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Quality Control of [ 189358-30-3 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 189358-30-3 ]

Product Details of [ 189358-30-3 ]

CAS No. :	189358-30-3	MDL No. :	MFCD11504864
Formula :	C₈H₈B₂O₄S₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	GERFEEQVJFVEBC-UHFFFAOYSA-N
M.W :	253.90	Pubchem ID :	46739143
Synonyms :

Safety of [ 189358-30-3 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P264-P270-P301+P312-P330-P501	UN#:	N/A
Hazard Statements:	H302	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 189358-30-3 ]

* 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 [ 189358-30-3 ]

[ 189358-30-3 ] Synthesis Path-Downstream 1~26

1
[ 189358-30-3 ]
(10bR,10cS)-2,7-Di-tert-butyl-4,9-diiodo-10b,10c-dimethyl-10b,10c-dihydro-pyrene [ No CAS ]
thiophene-dimethyldihydropyrene copolymer, low molecular weight, n ca.5 [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With sodium hydrogencarbonate In 1,2-dimethoxyethane

Reference： [1]Marsella, Michael J.; Wang, Zhi-Qiang; Mitchell, Reginald H. [Organic Letters, 2000, vol. 2, # 19, p. 2979 - 2982]

2
[ 146697-85-0 ]
[ 189358-30-3 ]
5,5'-bis[1''-[2'''-(trimethylsilyl)ethoxy]methyl}-imidazol-2''-yl]-2,2'-bithiophene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
29%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium hydrogencarbonate In 1,2-dimethoxyethane at 70℃; for 18h;

Reference： [1]Murata, Tsuyoshi; Morita, Yasushi; Nakasuji, Kazuhiro [Tetrahedron, 2005, vol. 61, # 25, p. 6056 - 6063]

3
[ 189358-30-3 ]
[ 518329-44-7 ]
5,5'-bis[1''-[2'''-(trimethylsilyl)ethoxy]methyl}-imidazol-4''-yl]-2,2'-bithiophene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
49%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium hydrogencarbonate In 1,2-dimethoxyethane at 70℃; for 18h;

Reference： [1]Murata, Tsuyoshi; Morita, Yasushi; Nakasuji, Kazuhiro [Tetrahedron, 2005, vol. 61, # 25, p. 6056 - 6063]

4
[ 1001590-56-2 ]
[ 189358-30-3 ]
[5'''''-(3,4,5-Tris-dodecyloxy-benzoyl)-[2,2';5',2'';5'',2''';5''',2'''';5'''',2''''']sexithiophen-5-yl]-(3,4,5-tris-dodecyloxy-phenyl)-methanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In tetrahydrofuran at 60℃; for 28h;

Reference： [1]Yasuda, Takuma; Kishimoto, Kenji; Kato, Takashi [Chemical Communications, 2006, # 32, p. 3399 - 3401]

5
[ 1001590-57-3 ]
[ 189358-30-3 ]
C₁₂₂H₁₉₀O₈S₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In tetrahydrofuran at 60℃; for 28h;

Reference： [1]Yasuda, Takuma; Kishimoto, Kenji; Kato, Takashi [Chemical Communications, 2006, # 32, p. 3399 - 3401]

6
[ 1001590-58-4 ]
[ 189358-30-3 ]
C₁₄₆H₂₃₈O₈S₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In tetrahydrofuran at 60℃; for 28h;

Reference： [1]Yasuda, Takuma; Kishimoto, Kenji; Kato, Takashi [Chemical Communications, 2006, # 32, p. 3399 - 3401]

7
[ 492-97-7 ]
[ 189358-30-3 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 2,2'-Bithiophene With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 3h; Stage #2: With Triisopropyl borate In tetrahydrofuran; hexane for 13h; cooling;

Reference： [1]Sakamoto, Kazuya; Takashima, Yoshinori; Yamaguchi, Hiroyasu; Harada, Akira [Journal of Organic Chemistry, 2007, vol. 72, # 2, p. 459 - 465]

