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CAS No.: | 25796-77-4 |
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Name: | 4H-Cyclopenta[2,1-b:3,4-b']dithiophen-4-one |
Article Data: | 17 |
Molecular Structure: | |
Formula: | C9H4OS2 |
Molecular Weight: | 192.262 |
Synonyms: | 4H-Cyclopenta[2,1-b:3,4-b']dithiophen-4-one |
Density: | 1.553 |
Melting Point: | 134.0 to 138.0 °C |
Boiling Point: | 349.6±17.0 °C(Predicted) |
PSA: | 73.55000 |
LogP: | 3.02100 |
bis(2-iodo-3-thienyl)methanone
4H-cyclopenta[2,1-b:3,4-b']dithiophen-4-one
Conditions | Yield |
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With copper In N,N-dimethyl-formamide Reflux; | 99% |
With copper In N,N-dimethyl-formamide for 15h; Ullmann reaction; Reflux; | 95% |
With copper In N,N-dimethyl-formamide for 15h; Ullmann coupling reaction; Heating; | 90% |
2,6-bis(trimethylsilyl)-4H-cyclopenta[2,1-b:3,4-b′]dithiophen-4-one
4H-cyclopenta[2,1-b:3,4-b']dithiophen-4-one
Conditions | Yield |
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With trifluoroacetic acid In chloroform at 20℃; for 1h; | 95% |
spiro[4H-cyclopenta[2,1-b;3,4-b']-dithiophene-4,2'-[1,3]dioxolan]
4H-cyclopenta[2,1-b:3,4-b']dithiophen-4-one
Conditions | Yield |
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With hydrogenchloride Hydrolysis; | 91% |
3,3'dibromo-2,2'-bithiophene
N,N-Dimethylcarbamoyl chloride
4H-cyclopenta[2,1-b:3,4-b']dithiophen-4-one
Conditions | Yield |
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Stage #1: 3,3'dibromo-2,2'-bithiophene With n-butyllithium In diethyl ether; hexane at -78℃; for 2h; Inert atmosphere; Stage #2: N,N-Dimethylcarbamoyl chloride In diethyl ether; hexane at -78 - 20℃; Inert atmosphere; | 79% |
Stage #1: 3,3'dibromo-2,2'-bithiophene With n-butyllithium In diethyl ether at -78℃; for 1h; Inert atmosphere; Stage #2: N,N-Dimethylcarbamoyl chloride In diethyl ether at -78 - 20℃; Inert atmosphere; | 76% |
Stage #1: 3,3'dibromo-2,2'-bithiophene With n-butyllithium In diethyl ether; hexane at -70℃; for 1h; Inert atmosphere; Stage #2: N,N-Dimethylcarbamoyl chloride In diethyl ether; hexane for 3h; Inert atmosphere; | 75.1% |
Stage #1: 3,3'dibromo-2,2'-bithiophene With n-butyllithium In diethyl ether at -78℃; for 2h; Stage #2: N,N-Dimethylcarbamoyl chloride In diethyl ether at 20℃; | 68% |
Stage #1: 3,3'dibromo-2,2'-bithiophene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Schlenk technique; Inert atmosphere; Stage #2: N,N-Dimethylcarbamoyl chloride In tetrahydrofuran; hexane at -78 - 0℃; for 3h; Schlenk technique; Inert atmosphere; | 58% |
2,3-thiophenedicarboxylic acid anhydride
A
4H-cyclopenta[2,1-b:3,4-b']dithiophen-4-one
B
4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-dione
Conditions | Yield |
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at 500℃; under 1 - 5 Torr; | A 1.2% B n/a |
3-thiophene carboxaldehyde
4H-cyclopenta[2,1-b:3,4-b']dithiophen-4-one
Conditions | Yield |
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Multi-step reaction with 3 steps 1: 94 percent / PCC / CH2Cl2 / 12 h / 20 °C 2: 90 percent / Cu / dimethylformamide / 15 h / Heating View Scheme | |
Multi-step reaction with 4 steps 1.1: n-butyllithium / diethyl ether; hexane / 0.5 h / -78 °C 1.2: -78 - 20 °C 2.1: n-butyllithium / diethyl ether; hexane / 0.5 h / -78 °C 2.2: -78 - 20 °C 3.1: pyridinium chlorochromate / dichloromethane / 12 h / 20 °C 4.1: copper / N,N-dimethyl-formamide / 15 h / Reflux View Scheme | |
Multi-step reaction with 4 steps 1.1: n-butyllithium / diethyl ether / -78 °C 1.2: -78 - 20 °C 2.1: n-butyllithium / diethyl ether / -23 - 20 °C 2.2: -23 - 20 °C 3.1: pyridinium chlorochromate / 1,2-dichloro-ethane / 80 °C 4.1: copper / N,N-dimethyl-formamide / Reflux View Scheme |
bis(2-iodothiophen-3-yl)methanol
4H-cyclopenta[2,1-b:3,4-b']dithiophen-4-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 94 percent / PCC / CH2Cl2 / 12 h / 20 °C 2: 90 percent / Cu / dimethylformamide / 15 h / Heating View Scheme | |
Multi-step reaction with 2 steps 1: pyridinium chlorochromate / dichloromethane / 12 h / 20 °C 2: copper / N,N-dimethyl-formamide / 15 h / Reflux View Scheme | |
Multi-step reaction with 2 steps 1: pyridinium chlorochromate / 1,2-dichloro-ethane / 80 °C 2: copper / N,N-dimethyl-formamide / Reflux View Scheme | |
Multi-step reaction with 2 steps 1: pyridinium chlorochromate / dichloromethane / 10 h / 25 °C 2: copper / N,N-dimethyl-formamide / 4 h / 120 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 2 steps 1: pyridinium chlorochromate / dichloromethane / 10 h / 25 °C 2: copper / N,N-dimethyl-formamide / 4 h / 120 °C / