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Heterocyclic Building Blocks
Thiadiazoles
4-bromobenzo[c][1,2,5]thiadiazole
4,7-Dibromo-5,6-bis(octyloxy)benzo[c][1,2,5]thiadiazole
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4-bromobenzo[c][1,2,5]thiadiazole

[ CAS No. 1192352-08-1 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 1192352-08-1
Chemical Structure| 1192352-08-1
Structure of 1192352-08-1 * Storage: {[proInfo.prStorage]}
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For Research Only 110K+ Compounds Competitive Price 1-2 Day Shipping

Quality Control of [ 1192352-08-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 1192352-08-1 ]

SDS Specification
Alternatived Products of [ 1192352-08-1 ]

Product Details of [ 1192352-08-1 ]

CAS No. :1192352-08-1 MDL No. :MFCD19440967
Formula : C22H34Br2N2O2S Boiling Point : -
Linear Structure Formula :- InChI Key :VGCVJZVDAAWTFC-UHFFFAOYSA-N
M.W : 550.39 Pubchem ID :67329181
Synonyms :

Calculated chemistry of [ 1192352-08-1 ]

Physicochemical Properties

Num. heavy atoms : 29
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.73
Num. rotatable bonds : 16
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 133.1
TPSA : 72.48 Ų

Pharmacokinetics

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) : -2.59 cm/s

Lipophilicity

Log Po/w (iLOGP) : 5.92
Log Po/w (XLOGP3) : 9.95
Log Po/w (WLOGP) : 8.69
Log Po/w (MLOGP) : 4.91
Log Po/w (SILICOS-IT) : 9.35
Consensus Log Po/w : 7.76

Druglikeness

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

Water Solubility

Log S (ESOL) : -8.69
Solubility : 0.00000111 mg/ml ; 0.000000002 mol/l
Class : Poorly soluble
Log S (Ali) : -11.4
Solubility : 0.0000000022 mg/ml ; 0.0 mol/l
Class : Insoluble
Log S (SILICOS-IT) : -9.98
Solubility : 0.000000057 mg/ml ; 0.0000000001 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 3.0
Synthetic accessibility : 3.77

Safety of [ 1192352-08-1 ]

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:

Application In Synthesis of [ 1192352-08-1 ]

* 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 [ 1192352-08-1 ]

[ 1192352-08-1 ] Synthesis Path-Downstream   1~76

  • 1
  • [ 1192352-08-1 ]
  • [ 193978-23-3 ]
  • [ 1192352-09-2 ]
YieldReaction ConditionsOperation in experiment
49% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In water; toluene at 90℃; for 240h; Inert atmosphere;
Reference： [1]Ruiping, Qin; Weiwei, Li; Cuihong, Li; Chun, Du; Veit, Clemens; Schleiermacher, Hans-Frieder; Andersson, Mattias; Zhishan, Bo; Zhengping, Liu; Inganaes, Olle; Wuerfel, Uli; Fengling, Zhang [Journal of the American Chemical Society, 2009, vol. 131, # 41, p. 14612 - 14613]
  • 2
  • [ 1192352-08-1 ]
  • [ 1313876-03-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0) / toluene / Inert atmosphere; Reflux 2: N-Bromosuccinimide / tetrahydrofuran / 0 - 20 °C
Reference： [1]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]
  • 3
  • [ 1192352-08-1 ]
  • [ 175922-79-9 ]
  • [ 1313876-01-5 ]
YieldReaction ConditionsOperation in experiment
79% With tetrakis(triphenylphosphine) palladium(0) In toluene Inert atmosphere; Reflux;
Reference： [1]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]
  • 4
  • 4,5-bis(octyloxy)benzene-1,2-diaminium dichloride [ No CAS ]
  • [ 1192352-08-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: triethylamine 2: bromine; acetic acid / dichloromethane
Multi-step reaction with 2 steps 1: triethylamine; thionyl chloride / dichloromethane / 6 h / 50 °C / Inert atmosphere 2: bromine; hydrogen bromide / 6 h / 120 °C
Multi-step reaction with 2 steps 1: triethylamine; thionyl chloride / dichloromethane / 20 h / Inert atmosphere; Reflux 2: bromine / dichloromethane; acetic acid / 48 h / 20 °C / Darkness
Multi-step reaction with 2 steps 1: triethylamine; thionyl chloride / dichloromethane / 6 h / Inert atmosphere; Reflux 2: bromine; acetic acid / dichloromethane / 48 h / 20 °C / Darkness

Reference： [1]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]
[2]Zeng, Shaohang; Yin, Lunxiang; Ji, Changyan; Jiang, Xueying; Li, Kechang; Li, Yanqin; Wang, Yue [Chemical Communications, 2012, vol. 48, # 86, p. 10627 - 10629]
[3]Chen, Long; Li, Xin; Ying, Weijiang; Zhang, Xiaoyu; Guo, Fuling; Li, Jing; Hua, Jianli [European Journal of Organic Chemistry, 2013, # 9, p. 1770 - 1780]
[4]Hu, Zijun; Liu, Kuan [Journal of Polymer Science, Part A: Polymer Chemistry, 2020]
  • 5
  • [ 1254353-37-1 ]
  • [ 1192352-08-1 ]
YieldReaction ConditionsOperation in experiment
93% With bromine; acetic acid In dichloromethane at 20℃; for 48h;
92% With bromine In dichloromethane; acetic acid at 20℃; for 48h; Darkness;
92% With N-Bromosuccinimide In acetic acid at 60℃; for 5h; Synthesis of compound 4a Compound 3 (1 g, 2.55 mmol) was dissolved in 20 mL of acetic acid and NBS (0.703 g, 5.1 mmol) was added in small portions. The mixture was stirred by heating at 60°C for 5 h. Then the mixture was poured into water and extracted with ether. Organic phase was dried over anhydrous MgSO4 and filtered. The solvent was then removed and compound 4 was obtained as light yellow powder with yield of 92 %. 1H NMR (CDCl3, 600 MHz, δ): 4.20 (t, J=6.68 Hz, 4H), 1.94-1.91 (m, 4H), 1.57-1.55 (m, 4H), 1.34-1.42 (m, 16H), 0.93 (t, J=6.78 Hz, 6H) ppm. The NMR data match well those presented in [5]. ESI, m/z =550,0 ([M-H]-)
91% With bromine; sodium acetate; acetic acid at 20℃; for 48h;
90% With hydrogen bromide; bromine at 120℃; for 6h;
74% With bromine; acetic acid In dichloromethane at 20℃; for 48h; Darkness;
73.4% With bromine; acetic acid In dichloromethane at 20℃; for 48h; Darkness;
With bromine; acetic acid In dichloromethane

Reference： [1]Yu, Jiangsheng; Zhao, Baofeng; Nie, Xuemei; Zhou, Baojin; Li, Yang; Hai, Jiefeng; Zhu, Enwei; Bian, Linyi; Wu, Hongbin; Tang, Weihua [New Journal of Chemistry, 2015, vol. 39, # 3, p. 2248 - 2255]
[2]Chen, Long; Li, Xin; Ying, Weijiang; Zhang, Xiaoyu; Guo, Fuling; Li, Jing; Hua, Jianli [European Journal of Organic Chemistry, 2013, # 9, p. 1770 - 1780]
[3]Kuznetsov, Petr M.; Nikitenko, Sergey L.; Kuznetsov, Ilya E.; Proshin, Pavel I.; Revina, Daria V.; Troshin, Pavel A.; Akkuratov, Alexander V. [Tetrahedron Letters, 2020, vol. 61, # 26]
[4]Cardone, Antonio; Martinelli, Carmela; Losurdo, Maria; Dilonardo, Elena; Bruno, Giovanni; Scavia, Guido; Destri, Silvia; Cosma, Pinalysa; Salamandra, Luigi; Reale, Andrea; Di Carlo, Aldo; Aguirre, Aranzazu; Milian-Medina, Begona; Gierschner, Johannes; Farinola, Gianluca M. [Journal of Materials Chemistry A, 2013, vol. 1, # 3, p. 715 - 727]
[5]Zeng, Shaohang; Yin, Lunxiang; Ji, Changyan; Jiang, Xueying; Li, Kechang; Li, Yanqin; Wang, Yue [Chemical Communications, 2012, vol. 48, # 86, p. 10627 - 10629]
[6]Location in patent: experimental part Li, Yaowen; Chen, Yujin; Liu, Xing; Wang, Zhong; Yang, Xiaoming; Tu, Yingfeng; Zhu, Xiulin [Macromolecules, 2011, vol. 44, # 16, p. 6370 - 6381]
[7]Hu, Zijun; Liu, Kuan [Journal of Polymer Science, Part A: Polymer Chemistry, 2020]
[8]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
  • [ 111-83-1 ]
  • [ 1192352-08-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: potassium carbonate 2: nitric acid; acetic acid / dichloromethane 3: hydrogenchloride; tin(ll) chloride / ethanol 4: triethylamine 5: bromine; acetic acid / dichloromethane
Multi-step reaction with 5 steps 1: potassium carbonate / N,N-dimethyl-formamide / 48 h / 100 °C / Inert atmosphere 2: nitric acid; acetic acid / dichloromethane / 41 h / 10 - 20 °C 3: hydrogenchloride; tin(II) chloride hydrate / ethanol; water / 85 °C 4: thionyl chloride; triethylamine / dichloromethane / 6 h / Reflux 5: bromine; acetic acid / dichloromethane / 48 h / 20 °C / Darkness
Multi-step reaction with 5 steps 1: potassium carbonate / acetone / 60 h / 65 °C / Inert atmosphere; Reflux 2: nitric acid; acetic acid / dichloromethane / 51 h / 0 - 20 °C 3: hydrogenchloride; tin(II) chloride hydrate / ethanol; water / 18 h / 85 °C / Inert atmosphere 4: triethylamine; thionyl chloride / dichloromethane / 6 h / 50 °C / Inert atmosphere 5: bromine; hydrogen bromide / 6 h / 120 °C
Multi-step reaction with 5 steps 1.1: potassium hydroxide / ethanol / 40 h / Inert atmosphere; Reflux 2.1: nitric acid / dichloromethane; acetic acid / 10 - 20 °C 2.2: 20 °C 3.1: tin(ll) chloride; hydrogenchloride / ethanol / 85 °C 4.1: triethylamine; thionyl chloride / dichloromethane / 20 h / Inert atmosphere; Reflux 5.1: bromine / dichloromethane; acetic acid / 48 h / 20 °C / Darkness
Multi-step reaction with 5 steps 1: potassium carbonate / acetone / Reflux 2: nitric acid; acetic acid / dichloromethane 3: hydrogen; palladium on activated charcoal / ethanol / 1520.1 Torr 4: thionyl chloride; triethylamine / dichloromethane 5: acetic acid; bromine; sodium acetate / 48 h / 20 °C
Multi-step reaction with 5 steps 1: potassium carbonate / N,N-dimethyl-formamide / 48 h / 100 °C / Inert atmosphere 2: nitric acid; sulfuric acid / dichloromethane / 1.5 h / 20 °C 3: hydrogenchloride; tin(ll) chloride / ethanol; water / 85 °C / Inert atmosphere 4: triethylamine; thionyl chloride / dichloromethane / 6 h / Inert atmosphere; Reflux 5: bromine; acetic acid / dichloromethane / 48 h / 20 °C / Darkness

Reference： [1]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]
[2]Li, Yaowen; Chen, Yujin; Liu, Xing; Wang, Zhong; Yang, Xiaoming; Tu, Yingfeng; Zhu, Xiulin [Macromolecules, 2011, vol. 44, # 16, p. 6370 - 6381]
[3]Zeng, Shaohang; Yin, Lunxiang; Ji, Changyan; Jiang, Xueying; Li, Kechang; Li, Yanqin; Wang, Yue [Chemical Communications, 2012, vol. 48, # 86, p. 10627 - 10629]
[4]Chen, Long; Li, Xin; Ying, Weijiang; Zhang, Xiaoyu; Guo, Fuling; Li, Jing; Hua, Jianli [European Journal of Organic Chemistry, 2013, # 9, p. 1770 - 1780]
[5]Cardone, Antonio; Martinelli, Carmela; Losurdo, Maria; Dilonardo, Elena; Bruno, Giovanni; Scavia, Guido; Destri, Silvia; Cosma, Pinalysa; Salamandra, Luigi; Reale, Andrea; Di Carlo, Aldo; Aguirre, Aranzazu; Milian-Medina, Begona; Gierschner, Johannes; Farinola, Gianluca M. [Journal of Materials Chemistry A, 2013, vol. 1, # 3, p. 715 - 727]
[6]Hu, Zijun; Liu, Kuan [Journal of Polymer Science, Part A: Polymer Chemistry, 2020]
  • 7
  • [ 4956-41-6 ]
  • [ 1192352-08-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: nitric acid; acetic acid / dichloromethane 2: hydrogenchloride; tin(ll) chloride / ethanol 3: triethylamine 4: bromine; acetic acid / dichloromethane
Multi-step reaction with 4 steps 1: nitric acid; acetic acid / dichloromethane / 41 h / 10 - 20 °C 2: hydrogenchloride; tin(II) chloride hydrate / ethanol; water / 85 °C 3: thionyl chloride; triethylamine / dichloromethane / 6 h / Reflux 4: bromine; acetic acid / dichloromethane / 48 h / 20 °C / Darkness
Multi-step reaction with 4 steps 1: nitric acid; acetic acid / dichloromethane / 51 h / 0 - 20 °C 2: hydrogenchloride; tin(II) chloride hydrate / ethanol; water / 18 h / 85 °C / Inert atmosphere 3: triethylamine; thionyl chloride / dichloromethane / 6 h / 50 °C / Inert atmosphere 4: bromine; hydrogen bromide / 6 h / 120 °C
Multi-step reaction with 4 steps 1.1: nitric acid / dichloromethane; acetic acid / 10 - 20 °C 1.2: 20 °C 2.1: tin(ll) chloride; hydrogenchloride / ethanol / 85 °C 3.1: triethylamine; thionyl chloride / dichloromethane / 20 h / Inert atmosphere; Reflux 4.1: bromine / dichloromethane; acetic acid / 48 h / 20 °C / Darkness
Multi-step reaction with 4 steps 1: nitric acid; acetic acid / dichloromethane 2: hydrogen; palladium on activated charcoal / ethanol / 1520.1 Torr 3: thionyl chloride; triethylamine / dichloromethane 4: acetic acid; bromine; sodium acetate / 48 h / 20 °C
Multi-step reaction with 4 steps 1: nitric acid; sulfuric acid / dichloromethane / 1.5 h / 20 °C 2: hydrogenchloride; tin(ll) chloride / ethanol; water / 85 °C / Inert atmosphere 3: triethylamine; thionyl chloride / dichloromethane / 6 h / Inert atmosphere; Reflux 4: bromine; acetic acid / dichloromethane / 48 h / 20 °C / Darkness

Reference： [1]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]
[2]Li, Yaowen; Chen, Yujin; Liu, Xing; Wang, Zhong; Yang, Xiaoming; Tu, Yingfeng; Zhu, Xiulin [Macromolecules, 2011, vol. 44, # 16, p. 6370 - 6381]
[3]Zeng, Shaohang; Yin, Lunxiang; Ji, Changyan; Jiang, Xueying; Li, Kechang; Li, Yanqin; Wang, Yue [Chemical Communications, 2012, vol. 48, # 86, p. 10627 - 10629]
[4]Chen, Long; Li, Xin; Ying, Weijiang; Zhang, Xiaoyu; Guo, Fuling; Li, Jing; Hua, Jianli [European Journal of Organic Chemistry, 2013, # 9, p. 1770 - 1780]
[5]Cardone, Antonio; Martinelli, Carmela; Losurdo, Maria; Dilonardo, Elena; Bruno, Giovanni; Scavia, Guido; Destri, Silvia; Cosma, Pinalysa; Salamandra, Luigi; Reale, Andrea; Di Carlo, Aldo; Aguirre, Aranzazu; Milian-Medina, Begona; Gierschner, Johannes; Farinola, Gianluca M. [Journal of Materials Chemistry A, 2013, vol. 1, # 3, p. 715 - 727]
[6]Hu, Zijun; Liu, Kuan [Journal of Polymer Science, Part A: Polymer Chemistry, 2020]
  • 8
  • [ 120-80-9 ]
  • [ 1192352-08-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: potassium carbonate 2: nitric acid; acetic acid / dichloromethane 3: hydrogenchloride; tin(ll) chloride / ethanol 4: triethylamine 5: bromine; acetic acid / dichloromethane
Multi-step reaction with 5 steps 1: potassium carbonate / N,N-dimethyl-formamide / 48 h / 100 °C / Inert atmosphere 2: nitric acid; acetic acid / dichloromethane / 41 h / 10 - 20 °C 3: hydrogenchloride; tin(II) chloride hydrate / ethanol; water / 85 °C 4: thionyl chloride; triethylamine / dichloromethane / 6 h / Reflux 5: bromine; acetic acid / dichloromethane / 48 h / 20 °C / Darkness
Multi-step reaction with 5 steps 1: potassium carbonate / acetone / 60 h / 65 °C / Inert atmosphere; Reflux 2: nitric acid; acetic acid / dichloromethane / 51 h / 0 - 20 °C 3: hydrogenchloride; tin(II) chloride hydrate / ethanol; water / 18 h / 85 °C / Inert atmosphere 4: triethylamine; thionyl chloride / dichloromethane / 6 h / 50 °C / Inert atmosphere 5: bromine; hydrogen bromide / 6 h / 120 °C
Multi-step reaction with 5 steps 1.1: potassium hydroxide / ethanol / 40 h / Inert atmosphere; Reflux 2.1: nitric acid / dichloromethane; acetic acid / 10 - 20 °C 2.2: 20 °C 3.1: tin(ll) chloride; hydrogenchloride / ethanol / 85 °C 4.1: triethylamine; thionyl chloride / dichloromethane / 20 h / Inert atmosphere; Reflux 5.1: bromine / dichloromethane; acetic acid / 48 h / 20 °C / Darkness
Multi-step reaction with 5 steps 1: potassium carbonate / acetone / Reflux 2: nitric acid; acetic acid / dichloromethane 3: hydrogen; palladium on activated charcoal / ethanol / 1520.1 Torr 4: thionyl chloride; triethylamine / dichloromethane 5: acetic acid; bromine; sodium acetate / 48 h / 20 °C
Multi-step reaction with 5 steps 1.1: sodium hydroxide / ethanol / 0.5 h / 60 °C 1.2: 40 h / 60 °C 2.1: acetic acid; nitric acid / dichloromethane / 40 h / 10 - 20 °C 3.1: hydrogenchloride; tin(ll) chloride / ethanol; water / 80 °C / Inert atmosphere 4.1: thionyl chloride; triethylamine / dichloromethane / Inert atmosphere; Reflux 5.1: acetic acid; bromine / dichloromethane / 48 h / 20 °C
Multi-step reaction with 5 steps 1: potassium carbonate / N,N-dimethyl-formamide / 48 h / 100 °C / Inert atmosphere 2: nitric acid; sulfuric acid / dichloromethane / 1.5 h / 20 °C 3: hydrogenchloride; tin(ll) chloride / ethanol; water / 85 °C / Inert atmosphere 4: triethylamine; thionyl chloride / dichloromethane / 6 h / Inert atmosphere; Reflux 5: bromine; acetic acid / dichloromethane / 48 h / 20 °C / Darkness

Reference： [1]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]
[2]Li, Yaowen; Chen, Yujin; Liu, Xing; Wang, Zhong; Yang, Xiaoming; Tu, Yingfeng; Zhu, Xiulin [Macromolecules, 2011, vol. 44, # 16, p. 6370 - 6381]
[3]Zeng, Shaohang; Yin, Lunxiang; Ji, Changyan; Jiang, Xueying; Li, Kechang; Li, Yanqin; Wang, Yue [Chemical Communications, 2012, vol. 48, # 86, p. 10627 - 10629]
[4]Chen, Long; Li, Xin; Ying, Weijiang; Zhang, Xiaoyu; Guo, Fuling; Li, Jing; Hua, Jianli [European Journal of Organic Chemistry, 2013, # 9, p. 1770 - 1780]
[5]Cardone, Antonio; Martinelli, Carmela; Losurdo, Maria; Dilonardo, Elena; Bruno, Giovanni; Scavia, Guido; Destri, Silvia; Cosma, Pinalysa; Salamandra, Luigi; Reale, Andrea; Di Carlo, Aldo; Aguirre, Aranzazu; Milian-Medina, Begona; Gierschner, Johannes; Farinola, Gianluca M. [Journal of Materials Chemistry A, 2013, vol. 1, # 3, p. 715 - 727]
[6]Yu, Jiangsheng; Zhao, Baofeng; Nie, Xuemei; Zhou, Baojin; Li, Yang; Hai, Jiefeng; Zhu, Enwei; Bian, Linyi; Wu, Hongbin; Tang, Weihua [New Journal of Chemistry, 2015, vol. 39, # 3, p. 2248 - 2255]
[7]Hu, Zijun; Liu, Kuan [Journal of Polymer Science, Part A: Polymer Chemistry, 2020]
  • 9
  • [ 156777-91-2 ]
  • [ 1192352-08-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: hydrogenchloride; tin(ll) chloride / ethanol 2: triethylamine 3: bromine; acetic acid / dichloromethane
Multi-step reaction with 3 steps 1: hydrogenchloride; tin(II) chloride hydrate / ethanol; water / 85 °C 2: thionyl chloride; triethylamine / dichloromethane / 6 h / Reflux 3: bromine; acetic acid / dichloromethane / 48 h / 20 °C / Darkness
Multi-step reaction with 3 steps 1: hydrogenchloride; tin(II) chloride hydrate / ethanol; water / 18 h / 85 °C / Inert atmosphere 2: triethylamine; thionyl chloride / dichloromethane / 6 h / 50 °C / Inert atmosphere 3: bromine; hydrogen bromide / 6 h / 120 °C
Multi-step reaction with 3 steps 1: tin(ll) chloride; hydrogenchloride / ethanol / 85 °C 2: triethylamine; thionyl chloride / dichloromethane / 20 h / Inert atmosphere; Reflux 3: bromine / dichloromethane; acetic acid / 48 h / 20 °C / Darkness
Multi-step reaction with 3 steps 1: hydrogen; palladium on activated charcoal / ethanol / 1520.1 Torr 2: thionyl chloride; triethylamine / dichloromethane 3: acetic acid; bromine; sodium acetate / 48 h / 20 °C
Multi-step reaction with 3 steps 1: hydrogenchloride; tin(ll) chloride / ethanol; water / 85 °C / Inert atmosphere 2: triethylamine; thionyl chloride / dichloromethane / 6 h / Inert atmosphere; Reflux 3: bromine; acetic acid / dichloromethane / 48 h / 20 °C / Darkness

