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Material Science
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Triptycene Series
2,3,6,7,12,13-Hexabromotriptycene
Material Science
Chemistry
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Organic Building Blocks
Triptycene Series
Benzene Compounds

[ CAS No. 55805-81-7 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 55805-81-7
Chemical Structure| 55805-81-7
Structure of 55805-81-7 * Storage: {[proInfo.prStorage]}
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Quality Control of [ 55805-81-7 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 55805-81-7 ]

SDS Specification
Alternatived Products of [ 55805-81-7 ]

Product Details of [ 55805-81-7 ]

CAS No. :55805-81-7 MDL No. :MFCD31700802
Formula : C20H8Br6 Boiling Point : -
Linear Structure Formula :- InChI Key :FXRWLRSFZAHEEL-UHFFFAOYSA-N
M.W : 727.70 Pubchem ID :23270035
Synonyms :

Calculated chemistry of [ 55805-81-7 ]

Physicochemical Properties

Num. heavy atoms : 26
Num. arom. heavy atoms : 18
Fraction Csp3 : 0.1
Num. rotatable bonds : 0
Num. H-bond acceptors : 0.0
Num. H-bond donors : 0.0
Molar Refractivity : 127.64
TPSA : 0.0 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -4.37 cm/s

Lipophilicity

Log Po/w (iLOGP) : 4.86
Log Po/w (XLOGP3) : 8.97
Log Po/w (WLOGP) : 9.25
Log Po/w (MLOGP) : 8.72
Log Po/w (SILICOS-IT) : 9.08
Consensus Log Po/w : 8.17

Druglikeness

Lipinski : 2.0
Ghose : None
Veber : 0.0
Egan : 1.0
Muegge : 3.0
Bioavailability Score : 0.17

Water Solubility

Log S (ESOL) : -10.52
Solubility : 0.0000000222 mg/ml ; 0.0 mol/l
Class : Insoluble
Log S (Ali) : -8.86
Solubility : 0.00000101 mg/ml ; 0.0000000014 mol/l
Class : Poorly soluble
Log S (SILICOS-IT) : -12.14
Solubility : 0.0000000005 mg/ml ; 0.0 mol/l
Class : Insoluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 3.41

Safety of [ 55805-81-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 55805-81-7 ]

* 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 [ 55805-81-7 ]

