[ CAS No. 1610471-69-6 ] {[proInfo.proName]}

Name: 1610471-69-6|4,4,4,4-(1,3,6,8-Pyrenetetrayl)tetrakis[benzenamine]|98%
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Quality Control of [ 1610471-69-6 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 1610471-69-6 ]

CAS No. :	1610471-69-6	MDL No. :	MFCD31700814
Formula :	C₄₀H₃₀N₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	XDTZQQXBFDIDSL-UHFFFAOYSA-N
M.W :	566.69	Pubchem ID :	101573330
Synonyms :

Safety of [ 1610471-69-6 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338	UN#:
Hazard Statements:	H302-H315-H319-H335	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1610471-69-6 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 1610471-69-6 ]

[ 1610471-69-6 ] Synthesis Path-Downstream 1~5

1
[ 128-63-2 ]
[ 214360-73-3 ]
[ 1610471-69-6 ]

Yield	Reaction Conditions	Operation in experiment
98%	With tetrakis-(triphenylphosphine)-palladium; potassium carbonate In 1,4-dioxane; lithium hydroxide monohydrate at 115℃; Inert atmosphere;
94%	With tetrakis-(triphenylphosphine)-palladium; potassium carbonate In 1,4-dioxane; lithium hydroxide monohydrate for 72h; Schlenk technique; Inert atmosphere; Reflux;
90%	With tetrakis-(triphenylphosphine)-palladium; potassium carbonate In 1,4-dioxane; lithium hydroxide monohydrate at 115℃; for 72h; Inert atmosphere;

90%	With tetrakis-(triphenylphosphine)-palladium; potassium carbonate In 1,4-dioxane; lithium hydroxide monohydrate at 115℃; for 72h; Inert atmosphere; Schlenk technique;
90%	With tetrakis-(triphenylphosphine)-palladium; potassium carbonate In 1,4-dioxane; lithium hydroxide monohydrate at 115℃; for 72h; Inert atmosphere; Schlenk technique; Glovebox;
86%	With tetrakis-(triphenylphosphine)-palladium; potassium carbonate In 1,4-dioxane; lithium hydroxide monohydrate at 110℃; for 72h; Inert atmosphere;
86%	With tetrakis-(triphenylphosphine)-palladium; potassium carbonate In 1,4-dioxane; lithium hydroxide monohydrate at 115℃; for 72h;
84%	With tetrakis-(triphenylphosphine)-palladium; potassium carbonate In 1,4-dioxane; lithium hydroxide monohydrate at 115℃; for 72h; Inert atmosphere;
84%	With tetrakis-(triphenylphosphine)-palladium; potassium carbonate In 1,4-dioxane; lithium hydroxide monohydrate at 115℃; for 72h; Inert atmosphere;
81%	With tetrakis-(triphenylphosphine)-palladium; potassium carbonate In 1,4-dioxane at 115℃; for 72h; Inert atmosphere;
75%	With tetrakis-(triphenylphosphine)-palladium; potassium carbonate In 1,4-dioxane for 72h; Reflux; Inert atmosphere;
75%	With tetrakis-(triphenylphosphine)-palladium; potassium carbonate In 1,4-dioxane; lithium hydroxide monohydrate at 115℃; for 72h;
70%	With tetrakis-(triphenylphosphine)-palladium; anhydrous potassium carbamate In 1,4-dioxane; lithium hydroxide monohydrate for 72h; Inert atmosphere; Reflux;
64%	With tetrakis-(triphenylphosphine)-palladium; potassium carbonate In 1,4-dioxane; lithium hydroxide monohydrate for 72h; Inert atmosphere; Reflux;
61%	With tetrakis-(triphenylphosphine)-palladium; potassium carbonate In 1,4-dioxane for 72h; Reflux; Inert atmosphere;
58%	With tetrakis-(triphenylphosphine)-palladium; potassium carbonate In 1,4-dioxane for 72h; Inert atmosphere; Reflux;
54%	With tetrakis-(triphenylphosphine)-palladium; potassium carbonate In 1,4-dioxane Inert atmosphere; Reflux;
	With tetrakis-(triphenylphosphine)-palladium; potassium carbonate In 1,4-dioxane; lithium hydroxide monohydrate
	With tetrakis-(triphenylphosphine)-palladium; potassium carbonate In 1,4-dioxane; lithium hydroxide monohydrate for 72h; Inert atmosphere; Reflux;	1,3,6,8-tetrakis(4-aminophenyl)pyrene (2) : 1,3,6,8- tetrabromopyrene (2.96 g, 5.72 mmol), 4- aminophenylboronic acid pinacol ester (6.0 g, 27.4 mmol), K2CO3 (4.4 g, 31.6 mmol), and Pd(PPh3)4 (0.66 g, 0.589 mmol) were introduced into a mixture of 1,4- dioxane (100 mL) and H2O (20 mL). The resulting mixture was refluxed under N2 atmosphere for 3 d. After cooling to room temperature, the solution was poured into water. The formed precipitate was filtered off, and washed with water and methanol, which was further purified by flash chromatography with acetone as eluent to afford the title compound as a yellow-brown solid. 1H NMR (400 MHz, d6-DMSO, 298K, TMS): d 8.13 (s, 4H), 7.79 (s, 2H), 7.35 (d, 8H, J=8.4 Hz), 6.77 (d, 8H, J=8.0 Hz), 5.32 (s, 8H) ppm.