8
[ 107-21-1 ]
[ 189358-30-3 ]
[ 925246-82-8 ]

Yield	Reaction Conditions	Operation in experiment
53%	In toluene at 80℃;

Reference： [1]Sakamoto, Kazuya; Takashima, Yoshinori; Yamaguchi, Hiroyasu; Harada, Akira [Journal of Organic Chemistry, 2007, vol. 72, # 2, p. 459 - 465]

9
[ 189358-30-3 ]
[ 737761-33-0 ]
polymer, M_w 4570, M_w/M_n 1.24 by GPC; monomer(s): 2,2\-bithiophene-5,5\-diboronic acid; tetra(4-bromobiphenyl)silane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
42%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In tetrahydrofuran for 16h; Heating;

Reference： [1]Liu, Xue-Ming; Lin, Tingting; Huang, Junchao; Hao, Xiao-Tao; Ong, Kian Soo; He, Chaobin [Macromolecules, 2005, vol. 38, # 10, p. 4157 - 4168]

10
[ 189358-30-3 ]
5,5'-bis(4''-imidazolyl)-2,2'-bithiophene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 49 percent / Pd(PPh₃)4; aq. NaHCO₃ / 1,2-dimethoxy-ethane / 18 h / 70 °C 2: 97 percent / aq. HCl / ethanol / 3 h / Heating

Reference： [1]Murata, Tsuyoshi; Morita, Yasushi; Nakasuji, Kazuhiro [Tetrahedron, 2005, vol. 61, # 25, p. 6056 - 6063]

11
[ 189358-30-3 ]
5,5'-bis(2''-imidazolyl)-2,2'-bithiophene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 29 percent / Pd(PPh₃)4; aq. NaHCO₃ / 1,2-dimethoxy-ethane / 18 h / 70 °C 2: 97 percent / aq. HCl / ethanol / 3 h / Heating

Reference： [1]Murata, Tsuyoshi; Morita, Yasushi; Nakasuji, Kazuhiro [Tetrahedron, 2005, vol. 61, # 25, p. 6056 - 6063]

12
[ 860438-16-0 ]
[ 189358-30-3 ]
poly(5,5''-dibromo-3',4'-dibutyl-4,4''-diperfluorobutyl[2,2';5',2'']terthiophene-co-2,2'-dithiophene-5,5'-diboric acid) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
31%	With sodium carbonate In water; benzene for 24h; Heating / reflux;	1 COMPARATIVE EXAMPLE 1Comparative Compound (A) shown below was prepared for comparison with Exemplifying compound (IV-36), a ϖ-conjugated compound of the present invention. The preparation process is described below.Tetrakis(triphenylphosphine)palladium (0.04 mmol) and 3 mL of an aqueous 2N sodium carbonate solution were added to a mixture solution of 5,5-dibromo-3',4'-dibutyl-4,4-diperfluorobutyl-[2,2';5',2]terthiophene (2 mmol) and 2,2'-dithiophene-5,5'-diboric acid (2 mmol) in 10 mL of benzene in a nitrogen atmosphere. The resulting mixture was refluxed for 24 hours. The reaction mixture was poured into a large amount of acetone to obtain a crude product of Comparative Compound (A). This crude product was purified by repeated reprecipitation to obtain the intended Comparative Compound (A) in a 31% yield. The obtained Comparative Compound (A) had a molecular weight of Mn: 19,300; Mw: 31,800 according to GPC measurement (solvent: chloroform).A field effect type organic transistor was prepared in the same manner as in Example 4 except that Comparative Compound (A) was used in place of Exemplifying compound (IV-36) used in Example 4. The mobility was measured in the same manner as in Example 4. The results are shown below.