[ 55805-81-7 ] Synthesis Path-Downstream   1~37

YieldReaction ConditionsOperation in experiment
Triptycen, Br2;
  • 2
  • tris(biphenyl-2,2'-diyl)zirconate (lithium(tetrahydrofuran)4)2 [ No CAS ]
  • [ 55805-81-7 ]
  • [ 1092921-61-3 ]
YieldReaction ConditionsOperation in experiment
9% In toluene at 20℃; for 48h; Inert atmosphere;
Reference： [1]Location in patent: experimental part Hilton, Cameron L.; Jamison, Christopher R.; Zane, Hannah K.; King, Benjamin T. [Journal of Organic Chemistry, 2009, vol. 74, # 1, p. 405 - 407]
  • 3
  • [ 477-75-8 ]
  • [ 55805-81-7 ]
Reference： [1]Chemistry - A European Journal,2014,vol. 20,p. 11291 - 11294,4
[2]Chemical Communications,2012,vol. 48,p. 1141 - 1143
[3]Journal of Organic Chemistry,2009,vol. 74,p. 405 - 407
[4]Macromolecules,2010,vol. 43,p. 5287 - 5294
[5]Angewandte Chemie - International Edition,2018,vol. 57,p. 3415 - 3420
    Angew. Chem.,2018,vol. 130,p. 3473 - 3478,6
  • 4
  • [ 55805-81-7 ]
  • [ 124-41-4 ]
  • 2,3,6,7,12,13-hexamethoxytriptycene [ No CAS ]
YieldReaction ConditionsOperation in experiment
With copper(I) bromide In toluene
Reference： [1]Location in patent: scheme or table Ghanem, Bader S.; Hashem, Mohammed; Harris, Kenneth D. M.; Msayib, Kadhum J.; Xu, Mingcan; Budd, Peter M.; Chaukura, Nhamo; Book, David; Tedds, Steven; Walton, Allan; McKeown, Neil B. [Macromolecules, 2010, vol. 43, # 12, p. 5287 - 5294]
  • 5
  • [ 55805-81-7 ]
  • [ 1227256-04-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: copper(I) bromide / toluene 2: boron tribromide / dichloromethane / 20 °C
Reference： [1]Ghanem, Bader S.; Hashem, Mohammed; Harris, Kenneth D. M.; Msayib, Kadhum J.; Xu, Mingcan; Budd, Peter M.; Chaukura, Nhamo; Book, David; Tedds, Steven; Walton, Allan; McKeown, Neil B. [Macromolecules, 2010, vol. 43, # 12, p. 5287 - 5294]
  • 6
  • [ 1013-88-3 ]
  • [ 55805-81-7 ]
  • N2,N3,N6,N7,N14,N15-hexakis(diphenylmethylene)triptycene-2,3,6,7,14,15-hexaamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
84% With tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene at 110℃; Inert atmosphere;
With tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene at 110℃; for 15h; Inert atmosphere;
Reference： [1]Rabbani, Mohammad Gulam; Reich, Thomas E.; Kassab, Refaie M.; Jackson, Karl T.; El-Kaderi, Hani M. [Chemical Communications, 2012, vol. 48, # 8, p. 1141 - 1143]
[2]Mahmood, Javeed; Kim, Seok-Jin; Noh, Hyuk-Jun; Jung, Sun-Min; Ahmad, Ishfaq; Li, Feng; Seo, Jeong-Min; Baek, Jong-Beom [Angewandte Chemie - International Edition, 2018, vol. 57, # 13, p. 3415 - 3420][Angew. Chem., 2018, vol. 130, # 13, p. 3473 - 3478,6]
  • 7
  • [ 55805-81-7 ]
  • C47H65N6(3+)*3BF4(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium t-butanolate; palladium diacetate; 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride / toluene / 16 h / 110 °C / Schlenk technique 2: tetrafluoroboric acid / diethyl ether / 16 h / Reflux
Reference： [1]Gonell, Sergio; Poyatos, Macarena; Peris, Eduardo [Angewandte Chemie - International Edition, 2013, vol. 52, # 27, p. 7009 - 7013][Angew. Chem., 2013, vol. 125, # 27, p. 7147 - 7151,6]
  • 8
  • [ 55805-81-7 ]
  • C56H77Cl3N6Pd3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium t-butanolate; palladium diacetate; 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride / toluene / 16 h / 110 °C / Schlenk technique 2.1: tetrafluoroboric acid / diethyl ether / 16 h / Reflux 3.1: potassium hexamethylsilazane / toluene; tetrahydrofuran / 0.17 h / 0 °C 3.2: 2.17 h / 0 - 20 °C