Reference： [1]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]
[2]Li, Yaowen; Chen, Yujin; Liu, Xing; Wang, Zhong; Yang, Xiaoming; Tu, Yingfeng; Zhu, Xiulin [Macromolecules, 2011, vol. 44, # 16, p. 6370 - 6381]
[3]Zeng, Shaohang; Yin, Lunxiang; Ji, Changyan; Jiang, Xueying; Li, Kechang; Li, Yanqin; Wang, Yue [Chemical Communications, 2012, vol. 48, # 86, p. 10627 - 10629]
[4]Chen, Long; Li, Xin; Ying, Weijiang; Zhang, Xiaoyu; Guo, Fuling; Li, Jing; Hua, Jianli [European Journal of Organic Chemistry, 2013, # 9, p. 1770 - 1780]
[5]Cardone, Antonio; Martinelli, Carmela; Losurdo, Maria; Dilonardo, Elena; Bruno, Giovanni; Scavia, Guido; Destri, Silvia; Cosma, Pinalysa; Salamandra, Luigi; Reale, Andrea; Di Carlo, Aldo; Aguirre, Aranzazu; Milian-Medina, Begona; Gierschner, Johannes; Farinola, Gianluca M. [Journal of Materials Chemistry A, 2013, vol. 1, # 3, p. 715 - 727]
[6]Hu, Zijun; Liu, Kuan [Journal of Polymer Science, Part A: Polymer Chemistry, 2020]
  • 10
  • [ 1192352-08-1 ]
  • [ 162717-58-0 ]
  • [ 1335248-04-8 ]
YieldReaction ConditionsOperation in experiment
92% With palladium diacetate; tris-(o-tolyl)phosphine In toluene at 95℃; for 24h; Inert atmosphere;
Reference： [1]Location in patent: experimental part Yi, Hunan; Al-Faifi, Solyman; Iraqi, Ahmed; Watters, Darren C.; Kingsley, James; Lidzey, David G. [Journal of Materials Chemistry, 2011, vol. 21, # 35, p. 13649 - 13656]
  • 11
  • tributyl(3-dodecylcyclopenta-1,3-dien-1-yl)stannane [ No CAS ]
  • [ 1192352-08-1 ]
  • [ 1325716-61-7 ]
YieldReaction ConditionsOperation in experiment
With bis-triphenylphosphine-palladium(II) chloride In tetrahydrofuran for 24h; Reflux; Inert atmosphere;
Reference： [1]Location in patent: experimental part Li, Yaowen; Chen, Yujin; Liu, Xing; Wang, Zhong; Yang, Xiaoming; Tu, Yingfeng; Zhu, Xiulin [Macromolecules, 2011, vol. 44, # 16, p. 6370 - 6381]
  • 12
  • [ 1192352-08-1 ]
  • [ 1192352-10-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: bis-triphenylphosphine-palladium(II) chloride / tetrahydrofuran / 24 h / Reflux; Inert atmosphere 2: N-Bromosuccinimide; acetic acid / chloroform / 20 h / 20 °C / Darkness
Multi-step reaction with 2 steps 1: tris(dibenzylideneacetone)dipalladium(0) chloroform complex; tris-(o-tolyl)phosphine / tetrahydrofuran / 20 h / Inert atmosphere; Reflux 2: N-Bromosuccinimide / N,N-dimethyl-formamide / 20 h / 20 °C / Darkness
Multi-step reaction with 2 steps 1: bis-triphenylphosphine-palladium(II) chloride / tetrahydrofuran / 40 h / 70 °C / Inert atmosphere 2: N-Bromosuccinimide / chloroform / 24 h / Darkness
Multi-step reaction with 2 steps 1: bis-triphenylphosphine-palladium(II) chloride / tetrahydrofuran / 24 h / Inert atmosphere; Reflux 2: N-Bromosuccinimide / chloroform; acetic acid / 20 °C / Inert atmosphere; Darkness

Reference： [1]Li, Yaowen; Chen, Yujin; Liu, Xing; Wang, Zhong; Yang, Xiaoming; Tu, Yingfeng; Zhu, Xiulin [Macromolecules, 2011, vol. 44, # 16, p. 6370 - 6381]
[2]Sun, Ying; Lin, Baoping; Yang, Hong; Gong, Xiaohui [Polymer, 2012, vol. 53, # 7, p. 1535 - 1542]
[3]Zeng, Shaohang; Yin, Lunxiang; Ji, Changyan; Jiang, Xueying; Li, Kechang; Li, Yanqin; Wang, Yue [Chemical Communications, 2012, vol. 48, # 86, p. 10627 - 10629]
[4]Lee, Tae Ho; Choi, Min Hee; Jeon, Sung Jae; Moon, Doo Kyung [Polymer, 2016, vol. 99, p. 756 - 766]
  • 13
  • [ 1192352-08-1 ]
  • [ 1325716-62-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: bis-triphenylphosphine-palladium(II) chloride / tetrahydrofuran / 24 h / Reflux; Inert atmosphere 2: N-Bromosuccinimide; acetic acid / chloroform / 20 h / 20 °C / Darkness
Reference： [1]Li, Yaowen; Chen, Yujin; Liu, Xing; Wang, Zhong; Yang, Xiaoming; Tu, Yingfeng; Zhu, Xiulin [Macromolecules, 2011, vol. 44, # 16, p. 6370 - 6381]
  • 14
  • [ 1192352-08-1 ]
  • [ 1325716-63-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: bis-triphenylphosphine-palladium(II) chloride / tetrahydrofuran / 24 h / Reflux; Inert atmosphere 2: N-Bromosuccinimide; acetic acid / chloroform / 20 h / 20 °C / Darkness
Reference： [1]Li, Yaowen; Chen, Yujin; Liu, Xing; Wang, Zhong; Yang, Xiaoming; Tu, Yingfeng; Zhu, Xiulin [Macromolecules, 2011, vol. 44, # 16, p. 6370 - 6381]
  • 15
  • [ 1192352-08-1 ]
  • [ 1325716-64-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: bis-triphenylphosphine-palladium(II) chloride / tetrahydrofuran / 24 h / Reflux; Inert atmosphere 2: N-Bromosuccinimide; acetic acid / chloroform / 20 h / 20 °C / Darkness
Reference： [1]Li, Yaowen; Chen, Yujin; Liu, Xing; Wang, Zhong; Yang, Xiaoming; Tu, Yingfeng; Zhu, Xiulin [Macromolecules, 2011, vol. 44, # 16, p. 6370 - 6381]
  • 16
  • [ 1192352-08-1 ]
  • [ 1325716-65-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: bis-triphenylphosphine-palladium(II) chloride / tetrahydrofuran / 24 h / Reflux; Inert atmosphere 2: N-Bromosuccinimide; acetic acid / chloroform / 20 h / 20 °C / Darkness
Reference： [1]Li, Yaowen; Chen, Yujin; Liu, Xing; Wang, Zhong; Yang, Xiaoming; Tu, Yingfeng; Zhu, Xiulin [Macromolecules, 2011, vol. 44, # 16, p. 6370 - 6381]
  • 17
  • [ 1192352-08-1 ]
  • [ 504441-11-6 ]
  • [ 1325716-59-3 ]
YieldReaction ConditionsOperation in experiment
With bis-triphenylphosphine-palladium(II) chloride In tetrahydrofuran for 24h; Reflux; Inert atmosphere;
Reference： [1]Location in patent: experimental part Li, Yaowen; Chen, Yujin; Liu, Xing; Wang, Zhong; Yang, Xiaoming; Tu, Yingfeng; Zhu, Xiulin [Macromolecules, 2011, vol. 44, # 16, p. 6370 - 6381]
  • 18
  • [ 1192352-08-1 ]
  • [ 54663-78-4 ]
  • [ 1192352-09-2 ]
YieldReaction ConditionsOperation in experiment
97% With bis-triphenylphosphine-palladium(II) chloride In toluene at 110℃; Inert atmosphere;
90% With bis-triphenylphosphine-palladium(II) chloride In toluene Inert atmosphere; Reflux;
87% With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; tris-(o-tolyl)phosphine In tetrahydrofuran for 20h; Inert atmosphere; Reflux;
85% With bis-triphenylphosphine-palladium(II) chloride In tetrahydrofuran for 24h; Inert atmosphere; Reflux; 2.3.3. 5,6-bis(octyloxy)-4,7-di(thiophen-2-yl)benzo[c][1,2,5]thiadiazole (3) A0 (0.826 g, 1.5 mmol), tributyl(thiophen-2-yl)stannane (1.231 g 3.3 mmol) and bis(triphenylphosphine)palladium(II) chloride (0.21 g, 0.3 mmol) were dissolved in 30 mL of anhydrous THF in a well-dried round flask under nitrogen atmosphere. After flushing with nitrogen, the reactant was heated to reflux for 24 h. After cooled to room temperature, the reaction mixture was poured into water. The product was extracted with ethyl acetate. The extracts were combined and washed with water and brine, then dried over Na2SO4. The filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on silica to give compound as a deep red crystal (0.710 g, 85%). 1H NMR (400 MHz, CDCl3): d (ppm) 8.47 (d, 2H), 7.50 (d, 2H), 7.23 (t, 2H), 4.10 (t, 4H), 1.91 (m, 4H), 1.41 (m, 4H), 1.34 - 1.29 (m, 16H), 0.89 (t, 6H). m/z 556.
78% With bis-triphenylphosphine-palladium(II) chloride In tetrahydrofuran for 24h; Reflux; Inert atmosphere;
0.96 g With bis-triphenylphosphine-palladium(II) chloride In tetrahydrofuran at 70℃; for 40h; Inert atmosphere;
With tris-(dibenzylideneacetone)dipalladium(0); tris-(o-tolyl)phosphine In toluene for 12h; Reflux;

