preecha; Prachumrak, Narid; Namuangruk, Supawadee; Jungsuttiwong, Siriporn; Keawin, Tinnagon; Sudyoadsuk, Taweesak; Promarak, Vinich [Journal of Materials Chemistry C, 2014, vol. 2, # 28, p. 5540 - 5552]

35
[ 286438-45-7 ]
[ 1068116-44-8 ]
[ 1618678-86-6 ]

Yield	Reaction Conditions	Operation in experiment
70%	With potassium phosphate; copper(l) iodide; trans-1,2-Diaminocyclohexane In toluene for 24h; Inert atmosphere; Reflux;

Reference： [1]Moonsin, Preecha; Prachumrak, Narid; Namuangruk, Supawadee; Jungsuttiwong, Siriporn; Keawin, Tinnagon; Sudyoadsuk, Taweesak; Promarak, Vinich [Journal of Materials Chemistry C, 2014, vol. 2, # 28, p. 5540 - 5552]

36
[ 286438-45-7 ]
[ 37500-95-1 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
73%	With potassium phosphate; copper(l) iodide; trans-1,2-Diaminocyclohexane In toluene for 24h; Inert atmosphere; Reflux;

Reference： [1]Moonsin, Preecha; Prachumrak, Narid; Namuangruk, Supawadee; Jungsuttiwong, Siriporn; Keawin, Tinnagon; Sudyoadsuk, Taweesak; Promarak, Vinich [Journal of Materials Chemistry C, 2014, vol. 2, # 28, p. 5540 - 5552]

37
[ 286438-45-7 ]
[ 86-74-8 ]
[ 2000210-24-0 ]

Yield	Reaction Conditions	Operation in experiment
87%	With potassium phosphate; copper(l) iodide; trans-1,2-Diaminocyclohexane In toluene for 24h; Inert atmosphere; Reflux;

Reference： [1]Sangchart, Tidaratana; Niroram, Arunroj; Kaewpuang, Teadkait; Prachumrak, Narid; Namuangruk, Supawadee; Sudyoadsuk, Taweesak; Keawin, Tinnagon; Saengsuwan, Sayant; Jungsuttiwong, Siriporn; Maensiri, Santi; Kungwan, Nawee; Promarak, Vinich [RSC Advances, 2015, vol. 5, # 34, p. 26569 - 26579]

38
[ 286438-45-7 ]
[ 33513-42-7 ]
[ 1450727-06-6 ]

Reference： [1]Journal of the American Chemical Society,2016,vol. 138,p. 802 - 805

39
[ 286438-45-7 ]
[ 76528-51-3 ]
[ 2241393-98-4 ]

Yield	Reaction Conditions	Operation in experiment
54%	With palladium diacetate; triethylamine; triphenylphosphine In N,N-dimethyl-formamide at 110℃; for 48h; Inert atmosphere;

Reference： [1]Zhao, Gang; Feng, Yan; Guang, Shanyi; Xu, Hongyao; Lin, Naibo; Liu, Xiangyang [RSC Advances, 2017, vol. 7, # 85, p. 53785 - 53796]

40
[ 286438-45-7 ]
[ 2241394-06-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: palladium diacetate; triphenylphosphine; triethylamine / N,N-dimethyl-formamide / 48 h / 110 °C / Inert atmosphere 2: triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide / 48 h / 80 °C / Inert atmosphere 3: sodium hydroxide / 1,4-dioxane / 4 h / 80 °C / Inert atmosphere

Reference： [1]Zhao, Gang; Feng, Yan; Guang, Shanyi; Xu, Hongyao; Lin, Naibo; Liu, Xiangyang [RSC Advances, 2017, vol. 7, # 85, p. 53785 - 53796]

41
[ 286438-45-7 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: palladium diacetate; triphenylphosphine; triethylamine / N,N-dimethyl-formamide / 48 h / 110 °C / Inert atmosphere 2: triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide / 48 h / 80 °C / Inert atmosphere

Reference： [1]Zhao, Gang; Feng, Yan; Guang, Shanyi; Xu, Hongyao; Lin, Naibo; Liu, Xiangyang [RSC Advances, 2017, vol. 7, # 85, p. 53785 - 53796]

42
[ 286438-45-7 ]
[ 2183479-32-3 ]