Reference： [1]Gonell, Sergio; Poyatos, Macarena; Peris, Eduardo [Angewandte Chemie - International Edition, 2013, vol. 52, # 27, p. 7009 - 7013][Angew. Chem., 2013, vol. 125, # 27, p. 7147 - 7151,6]
  • 9
  • [ 55805-81-7 ]
  • C47H62Au3Cl3N6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium t-butanolate; palladium diacetate; 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride / toluene / 16 h / 110 °C / Schlenk technique 2.1: tetrafluoroboric acid / diethyl ether / 16 h / Reflux 3.1: potassium hexamethylsilazane / toluene; tetrahydrofuran / 0.17 h / 0 °C 3.2: air / 2 h / 20 °C / Darkness
Reference： [1]Gonell, Sergio; Poyatos, Macarena; Peris, Eduardo [Angewandte Chemie - International Edition, 2013, vol. 52, # 27, p. 7009 - 7013][Angew. Chem., 2013, vol. 125, # 27, p. 7147 - 7151,6]
  • 10
  • [ 55805-81-7 ]
  • [ 75-64-9 ]
  • C44H68N6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
99% With palladium diacetate; sodium t-butanolate; 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride In toluene at 110℃; for 16h; Schlenk technique;
Reference： [1]Gonell, Sergio; Poyatos, Macarena; Peris, Eduardo [Angewandte Chemie - International Edition, 2013, vol. 52, # 27, p. 7009 - 7013][Angew. Chem., 2013, vol. 125, # 27, p. 7147 - 7151,6]
  • 11
  • [ 381218-96-8 ]
  • [ 55805-81-7 ]
  • 2,3,6,7,14,15-hexa(4-terpyridinylphenyl)triptycene [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In methanol; water; toluene for 48h; Inert atmosphere; Reflux;
Reference： [1]Xie, Ting-Zheng; Guo, Kai; Huang, Mingjun; Lu, Xiaocun; Liao, Sheng-Yun; Sarkar, Rajarshi; Moorefield, Charles N.; Cheng, Stephen Z. D.; Wesdemiotis, Chrys; Newkome, George R. [Chemistry - A European Journal, 2014, vol. 20, # 36, p. 11291 - 11294]
  • 12
  • [ 55805-81-7 ]
  • 2,3,6,7,14,15-hexaethynyltriptycene [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: bis-triphenylphosphine-palladium(II) chloride; triphenylphosphine; copper(l) iodide; triethylamine / tetrahydrofuran / 18 h / 70 °C / Inert atmosphere; Schlenk technique 2: tetrabutyl ammonium fluoride / tetrahydrofuran / 25 °C
Reference： [1]Moylan, Claire; Rogers, Luke; Shaker, Yasser M.; Davis, Mia; Eckhardt, Hans-Georg; Eckert, Raphael; Ryan, Aoife A.; Senge, Mathias O. [European Journal of Organic Chemistry, 2016, vol. 2016, # 1, p. 185 - 195]
  • 13
  • [ 55805-81-7 ]
  • C17H26Si [ No CAS ]
  • C134H158Si6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; triphenylphosphine In tetrahydrofuran at 70℃; for 24h; Inert atmosphere; Schlenk technique;
Reference： [1]Moylan, Claire; Rogers, Luke; Shaker, Yasser M.; Davis, Mia; Eckhardt, Hans-Georg; Eckert, Raphael; Ryan, Aoife A.; Senge, Mathias O. [European Journal of Organic Chemistry, 2016, vol. 2016, # 1, p. 185 - 195]
  • 14
  • [ 55805-81-7 ]
  • [ 87199-17-5 ]
  • 2,3,6,7,14,15-hexa(4′-formylphenyl)triptycene [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With tetrakis-(triphenylphosphine)-palladium; Cs2CO3 In tetrahydrofuran at 65℃; Inert atmosphere;
70% With tetrakis-(triphenylphosphine)-palladium; Cs2CO3 In tetrahydrofuran at 65℃; for 18h; Inert atmosphere;
64% With tetrakis-(triphenylphosphine)-palladium; Cs2CO3 In tetrahydrofuran at 65℃; Inert atmosphere; Schlenk technique;
48.6% With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); Cs2CO3 In tetrahydrofuran for 48h; Inert atmosphere; Reflux;
48.6% With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); Cs2CO3 In tetrahydrofuran for 48h; Inert atmosphere; Reflux;