Reference： [1]Liu, Fangbin; Li, Hui; Wu, Yishi; Gu, Chunling; Fu, Hongbing [RSC Advances, 2015, vol. 5, # 112, p. 92151 - 92158]
[2]Cardone, Antonio; Martinelli, Carmela; Losurdo, Maria; Dilonardo, Elena; Bruno, Giovanni; Scavia, Guido; Destri, Silvia; Cosma, Pinalysa; Salamandra, Luigi; Reale, Andrea; Di Carlo, Aldo; Aguirre, Aranzazu; Milian-Medina, Begona; Gierschner, Johannes; Farinola, Gianluca M. [Journal of Materials Chemistry A, 2013, vol. 1, # 3, p. 715 - 727]
[3]Location in patent: experimental part Sun, Ying; Lin, Baoping; Yang, Hong; Gong, Xiaohui [Polymer, 2012, vol. 53, # 7, p. 1535 - 1542]
[4]Lee, Tae Ho; Choi, Min Hee; Jeon, Sung Jae; Moon, Doo Kyung [Polymer, 2016, vol. 99, p. 756 - 766]
[5]Location in patent: experimental part Li, Yaowen; Chen, Yujin; Liu, Xing; Wang, Zhong; Yang, Xiaoming; Tu, Yingfeng; Zhu, Xiulin [Macromolecules, 2011, vol. 44, # 16, p. 6370 - 6381]
[6]Zeng, Shaohang; Yin, Lunxiang; Ji, Changyan; Jiang, Xueying; Li, Kechang; Li, Yanqin; Wang, Yue [Chemical Communications, 2012, vol. 48, # 86, p. 10627 - 10629]
[7]Jung, In Hwan; Kim, Hoyeon; Lee, Wonho; Jung, Byung Jun; Woo, Han Young; Yoo, Seunghyup; Shim, Hong-Ku [Journal of Nanoscience and Nanotechnology, 2014, vol. 14, # 8, p. 6422 - 6426]
  • 19
  • [ 1192352-08-1 ]
  • (4-decylthiophene-2-yl)tributylstannane [ No CAS ]
  • [ 1325716-60-6 ]
YieldReaction ConditionsOperation in experiment
With bis-triphenylphosphine-palladium(II) chloride In tetrahydrofuran for 24h; Reflux; Inert atmosphere;
Reference： [1]Location in patent: experimental part Li, Yaowen; Chen, Yujin; Liu, Xing; Wang, Zhong; Yang, Xiaoming; Tu, Yingfeng; Zhu, Xiulin [Macromolecules, 2011, vol. 44, # 16, p. 6370 - 6381]
  • 20
  • [ 1192352-08-1 ]
  • tributyl(4-hexyl-2-thienyl)stannane [ No CAS ]
  • [ 1325716-58-2 ]
YieldReaction ConditionsOperation in experiment
With bis-triphenylphosphine-palladium(II) chloride In tetrahydrofuran for 24h; Reflux; Inert atmosphere;
Reference： [1]Location in patent: experimental part Li, Yaowen; Chen, Yujin; Liu, Xing; Wang, Zhong; Yang, Xiaoming; Tu, Yingfeng; Zhu, Xiulin [Macromolecules, 2011, vol. 44, # 16, p. 6370 - 6381]
  • 21
  • 4,5-bis(octyloxy)benzene-1,2-diaminium chloride [ No CAS ]
  • [ 1192352-08-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: thionyl chloride; triethylamine / dichloromethane / 6 h / Reflux 2: bromine; acetic acid / dichloromethane / 48 h / 20 °C / Darkness
Reference： [1]Li, Yaowen; Chen, Yujin; Liu, Xing; Wang, Zhong; Yang, Xiaoming; Tu, Yingfeng; Zhu, Xiulin [Macromolecules, 2011, vol. 44, # 16, p. 6370 - 6381]
  • 22
  • [ 251-41-2 ]
  • [ 1192352-08-1 ]
  • [ 1357562-33-4 ]
YieldReaction ConditionsOperation in experiment
79% Stage #1: thieno[3,2-b]thiophene With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 1h; Inert atmosphere; Stage #2: With trimethyltin(IV)chloride In tetrahydrofuran; hexane at 0 - 20℃; Inert atmosphere; Stage #3: 4,7-dibromo-5,6-bis(octyloxy)benzo-[c][1,2,5]-thiadiazole With bis-triphenylphosphine-palladium(II) chloride In tetrahydrofuran; hexane for 24h; Inert atmosphere; Reflux;
Reference： [1]Location in patent: experimental part Wang, Xiaochen; Sun, Yeping; Chen, Song; Guo, Xia; Zhang, Maojie; Li, Xiaoyu; Li, Yongfang; Wang, Haiqiao [Macromolecules, 2012, vol. 45, # 3, p. 1208 - 1216]
  • 23
  • [ 251-41-2 ]
  • [ 1192352-08-1 ]
  • [ 1357562-34-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / 0 °C / Inert atmosphere 1.2: 0 - 20 °C / Inert atmosphere 1.3: 24 h / Inert atmosphere; Reflux 2.1: N-Bromosuccinimide; acetic acid / chloroform / 20 °C / Darkness; Inert atmosphere
Reference： [1]Wang, Xiaochen; Sun, Yeping; Chen, Song; Guo, Xia; Zhang, Maojie; Li, Xiaoyu; Li, Yongfang; Wang, Haiqiao [Macromolecules, 2012, vol. 45, # 3, p. 1208 - 1216]
  • 24
  • [ 13331-23-2 ]
  • [ 1192352-08-1 ]
  • [ 1393643-24-7 ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran; water Inert atmosphere;
Reference： [1]Location in patent: scheme or table Wang, Xiaochen; Sun, Yeping; Chen, Song; Guo, Xia; Zhang, Maojie; Li, Xiaoyu; Li, Yongfang; Wang, Haiqiao [Macromolecules, 2012, vol. 45, # 3, p. 1208 - 1216]
  • 25
  • [ 6165-68-0 ]
  • [ 1192352-08-1 ]
  • [ 1192352-09-2 ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran; water Inert atmosphere;
Reference： [1]Location in patent: scheme or table Wang, Xiaochen; Sun, Yeping; Chen, Song; Guo, Xia; Zhang, Maojie; Li, Xiaoyu; Li, Yongfang; Wang, Haiqiao [Macromolecules, 2012, vol. 45, # 3, p. 1208 - 1216]
  • 26
  • [ 1192352-08-1 ]
  • [ 1357562-35-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran; water / Inert atmosphere 2: N-Bromosuccinimide; acetic acid / chloroform / Inert atmosphere
Reference： [1]Wang, Xiaochen; Sun, Yeping; Chen, Song; Guo, Xia; Zhang, Maojie; Li, Xiaoyu; Li, Yongfang; Wang, Haiqiao [Macromolecules, 2012, vol. 45, # 3, p. 1208 - 1216]
  • 27
  • [ 1192352-08-1 ]
  • [ 1391851-93-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: acetic acid; zinc / water / 16 h / 60 °C 2: water; acetic acid / 60 °C 3: tetrakis(triphenylphosphine) palladium(0) / toluene / 36 h / Inert atmosphere; Reflux
Reference： [1]Li, Shuang; He, Zhicai; Yu, Jian; Chen, Su'An; Zhong, Aoshu; Wu, Hongbin; Zhong, Cheng; Qin, Jingui; Li, Zhen [Journal of Polymer Science, Part A: Polymer Chemistry, 2012, vol. 50, # 14, p. 2819 - 2828]
  • 28
  • [ 1192352-08-1 ]
  • [ 1391851-94-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: acetic acid; zinc / water / 16 h / 60 °C 2: water; acetic acid / 60 °C 3: tetrakis(triphenylphosphine) palladium(0) / toluene / 36 h / Inert atmosphere; Reflux 4: trichlorophosphate / 1,2-dichloro-ethane / Reflux
Reference： [1]Li, Shuang; He, Zhicai; Yu, Jian; Chen, Su'An; Zhong, Aoshu; Wu, Hongbin; Zhong, Cheng; Qin, Jingui; Li, Zhen [Journal of Polymer Science, Part A: Polymer Chemistry, 2012, vol. 50, # 14, p. 2819 - 2828]
  • 29
  • [ 1192352-08-1 ]
  • 3,6-dibromo-4,5-bis(octyloxy)cyclohexa-3,5-diene-1,2-diamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With acetic acid; zinc In water at 60℃; for 16h;
Reference： [1]Location in patent: experimental part Li, Shuang; He, Zhicai; Yu, Jian; Chen, Su'An; Zhong, Aoshu; Wu, Hongbin; Zhong, Cheng; Qin, Jingui; Li, Zhen [Journal of Polymer Science, Part A: Polymer Chemistry, 2012, vol. 50, # 14, p. 2819 - 2828]
  • 30
  • [ 1192352-08-1 ]
  • [ 1427163-49-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: tetrakis(triphenylphosphine) palladium(0); copper(l) iodide; triethylamine / 24 h / 70 °C / Inert atmosphere 2: tetrabutyl ammonium fluoride / dichloromethane / 0.5 h / 20 °C / Inert atmosphere 3: tetrakis(triphenylphosphine) palladium(0); copper(l) iodide; triethylamine / 24 h / 20 °C / Inert atmosphere
Reference： [1]Du, Chun; Li, Weiwei; Li, Cuihong; Bo, Zhishan [Journal of Polymer Science, Part A: Polymer Chemistry, 2013, vol. 51, # 2, p. 383 - 393]
  • 31
  • [ 1192352-08-1 ]
  • [ 1427163-48-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); copper(l) iodide; triethylamine / 24 h / 70 °C / Inert atmosphere 2: tetrabutyl ammonium fluoride / dichloromethane / 0.5 h / 20 °C / Inert atmosphere
Reference： [1]Du, Chun; Li, Weiwei; Li, Cuihong; Bo, Zhishan [Journal of Polymer Science, Part A: Polymer Chemistry, 2013, vol. 51, # 2, p. 383 - 393]
  • 32
  • [ 1192352-08-1 ]
  • [ 1066-54-2 ]
  • [ 1427163-47-0 ]
YieldReaction ConditionsOperation in experiment
92% With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine at 70℃; for 24h; Inert atmosphere;
Reference： [1]Du, Chun; Li, Weiwei; Li, Cuihong; Bo, Zhishan [Journal of Polymer Science, Part A: Polymer Chemistry, 2013, vol. 51, # 2, p. 383 - 393]
  • 33
  • [ 1192352-08-1 ]
  • [ 1420991-86-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: zinc; acetic acid / 3 h / 80 °C / Inert atmosphere 1.2: 24 h / 60 °C / Inert atmosphere; Reflux 2.1: bis-triphenylphosphine-palladium(II) chloride / toluene / 48 h / 80 °C / Inert atmosphere; Reflux
Reference： [1]Song, Ho Jun; Lee, Tae Ho; Han, Myung Hee; Lee, Jang Yong; Moon, Doo Kyung [Polymer, 2013, vol. 54, # 3, p. 1072 - 1079]
  • 34
  • [ 1192352-08-1 ]
  • [ 1420991-87-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: zinc; acetic acid / 3 h / 80 °C / Inert atmosphere 1.2: 24 h / 60 °C / Inert atmosphere; Reflux 2.1: bis-triphenylphosphine-palladium(II) chloride / toluene / 48 h / 80 °C / Inert atmosphere; Reflux 3.1: N-Bromosuccinimide / tetrahydrofuran / 24 h / 20 °C / Inert atmosphere
