[ CAS No. 84907-55-1 ] {[proInfo.proName]}

Name: 84907-55-1|4,4'-(Ethyne-1,2-diyl)dibenzaldehyde|98%
Brand: Ambeed
SKU: A714394
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Quality Control of [ 84907-55-1 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 84907-55-1 ]

CAS No. :	84907-55-1	MDL No. :	MFCD01573051
Formula :	C₁₆H₁₀O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	IZJKYSQCRNPJHX-UHFFFAOYSA-N
M.W :	234.25	Pubchem ID :	14169731
Synonyms :

Safety of [ 84907-55-1 ]

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

Application In Synthesis of [ 84907-55-1 ]

* 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 [ 84907-55-1 ]

[ 84907-55-1 ] Synthesis Path-Downstream 1~42

1
[ 2789-88-0 ]
[ 84907-55-1 ]

Yield	Reaction Conditions	Operation in experiment
	(i) NBS, (PhCO)2O₂, CCl₄, (ii) hexamethylenetetramine, CHCl₃, (iii) aq. AcOH; Multistep reaction;

Reference： [1]Drefahl,G.; Ploetner,G. [Chemische Berichte, 1960, vol. 93, p. 990 - 998]

2
[ 100-44-7 ]
[ 84907-55-1 ]
[ 21850-32-8 ]

Yield	Reaction Conditions	Operation in experiment
	(i) Mg, Et₂O, (ii) /BRN= 6201824/, xylene, (iii) I₂, xylene; Multistep reaction;

Reference： [1]Drefahl,G.; Ploetner,G. [Chemische Berichte, 1960, vol. 93, p. 990 - 998]

4
[ 2789-89-1 ]
[ 33513-42-7 ]
[ 84907-55-1 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; n-butyllithium Yield given. Multistep reaction;

Reference： [1]Raston, Ilona; Wennerstroem, Olof [Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1982, vol. 36, # 10, p. 655 - 660]

5
[ 84907-55-1 ]
4,4'-bis(bromomethyl)tolan bistriphenylphosphonium salt [ No CAS ]
all-cis-<2₈>paracyclophanetetrayne [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With lithium ethoxide In N,N-dimethyl-formamide at -40℃;

Reference： [1]Raston, Ilona; Wennerstroem, Olof [Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1982, vol. 36, # 10, p. 655 - 660]

6
[ 84907-55-1 ]
[ 84907-57-3 ]

Yield	Reaction Conditions	Operation in experiment
93%	With sodium tetrahydroborate In ethanol

Reference： [1]Raston, Ilona; Wennerstroem, Olof [Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1982, vol. 36, # 10, p. 655 - 660]

7
[ 17610-00-3 ]
[ 126136-05-8 ]
[ 84907-55-1 ]
C₁₃₈H₁₈₆N₈ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With chloranil; trichloroacetic acid 1.) CH₃CN, CH₂Cl₂, r.t., 1 day, 2.) CH₃CN, CH₂Cl₂, THF, 1 day; Yield given. Multistep reaction;

Reference： [1]Kawabata, Shigeki; Tanabe, Nobuhiro; Osuka, Atsuhiro [Chemistry Letters, 1994, # 10, p. 1797 - 1800]

8
[ 17610-00-3 ]
[ 126136-05-8 ]
[ 84907-55-1 ]
C₁₃₈H₁₈₆N₈ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With chloranil; trichloroacetic acid 1.) CH₃CN, CH₂Cl₂, 1 d, 2.) THF, 1 d; Yield given. Multistep reaction;

Reference： [1]Osuka, Atsuhiro; Tanabe, Nobuhiro; Kawabata, Shigeki; Yamazaki, Iwao; Nishimura, Yoshinobu [Journal of Organic Chemistry, 1995, vol. 60, # 22, p. 7177 - 7185]

9
[ 172508-29-1 ]
[ 84907-55-1 ]

Yield	Reaction Conditions	Operation in experiment
98%	With tris(tert-butyl(3,5-dimethylphenyl)amino)(propylidyne)molybdenum; tris(2-hydroxy-3-isopropylbenzyl)methane In Carbon tetrachloride at 40℃; for 2h; Molecular sieve; Inert atmosphere; Glovebox;
96%	With C₃₄H₄₄MoO₃Si In Carbon tetrachloride at 40℃; for 16h; Inert atmosphere; Molecular sieve;
96%	In Carbon tetrachloride at 40℃; for 16h; Molecular sieve;	6.B For 5 molecular sieves-driven closed-system alkyne metathesis reactions (method B): General procedure: The ligand (L7b-L7c) (0.003 mmol) and the precursor (2.0 mg, 0.003 mmol) were premixed in dry carbon tetrachloride for 5 minutes to generate the catalyst in situ. Subsequently, the substrate (0.1 mmol) was added with 5 molecular sieves (150 mg for entries 1-4 and 300 mg for entries 4-5) and internal standard. The stirring was continued for 5-7 h for entries 4 and 5 and 16-20 h for entries 1-3 and 6 in a closed system with regular monitoring of the reaction by NMR.