Reference： [1]Li, Hui; Chen, Fengqian; Guan, Xinyu; Li, Jiali; Li, Cuiyan; Tang, Bin; Valtchev, Valentin; Yan, Yushan; Qiu, Shilun; Fang, Qianrong [Journal of the American Chemical Society, 2021, vol. 143, # 7, p. 2654 - 2659]
[2]Yu, Chengyang; Li, Hui; Wang, Yujie; Suo, Jinqun; Guan, Xinyu; Wang, Rui; Valtchev, Valentin; Yan, Yushan; Qiu, Shilun; Fang, Qianrong [Angewandte Chemie - International Edition, 2022, vol. 61, # 13][Angew. Chem., 2022, vol. 134, # 13]
[3]Moylan, Claire; Rogers, Luke; Shaker, Yasser M.; Davis, Mia; Eckhardt, Hans-Georg; Eckert, Raphael; Ryan, Aoife A.; Senge, Mathias O. [European Journal of Organic Chemistry, 2016, vol. 2016, # 1, p. 185 - 195]
[4]Li, Zonglong; Sheng, Li; Wang, Hangchao; Wang, Xiaolin; Li, Mingyang; Xu, Yulong; Cui, Hao; Zhang, Haitian; Liang, Hongmei; Xu, Hong; He, Xiangming [Journal of the American Chemical Society, 2021, vol. 143, # 1, p. 92 - 96]
[5]Li, Zonglong; Sheng, Li; Hsueh, Chouhung; Wang, Xiaolin; Cui, Hao; Gao, Hongqiang; Wu, Yanzhou; Wang, Jianlong; Tang, Yaping; Xu, Hong; He, Xiangming [Chemistry of Materials, 2021, vol. 33, # 24, p. 9618 - 9623]
  • 15
  • [ 55805-81-7 ]
  • [ 126747-14-6 ]
  • 2,3,6,7,14,15-hexakis(4-cyanophenyl)triptycene [ No CAS ]
YieldReaction ConditionsOperation in experiment
63% With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In tetrahydrofuran at 65℃; Inert atmosphere; Schlenk technique;
Reference： [1]Moylan, Claire; Rogers, Luke; Shaker, Yasser M.; Davis, Mia; Eckhardt, Hans-Georg; Eckert, Raphael; Ryan, Aoife A.; Senge, Mathias O. [European Journal of Organic Chemistry, 2016, vol. 2016, # 1, p. 185 - 195]
  • 16
  • [ 55805-81-7 ]
  • [ 150255-96-2 ]
  • 2,3,6,7,14,15-hexakis(3-cyanophenyl)triptycene [ No CAS ]
YieldReaction ConditionsOperation in experiment
61% With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In tetrahydrofuran at 65℃; Inert atmosphere; Schlenk technique;
Reference： [1]Moylan, Claire; Rogers, Luke; Shaker, Yasser M.; Davis, Mia; Eckhardt, Hans-Georg; Eckert, Raphael; Ryan, Aoife A.; Senge, Mathias O. [European Journal of Organic Chemistry, 2016, vol. 2016, # 1, p. 185 - 195]
  • 17
  • [ 55805-81-7 ]
  • [ 99768-12-4 ]
  • C68H50O12 [ No CAS ]
YieldReaction ConditionsOperation in experiment
66% With potassium phosphate; SPhos Pd G3 In tetrahydrofuran; water Inert atmosphere; Reflux;
With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In tetrahydrofuran at 65℃; Inert atmosphere; Schlenk technique;
Reference： [1]Li, Penghao; Li, Peng; Ryder, Matthew R.; Liu, Zhichang; Stern, Charlotte L.; Farha, Omar K.; Stoddart, J. Fraser [Angewandte Chemie - International Edition, 2019, vol. 58, # 6, p. 1664 - 1669][Angew. Chem., 2019, vol. 131, p. 1678 - 1683,6]
[2]Moylan, Claire; Rogers, Luke; Shaker, Yasser M.; Davis, Mia; Eckhardt, Hans-Georg; Eckert, Raphael; Ryan, Aoife A.; Senge, Mathias O. [European Journal of Organic Chemistry, 2016, vol. 2016, # 1, p. 185 - 195]
  • 18
  • [ 55805-81-7 ]
  • [ 10365-98-7 ]
  • 2,3,6,7,14,15-hexakis(3-methoxyphenyl)triptycene [ No CAS ]
YieldReaction ConditionsOperation in experiment