Reference： [1]Song, Ho Jun; Lee, Tae Ho; Han, Myung Hee; Lee, Jang Yong; Moon, Doo Kyung [Polymer, 2013, vol. 54, # 3, p. 1072 - 1079]
  • 35
  • [ 1192352-08-1 ]
  • [ 1383842-45-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: zinc; acetic acid / 3 h / 80 °C / Inert atmosphere; Reflux 1.2: 24 h / 60 °C / Inert atmosphere; Reflux 2.1: bis-triphenylphosphine-palladium(II) chloride / toluene / 48 h / 80 °C / Inert atmosphere; Reflux
Reference： [1]Song, Ho Jun; Lee, Tae Ho; Han, Myung Hee; Lee, Jang Yong; Moon, Doo Kyung [Polymer, 2013, vol. 54, # 3, p. 1072 - 1079]
  • 36
  • [ 1192352-08-1 ]
  • [ 1383842-47-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: zinc; acetic acid / 3 h / 80 °C / Inert atmosphere; Reflux 1.2: 24 h / 60 °C / Inert atmosphere; Reflux 2.1: bis-triphenylphosphine-palladium(II) chloride / toluene / 48 h / 80 °C / Inert atmosphere; Reflux 3.1: N-Bromosuccinimide / tetrahydrofuran / 24 h / 20 °C / Inert atmosphere
Reference： [1]Song, Ho Jun; Lee, Tae Ho; Han, Myung Hee; Lee, Jang Yong; Moon, Doo Kyung [Polymer, 2013, vol. 54, # 3, p. 1072 - 1079]
  • 37
  • [ 1192352-08-1 ]
  • [ 134-81-6 ]
  • [ 1420991-84-9 ]
YieldReaction ConditionsOperation in experiment
63.4% Stage #1: 4,7-dibromo-5,6-bis(octyloxy)benzo-[c][1,2,5]-thiadiazole With acetic acid; zinc at 80℃; for 3h; Inert atmosphere; Stage #2: benzil In acetic acid at 60℃; for 24h; Inert atmosphere; Reflux; 4 2.4 5,8-dibromo-6,7-bis(octyloxy)-2,3-diphenylquinoxaline Under a nitrogen atmosphere, 4,7-dibromo-5,6-bis(octyloxy)benzo[c] [1,2,5]thiadiazole (4.0 g, 7.27 mmol) and zinc (5.88 g 90.0 mmol) dust were dissolved in 110 ml acetic acid. The mixture was refluxed for 3 h at 80 °C. After cooling to room temperature, the reaction mixture was washed with a NaOH solution. The solids that resulted after evaporation of the organic solvent and benzil (3.36 g, 15.92 mmol) were dissolved in 110 ml acetic acid. The mixture was refluxed for 1 day at 60 °C. After cooling to room temperature, an orange colored mixture was observed. After filtration, the reaction mixture was purified by column chromatography on silica gel (dichloromethane as eluent) to obtain the product as a green solid (3.2 g, 63.4%) 1H NMR (400 MHz; CDCl3; Me4Si): 7.62(d, 4H; Ar) 7.37(m, 6H; Ar) 4.20(t, 4H; CH2) 1.92(m, 4H; CH2) 1.55(m, 4H; CH2) 1.33(m, 16H; CH2) 0.90(t, 6H; CH3) 13C NMR (100 MHz; CDCl3; Me4Si): 153.81; 152.69; 138.24; 137.14; 130.22; 129.25; 128.30; 117.26; 74.86; 31.88; 30.33; 29.45; 29.31; 26.07; 22.70; 14.13. Anal. Calcd for: C36H44Br2N2O2: C, 62.07; H, 6.37; N, 4.02; O, 4.59 found: C, 61.20; H, 6.44; N, 3.92; O, 4.99.
Reference： [1]Song, Ho Jun; Lee, Tae Ho; Han, Myung Hee; Lee, Jang Yong; Moon, Doo Kyung [Polymer, 2013, vol. 54, # 3, p. 1072 - 1079]
  • 38
  • [ 1192352-08-1 ]
  • [ 84-11-7 ]
  • [ 1383842-43-0 ]
YieldReaction ConditionsOperation in experiment
58.9% Stage #1: 4,7-dibromo-5,6-bis(octyloxy)benzo-[c][1,2,5]-thiadiazole With acetic acid; zinc at 80℃; for 3h; Inert atmosphere; Reflux; Stage #2: 9,10-phenanthrenequinone In acetic acid at 60℃; for 24h; Inert atmosphere; Reflux; 7 2.7 10,13-dibromo-11,12-bis(octyloxy)dibenzo[a,c]phenazine Under a nitrogen atmosphere, 4,7-dibromo-5,6-bis(octyloxy)benzo[c] [1,2,5]thiadiazole (1.75 g, 3.18 mmol) and zinc (2.58 g 39.4 mmol) dust were dissolved in 110 ml acetic acid. The mixture was refluxed for 3 h at 80 °C. After cooling to room temperature, the reaction mixture was washed with a NaOH solution. The solids that resulted after the evaporation of the organic solvent and 9,10-phenanthrenequinone (1.46 g, 7.0 mmol) were dissolved in 110 ml acetic acid. The mixture was refluxed for 1 day at 60 °C. After cooling to room temperature, an orange colored mixture was observed. After filtration, the reaction mixture was purified by column chromatography on silica gel (dichloromethane as eluent) to obtain the product as a light-yellow solid (1.3 g, 58.9%) 1H NMR (400 MHz; CDCl3; Me4Si): 9.29 (d, 2H; Ar) 8.41 (t, 2H; Ar) 7.68 (m, 4H; Ar) 4.27(t, 4H; CH2) 1.96(t, 4H; CH2) 1.59(m, 4H; CH2) 1.42(m, 16H; CH2) 0.91(t, 6H; CH3). 13C NMR (100 MHz; CDCl3; Me4Si): 153.91; 141.80; 137.92; 132.00; 130.49; 129.47; 127.96; 126.71; 122.73; 117.21; 74.94; 31.90; 30.41; 29.50; 29.35; 26.12; 22.72; 14.14. Anal. Calcd for: C36H42Br2N2O2: C, 62.26; H, 6.10; N, 4.03; O, 4.61 Found: C, 60.16; H, 5.78; N, 3.79; O, 5.11.
Reference： [1]Song, Ho Jun; Lee, Tae Ho; Han, Myung Hee; Lee, Jang Yong; Moon, Doo Kyung [Polymer, 2013, vol. 54, # 3, p. 1072 - 1079]
  • 39
  • [ 1192352-08-1 ]
  • [ 201802-67-7 ]
  • 7-bromo-4-[4-(diphenylamino)phenyl]-5,6-bis(octyloxy)benzo[c][1,2,5]thiadiazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
46.3% Stage #1: 4,7-dibromo-5,6-bis(octyloxy)benzo-[c][1,2,5]-thiadiazole With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at 55℃; for 0.5h; Inert atmosphere; Stage #2: 4-(diphenylamino)phenyl boronic acid In tetrahydrofuran; water for 12h; Inert atmosphere; Reflux;
Reference： [1]Chen, Long; Li, Xin; Ying, Weijiang; Zhang, Xiaoyu; Guo, Fuling; Li, Jing; Hua, Jianli [European Journal of Organic Chemistry, 2013, # 9, p. 1770 - 1780]
  • 40
  • [ 1192352-08-1 ]
  • (Z)-2-cyano-3-(4-{7-[4-(diphenylamino)phenyl]-5,6-bis(octyloxy)benzo[c][1,2,5]thiadiazol-4-yl}phenyl)acrylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran; water / 0.5 h / 55 °C / Inert atmosphere 1.2: 12 h / Inert atmosphere; Reflux 2.1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran; water / 0.5 h / 55 °C / Inert atmosphere 2.2: 12 h / Inert atmosphere; Reflux 3.1: ammonium acetate / acetic acid / 12 h / Reflux; Inert atmosphere
Reference： [1]Chen, Long; Li, Xin; Ying, Weijiang; Zhang, Xiaoyu; Guo, Fuling; Li, Jing; Hua, Jianli [European Journal of Organic Chemistry, 2013, # 9, p. 1770 - 1780]
  • 41
  • [ 1192352-08-1 ]
  • (Z)-2-cyano-3-(5-{7-[4-(diphenylamino)phenyl]-5,6-bis(octyloxy)benzo[c][1,2,5]thiadiazol-4-yl}furan-2-yl)acrylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran; water / 0.5 h / 55 °C / Inert atmosphere 1.2: 12 h / Inert atmosphere; Reflux 2.1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran; water / 0.5 h / 55 °C / Inert atmosphere 2.2: 12 h / Inert atmosphere; Reflux 3.1: ammonium acetate / acetic acid / 12 h / Reflux; Inert atmosphere
Reference： [1]Chen, Long; Li, Xin; Ying, Weijiang; Zhang, Xiaoyu; Guo, Fuling; Li, Jing; Hua, Jianli [European Journal of Organic Chemistry, 2013, # 9, p. 1770 - 1780]
  • 42
  • [ 1192352-08-1 ]
  • (Z)-2-cyano-3-(5-{7-[4-(diphenylamino)phenyl]-5,6-bis(octyloxy)benzo[c][1,2,5]thiadiazol-4-yl}thiophen-2-yl)acrylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran; water / 0.5 h / 55 °C / Inert atmosphere 1.2: 12 h / Inert atmosphere; Reflux 2.1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran; water / 0.5 h / 55 °C / Inert atmosphere 2.2: 12 h / Inert atmosphere; Reflux 3.1: ammonium acetate / acetic acid / 12 h / Reflux; Inert atmosphere
Reference： [1]Chen, Long; Li, Xin; Ying, Weijiang; Zhang, Xiaoyu; Guo, Fuling; Li, Jing; Hua, Jianli [European Journal of Organic Chemistry, 2013, # 9, p. 1770 - 1780]
  • 43
  • [ 1192352-08-1 ]
  • 4-{7-[4-(diphenylamino)phenyl]-5,6-bis(octyloxy)benzo[c][1,2,5]thiadiazol-4-yl}benzaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran; water / 0.5 h / 55 °C / Inert atmosphere 1.2: 12 h / Inert atmosphere; Reflux 2.1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran; water / 0.5 h / 55 °C / Inert atmosphere 2.2: 12 h / Inert atmosphere; Reflux
Reference： [1]Chen, Long; Li, Xin; Ying, Weijiang; Zhang, Xiaoyu; Guo, Fuling; Li, Jing; Hua, Jianli [European Journal of Organic Chemistry, 2013, # 9, p. 1770 - 1780]
  • 44
  • [ 1192352-08-1 ]
  • 5-{7-[4-(diphenylamino)phenyl]-5,6-bis(octyloxy)benzo[c][1,2,5]thiadiazol-4-yl}furan-2-carbaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran; water / 0.5 h / 55 °C / Inert atmosphere 1.2: 12 h / Inert atmosphere; Reflux 2.1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran; water / 0.5 h / 55 °C / Inert atmosphere 2.2: 12 h / Inert atmosphere; Reflux
Reference： [1]Chen, Long; Li, Xin; Ying, Weijiang; Zhang, Xiaoyu; Guo, Fuling; Li, Jing; Hua, Jianli [European Journal of Organic Chemistry, 2013, # 9, p. 1770 - 1780]