95%	With C₅₇H₃₂F₂₄NO₂P₂Re In toluene at 100℃; for 16h; Schlenk technique; Molecular sieve; Inert atmosphere;
93%	With [Re(≡CCH₂Ph)(^4-CF3-PhPO)₂(py)] In toluene at 100℃; for 8h; Molecular sieve; Inert atmosphere; Schlenk technique;
80%	With C₂₅H₂₆MoNO₃⁽¹⁺⁾*I^(1-) In Carbon tetrachloride at 40℃; Inert atmosphere;
47%	With 2-(trifluoromethyl)phenol; CH₃CH₂CMo[N(t-Bu)(3,5-C₆H₃Me₂)]3 In various solvent(s) at 30℃; for 22h;
46%	With dichloromethane In toluene
46%	With dichloromethane In toluene at 80℃;

Reference： [1]Du, Ya; Yang, Haishen; Zhu, Chengpu; Ortiz, Michael; Okochi, Kenji D.; Shoemaker, Richard; Jin, Yinghua; Zhang, Wei [Chemistry - A European Journal, 2016, vol. 22, # 23, p. 7959 - 7963]
[2]Yang, Haishen; Liu, Zhenning; Zhang, Wei [Advanced Synthesis and Catalysis, 2013, vol. 355, # 5, p. 885 - 890]
[3]Current Patent Assignee: UNIVERSITY OF COLORADO (SYSTEM) - US2013/261295, 2013, A1 Location in patent: Paragraph 0281; 0282
[4]Cui, Mingxu; Bai, Wei; Sung, Herman H. Y.; Williams, Ian D.; Jia, Guochen [Journal of the American Chemical Society, 2020, vol. 142, # 31, p. 13339 - 13344]
[5]Cui, Mingxu; Sung, Herman H. Y.; Williams, Ian D.; Jia, Guochen [Journal of the American Chemical Society, 2022, vol. 144, # 14, p. 6349 - 6360]
[6]Jyothish, Kuthanapillil; Wang, Qi; Zhang, Wei [Advanced synthesis and catalysis, 2012, vol. 354, # 11-12, p. 2073 - 2078,6]
[7]Zhang, Wei; Kraft, Stefan; Moore, Jeffrey S. [Journal of the American Chemical Society, 2004, vol. 126, # 1, p. 329 - 335]
[8]Fuerstner, Alois; Mathes, Christian; Lehmann, Christian W. [Chemistry - A European Journal, 2001, vol. 7, # 24, p. 5299 - 5317]
[9]Fuerstner, Alois; Mathes, Christian [Organic Letters, 2001, vol. 3, # 2, p. 221 - 223]

10
[ 652974-14-6 ]
[ 84907-55-1 ]

Yield	Reaction Conditions	Operation in experiment
83%	With 4-nitro-phenol; CH₃CH₂CMo[N(t-Bu)(3,5-C₆H₃Me₂)]3 In various solvent(s) at 30℃; for 22h;

Reference： [1]Zhang, Wei; Kraft, Stefan; Moore, Jeffrey S. [Journal of the American Chemical Society, 2004, vol. 126, # 1, p. 329 - 335]

11
[ 107-97-1 ]
[ 120329-58-0 ]
[ 84907-55-1 ]
C₁₄₀H₂₀N₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
58%	In chlorobenzene for 10h; Heating;

Reference： [1]Atienza, Carmen; Insuasty, Braulio; Seoane, Carlos; Martin, Nazario; Ramey, Jeff; Rahman, G. M. Aminur; Guldi, Dirk M. [Journal of Materials Chemistry, 2005, vol. 15, # 1, p. 124 - 132]

12
[ 120329-58-0 ]
[ 84907-55-1 ]
octylamino-acetic acid [ No CAS ]
C₁₅₄H₄₈N₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
58%	In chlorobenzene for 10h; Heating;