44% With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In tetrahydrofuran at 65℃; Inert atmosphere; Schlenk technique;
Reference： [1]Moylan, Claire; Rogers, Luke; Shaker, Yasser M.; Davis, Mia; Eckhardt, Hans-Georg; Eckert, Raphael; Ryan, Aoife A.; Senge, Mathias O. [European Journal of Organic Chemistry, 2016, vol. 2016, # 1, p. 185 - 195]
  • 19
  • [ 55805-81-7 ]
  • [ 28611-39-4 ]
  • 2,3,6,7,14,15-hexakis[(4-dimethylamino)phenyl]triptycene [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 65℃; Inert atmosphere; Schlenk technique;
Reference： [1]Moylan, Claire; Rogers, Luke; Shaker, Yasser M.; Davis, Mia; Eckhardt, Hans-Georg; Eckert, Raphael; Ryan, Aoife A.; Senge, Mathias O. [European Journal of Organic Chemistry, 2016, vol. 2016, # 1, p. 185 - 195]
  • 20
  • [ 870238-65-6 ]
  • [ 55805-81-7 ]
  • C86H86Si6 [ No CAS ]
Reference： [1]European Journal of Organic Chemistry,2016,vol. 2016,p. 185 - 195
  • 21
  • [ 55805-81-7 ]
  • [ 73183-34-3 ]
  • 2,3,6,7,14,15-hexakis(boronic acid pinacol ester)triptycene [ No CAS ]
YieldReaction ConditionsOperation in experiment
36% With bis-triphenylphosphine-palladium(II) chloride; caesium carbonate In 1,2-dichloro-ethane at 65℃; Inert atmosphere; Schlenk technique;
Reference： [1]Moylan, Claire; Rogers, Luke; Shaker, Yasser M.; Davis, Mia; Eckhardt, Hans-Georg; Eckert, Raphael; Ryan, Aoife A.; Senge, Mathias O. [European Journal of Organic Chemistry, 2016, vol. 2016, # 1, p. 185 - 195]
  • 22
  • [ 84110-40-7 ]
  • [ 55805-81-7 ]
  • 2,3,6,7,14,15-hexakis(2-methylpropyl)triptycene [ No CAS ]
YieldReaction ConditionsOperation in experiment
32% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate In tetrahydrofuran at 80℃; for 18h; Inert atmosphere; Schlenk technique;
Reference： [1]Moylan, Claire; Rogers, Luke; Shaker, Yasser M.; Davis, Mia; Eckhardt, Hans-Georg; Eckert, Raphael; Ryan, Aoife A.; Senge, Mathias O. [European Journal of Organic Chemistry, 2016, vol. 2016, # 1, p. 185 - 195]
  • 23
  • [ 98139-72-1 ]
  • [ 55805-81-7 ]
  • 2,3,6,7,14,15-hexakis(3-methylbutyl)triptycene [ No CAS ]
YieldReaction ConditionsOperation in experiment
36% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate In tetrahydrofuran at 80℃; for 18h; Inert atmosphere; Schlenk technique;
Reference： [1]Moylan, Claire; Rogers, Luke; Shaker, Yasser M.; Davis, Mia; Eckhardt, Hans-Georg; Eckert, Raphael; Ryan, Aoife A.; Senge, Mathias O. [European Journal of Organic Chemistry, 2016, vol. 2016, # 1, p. 185 - 195]
  • 24
  • [ 16343-08-1 ]
  • [ 55805-81-7 ]
  • 2,3,6,7,14,15-hexahexyltriptycene [ No CAS ]
YieldReaction ConditionsOperation in experiment
21% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate In tetrahydrofuran at 80℃; for 18h; Inert atmosphere; Schlenk technique;
Reference： [1]Moylan, Claire; Rogers, Luke; Shaker, Yasser M.; Davis, Mia; Eckhardt, Hans-Georg; Eckert, Raphael; Ryan, Aoife A.; Senge, Mathias O. [European Journal of Organic Chemistry, 2016, vol. 2016, # 1, p. 185 - 195]
  • 25
  • [ 55805-81-7 ]
  • [ 1066-54-2 ]
  • 2,3,6,7,14,15-hexakis(trimethylsilylethynyl)triptycene [ No CAS ]
YieldReaction ConditionsOperation in experiment