Reference： [1]Ascherl, Laura; Evans, Emrys W.; Gorman, Jeffrey; Orsborne, Sarah; Bessinger, Derya; Bein, Thomas; Friend, Richard H.; Auras, Florian [Journal of the American Chemical Society, 2019, vol. 141, # 39, p. 15693 - 15699]
[2]Liu, Shuyang; Tian, Miao; Bu, Xiubin; Tian, Hua; Yang, Xiaobo [Chemistry - A European Journal, 2021, vol. 27, # 28, p. 7738 - 7744]
[3]Auras, Florian; Ascherl, Laura; Hakimioun, Amir H.; Margraf, Johannes T.; Hanusch, Fabian C.; Reuter, Stephan; Bessinger, Derya; Döblinger, Markus; Hettstedt, Christina; Karaghiosoff, Konstantin; Herbert, Simon; Knochel, Paul; Clark, Timothy; Bein, Thomas [Journal of the American Chemical Society, 2016, vol. 138, # 51, p. 16703 - 16710]
[4]Keller, Niklas; Bessinger, Derya; Reuter, Stephan; Calik, Mona; Ascherl, Laura; Hanusch, Fabian C.; Auras, Florian; Bein, Thomas [Journal of the American Chemical Society, 2017, vol. 139, # 24, p. 8194 - 8199]
[5]Bessinger, Derya; Ascherl, Laura; Auras, Florian; Bein, Thomas [Journal of the American Chemical Society, 2017, vol. 139, # 34, p. 12035 - 12042]
[6]Grunenberg, Lars; Savasci, Gökcen; Terban, Maxwell W.; Duppel, Viola; Moudrakovski, Igor; Etter, Martin; Dinnebier, Robert E.; Ochsenfeld, Christian; Lotsch, Bettina V. [Journal of the American Chemical Society, 2021, vol. 143, # 9, p. 3430 - 3438]
[7]Chen, Chuan-Jie; Gu, Zhi-Guo; Han, Wang-Kang; Lu, Hui-Shu; Niu, Tengfei; Yan, Xiaodong [Angewandte Chemie - International Edition, 2021, vol. 60, # 33, p. 17881 - 17886][Angew. Chem., 2021, vol. 133, # 33, p. 18025 - 18030]
[8]Yan, Dong; Wang, Zhifang; Cheng, Peng; Chen, Yao; Zhang, Zhenjie [Angewandte Chemie - International Edition, 2021, vol. 60, # 11, p. 6055 - 6060][Angew. Chem., 2021, vol. 133, # 11, p. 6120 - 6125,6]
[9]Chen, Yao; Cheng, Peng; Jin, Fazheng; Lin, En; Qiao, Shan; Wang, Zhifang; Xiong, Fanhao; Yan, Dong; Yang, Yi; Zhang, Zhenjie [Journal of Materials Chemistry A, 2021, vol. 9, # 48, p. 27434 - 27441]
[10]Kang, Chengjun; Zhang, Zhaoqiang; Wee, Vanessa; Usadi, Adam K.; Calabro, David C.; Baugh, Lisa Saunders; Wang, Shun; Wang, Yuxiang; Zhao, Dan [Journal of the American Chemical Society, 2020, vol. 142, # 30, p. 12995 - 13002]
[11]Huang, Ning; Wang, Ping; Addicoat, Matthew A.; Heine, Thomas; Jiang, Donglin [Angewandte Chemie - International Edition, 2017, vol. 56, # 18, p. 4982 - 4986][Angew. Chem., 2017, vol. 129, # 18, p. 5064 - 5068]
[12]Li, Wenqian; Huang, Xiaofeng; Zeng, Tengwu; Liu, Yahu A.; Hu, Weibo; Yang, Hui; Zhang, Yue-Biao; Wen, Ke [Angewandte Chemie - International Edition, 2021, vol. 60, # 4, p. 1869 - 1874][Angew. Chem., 2021, vol. 133, # 4, p. 1897 - 1902,6]
[13]Jin, Shangbin; Sakurai, Tsuneaki; Kowalczyk, Tim; Dalapati, Sasanka; Xu, Fei; Wei, Hao; Chen, Xiong; Gao, Jia; Seki, Shu; Irle, Stephan; Jiang, Donglin [Chemistry - A European Journal, 2014, vol. 20, # 45, p. 14608 - 14613]
[14]Li, Chunzhi; Li, He; Li, Zhongping; Munyentwali, Alexis; Shui, Hengfu; Zhou, Mingan [Chemistry - An Asian Journal, 2022]
[15]Chen, Xiong; Huang, Ning; Gao, Jia; Xu, Hong; Xu, Fei; Jiang, Donglin [Chemical Communications, 2014, vol. 50, # 46, p. 6161 - 6163]
[16]Chen, Xiong; Feng, Xiao; Han, Songjie; Li, Chunzhi; Li, He; Li, Ziping; Liu, Xiaoming; Shao, Pengpeng; Xia, Hong [Journal of Materials Chemistry A, 2020, vol. 8, # 17, p. 8706 - 8715]
[17]Mi, Zhen; Yang, Peng; Wang, Rong; Unruangsri, Junjuda; Yang, Wuli; Wang, Changchun; Guo, Jia [Journal of the American Chemical Society, 2019, vol. 141, # 36, p. 14433 - 14442]
[18]Balch, Halleh B.; Evans, Austin M.; Dasari, Raghunath R.; Li, Hong; Li, Ruofan; Thomas, Simil; Wang, Danqing; Bisbey, Ryan P.; Slicker, Kaitlin; Castano, Ioannina; Xun, Sangni; Jiang, Lili; Zhu, Chenhui; Gianneschi, Nathan; Ralph, Daniel C.; Brédas, Jean-Luc; Marder, Seth R.; Dichtel, William R.; Wang, Feng [Journal of the American Chemical Society, 2020, vol. 142, # 50, p. 21131 - 21139]
[19]Current Patent Assignee: STATE UNIVERSITY SYSTEM OF FLORIDA - WO2021/97324, 2021, A1 Location in patent: Paragraph 00126; 00128