13
[ 63697-96-1 ]
[ 1122-91-4 ]
[ 84907-55-1 ]

Yield	Reaction Conditions	Operation in experiment
98%	With copper(l) iodide; diisopropylamine In toluene at 20℃; for 4h;
92%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; triphenylphosphine In N,N-dimethyl-formamide at 70℃; for 12h; Inert atmosphere; Sealed tube;
88%	With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine In tetrahydrofuran at 85℃; Inert atmosphere;

79%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In tetrahydrofuran at 85℃; for 44h; Inert atmosphere;
69%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 50℃;
65%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 80℃; for 12h; Inert atmosphere;
63%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; copper(l) iodide; triethylamine; XPhos In toluene at 80℃; for 7h; Schlenk technique; Inert atmosphere;
	With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine In tetrahydrofuran at 85℃;

Reference： [1]Orita, Akihiro; Ye, Fangguo; Babu, Govindarajulu; Ikemoto, Tomohiro; Otera, Junzo [Canadian Journal of Chemistry, 2005, vol. 83, # 6-7, p. 716 - 727]
[2]Borozdina, Yulia B.; Mostovich, Evgeny; Enkelmann, Volker; Wolf, Bernd; Cong, Pham T.; Tutsch, Ulrich; Lang, Michael; Baumgarten, Martin [Journal of Materials Chemistry C, 2014, vol. 2, # 32, p. 6618 - 6629]
[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]Eisterhold, Andrew M.; Puangsamlee, Thamon; Otterbach, Steffen; Bräse, Stefan; Weis, Patrick; Wang, Xiqu; Kutonova, Ksenia V.; Miljanić, Ognjen Š. [Organic Letters, 2021, vol. 23, # 3, p. 781 - 785]
[5]Location in patent: scheme or table Hu, Laixing; Kully, Maureen L.; Boykin, David W.; Abood, Norman [Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 13, p. 3374 - 3377]
[6]Alahakoon, Sampath B.; Thompson, Christina M.; Nguyen, Amy X.; Occhialini, Gino; McCandless, Gregory T.; Smaldone, Ronald A. [Chemical Communications, 2016, vol. 52, # 13, p. 2843 - 2845]
[7]Yin, Jiangliang; Tan, Meiling; Wu, Di; Jiang, Ruyong; Li, Chengming; You, Jingsong [Angewandte Chemie - International Edition, 2017, vol. 56, # 42, p. 13094 - 13098][Angew. Chem., 2017, vol. 56, p. 13274 - 13278,5]
[8]Zhang, Bing; Mao, Haiyan; Matheu, Roc; Reimer, Jeffrey A.; Alshmimri, Sultan A.; Alshihri, Saeed; Yaghi, Omar M. [Journal of the American Chemical Society, 2019, vol. 141, # 29, p. 11420 - 11424]

14
[ 75-20-7 ]
[ 1122-91-4 ]
[ 84907-55-1 ]

Yield	Reaction Conditions	Operation in experiment
14%	With potassium carbonate In tetrahydrofuran at 65℃; for 12h;

Reference： [1]Zhang, Weiwei; Wu, Huayue; Liu, Zhiqing; Zhong, Ping; Zhang, Lin; Huang, Xiaobo; Cheng, Jiang [Chemical Communications, 2006, # 46, p. 4826 - 4828]

15
[ 1122-91-4 ]
[ 84907-55-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 97 percent / CuI; Pd₂(dba)3; PPh₃ / Et₃N / 24 h / 80 °C 2: 47 percent / CH3CH2CMo[N(t-Bu)(3,5-C6H3Me2)]3; α,α,α-trifluoro-o-cresol / various solvent(s) / 22 h / 30 °C / 5 Torr
	Multi-step reaction with 2 steps 1: 96 percent / CuI; Pd₂(dba)3; PPh₃ / Et₃N / 24 h / 80 °C 2: 83 percent / CH₃CH₂CMo[N(t-Bu)(3,5-C₆H₃Me₂)]3; p-nitrophenol / various solvent(s) / 22 h / 30 °C / 1 Torr
	Multi-step reaction with 3 steps 1: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine / 12 h / 80 °C / Inert atmosphere 2: potassium carbonate / methanol; dichloromethane / 3 h / 20 °C 3: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine / 12 h / 80 °C / Inert atmosphere