67% With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; triphenylphosphine In tetrahydrofuran at 70℃; for 18h; Inert atmosphere; Schlenk technique;
Reference： [1]Moylan, Claire; Rogers, Luke; Shaker, Yasser M.; Davis, Mia; Eckhardt, Hans-Georg; Eckert, Raphael; Ryan, Aoife A.; Senge, Mathias O. [European Journal of Organic Chemistry, 2016, vol. 2016, # 1, p. 185 - 195]
  • 26
  • (pinacolato)BC6H4C6H4(OMe)2C6H4Cl [ No CAS ]
  • [ 55805-81-7 ]
  • C140H116Cl6O12 [ No CAS ]
YieldReaction ConditionsOperation in experiment
69% With tetrakis(triphenylphosphine) palladium(0); sodium hydroxide In tetrahydrofuran; water at 90℃; for 4h; Inert atmosphere;
Reference： [1]Li, Penghao; Zakharov, Lev N.; Jasti, Ramesh [Angewandte Chemie - International Edition, 2017, vol. 56, # 19, p. 5237 - 5241][Angew. Chem., 2017, vol. 129, p. 5321 - 5325]
  • 27
  • [ 55805-81-7 ]
  • [ 620595-36-0 ]
  • 2,3,6,7,12,13-hexa-(3’-carbonyl-4’-hydroxyphenyl)triptycene [ No CAS ]
YieldReaction ConditionsOperation in experiment
93% With potassium fluoride; tris-(dibenzylideneacetone)dipalladium(0); tri tert-butylphosphoniumtetrafluoroborate In tetrahydrofuran; water at 80℃; for 16h;
Reference： [1]Reinhard, Dennis; Zhang, Wen-Shan; Rominger, Frank; Curticean, Ronald; Wacker, Irene; Schröder, Rasmus R.; Mastalerz, Michael [Chemistry - A European Journal, 2018, vol. 24, # 44, p. 11433 - 11437]
  • 28
  • [ 55805-81-7 ]
  • methyl 4-((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethynyl)benzoate [ No CAS ]
  • C116H74O12 [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% With potassium phosphate; (2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1 ‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl)]palladium(II) methanesulfonate In tetrahydrofuran; water Reflux; Inert atmosphere;
Reference： [1]Li, Penghao; Chen, Zhijie; Ryder, Matthew R.; Stern, Charlotte L.; Guo, Qing-Hui; Wang, Xingjie; Farha, Omar K.; Stoddart, J. Fraser [Journal of the American Chemical Society, 2019, vol. 141, # 33, p. 12998 - 13002]
  • 29
  • [ 110-00-9 ]
  • [ 55805-81-7 ]
  • 1,4,6,8,11,13,15,18-octahydro-1,4:8,11:15,18-triepoxy-6,13-[2′,3′]-naphthalenopentacene [ No CAS ]
YieldReaction ConditionsOperation in experiment
64% With n-butyllithium In tetrahydrofuran at -40℃; for 1h; Inert atmosphere; 4 Synthesis of compound 5 Add compound 4 to a 100mL two-necked flask (0.5g, 0.687mmol), Furan 1.5mL Anhydrous tetrahydrofuran 60mL, under nitrogen protection, Cool to -40°C. Slowly add 1mL (2.5M) n-butyllithium dropwise, continue to stir for 1h, The reaction was quenched by adding 2 mL of methanol, and the temperature was raised to room temperature. The solvent was removed under reduced pressure, the solid was dissolved in dichloromethane, Filter, crystallize the filtrate with petroleum ether, and filter to obtain compound 5 (0.2g), The yield was 64%.
60% With n-butyllithium In tetrahydrofuran at -40℃; for 1h; Inert atmosphere;
Reference： [1]Current Patent Assignee: BEIJING UNIVERSITY OF CHEMICAL TECHNOLOGY - CN112299982, 2021, A Location in patent: Paragraph 0094; 0099-0101
[2]Duan, Yuxiao; Zhang, Guowei; Liu, Xinyue; Shi, Fenghui; Wang, Tingting; Yan, Hongchen; Xu, Hu; Zhang, Lei [Journal of Organic Chemistry, 2022, vol. 87, # 14, p. 8841 - 8848]