  • 45
  • [ 1192352-08-1 ]
  • 5-{7-[4-(diphenylamino)phenyl]-5,6-bis(octyloxy)benzo[c][1,2,5]thiadiazol-4-yl}thiophene-2-carbaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran; water / 0.5 h / 55 °C / Inert atmosphere 1.2: 12 h / Inert atmosphere; Reflux 2.1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran; water / 0.5 h / 55 °C / Inert atmosphere 2.2: 12 h / Inert atmosphere; Reflux
Reference： [1]Chen, Long; Li, Xin; Ying, Weijiang; Zhang, Xiaoyu; Guo, Fuling; Li, Jing; Hua, Jianli [European Journal of Organic Chemistry, 2013, # 9, p. 1770 - 1780]
  • 46
  • [ 86723-23-1 ]
  • [ 1192352-08-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: thionyl chloride; triethylamine / dichloromethane 2: acetic acid; bromine; sodium acetate / 48 h / 20 °C
Reference： [1]Cardone, Antonio; Martinelli, Carmela; Losurdo, Maria; Dilonardo, Elena; Bruno, Giovanni; Scavia, Guido; Destri, Silvia; Cosma, Pinalysa; Salamandra, Luigi; Reale, Andrea; Di Carlo, Aldo; Aguirre, Aranzazu; Milian-Medina, Begona; Gierschner, Johannes; Farinola, Gianluca M. [Journal of Materials Chemistry A, 2013, vol. 1, # 3, p. 715 - 727]
  • 47
  • [ 1192352-08-1 ]
  • [ 121359-48-6 ]
  • 4,7-di(thiazol-2-yl)-5,6-dioctyloxy-benzo[c][1,2,5]thiadiazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
97% With tetrakis(triphenylphosphine) palladium(0) In toluene at 115℃; for 48h; Inert atmosphere;
Reference： [1]Zaborova, Elena; Chavez, Patricia; Bechara, Rony; Leveque, Patrick; Heiser, Thomas; Mery, Stephane; Leclerc, Nicolas [Chemical Communications, 2013, vol. 49, # 85, p. 9938 - 9940]
  • 48
  • [ 1192352-08-1 ]
  • 5-(N,N-diphenylamino)-2-(tri-n-butylstannyl)thiophene [ No CAS ]
  • 5-(7-bromo-5,6-bis(octyloxy)benzo[c][1,2,5]thiadiazol-4-yl)-N,N-diphenylthiophen-2-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
40% With tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide for 20h; Reflux; Inert atmosphere;
Reference： [1]Zhang, Xiaoyu; Chen, Long; Li, Xin; Mao, Jiangyi; Wu, Wenjun; Agren, Hans; Hua, Jianli [Journal of Materials Chemistry C, 2014, vol. 2, # 20, p. 4063 - 4072]
  • 49
  • [ 1192352-08-1 ]
  • [ 1383842-42-9 ]
YieldReaction ConditionsOperation in experiment
With sodium tetrahydroborate In tetrahydrofuran at 20℃; for 12h; Inert atmosphere; To a mixture of compound (1) (0.95g, 1.73mmol), dry tetrahydrofuran (THF, 20mL), ethanol (40mL) and sodium borohydride (NaBH4, 0.99g, 25.95mmol) was added a degassed mixture under stirring at 0°C. The mixture was agitated for 12h under the protection of nitrogen at room temperature (RT), and then the mixture was poured into 100mL of distilled water, and extracted with anhydrous diethyl ether (3×20mL). The combined organic layer was dried over anhydrous magnesium sulfate (MgSO4) and the solvent was removed off by rotary evaporation.
With sodium tetrahydroborate In tetrahydrofuran; ethanol at 0 - 20℃; for 12h; Inert atmosphere; 2.1 4.2.1 5,8-Dibromo-2,3-bis(4-methoxyphenyl)-6,7-bis(octyloxy)quinoxaline (3) 4,7-Dibromo-5,6-bis(octyloxy)benzo[c][1,2,5]thiadiazole (1) (1.10g, 2.00mmol) and sodium borohydride (1.14g, 26.00mmol) were mixed with ethanol (40mL) and THF (20mL) at 0°C, and stirred for 12h at room temperature (RT) under nitrogen atmosphere. After quenched with distilled water (100mL), the mixture was extracted with anhydrous diethyl ether (30mL×3). The combined organic layer was dried over anhydrous magnesium sulfate (MgSO4) and filtered. The filtration was distilled to remove off the solvent and the compound 2 of 2,3-diamino-5,6-bis(octyloxy)-1,4-dibromobenzene was obtained and directly used in the next step. To a solution of compound 2 in ethanol (30mL) and acetic acid (60mL) was added 1,2-bis(4-meth-oxyphenyl)ethane-1,2-dione (0.54g, 2.00mmol). The mixture was refluxed under stirring for 12h in nitrogen atmosphere. After cooled to RT, the mixture was extracted with DCM (30mL×3). The combined organic layer was dried over anhydrous MgSO4 and distilled to remove off solvent. The residue was purified by silica gel column chromatography using mixed solvent of petroleum ether (PE)-DCM (V/V, 2/1) as eluent to obtain compound 3 as a yellow solid (1.02g, 67.5%). 1H NMR (400MHz, CDCl3, TMS), δ (ppm): 7.26 (d, J=8.4Hz, 4H), 6.88 (d, J=8.4Hz, 4H), 4.19 (t, J=6.5Hz, 4H), 3.84 (s, 6H), 1.94-1.86 (m, 4H), 1.36-1.25 (m, 20H), 0.90-0.88 (m, 6H). MALDI- TOF MS (m/z) for C38H48Br2N2O2, Calcd: 758.19, Found: 758.24
Reference： [1]Fan, Qunping; Liu, Yu; Xiao, Manjun; Tan, Hua; Wang, Yafei; Su, Wenyan; Yu, Delong; Yang, Renqiang; Zhu, Weiguo [Organic electronics, 2014, vol. 15, # 11, p. 3375 - 3383]
[2]Su, Wenyan; Xiao, Manjun; Fan, Qunping; Zhong, Juan; Chen, Jianhua; Dang, Dongfeng; Shi, Junwei; Xiong, Wenjin; Duan, Xongwei; Tan, Hua; Liu, Yu; Zhu, Weiguo [Organic electronics, 2015, vol. 17, p. 129 - 137]
  • 50
  • [ 1192352-08-1 ]
  • 10,13-dibromo-11,12-bis(octyloxy)phenanthro[4,5-abc]phenazine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium tetrahydroborate / tetrahydrofuran / 12 h / 20 °C / Inert atmosphere 2: acetic acid / 12 h / Reflux; Inert atmosphere
Reference： [1]Fan, Qunping; Liu, Yu; Xiao, Manjun; Tan, Hua; Wang, Yafei; Su, Wenyan; Yu, Delong; Yang, Renqiang; Zhu, Weiguo [Organic electronics, 2014, vol. 15, # 11, p. 3375 - 3383]
  • 51
  • [ 1192352-08-1 ]
  • 11,12-bis(octyloxy)-10,13-di(thiophen-2-yl)phenanthro[4,5-abc]phenazine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: sodium tetrahydroborate / tetrahydrofuran / 12 h / 20 °C / Inert atmosphere 2: acetic acid / 12 h / Reflux; Inert atmosphere 3: tetrakis(triphenylphosphine) palladium(0) / 24 h / Inert atmosphere; Reflux
Reference： [1]Fan, Qunping; Liu, Yu; Xiao, Manjun; Tan, Hua; Wang, Yafei; Su, Wenyan; Yu, Delong; Yang, Renqiang; Zhu, Weiguo [Organic electronics, 2014, vol. 15, # 11, p. 3375 - 3383]
  • 52
  • [ 1192352-08-1 ]
  • 10,13-bis(5-bromothiophen-2-yl)-11,12-bis(octyloxy)-phenanthro[4,5-abc]-phenazine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: sodium tetrahydroborate / tetrahydrofuran / 12 h / 20 °C / Inert atmosphere 2: acetic acid / 12 h / Reflux; Inert atmosphere 3: tetrakis(triphenylphosphine) palladium(0) / 24 h / Inert atmosphere; Reflux 4: N-Bromosuccinimide / 5 h / 20 °C / Inert atmosphere
Reference： [1]Fan, Qunping; Liu, Yu; Xiao, Manjun; Tan, Hua; Wang, Yafei; Su, Wenyan; Yu, Delong; Yang, Renqiang; Zhu, Weiguo [Organic electronics, 2014, vol. 15, # 11, p. 3375 - 3383]
  • 53
  • [ 1192352-08-1 ]
  • 5,8-dibromo-2,3-bis(4-methoxyphenyl)-6,7-bis(octyloxy)quinoxaline [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium tetrahydroborate / ethanol; tetrahydrofuran / 12 h / 0 - 20 °C / Inert atmosphere 2: acetic acid / ethanol / 12 h / Reflux; Inert atmosphere
Reference： [1]Su, Wenyan; Xiao, Manjun; Fan, Qunping; Zhong, Juan; Chen, Jianhua; Dang, Dongfeng; Shi, Junwei; Xiong, Wenjin; Duan, Xongwei; Tan, Hua; Liu, Yu; Zhu, Weiguo [Organic electronics, 2015, vol. 17, p. 129 - 137]
  • 54
  • [ 1192352-08-1 ]
  • 2,3-bis(4-methoxyphenyl)-6,7-bis(octylox)-5,8-di(thiophen-2-yl)quinoxaline [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: sodium tetrahydroborate / ethanol; tetrahydrofuran / 12 h / 0 - 20 °C / Inert atmosphere 2: acetic acid / ethanol / 12 h / Reflux; Inert atmosphere 3: tetrakis(triphenylphosphine) palladium(0) / toluene / 24 h / Reflux; Inert atmosphere
Reference： [1]Su, Wenyan; Xiao, Manjun; Fan, Qunping; Zhong, Juan; Chen, Jianhua; Dang, Dongfeng; Shi, Junwei; Xiong, Wenjin; Duan, Xongwei; Tan, Hua; Liu, Yu; Zhu, Weiguo [Organic electronics, 2015, vol. 17, p. 129 - 137]
  • 55
  • [ 1192352-08-1 ]
  • 5,8-bis(5-bromothiophen-2-yl)-2,3-bis(4-methoxyphenyl)-6,7-bis(octyloxy)quinoxaline [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: sodium tetrahydroborate / ethanol; tetrahydrofuran / 12 h / 0 - 20 °C / Inert atmosphere 2: acetic acid / ethanol / 12 h / Reflux; Inert atmosphere 3: tetrakis(triphenylphosphine) palladium(0) / toluene / 24 h / Reflux; Inert atmosphere 4: N-Bromosuccinimide / tetrahydrofuran / 5 h / 20 °C
Reference： [1]Su, Wenyan; Xiao, Manjun; Fan, Qunping; Zhong, Juan; Chen, Jianhua; Dang, Dongfeng; Shi, Junwei; Xiong, Wenjin; Duan, Xongwei; Tan, Hua; Liu, Yu; Zhu, Weiguo [Organic electronics, 2015, vol. 17, p. 129 - 137]
  • 56
  • [ 1192352-08-1 ]
  • [ 54663-78-4 ]