	Multi-step reaction with 3 steps 1: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine / tetrahydrofuran / 20 °C / Inert atmosphere 2: potassium hydroxide / methanol / 1 h / 20 °C 3: copper(l) iodide; triethylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / tetrahydrofuran / 85 °C / Inert atmosphere
	Multi-step reaction with 3 steps 1: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine / tetrahydrofuran / 13 h / 65 °C / Inert atmosphere 2: potassium carbonate / methanol / 5 h / 20 °C 3: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; copper(l) iodide; triethylamine; XPhos / toluene / 7 h / 80 °C / Schlenk technique; Inert atmosphere
	Multi-step reaction with 3 steps 1: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine / tetrahydrofuran / 85 °C 2: potassium hydroxide / methanol 3: copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine / tetrahydrofuran / 85 °C
	Multi-step reaction with 3 steps 1: triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide / tetrahydrofuran / 3 h / 20 °C / Inert atmosphere 2: potassium hydroxide / methanol / 20 °C / Inert atmosphere 3: triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide / tetrahydrofuran / 44 h / 85 °C / Inert atmosphere

Reference： [1]Zhang, Wei; Kraft, Stefan; Moore, Jeffrey S. [Journal of the American Chemical Society, 2004, vol. 126, # 1, p. 329 - 335]
[2]Zhang, Wei; Kraft, Stefan; Moore, Jeffrey S. [Journal of the American Chemical Society, 2004, vol. 126, # 1, p. 329 - 335]
[3]Alahakoon, Sampath B.; Thompson, Christina M.; Nguyen, Amy X.; Occhialini, Gino; McCandless, Gregory T.; Smaldone, Ronald A. [Chemical Communications, 2016, vol. 52, # 13, p. 2843 - 2845]
[4]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]
[5]Yin, Jiangliang; Tan, Meiling; Wu, Di; Jiang, Ruyong; Li, Chengming; You, Jingsong [Angewandte Chemie - International Edition, 2017, vol. 56, # 42, p. 13094 - 13098][Angew. Chem., 2017, vol. 56, p. 13274 - 13278,5]
[6]Zhang, Bing; Mao, Haiyan; Matheu, Roc; Reimer, Jeffrey A.; Alshmimri, Sultan A.; Alshihri, Saeed; Yaghi, Omar M. [Journal of the American Chemical Society, 2019, vol. 141, # 29, p. 11420 - 11424]
[7]Eisterhold, Andrew M.; Puangsamlee, Thamon; Otterbach, Steffen; Bräse, Stefan; Weis, Patrick; Wang, Xiqu; Kutonova, Ksenia V.; Miljanić, Ognjen Š. [Organic Letters, 2021, vol. 23, # 3, p. 781 - 785]

16
[ 84907-55-1 ]
[ 5140-98-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 93 percent / NaBH₄ / ethanol 2: 83 percent / 30percent HBr / acetic acid

Reference： [1]Raston, Ilona; Wennerstroem, Olof [Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1982, vol. 36, # 10, p. 655 - 660]

17
[ 84907-55-1 ]
all-cis-<2₈>paracyclophanetetrayne [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 93 percent / NaBH₄ / ethanol 2: 83 percent / 30percent HBr / acetic acid 3: 87 percent / dimethylformamide / 154 °C 4: LiOEt / dimethylformamide / -40 °C

Reference： [1]Raston, Ilona; Wennerstroem, Olof [Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1982, vol. 36, # 10, p. 655 - 660]

18
[ 84907-55-1 ]
4,4'-bis(bromomethyl)tolan bistriphenylphosphonium salt [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 93 percent / NaBH₄ / ethanol 2: 83 percent / 30percent HBr / acetic acid 3: 87 percent / dimethylformamide / 154 °C

Reference： [1]Raston, Ilona; Wennerstroem, Olof [Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1982, vol. 36, # 10, p. 655 - 660]

19
[ 1189131-43-8 ]
[ 84907-55-1 ]
[ 1189131-44-9 ]

Yield	Reaction Conditions	Operation in experiment
53%	In 1,4-dioxane at 20℃; for 17h;

20
[ 84907-55-1 ]
[ 253598-65-1 ]
[ 1189131-43-8 ]

Yield	Reaction Conditions	Operation in experiment
77%	With potassium <i>tert</i>-butylate In tetrahydrofuran at 0℃; for 4h;
77%	With potassium <i>tert</i>-butylate In tetrahydrofuran at 0℃; for 4h;