  • 30
  • [ 55805-81-7 ]
  • N-(diphenylmethylene)-2,6-bis(1-methylethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenamine [ No CAS ]
  • C170H164N6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In tetrahydrofuran; water at 80℃; for 72h; Inert atmosphere;
Reference： [1]Li, Hui; Chen, Fengqian; Guan, Xinyu; Li, Jiali; Li, Cuiyan; Tang, Bin; Valtchev, Valentin; Yan, Yushan; Qiu, Shilun; Fang, Qianrong [Journal of the American Chemical Society, 2021, vol. 143, # 7, p. 2654 - 2659]
  • 31
  • [ 201230-82-2 ]
  • [ 55805-81-7 ]
  • [ 71-36-3 ]
  • hexabutyl triptycene-2,3,6,7,14,15-hexacarboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
69% Stage #1: 2,3,6,7,12,13-hexabromotriptycene; butan-1-ol With palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; N-ethyl-N,N-diisopropylamine In 5,5-dimethyl-1,3-cyclohexadiene at 20℃; for 1h; Inert atmosphere; Glovebox; Stage #2: carbon monoxide In 5,5-dimethyl-1,3-cyclohexadiene at 120 - 140℃; for 48h; Autoclave; Carboxylic Esters 1a-8a on a Gram Scale: Typical Procedure C General procedure: hetero)arene (5 mmol), Pd(OAc)2 (0.12 g, 0.75 mmol), and rac-BINAP (0.46 g, 0.75 mmol). Next, a N2 saturated mixture of xylenes(55 mL), nBuOH (45 mL), and DIPEA (6.5 mL) was added to the reactionbottle and the mixture was stirred for 1.0 h at r.t. to give a yellowgreento red-brown solution. The resulting solution was transferredto an autoclave, which was then charged with 30 atm of CO, heated to120 °C and then held at 140 °C for 48 h. The mixture was allowed tocool to r.t., the CO gas was released slowly in a well-ventilated hoodand the solution was concentrated. Purification by column chromatography(PE/EtOAc 10:1 to 2:1) gave carboxylic esters 1a-8a (95->99% conversion, 65-92% yield)
Reference： [1]Wu, Weilong; Jing, Yongkang; Zhang, Deyi; Yan, Xianghe; Liang, Rong; Lu, Zhiqiang; Ji, Baoming [Synthesis, 2022, vol. 54, # 2, p. 403 - 410]
  • 32
  • [ 55805-81-7 ]
  • [ 945681-56-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; N-ethyl-N,N-diisopropylamine / 5,5-dimethyl-1,3-cyclohexadiene / 1 h / 20 °C / Inert atmosphere; Glovebox 1.2: 48 h / 120 - 140 °C / 22801.5 Torr / Autoclave 2.1: potassium hydroxide / tetrahydrofuran; water / Reflux
Reference： [1]Wu, Weilong; Jing, Yongkang; Zhang, Deyi; Yan, Xianghe; Liang, Rong; Lu, Zhiqiang; Ji, Baoming [Synthesis, 2022, vol. 54, # 2, p. 403 - 410]
  • 33
  • [ 55805-81-7 ]
  • [ 17534-15-5 ]
  • C38H20S6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
54% With potassium carbonate In N,N-dimethyl-formamide at 150℃; for 12h; Inert atmosphere;
Reference： [1]Hu, Zhaobo; Ruan, Huapeng; Song, You; Tang, Shuxuan; Wang, Xinping; Zhao, Yue [Chemical Communications, 2022, vol. 58, # 12, p. 1986 - 1989]
  • 34
  • 3-fluoro-4-formylbenzeneboronic acid [ No CAS ]
  • [ 55805-81-7 ]
  • 2,3,6,7,14,15-hexa(3’-fluorine-4′-formylphenyl)triptycene [ No CAS ]
YieldReaction ConditionsOperation in experiment
53% With tetrakis-(triphenylphosphine)-palladium; Cs2CO3 In tetrahydrofuran at 65℃; for 18h; Inert atmosphere;