  • [ 1334686-70-2 ]
YieldReaction ConditionsOperation in experiment
92% With tetrakis(triphenylphosphine) palladium(0) In toluene at 110℃; for 48h; Inert atmosphere;
Reference： [1]Yu, Jiangsheng; Zhao, Baofeng; Nie, Xuemei; Zhou, Baojin; Li, Yang; Hai, Jiefeng; Zhu, Enwei; Bian, Linyi; Wu, Hongbin; Tang, Weihua [New Journal of Chemistry, 2015, vol. 39, # 3, p. 2248 - 2255]
  • 57
  • [ 42244-53-1 ]
  • [ 1192352-08-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: acetic acid; nitric acid / dichloromethane / 40 h / 10 - 20 °C 2: hydrogenchloride; tin(ll) chloride / ethanol; water / 80 °C / Inert atmosphere 3: thionyl chloride; triethylamine / dichloromethane / Inert atmosphere; Reflux 4: acetic acid; bromine / dichloromethane / 48 h / 20 °C
Reference： [1]Yu, Jiangsheng; Zhao, Baofeng; Nie, Xuemei; Zhou, Baojin; Li, Yang; Hai, Jiefeng; Zhu, Enwei; Bian, Linyi; Wu, Hongbin; Tang, Weihua [New Journal of Chemistry, 2015, vol. 39, # 3, p. 2248 - 2255]
  • 58
  • [ 143-15-7 ]
  • [ 1192352-08-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: sodium hydroxide / ethanol / 0.5 h / 60 °C 1.2: 40 h / 60 °C 2.1: acetic acid; nitric acid / dichloromethane / 40 h / 10 - 20 °C 3.1: hydrogenchloride; tin(ll) chloride / ethanol; water / 80 °C / Inert atmosphere 4.1: thionyl chloride; triethylamine / dichloromethane / Inert atmosphere; Reflux 5.1: acetic acid; bromine / dichloromethane / 48 h / 20 °C
Reference： [1]Yu, Jiangsheng; Zhao, Baofeng; Nie, Xuemei; Zhou, Baojin; Li, Yang; Hai, Jiefeng; Zhu, Enwei; Bian, Linyi; Wu, Hongbin; Tang, Weihua [New Journal of Chemistry, 2015, vol. 39, # 3, p. 2248 - 2255]
  • 59
  • [ 171418-24-9 ]
  • [ 1192352-08-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: hydrogenchloride; tin(ll) chloride / ethanol; water / 80 °C / Inert atmosphere 2: thionyl chloride; triethylamine / dichloromethane / Inert atmosphere; Reflux 3: acetic acid; bromine / dichloromethane / 48 h / 20 °C
Reference： [1]Yu, Jiangsheng; Zhao, Baofeng; Nie, Xuemei; Zhou, Baojin; Li, Yang; Hai, Jiefeng; Zhu, Enwei; Bian, Linyi; Wu, Hongbin; Tang, Weihua [New Journal of Chemistry, 2015, vol. 39, # 3, p. 2248 - 2255]
  • 60
  • 4,5-bis(dodecyloxy)benzene-1,2-diaminium chloride [ No CAS ]
  • [ 1192352-08-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: thionyl chloride; triethylamine / dichloromethane / Inert atmosphere; Reflux 2: acetic acid; bromine / dichloromethane / 48 h / 20 °C
Reference： [1]Yu, Jiangsheng; Zhao, Baofeng; Nie, Xuemei; Zhou, Baojin; Li, Yang; Hai, Jiefeng; Zhu, Enwei; Bian, Linyi; Wu, Hongbin; Tang, Weihua [New Journal of Chemistry, 2015, vol. 39, # 3, p. 2248 - 2255]
  • 61
  • [ 1192352-08-1 ]
  • [ 1334686-71-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0) / toluene / 48 h / 110 °C / Inert atmosphere 2: N-Bromosuccinimide / tetrahydrofuran / 18 h / 0 - 20 °C / Darkness
Reference： [1]Yu, Jiangsheng; Zhao, Baofeng; Nie, Xuemei; Zhou, Baojin; Li, Yang; Hai, Jiefeng; Zhu, Enwei; Bian, Linyi; Wu, Hongbin; Tang, Weihua [New Journal of Chemistry, 2015, vol. 39, # 3, p. 2248 - 2255]
  • 62
  • [ 1192352-08-1 ]
  • [ 1461-22-9 ]
  • 5,6-bis(octyloxy)-4,7-bis(5-(tributylstannyl)thiophen-2-yl) benzo[c][1,2,5]thiadiazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
42% Stage #1: 4,7-dibromo-5,6-bis(octyloxy)benzo-[c][1,2,5]-thiadiazole With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 1h; Inert atmosphere; Stage #2: tributyltin chloride In tetrahydrofuran at -78 - 20℃; for 1h;
Reference： [1]Liu, Fangbin; Li, Hui; Wu, Yishi; Gu, Chunling; Fu, Hongbing [RSC Advances, 2015, vol. 5, # 112, p. 92151 - 92158]
  • 63
  • [ 1192352-08-1 ]
  • 5-(7-(4-(bis(4-(octyloxy)phenyl)amino)phenyl)-5,6-bis(octyloxy)benzo[c][1,2,5]thiadiazol-4-yl)thiophene-2-carbaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / water; tetrahydrofuran / 0.25 h / 50 °C / Inert atmosphere 1.2: 6 h / 60 °C / Inert atmosphere 2.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / water; tetrahydrofuran / 0.25 h / 50 °C / Inert atmosphere 2.2: 12 h / Inert atmosphere; Reflux
Reference： [1]Mao, Jiangyi; Zhang, Xiaoyu; Liu, Shih-Hung; Shen, Zhongjin; Li, Xing; Wu, Wenjun; Chou, Pi-Tai; Hua, Jianli [Electrochimica Acta, 2015, vol. 179, p. 179 - 186]
  • 64
  • [ 1192352-08-1 ]
  • C67H84N6O5S3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / water; tetrahydrofuran / 0.25 h / 50 °C / Inert atmosphere 1.2: 6 h / 60 °C / Inert atmosphere 2.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / water; tetrahydrofuran / 0.25 h / 50 °C / Inert atmosphere 2.2: 12 h / Inert atmosphere; Reflux 3.1: sodium hydroxide / water; ethanol / 12 h / Inert atmosphere; Reflux
Reference： [1]Mao, Jiangyi; Zhang, Xiaoyu; Liu, Shih-Hung; Shen, Zhongjin; Li, Xing; Wu, Wenjun; Chou, Pi-Tai; Hua, Jianli [Electrochimica Acta, 2015, vol. 179, p. 179 - 186]
  • 65
  • [ 1192352-08-1 ]
  • (4-{bis[4-(octyloxy)phenyl]amino}phenyl)boronic acid [ No CAS ]
  • 4-(7-bromo-5,6-bis(octyloxy)benzo[c][1,2,5]thiadiazol-4-yl)-N,N-bis(4-(octyloxy)phenyl)aniline [ No CAS ]
YieldReaction ConditionsOperation in experiment
78.1% Stage #1: 4,7-dibromo-5,6-bis(octyloxy)benzo-[c][1,2,5]-thiadiazole With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at 50℃; for 0.25h; Inert atmosphere; Stage #2: (4-{bis[4-(octyloxy)phenyl]amino}phenyl)boronic acid In tetrahydrofuran; water at 60℃; for 6h; Inert atmosphere; 2.3.1. 4-(7-bromobenzo[c][1,2,5]thiadiazol-4-yl)-N,N-bis(4-(octyloxy) phenyl) aniline (1) General procedure: Under an argon atmosphere, a mixture of 4,7-dibromobenzo[c][1,2,5]thiadiazole (290 mg, 1 mmol) and Pd(PPh3)4 (100 mg,0.087 mmol) and K2CO3 (1.00 g, 7.25 mmol) in deionized water (5 mL) and THF (15 mL) was heated to 50°C and stirred for 15 min, then a solution of (4-(bis(4-(octyloxy)phenyl)amino)phenyl)boronic acid (550 mg, 1 mmol) in THF (5 mL) was injected slowly.Then the mixture was heated to 60°C and reacted for 6 h. After cooling down, the raw product was extracted using CH2Cl2 (DCM) and water for three times. The organic layers were combined anddried by anhydrous MgSO4. After filtration, the solvent was removed under reduced pressure and the residue was purified by chromatography on a silica gel column with DCM/PE (petroleumether) (1:3 by volume) to give 1 as red solid (500 mg, 70.1% yield).
Reference： [1]Mao, Jiangyi; Zhang, Xiaoyu; Liu, Shih-Hung; Shen, Zhongjin; Li, Xing; Wu, Wenjun; Chou, Pi-Tai; Hua, Jianli [Electrochimica Acta, 2015, vol. 179, p. 179 - 186]
  • 66
  • [ 1192352-08-1 ]
  • [ 1326239-98-8 ]
  • [ 1357562-33-4 ]
YieldReaction ConditionsOperation in experiment
89% With bis-triphenylphosphine-palladium(II) chloride In tetrahydrofuran for 24h; Inert atmosphere; Reflux; 2.3.4. 5,6-bis(octyloxy)-4,7-di(thieno[3,2-b]thiophen-2-yl)benzo[c][1,2,5]thiadiazole (4) A0 (0.826 g, 1.5 mmol), trimethyl(thieno[3,2-b]thiophen-2-yl)stannane (1.000 g 3.3 mmol) and bis(triphenylphosphine)palladium(II) chloride (0.21 g, 0.3 mmol) were dissolved in 60 mL of anhydrous THF in a well-dried round flask under nitrogen atmosphere. After flushing with nitrogen, the reactant was heated to reflux for 24 h. After cooled to room temperature, the reaction mixture was poured into water. The product was extracted with ethyl acetate. The extracts were combined and washed with water and brine, then dried over Na2SO4. The filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on silica to give compound as a deep red oil (0.893 g, 89%). 1H NMR (400 MHz, CDCl3): d (ppm) 8.80 (s, 2H), 7.46 (d, 2H), 7.31 (d, 2H), 4.16 (t, 4H), 1.98 (m, 4H), 1.455 (m, 4H), 1.33 - 1.28 (m, 16H), 0.89 (t, 6H). m/z 668.
Reference： [1]Lee, Tae Ho; Choi, Min Hee; Jeon, Sung Jae; Moon, Doo Kyung [Polymer, 2016, vol. 99, p. 756 - 766]
  • 67
  • [ 1192352-08-1 ]
  • [ 1326239-98-8 ]
  • [ 1357562-34-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: bis-triphenylphosphine-palladium(II) chloride / tetrahydrofuran / 24 h / Inert atmosphere; Reflux 2: N-Bromosuccinimide / chloroform; acetic acid / 20 °C / Inert atmosphere; Darkness
Reference： [1]Lee, Tae Ho; Choi, Min Hee; Jeon, Sung Jae; Moon, Doo Kyung [Polymer, 2016, vol. 99, p. 756 - 766]
  • 68
  • [ 1192352-08-1 ]
  • [ 133144-35-1 ]
  • [ 1335248-04-8 ]
YieldReaction ConditionsOperation in experiment