Reference： [1]Figueira-Duarte, Teresa M.; Clifford, John; Amendola, Vincenzo; Gegout, Aline; Olivier, Jean; Cardinali, Francois; Meneghetti, Moreno; Armaroli, Nicola; Nierengarten, Jean-Francois [Chemical Communications, 2006, # 19, p. 2054 - 2056]
[2]Location in patent: experimental part Figueira-Duarte, Teresa M.; Gegout, Aline; Olivier, Jean; Cardinali, Francois; Nierengarten, Jean-Francois [European Journal of Organic Chemistry, 2009, # 23, p. 3879 - 3884]

21
[ 872554-92-2 ]
[ 84907-55-1 ]
[ 872554-87-5 ]

Yield	Reaction Conditions	Operation in experiment
76%	With n-butyllithium; potassium <i>tert</i>-butylate; diethyl chlorophosphate In tetrahydrofuran; hexane under N2; BuLi in hexane (-78°C) added to Fe complex in THF; stirred (5 min); dialdehyde in THF added (-78°C); stirred (1 h); ClP(O)(OEt)2 added (-78°C); stirred (room temp., 1 h); t-BuOK added (-78°C); stirred(room temp.,2h); subjected to usual work up with aq. NH4Cl-CH2Cl2; combined org. layer washed with brine; dried (anhyd. MgSO4); evapd.; column chromd. (silica gel); elem. anal.;

Reference： [1]Orita, Akihiro; Ye, Fangguo; Babu, Govindarajulu; Ikemoto, Tomohiro; Otera, Junzo [Canadian Journal of Chemistry, 2005, vol. 83, # 6-7, p. 716 - 727]

22
[ 1189131-43-8 ]
[ 84907-55-1 ]
[ 1189131-44-9 ]
C₃₀₆H₄₉₈O₁₈ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 53% 2: 17%	With dicobalt octacarbonyl In 1,4-dioxane at 20℃; for 24h;

Reference： [1]Location in patent: experimental part Figueira-Duarte, Teresa M.; Gegout, Aline; Olivier, Jean; Cardinali, Francois; Nierengarten, Jean-Francois [European Journal of Organic Chemistry, 2009, # 23, p. 3879 - 3884]

23
[ 61440-86-6 ]
[ 84907-55-1 ]
[ 1189131-46-1 ]

Yield	Reaction Conditions	Operation in experiment
49%	With dicobalt octacarbonyl In 1,4-dioxane at 20℃; for 12h;

24
[ 84907-55-1 ]
4-(N-isopropylamidino)-1,2-phenylenediamine hydrochloride [ No CAS ]
C₃₆H₃₄N₈*ClH [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With p-benzoquinone In ethanol Reflux;

Reference： [1]Location in patent: scheme or table Hu, Laixing; Kully, Maureen L.; Boykin, David W.; Abood, Norman [Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 13, p. 3374 - 3377]

25
[ 1122-91-4 ]
[ 471-25-0 ]
[ 84907-55-1 ]

Yield	Reaction Conditions	Operation in experiment
97%	With bis-triphenylphosphine-palladium(II) chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1,4-di(diphenylphosphino)-butane In dimethyl sulfoxide at 80℃; for 1.5h;
62%	With bis-triphenylphosphine-palladium(II) chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine In dimethyl sulfoxide at 80℃;
	With bis-triphenylphosphine-palladium(II) chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1,4-di(diphenylphosphino)-butane In dimethyl sulfoxide at 80℃; for 3h;

Reference： [1]Location in patent: experimental part Park, Kyungho; Bae, Goun; Moon, Jeongju; Choe, Jaehoon; Song, Kwang Ho; Lee, Sunwoo [Journal of Organic Chemistry, 2010, vol. 75, # 18, p. 6244 - 6251]
[2]Zhang, Guanyu; Zhao, Ning; Bobadova-Parvanova, Petia; Wang, Maodie; Fronczek, Frank R.; Smith, Kevin M.; Vicente, M. Graça H. [Journal of Physical Chemistry A, 2018, vol. 122, # 30, p. 6256 - 6265]
[3]Cho, Eunjeong; Kim, Myungjin; Jayaraman, Aravindan; Kim, Jimin; Lee, Sunwoo [European Journal of Organic Chemistry, 2018, vol. 2018, # 6, p. 781 - 784]