Reference： [1]Current Patent Assignee: CANON INC. - US7462726, 2008, B2 Location in patent: Page/Page column 24-25

13
5,5''''-dibromo-3',4',3''',4'''-tetradecyl-4,4''''-diperfluorooctyl[2,2';5',2'';5'',2''';5''',2'''']quinquethiophene [ No CAS ]
[ 189358-30-3 ]
poly(5,5''''-dibromo-3',4',3''',4'''-tetradecyl-4,4''''-diperfluorooctyl[2,2';5',2'';5'',2''';5''',2'''']quinquethiophene-co-2,2'-dithiophene-5,5'-diboric acid) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
28%	With sodium carbonate In water; benzene for 24h; Heating / reflux;	3 COMPARATIVE EXAMPLE 2Comparative Compound (B) shown below was prepared for comparison with Exemplifying compound (IV-10), a ϖ-conjugated compound of the present invention. The preparation process is described below.Tetrakis(triphenylphosphine)palladium (0.02 mmol) and 3 mL of an aqueous 2N sodium carbonate solution were added to a mixture liquid of 5,5-dibromo-3,4-dibutyl-3',4'-diperfluorobutyl-[2,2';5',2;5,2';5',2]quinquethiophene (1.0 mmol), 4,4'-biphenyl-bisboric acid (1.0 mmol), and 8 mL of benzene in a nitrogen atmosphere. The resulting mixture was refluxed for 24 hours. The reaction mixture was poured into a large amount of acetone to obtain a crude product. This crude product was purified by repeated reprecipitation to obtain the intended Comparative Compound (B) in a 29% yield. The obtained Comparative Compound (B) had a molecular weight of Mn: 21,300; Mw: 30,000 according to GPC measurement (solvent: chloroform).A field effect type organic transistor was prepared in the same manner as in Example 5 except that Comparative Compound (B) was used in place of Exemplifying compound (IV-10) used in Example 5. The mobility was measured in the same manner as in Example 4. The results are shown below.

Reference： [1]Current Patent Assignee: CANON INC. - US7462726, 2008, B2 Location in patent: Page/Page column 27

14
[ 1080498-61-8 ]
[ 189358-30-3 ]
[ 1082540-33-7 ]

Yield	Reaction Conditions	Operation in experiment
	With palladium diacetate; potassium carbonate; tris-(o-tolyl)phosphine In N,N-dimethyl-formamide at 90℃; for 4h; Inert atmosphere;

Reference： [1]Sharmoukh; Ko, Kyoung Chul; Park, So Yeon; Ko, Ju Hong; Lee, Ji Min; Noh, Changho; Lee, Jin Yong; Son, Seung Uk [Organic Letters, 2008, vol. 10, # 23, p. 5365 - 5368]

15
[ 1053242-36-6 ]
[ 189358-30-3 ]
[ 1369484-62-7 ]

Yield	Reaction Conditions	Operation in experiment
11%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate In 1,2-dimethoxyethane; water Reflux;	4.2.1. 2,5'-Di-n-butylquaterthiophene (1a) A mixture of n-butyl-iodothiophene 3a (0.99 g, 4.37 mmol), Pd(PPh3)4 (0.28 g, 0.24 mmol), and sodium carbonate (2.0 g) in 1,2-dimethoxyethane (20 ml) and water (30 ml) was heated under reflux, and a solution of 2,5'-bithiophene boronic acid 5 (0.55 g, 2.19 mmol) in 1,2-dimethoxyethane (20 ml) was added dropwise. The mixture was heated under reflux overnight and cooled. After quenching with water (50 ml), the aqueous layer was extracted with CS2 three times. The combined organic layers were washed with water and dried over anhydrous MgSO4. After evaporation of the solvent, the crude product was purified by silica gel column chromatography using hexane/CS2 (1:1, v/v) and finally CS2 as eluent, and recrystallization from chloroform/hexane to afford 1 as a pale yellow solid (0.11 g, 11%). Mp=175 °C (TG/DTA). IR (KBr, cm-1): 3077, 2924, 2858, 2364, 1751, 1458, 1373, 1192, 1076, 794. 1H NMR (300 MHz, CDCl3): δ 0.96 (t, 6H, J=7.4 Hz), 1.42 (m, 4H), 1.69 (m, 4H), 2.82 (t, 4H, J=7.5 Hz), 6.98 (d, 2H, J=0.96 Hz), 7.05 (q, 4H, J=3.3 Hz), 7.14 (d, 2H, J=0.9 Hz). 13C NMR (300 MHz, CDCl3): δ 13.83, 22.18, 29.77, 33.63, 117.07, 122.82, 123.47, 123.85, 134.67, 135.41, 138.29, 146.96. MS (EIMS, m/z): 442 (M+). Elemental analysis: calcd for C24H26S4: C, 65.16; H, 5.88; S, 28.96. Found: C, 65.05; H, 5.70; S, 28.78.