Yield	Reaction Conditions	Operation in experiment
74.56%	With ammonium cerium (IV) nitrate; sulfuric acid In dichloromethane at 0℃; for 1h;	1 Synthesis of 2,7-dibromo-9,9-dodecyl-1,6-dinitro-9H-fluorene Dissolve fluorene (5.00 g, 30.08 mmol) in 40 mL of chloroform solution.A solution of Br2 (3.08 mL) dissolved in 15 mL of chloroform was added dropwise to the above solution and stirred at 0°C for 10 hours in the dark.Stop the reaction and pour the mixed solution into aqueous Na2S2O3 solution.Extract with dichloromethane (15 mL × 3), combine the organic layers with deionized water (25 mL × 3) and saturated brine (20 mL), dry the organic layer over anhydrous magnesium sulfate, and remove the solvent using a rotary evaporator.The crude product is recrystallized from absolute ethanol solution.A white solid of 2,7-dibromo-fluorene (7.04 g, 72.2%) was obtained;2,7-Dibromo-fluorene (6.40 g, 19.75 mmol) and tetrabutylammonium bromide (0.10 g, 0.31 mmol) obtained from the previous reactionDissolve 1-bromododecane (10 mL, 41.65 mmol) in 60 mL of toluene and 25 mL of 50 wt% NaOH aqueous solution, and argon at 80 °C for 24 hours under reflux.Stop the reaction and extract the solution with ethyl acetate (25mL x 3). Combine the organic layers with deionized water (25mL x 3)After washing with saturated brine (30 mL), the organic layer was dried over anhydrous magnesium sulfate and the solvent was removed using a rotary evaporator.The crude product was separated by a chromatography column (petroleum ether:dichloromethane=4:1) to give 2,7-dibromo-9,9-didodecyl-fluorene as a pale yellow solid (11.30 g, 86.6%). );Finally, the resulting 2,7-dibromo-9,9-didodecyl-fluorene (2.00 g, 3.03 mmol) was reacted in the previous step.Dissolve in 60 mL of dichloromethane, add 10 mL of concentrated sulfuric acid, and cool to 0 °C.Ammonium cerium nitrate (4.98 g, 9.08 mmol) was added in portions to the above mixed solution and the reaction was stirred for 1 hour.Stop the reaction by adding 50 mL of deionized water and extract with dichloromethane (15 mL x 3).The organic phase was washed with deionized water (25 mL×3) and saturated brine (20 mL), respectively.Dry the organic layer by adding anhydrous magnesium sulfate,The solvent was removed using a rotary evaporator and the crude product was separated on a chromatography column (petroleum ether: dichloromethane = 4:1).The orange-yellow product 2,7-dibromo-9,9-didoceyl-1,6-dinitrofluorene (1.7 g, 74.56%) was obtained.

Reference： [1]Current Patent Assignee: GUILIN UNIVERSITY OF TECHNOLOGY - CN107686448, 2018, A Location in patent: Paragraph 0014; 0015; 0016; 0017

43
[ 286438-45-7 ]
[ 1066-45-1 ]
[ 1312429-68-7 ]

Yield	Reaction Conditions	Operation in experiment
96%	Stage #1: 2,7-dibromo-9,9-di-n-dodecylfluorene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Stage #2: trimethyltin(IV)chloride In tetrahydrofuran; hexane at -78 - 20℃; for 12h;

Reference： [1]Gon, Masayuki; Tanaka, Kazuo; Chujo, Yoshiki [Angewandte Chemie - International Edition, 2018, vol. 57, # 22, p. 6546 - 6551][Angew. Chem., 2018, vol. 130, p. 6656 - 6661,6]

44
[ 286438-45-7 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide / 12.5 h / 20 - 70 °C / Alkaline conditions 2: tetrabutyl ammonium fluoride / 0.5 h / 20 °C 3: sodium hydroxide / methanol / 10 h / 20 °C / Inert atmosphere

Reference： [1]Tian, Zhuanzhuan; Yang, Xiaolong; Liu, Boao; Zhao, Jiang; Zhong, Daokun; Wu, Yong; Zhou, Guijiang; Wong, Wai-Yeung [Journal of Materials Chemistry C, 2018, vol. 6, # 22, p. 6023 - 6032]

45
[ 286438-45-7 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide / 12.5 h / 20 - 70 °C / Alkaline conditions 2: tetrabutyl ammonium fluoride / 0.5 h / 20 °C 3: sodium hydroxide / dichloromethane; methanol / 10 h / 20 °C / Inert atmosphere