26
[ 1122-91-4 ]
[ 142-45-0 ]
[ 84907-55-1 ]

Yield	Reaction Conditions	Operation in experiment
83%	With bis-triphenylphosphine-palladium(II) chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1,4-di(diphenylphosphino)-butane In dimethyl sulfoxide at 110℃; for 1.5h;

27
[ 172508-29-1 ]
[ 503-17-3 ]
[ 84907-55-1 ]

Yield	Reaction Conditions	Operation in experiment
71%	With tris[N-(tert-butyl)(3,5-dimethylphenyl)amido]molybdenum(VI) propylidyne; tris(2-hydroxy-5-nitro-benzyl)amine In tetrachloromethane at 40℃; for 7h; Inert atmosphere;

Reference： [1]Jyothish, Kuthanapillil; Zhang, Wei [Angewandte Chemie - International Edition, 2011, vol. 50, # 15, p. 3435 - 3438]

28
[ 762-42-5 ]
[ 84907-55-1 ]
C₂₈H₂₂O₁₀ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With C₄₇H₃₇Cl₂OP₂Ru In benzene at 70℃; for 22h; chemoselective reaction;

Reference： [1]Location in patent: experimental part Wu, Chung-Yeh; Lin, Ying-Chih; Chou, Pi-Tai; Wang, Yu; Liu, Yi-Hung [Dalton Transactions, 2011, vol. 40, # 14, p. 3748 - 3753]

29
[ 75-20-7 ]
[ 15164-44-0 ]
[ 84907-55-1 ]

Yield	Reaction Conditions	Operation in experiment
87%	With copper(l) iodide; palladium diacetate; triethylamine; triphenylphosphine In acetonitrile at 20℃; Inert atmosphere;	4.2. General procedure for Pd-catalyzed coupling reaction of calcium carbide with aryl iodides General procedure: A 100 mL round bottom flask with a magnetic stir bar was charged with copper iodide (0.1 equiv), palladium acetate (0.05 equiv), and triphenylphosphine (0.1 equiv) in acetonitrile. The solution was degassed with nitrogen for 20 min. Then, triethylamine (3 equiv), aryl iodides (1 equiv), and calcium carbide (3 equiv) were added. The mixture was stirred at room temperature overnight under nitrogen atmosphere. The reaction mixture was then filtrated through a short plug of silica gel and washed with hexane. The filtrate was evaporated under vacuum to give the desired compound.

Reference： [1]Location in patent: experimental part Chuentragool, Padon; Vongnam, Kunnigar; Rashatasakhon, Paitoon; Sukwattanasinitt, Mongkol; Wacharasindhu, Sumrit [Tetrahedron, 2011, vol. 67, # 42, p. 8177 - 8182]

30
[ 14384-45-3 ]
[ 84907-55-1 ]
2-(4-{2-[4-(1,3-dihydroxy-4,4,5,5-tetramethyl-imidazolidine-2-yl)phenyl]ethynyl}phenyl)-4,4,5,5-tetramethylimidazolidine-1,3-diol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98%	In toluene at 110℃; Inert atmosphere;
98%	In toluene Inert atmosphere; Reflux;

Reference： [1]Borozdina, Yulia B.; Mostovich, Evgeny; Enkelmann, Volker; Wolf, Bernd; Cong, Pham T.; Tutsch, Ulrich; Lang, Michael; Baumgarten, Martin [Journal of Materials Chemistry C, 2014, vol. 2, # 32, p. 6618 - 6629]
[2]Borozdina, Yulia B.; Mostovich, Evgeny A.; Cong, Pham Thanh; Postulka, Lars; Wolf, Bernd; Lang, Michael; Baumgarten, Martin [Journal of Materials Chemistry C, 2017, vol. 5, # 35, p. 9053 - 9065]

31
[ 14384-45-3 ]
[ 84907-55-1 ]
C₂₈H₃₂N₄O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: toluene / 110 °C / Inert atmosphere 2: sodium periodate / water; dichloromethane / 0 - 5 °C

32
[ 77123-57-0 ]
[ 84907-55-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: potassium carbonate / methanol; dichloromethane / 3 h / 20 °C 2: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine / 12 h / 80 °C / Inert atmosphere
	Multi-step reaction with 2 steps 1: potassium hydroxide / methanol / 1 h / 20 °C 2: copper(l) iodide; triethylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / tetrahydrofuran / 85 °C / Inert atmosphere
	Multi-step reaction with 2 steps 1: potassium carbonate / methanol / 5 h / 20 °C 2: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; copper(l) iodide; triethylamine; XPhos / toluene / 7 h / 80 °C / Schlenk technique; Inert atmosphere