Reference： [1]Location in patent: experimental part Ashizawa, Minoru; Niimura, Takuro; Yu, Yan; Tsuboi, Kazuma; Matsumoto, Hidetoshi; Yamada, Ryo; Kawauchi, Susumu; Tanioka, Akihiko; Mori, Takehiko [Tetrahedron, 2012, vol. 68, # 13, p. 2790 - 2798]

16
2-n-octyl-5-iodothiophene [ No CAS ]
[ 189358-30-3 ]
5,5'''-dioctyl-2,2',5',2'',5'',2'''-quaterthiophene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
7%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate In 1,2-dimethoxyethane; water Reflux;	4.2.1. 2,5'-Di-n-butylquaterthiophene (1a) General procedure: A mixture of n-butyl-iodothiophene 3a (0.99 g, 4.37 mmol), Pd(PPh3)4 (0.28 g, 0.24 mmol), and sodium carbonate (2.0 g) in 1,2-dimethoxyethane (20 ml) and water (30 ml) was heated under reflux, and a solution of 2,5'-bithiophene boronic acid 5 (0.55 g, 2.19 mmol) in 1,2-dimethoxyethane (20 ml) was added dropwise. The mixture was heated under reflux overnight and cooled. After quenching with water (50 ml), the aqueous layer was extracted with CS2 three times. The combined organic layers were washed with water and dried over anhydrous MgSO4. After evaporation of the solvent, the crude product was purified by silica gel column chromatography using hexane/CS2 (1:1, v/v) and finally CS2 as eluent, and recrystallization from chloroform/hexane to afford 1 as a pale yellow solid (0.11 g, 11%).

17
[ 710338-91-3 ]
[ 189358-30-3 ]
5,5'''-dihexyl-2,2':5',2'':5'',2'''-quaterthiophene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
20%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate In 1,2-dimethoxyethane; water Reflux;	4.2.1. 2,5'-Di-n-butylquaterthiophene (1a) General procedure: A mixture of n-butyl-iodothiophene 3a (0.99 g, 4.37 mmol), Pd(PPh3)4 (0.28 g, 0.24 mmol), and sodium carbonate (2.0 g) in 1,2-dimethoxyethane (20 ml) and water (30 ml) was heated under reflux, and a solution of 2,5'-bithiophene boronic acid 5 (0.55 g, 2.19 mmol) in 1,2-dimethoxyethane (20 ml) was added dropwise. The mixture was heated under reflux overnight and cooled. After quenching with water (50 ml), the aqueous layer was extracted with CS2 three times. The combined organic layers were washed with water and dried over anhydrous MgSO4. After evaporation of the solvent, the crude product was purified by silica gel column chromatography using hexane/CS2 (1:1, v/v) and finally CS2 as eluent, and recrystallization from chloroform/hexane to afford 1 as a pale yellow solid (0.11 g, 11%).

18
[ 1261867-49-5 ]
[ 189358-30-3 ]
[ 1369484-64-9 ]

Yield	Reaction Conditions	Operation in experiment
30%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate In 1,2-dimethoxyethane; water Reflux;	4.2.1. 2,5'-Di-n-butylquaterthiophene (1a) General procedure: A mixture of n-butyl-iodothiophene 3a (0.99 g, 4.37 mmol), Pd(PPh3)4 (0.28 g, 0.24 mmol), and sodium carbonate (2.0 g) in 1,2-dimethoxyethane (20 ml) and water (30 ml) was heated under reflux, and a solution of 2,5'-bithiophene boronic acid 5 (0.55 g, 2.19 mmol) in 1,2-dimethoxyethane (20 ml) was added dropwise. The mixture was heated under reflux overnight and cooled. After quenching with water (50 ml), the aqueous layer was extracted with CS2 three times. The combined organic layers were washed with water and dried over anhydrous MgSO4. After evaporation of the solvent, the crude product was purified by silica gel column chromatography using hexane/CS2 (1:1, v/v) and finally CS2 as eluent, and recrystallization from chloroform/hexane to afford 1 as a pale yellow solid (0.11 g, 11%).