92% With bis-triphenylphosphine-palladium(II) chloride In tetrahydrofuran for 24h; Inert atmosphere; Reflux; 2.3.4. 5,6-bis(octyloxy)-4,7-di(thieno[3,2-b]thiophen-2-yl)benzo[c][1,2,5]thiadiazole (4) A0 (0.826 g, 1.5 mmol), 2,2'-bithiophen-5-yltrimethylstannane (1.086 g 3.3 mmol) and bis(triphenylphosphine)palladium(II) chloride (0.21 g, 0.3 mmol) were dissolved in 60 mL of anhydrous THF in a well-dried round flask under nitrogen atmosphere. After flushing with nitrogen, the reactant was heated to reflux for 24 h. After cooled to room temperature, the reaction mixture was poured into water. The product was extracted with ethyl acetate. The extracts were combined and washed with water and brine, then dried over Na2SO4. The filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on silica to give compound as a deep red crystal (0.995 g, 92%). 1H NMR (400 MHz, CDCl3): d (ppm) 8.51 (d, 2H), 7.31 (d, 2H), 7.29 (d, 2H), 7.27 (d, 2H), 7.07 (t, 2H), 4.17 (t, 4H), 1.98 (m, 4H), 1.50 (m, 4H), 1.36 - 1.29 (m, 16H), 0.88 (t, 6H). m/z 720.
Reference： [1]Lee, Tae Ho; Choi, Min Hee; Jeon, Sung Jae; Moon, Doo Kyung [Polymer, 2016, vol. 99, p. 756 - 766]
  • 69
  • [ 1192352-08-1 ]
  • 4-(5-bromo-thiophen-2-yl)-7-(5'-octyl-[2,2']bithiophenyl-5-yl)-5,6-bis-octyloxy-benzo[1,2,5]thiadiazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide / 24 h / 90 °C / Inert atmosphere 2.1: n-butyllithium / tetrahydrofuran; hexane / 4 h / -70 °C 2.2: 18 h / 23 °C 2.3: 6 h / 80 °C / Sonication; Inert atmosphere 3.1: N-Bromosuccinimide / tetrahydrofuran / 18 h / 23 °C / Darkness
Reference： [1]Current Patent Assignee: MERCK KGAA - KR2015/24386, 2015, A
  • 70
  • [ 1192352-08-1 ]
  • 4-(5'-octyl-[2,2']bithiophenyl-5-yl)-5,6-bis-octyloxy-benzo[1,2,5]thiadiazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide / 24 h / 90 °C / Inert atmosphere 2.1: n-butyllithium / tetrahydrofuran; hexane / 4 h / -70 °C 2.2: 18 h / 23 °C 2.3: 6 h / 80 °C / Sonication; Inert atmosphere
Reference： [1]Current Patent Assignee: MERCK KGAA - KR2015/24386, 2015, A
  • 71
  • [ 1192352-08-1 ]
  • [ 54663-78-4 ]
  • 4-bromo-5,6-bis-octyloxy-7-thiophen-2-yl-benzo[1,2,5]thiadiazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
44% With bis-triphenylphosphine-palladium(II) chloride In N,N-dimethyl-formamide at 90℃; for 24h; Inert atmosphere; 1.2 Synthesis of 4-bromo-5,6-bis-octyloxy-7-thiophen-2-yl-benzo[1,2,5]thiadiazole 4,7-dibromo-5,6-bis-octyloxy-benzo[1,2,5]thiadiazole (10 g; 18 mmol), Bis(triphenylphosphine)palladium(II) chloride (0.25 g; 0.36 mmol) and tributyl-thiophen-2-yl-stannane (5.7 ml; 18 mmol) were dissolved in degassed dry N,N-dimethylformamide (180 cm3). The reaction mixture was heated at 90°C for 24 hours under nitrogen. The N,N-dimethylformamide was evaporated in vacuo and the resulting oil was dissolved in petroleum ether (50 cm3) and purified by column chromatography (using petroleum ether 40-60 °C and dichloromethane mixture 70:30 as eluent; Silica gel) to give the desired product as a yellow oil (4.4 g, 44%).
Reference： [1]Current Patent Assignee: MERCK KGAA - KR2015/24386, 2015, A Location in patent: Paragraph 0349-0351
  • 72
  • [ 1192352-08-1 ]
  • [ 1066-54-2 ]
  • [ 1427163-48-1 ]
YieldReaction ConditionsOperation in experiment
40% Stage #1: 4,7-dibromo-5,6-bis(octyloxy)benzo-[c][1,2,5]-thiadiazole; trimethylsilylacetylene With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 70℃; for 24h; Inert atmosphere; Stage #2: With potassium fluoride In methanol; dichloromethane for 4h; Reflux;
Reference： [1]Hu, Zijun; Liu, Kuan [Journal of Polymer Science, Part A: Polymer Chemistry, 2020]
  • 73
  • [ 1192352-08-1 ]
  • [ 86134-26-1 ]
  • C48H70Br2N4O4S3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
24% With tetrakis(triphenylphosphine) palladium(0) In toluene for 24h; Inert atmosphere; Reflux; Synthesis of compound M2 Compound 4a (1.0 g, 1.82 mmol) and 2,5-bis(trimethylstannyl)thiophene (0.15 g, 0.36 mmol) were placed under argon in a two-necked round-bottom flask equipped with a reflux condenser. Then toluene (50 mL) and tetrakis(triphenylphosphine)palladium(0) (10 mg) were added. The mixture was heated at reflux within 24 h, and then the solvent was removed by reduced pressure evaporation. Crude product was purified by column chromatography (toluene/hexane, 1:2) to give M2. Yield = 24 %. 1H NMR (CDCl3, 600 MHz, δ): 8.51 (s, 2H), 4.20 (t, J=13.32 Hz, 4H), 4.12 (t, J=14.93 Hz, 4H), 1.92 (m, 4H), 1.55 (m, 4H), 1.21-1.43 (m, 40H), 0.88 (t, J=13.83 Hz, 6H), 0.81 (t, J=13.72 Hz, 6H) ppm. 13C NMR (CDCl3, 126 MHz, δ): 154.79, 152.08, 151.64, 149.98, 135.85, 130.77, 118.52, 105.23, 31.85, 30.35, 29.51, 29.33, 26.12, 26.00, 22.65, 14.07 ppm. ESI, m/z =1022,0 ([M-H]-) Chemical analysis (%) for C48H70Br2N4O4S3: C, 56.35; H, 6.90; Br, 15.62; N, 5.48; O, 6.26; S, 9.40; found C, 56.46; H, 6.83; N, 5.50; S, 9.19.
Reference： [1]Kuznetsov, Petr M.; Nikitenko, Sergey L.; Kuznetsov, Ilya E.; Proshin, Pavel I.; Revina, Daria V.; Troshin, Pavel A.; Akkuratov, Alexander V. [Tetrahedron Letters, 2020, vol. 61, # 26]
  • 74
  • [ 1192352-08-1 ]
  • [ 54663-78-4 ]
  • 2,5-bis(tributylstannyl)thiophene [ No CAS ]
  • (2,5-bis(5,6-bis(octyloxy)-7-(thiophen-2-yl)benzo[c][1,2,5]thiadiazol-4-yl)thiophene) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 4,7-dibromo-5,6-bis(octyloxy)benzo-[c][1,2,5]-thiadiazole; tributyl(thien-2-yl)stannane With tetrakis(triphenylphosphine) palladium(0) In toluene for 24h; Inert atmosphere; Reflux; Stage #2: 2,5-bis(tributylstannyl)thiophene In toluene for 24h; Inert atmosphere; Reflux; 4.2. Synthesis of A3-A8 General procedure: Corresponding dibrominated derivatives of acceptor building blocks(3 eq) and 2-(tributylstannyl) thiophene (1 eq) were dissolved inanhydrous toluene (50 mL) in a three-necked round-bottom flask. Themixture was deaerated and Pd(PPh3)4 (0.023 g, 0.015 eq) was addedunder argon. The mixture was heated at refilux for 24 h and then cooledto the room temperature. 2,5-bis(tributylstannyl)thiophene (7 eq) wasadded and reaction mixture was heated at refilux for another 24 h. Aftercooling to room temperature, the mixture was washed with water,organic phase collected, dried over MgSO4 and concentrated at the rotaryevaporator. The target compounds A3-A8 were separated from theside products and starting compounds by column chromatography onSiO2 (light petroleum-toluene mixtures as eluent) and further purifiedby preparative GPC.A3 (2,5-bis(5,6-bis(octyloxy)-7-(thiophen-2-yl)benzo[c][1,2,5]thiadiazol-4-yl)thiophene):1H NMR (CDCl3, 500 MHz): (ppm) 8.60 (s, 2H),8.50 (dd, J = 4.1 Hz, 1.2 Hz, 2H), 7.52 (dd, J = 4.1 Hz, 1.2 Hz, 2H), 7.25(m, 2H), 4.15 (m, 8H), 1.95-2.01 (m, 8H), 1.47 (m, 8H), 1.23-1.35 (m,36H), 0.90 (t, J = 6.7 Hz, 6H), 0.83 (t, J = 6.9 Hz, 6H) 13C NMR (CDCl3,126 MHz): (ppm) 152.38, 152.24, 151.24, 136.37, 134.38, 130.72,127.48, 126.93, 118.01, 117.75, 74.59, 74.54, 32.01, 30.61, 30.54,29.82, 29.71, 29.50, 29.46, 26.20, 26.18, 22.84, 22.80, 14.27, 14.21Calculated for C56H76N4O4S5 C, 65.33; H, 7.44; N, 5.44; O, 6.22; S,15.57, Found: C 65.02, H 7.52, N 5.51, S 15.48.
Reference： [1]Akkuratov, Alexander V.; Klimovich, Irina V.; Martynov, Ilya V.; Mazaleva, Olga; Peregudov, Alexander S.; Prudnov, Fedor A.; Shestakov, Alexander F.; Troshin, Pavel A.; Tukachev, Nikita V.; Zhugayevych, Andriy [Dyes and Pigments, 2021, vol. 185]
  • 75
  • [ 1192352-08-1 ]
  • (2,5-bis(7-(5-bromothiophen-2-yl)-5,6-bis(octyloxy)benzo[c][1,2,5]thiadiazol-4-yl)thiophene) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: tetrakis(triphenylphosphine) palladium(0) / toluene / 24 h / Inert atmosphere; Reflux 1.2: 24 h / Inert atmosphere; Reflux 2.1: N-Bromosuccinimide / 1,2-dichloro-benzene / 1 h / 60 °C
Reference： [1]Akkuratov, Alexander V.; Klimovich, Irina V.; Martynov, Ilya V.; Mazaleva, Olga; Peregudov, Alexander S.; Prudnov, Fedor A.; Shestakov, Alexander F.; Troshin, Pavel A.; Tukachev, Nikita V.; Zhugayevych, Andriy [Dyes and Pigments, 2021, vol. 185]
  • 76
  • [ 1192352-08-1 ]
  • (4,4-bis(2-ethylhexyl)-4H-cyclopenta[2,1-b:3,4-b’]dithiophen-2-yl)trimethylstannane [ No CAS ]
  • C72H108N2O2S5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran
Reference： [1]Shi, Yanan; Pan, Junxiu; Zhang, Hao; Yang, Chen; Zhang, Ziqi; Deng, Dan; Zhang, Jianqi; Lu, Kun; Wei, Zhixiang [Organic electronics, 2021, vol. 93]

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