	Multi-step reaction with 2 steps 1: potassium hydroxide / methanol 2: copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine / tetrahydrofuran / 85 °C
	Multi-step reaction with 2 steps 1: potassium hydroxide / methanol / 20 °C / Inert atmosphere 2: triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide / tetrahydrofuran / 44 h / 85 °C / Inert atmosphere

Reference： [1]Alahakoon, Sampath B.; Thompson, Christina M.; Nguyen, Amy X.; Occhialini, Gino; McCandless, Gregory T.; Smaldone, Ronald A. [Chemical Communications, 2016, vol. 52, # 13, p. 2843 - 2845]
[2]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]Yin, Jiangliang; Tan, Meiling; Wu, Di; Jiang, Ruyong; Li, Chengming; You, Jingsong [Angewandte Chemie - International Edition, 2017, vol. 56, # 42, p. 13094 - 13098][Angew. Chem., 2017, vol. 56, p. 13274 - 13278,5]
[4]Zhang, Bing; Mao, Haiyan; Matheu, Roc; Reimer, Jeffrey A.; Alshmimri, Sultan A.; Alshihri, Saeed; Yaghi, Omar M. [Journal of the American Chemical Society, 2019, vol. 141, # 29, p. 11420 - 11424]
[5]Eisterhold, Andrew M.; Puangsamlee, Thamon; Otterbach, Steffen; Bräse, Stefan; Weis, Patrick; Wang, Xiqu; Kutonova, Ksenia V.; Miljanić, Ognjen Š. [Organic Letters, 2021, vol. 23, # 3, p. 781 - 785]

33
[ 84907-55-1 ]
hexa(4-formylphenyl)benzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
55%	With dicobalt octacarbonyl In 1,4-dioxane at 160℃; for 1h; Microwave irradiation; Inert atmosphere;
	With dicobalt octacarbonyl In 1,4-dioxane at 120℃; Microwave irradiation;

Reference： [1]Alahakoon, Sampath B.; Thompson, Christina M.; Nguyen, Amy X.; Occhialini, Gino; McCandless, Gregory T.; Smaldone, Ronald A. [Chemical Communications, 2016, vol. 52, # 13, p. 2843 - 2845]
[2]Zhang, Bing; Mao, Haiyan; Matheu, Roc; Reimer, Jeffrey A.; Alshmimri, Sultan A.; Alshihri, Saeed; Yaghi, Omar M. [Journal of the American Chemical Society, 2019, vol. 141, # 29, p. 11420 - 11424]

34
C₃₆H₄₄N₂O₂ [ No CAS ]
[ 84907-55-1 ]
C₁₅₆H₁₅₀N₆O₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
51%	With trifluoroacetic acid In chloroform at 20℃; for 96h; Molecular sieve;

Reference： [1]Kinney, Zacharias J.; Hartley, C. Scott [Journal of the American Chemical Society, 2017, vol. 139, # 13, p. 4821 - 4827]

35
[ 14384-45-3 ]
[ 84907-55-1 ]
2-(4-{2-[4-(1-oxyl-4,4,5,5-tetramethyl-4H,5H-imidazolin-2-yl)phenyl]ethynyl}phenyl)-4,4,5,5-tetramethylimidazoline-1-oxyl-3-oxo [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: toluene / Inert atmosphere; Reflux 2: manganese(IV) oxide / nitromethane / 0.58 h / 20 °C

Reference： [1]Borozdina, Yulia B.; Mostovich, Evgeny A.; Cong, Pham Thanh; Postulka, Lars; Wolf, Bernd; Lang, Michael; Baumgarten, Martin [Journal of Materials Chemistry C, 2017, vol. 5, # 35, p. 9053 - 9065]

36
silver hexafluoroantimonate [ No CAS ]
sodium hexafluoroantimonate [ No CAS ]
[ 66-77-3 ]
[ 84907-55-1 ]
2,3,9,10-tetrakis(4-formylphenyl)naphtho[2,1,8-def]chromenium hexafluoroantimonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%	With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver(l) oxide In 1,2-dichloro-ethane at 120℃; for 24h; Schlenk technique; Inert atmosphere;