19
[ 1369484-78-5 ]
[ 189358-30-3 ]
[ 1369484-66-1 ]

Yield	Reaction Conditions	Operation in experiment
21%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate In 1,2-dimethoxyethane; water Reflux;	4.2.1. 2,5'-Di-n-butylquaterthiophene (1a) General procedure: A mixture of n-butyl-iodothiophene 3a (0.99 g, 4.37 mmol), Pd(PPh3)4 (0.28 g, 0.24 mmol), and sodium carbonate (2.0 g) in 1,2-dimethoxyethane (20 ml) and water (30 ml) was heated under reflux, and a solution of 2,5'-bithiophene boronic acid 5 (0.55 g, 2.19 mmol) in 1,2-dimethoxyethane (20 ml) was added dropwise. The mixture was heated under reflux overnight and cooled. After quenching with water (50 ml), the aqueous layer was extracted with CS2 three times. The combined organic layers were washed with water and dried over anhydrous MgSO4. After evaporation of the solvent, the crude product was purified by silica gel column chromatography using hexane/CS2 (1:1, v/v) and finally CS2 as eluent, and recrystallization from chloroform/hexane to afford 1 as a pale yellow solid (0.11 g, 11%).

20
[ 189358-30-3 ]
[ 98593-05-6 ]
[ 1286715-24-9 ]

Yield	Reaction Conditions	Operation in experiment
12%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate In 1,2-dimethoxyethane; water Reflux;	4.2.1. 2,5'-Di-n-butylquaterthiophene (1a) General procedure: A mixture of n-butyl-iodothiophene 3a (0.99 g, 4.37 mmol), Pd(PPh3)4 (0.28 g, 0.24 mmol), and sodium carbonate (2.0 g) in 1,2-dimethoxyethane (20 ml) and water (30 ml) was heated under reflux, and a solution of 2,5'-bithiophene boronic acid 5 (0.55 g, 2.19 mmol) in 1,2-dimethoxyethane (20 ml) was added dropwise. The mixture was heated under reflux overnight and cooled. After quenching with water (50 ml), the aqueous layer was extracted with CS2 three times. The combined organic layers were washed with water and dried over anhydrous MgSO4. After evaporation of the solvent, the crude product was purified by silica gel column chromatography using hexane/CS2 (1:1, v/v) and finally CS2 as eluent, and recrystallization from chloroform/hexane to afford 1 as a pale yellow solid (0.11 g, 11%).

21
[ 1268704-11-5 ]
[ 189358-30-3 ]
2,5'-bis(3-(N-nonyl-N-benzoylamino)-5-(N'-methyl-N'-phenylaminocarbonyl)benzen-1-yl)-[5,2']bithiophene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
19%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In tetrahydrofuran; water Reflux;

Reference： [1]Yamakado, Ryohei; Mikami, Koichiro; Takagi, Koji; Azumaya, Isao; Sugimoto, Shinri; Matsuoka, Shin-Ichi; Suzuki, Masato; Katagiri, Kosuke; Uchiyama, Masanobu; Muranaka, Atsuya [Chemistry - A European Journal, 2013, vol. 19, # 36, p. 11853 - 11857]

22
[ 5419-55-6 ]
[ 492-97-7 ]
[ 189358-30-3 ]

Yield	Reaction Conditions	Operation in experiment
83%	Stage #1: Triisopropyl borate; 2,2'-Bithiophene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 4h; Stage #2: With hydrogenchloride In tetrahydrofuran; hexane; water