Reference： [1]Tian, Zhuanzhuan; Yang, Xiaolong; Liu, Boao; Zhao, Jiang; Zhong, Daokun; Wu, Yong; Zhou, Guijiang; Wong, Wai-Yeung [Journal of Materials Chemistry C, 2018, vol. 6, # 22, p. 6023 - 6032]

46
[ 286438-45-7 ]
[ 87199-17-5 ]
[ 2229046-04-0 ]

Yield	Reaction Conditions	Operation in experiment
	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In water Inert atmosphere; Reflux;
81%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate In ethanol; toluene Inert atmosphere; Reflux;

Reference： [1]Zhang, Fang; Zhang, Rong; Liang, Xiaozhong; Guo, Kunpeng; Han, Zhaoxiang; Lu, Xiaoqing; Xie, Jingjuan; Li, Jie; Li, Da; Tian, Xia [Dyes and Pigments, 2018, vol. 155, p. 225 - 232]
[2]Sarikaya, Semiha Yildirim; Alidagi, Husniye Ardic; Cetindere, Seda [Journal of Fluorescence, 2023, vol. 33, # 1, p. 297 - 304]

47
[ 286438-45-7 ]
[ 2570453-46-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: copper(l) iodide; N-ethyl-N,N-diisopropylamine; bis-triphenylphosphine-palladium(II) chloride / 20 h / 75 °C / Inert atmosphere; Schlenk technique 2: potassium carbonate; methanol / diethyl ether / 5 h / 20 °C / Inert atmosphere; Schlenk technique 3: N-ethyl-N,N-diisopropylamine / dichloromethane / 48 h / 35 °C / Inert atmosphere; Schlenk technique

Reference： [1]Bassetti, Mauro; Battocchio, Chiara; Carlini, Laura; Cerra, Sara; Familiari, Giuseppe; Fontana, Laura; Fratoddi, Ilaria; Matassa, Roberto; Rossi, Enrico; Venditti, Iole [Inorganica Chimica Acta, 2021, vol. 516]

48
[ 286438-45-7 ]
[ 2584765-65-9 ]

Yield	Reaction Conditions	Operation in experiment
85%	With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In diethyl ether; hexane at -78 - 20℃;

Reference： [1]Baser-Kirazli, Nurcan; Lalancette, Roger A.; Jäkle, Frieder [Organometallics, 2021, vol. 40, # 4, p. 520 - 528]

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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CAS No. :	286438-45-7	MDL No. :	MFCD03427214
Formula :	C₃₇H₅₆Br₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	KFOUJVGPGBSIFB-UHFFFAOYSA-N
M.W :	660.65	Pubchem ID :	5140914
Synonyms :

Num. heavy atoms :	39
Num. arom. heavy atoms :	12
Fraction Csp3 :	0.68
Num. rotatable bonds :	22
Num. H-bond acceptors :	0.0
Num. H-bond donors :	0.0
Molar Refractivity :	185.54
TPSA :	0.0 Å²

GI absorption :	Low
BBB permeant :	No
P-gp substrate :	Yes
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	2.25 cm/s

Log Po/w (iLOGP) :	8.35
Log Po/w (XLOGP3) :	17.72
Log Po/w (WLOGP) :	14.1
Log Po/w (MLOGP) :	9.87
Log Po/w (SILICOS-IT) :	14.77
Consensus Log Po/w :	12.96

[ CAS No. 286438-45-7 ] {[proInfo.proName]}

Quality Control of [ 286438-45-7 ]

Related Doc. of [ 286438-45-7 ]

Product Details of [ 286438-45-7 ]

Calculated chemistry of [ 286438-45-7 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 286438-45-7 ]

Application In Synthesis of [ 286438-45-7 ]

[ 286438-45-7 ] Synthesis Path-Upstream 1~4

[ 286438-45-7 ] Synthesis Path-Downstream 1~48

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Lipinski :	2.0
Ghose :	None
Veber :	1.0
Egan :	1.0
Muegge :	4.0
Bioavailability Score :	0.17

Log S (ESOL) :	-13.88
Solubility :	0.0 mg/ml ; 0.0 mol/l
Class :	Insoluble
Log S (Ali) :	-17.94
Solubility :	7.6e-16 mg/ml ; 1.15e-18 mol/l
Class :	Insoluble
Log S (SILICOS-IT) :	-16.17
Solubility :	0.0 mg/ml ; 6.75e-17 mol/l
Class :	Insoluble

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	3.0
Synthetic accessibility :	5.09

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