Reference： [1]Yin, Jiangliang; Tan, Meiling; Wu, Di; Jiang, Ruyong; Li, Chengming; You, Jingsong [Angewandte Chemie - International Edition, 2017, vol. 56, # 42, p. 13094 - 13098][Angew. Chem., 2017, vol. 56, p. 13274 - 13278,5]

37
[ 84907-55-1 ]
4,4'-(2,2-dichloroacetyl)dibenzaldehyde [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
43%	With trichloroisocyanuric acid; water In acetonitrile at 25℃; for 12h;

Reference： [1]Cho, Eunjeong; Kim, Myungjin; Jayaraman, Aravindan; Kim, Jimin; Lee, Sunwoo [European Journal of Organic Chemistry, 2018, vol. 2018, # 6, p. 781 - 784]

38
[ 938-75-0 ]
[ 109-63-7 ]
[ 84907-55-1 ]
C₅₂H₅₂B₂F₄N₄O₈ [ No CAS ]
C₄₃H₄₂BF₂N₃O₇ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 28% 2: 6%	Stage #1: 3,4-dimethyl-1H-pyrrole-2-carboxylic acid ethyl ester; boron trifluoride diethyl etherate; tolan-4,4'-dicarbaldehyde In dichloromethane at 20℃; for 24h; Inert atmosphere; Stage #2: With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane for 1h; Inert atmosphere; Stage #3: With boron trifluoride diethyl etherate; triethylamine In dichloromethane at 0 - 20℃; for 8h; Inert atmosphere;

Reference： [1]Zhang, Guanyu; Zhao, Ning; Bobadova-Parvanova, Petia; Wang, Maodie; Fronczek, Frank R.; Smith, Kevin M.; Vicente, M. Graça H. [Journal of Physical Chemistry A, 2018, vol. 122, # 30, p. 6256 - 6265]

39
N-phenyl-4,5-dimethyl-1,3-thiazolium hexafluorophosphate salt [ No CAS ]
[ 84907-55-1 ]
4,5-bis(4-formylphenyl)-1,2-dimethylthiazolo[3,2-a]quinolizin-10-iumhexafluorophopsphate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; sodium acetate; silver trifluoromethanesulfonate In 1,2-dichloro-ethane at 27℃; for 18h; Schlenk technique; Inert atmosphere; Darkness;

Reference： [1]Dutta, Champak; Sainaba, Arppitha Baby; Choudhury, Joyanta [Chemical Communications, 2019, vol. 55, # 6, p. 854 - 857]

40
N-methoxyazulene-1-carboxamide [ No CAS ]
[ 84907-55-1 ]
4,4'-(2-methoxy-1-oxo-1,2-dihydroazuleno[1,2-c]pyridine-3,4-diyl)dibenzaldehyde [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	With oxygen; palladium diacetate; potassium iodide In N,N-dimethyl-formamide at 120℃; for 4h;

Reference： [1]Han, Gi Uk; Son, Jeong-Yu; Park, Dahee; Eom, Hyeonsik; Lee, Kyungsup; Noh, Hee Chan; Lee, Kooyeon; Lee, Phil Ho [Advanced Synthesis and Catalysis, 2020, vol. 362, # 21, p. 4749 - 4754]

41
[ 108-24-7 ]
[ 84907-55-1 ]
C₇₂H₄₈O₁₂ [ No CAS ]
C₇₂H₄₈O₁₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: tolan-4,4'-dicarbaldehyde With 3-ethyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazolium bromide; triethylamine In dichloromethane for 66h; Inert atmosphere; Reflux; Stage #2: acetic anhydride With sulfuric acid at 20℃; Inert atmosphere; Overall yield = 23 percent; Overall yield = 467 mg;

Reference： [1]Eisterhold, Andrew M.; Puangsamlee, Thamon; Otterbach, Steffen; Bräse, Stefan; Weis, Patrick; Wang, Xiqu; Kutonova, Ksenia V.; Miljanić, Ognjen Š. [Organic Letters, 2021, vol. 23, # 3, p. 781 - 785]

42
[ 84907-55-1 ]
C₆₄H₄₀O₈ [ No CAS ]
C₆₄H₄₀O₈ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 3-ethyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazolium bromide; triethylamine In dichloromethane for 66h; Inert atmosphere; Reflux; Overall yield = 1.39 g;

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H200	Unstable explosive
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H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 84907-55-1 ] {[proInfo.proName]}

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[ 84907-55-1 ] Synthesis Path-Downstream 1~42

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