2
[ 1610471-69-6 ]
[ 100-52-7 ]
(1E,1'E,1''E,1'''E)-N,N',N'',N'''-(pyrene-1,3,6,8-tetrayltetrakis(benzene-4,1-diyl))tetrakis(1-phenylmethanimine) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With magnesium sulfate In neat (no solvent) at 70℃; Sealed tube;

Reference： [1]Auras, Florian; Ascherl, Laura; Hakimioun, Amir H.; Margraf, Johannes T.; Hanusch, Fabian C.; Reuter, Stephan; Bessinger, Derya; Döblinger, Markus; Hettstedt, Christina; Karaghiosoff, Konstantin; Herbert, Simon; Knochel, Paul; Clark, Timothy; Bein, Thomas [Journal of the American Chemical Society, 2016, vol. 138, # 51, p. 16703 - 16710]

3
[ 1610471-69-6 ]
[ 135822-72-9 ]
C₂₀₈H₁₃₆N₂₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76.8%	With acetic acid In 1,3-dioxane; water; 1,3,5-trimethyl-benzene at 120℃; for 168h;

Reference： [1]Mi, Zhen; Yang, Peng; Wang, Rong; Unruangsri, Junjuda; Yang, Wuli; Wang, Changchun; Guo, Jia [Journal of the American Chemical Society, 2019, vol. 141, # 36, p. 14433 - 14442]

4
[ 1398053-00-3 ]
[ 106-40-1 ]
[ 1610471-69-6 ]

Yield	Reaction Conditions	Operation in experiment
75%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In 1,4-dioxane at 100℃; for 48h; Inert atmosphere;

Reference： [1]Chen, Tao; El-Mahdy, Ahmed F. M.; Kuo, Shiao-Wei; Wang, Hao-Xin; Yamauchi, Yusuke; Zakaria, Mohamed Barakat [Journal of Materials Chemistry A, 2020, vol. 8, # 47, p. 25148 - 25155]

5
[ 129-00-0 ]
[ 1610471-69-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: bromine / nitrobenzene / 18 h / 120 °C 2: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate / 1,4-dioxane; water / 72 h / Inert atmosphere; Reflux

Reference： [1]Current Patent Assignee: STATE UNIVERSITY SYSTEM OF FLORIDA - WO2021/97324, 2021, A1

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[ CAS No. 1610471-69-6 ] {[proInfo.proName]}

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[ 1610471-69-6 ] Synthesis Path-Downstream 1~5

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