Reference： [1]Yu, Chengyang; Li, Hui; Wang, Yujie; Suo, Jinqun; Guan, Xinyu; Wang, Rui; Valtchev, Valentin; Yan, Yushan; Qiu, Shilun; Fang, Qianrong [Angewandte Chemie - International Edition, 2022, vol. 61, # 13][Angew. Chem., 2022, vol. 134, # 13]
  • 35
  • [ 55805-81-7 ]
  • C56H32O9 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: n-butyllithium / tetrahydrofuran / 1 h / -40 °C / Inert atmosphere 2: 3,6-di(2'-pyridyl)-1,2,4,5-tetrazine / chloroform / 72 h / 20 °C / Inert atmosphere
Reference： [1]Duan, Yuxiao; Zhang, Guowei; Liu, Xinyue; Shi, Fenghui; Wang, Tingting; Yan, Hongchen; Xu, Hu; Zhang, Lei [Journal of Organic Chemistry, 2022, vol. 87, # 14, p. 8841 - 8848]
  • 36
  • [ 55805-81-7 ]
  • C56H26O6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: n-butyllithium / tetrahydrofuran / 1 h / -40 °C / Inert atmosphere 2: 3,6-di(2'-pyridyl)-1,2,4,5-tetrazine / chloroform / 72 h / 20 °C / Inert atmosphere 3: 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium iodide / tetrahydrofuran / 3 h / Reflux
Reference： [1]Duan, Yuxiao; Zhang, Guowei; Liu, Xinyue; Shi, Fenghui; Wang, Tingting; Yan, Hongchen; Xu, Hu; Zhang, Lei [Journal of Organic Chemistry, 2022, vol. 87, # 14, p. 8841 - 8848]
  • 37
  • [ 55805-81-7 ]
  • [ 3034-86-4 ]
  • hexamethyl 4,4',4",4"",4"",4'""-((9,10-dihydro-9,10-[1,2]benzenoanthracene-2,3,6,7,14,15-hexayl)hexakis(ethyn-2,1-diyl))hexabenzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
41.5% With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; triethylamine; triphenylphosphine for 48h; Reflux; Schlenk technique; 2.1 (Step 1)
Synthesis of Hexamethyl 4,4',4",4"",4"",4'""-((9,10-dihydro-9,10-[1,2]benzenoanthracene-2,3,6,7,14,15-hexayl)hexakis(ethyn-2,1-diyl))hexabenzoate
To a 100 mL Schlenk flask were added 2,3,6,7,14,15-hexabromo-9,10-dihydro-9,10-[1,2]benzenoanthracene (0.737 g, 1.01 mmol), CuI (43.0 mg, 0.226 mmol), PdCl2(PPh3)2 (98.6 mg, 0.104 mmol), PPh3 (53.5 mg, 0.204 mmol) and methyl 4-ethynylbenzoate (1.30 g, 8.14 mmol), followed by addition of 22 mL of degassed triethylamine. The mixture was heated under reflux with stirring for two days, and the solvent was then distilled off under reduced pressure. It was dissolved in dichloromethane and washed with a saturated aqueous sodium chloride solution. The organic layer was dried over magnesium sulfate and subjected to filtration, and the solvent was then distilled off under reduced pressure with a rotary evaporator. Purification was carried out by silica gel column chromatography (dichloromethane-ethyl acetate), and the solvent was then distilled off under reduced pressure with a rotary evaporator to obtain a solid. The obtained solid was reprecipitated with ethyl acetate and hexane and subjected to suction filtration to obtain hexamethyl 4,4',4",4'",4"",4'""-((9,10-dihydro-9,10-[1,2]benzenoanthracene-2,3,6,7,14,15-hexayl)hexakis (ethyn-2,1-diyl))hexabenzoate (0.504 g, 0.419 mmol) as a brown solid (yield: 41.5%).
Reference： [1]Current Patent Assignee: RIKKYO EDUCATIONAL CORP - US2022/64190, 2022, A1 Location in patent: Paragraph 0177; 0178

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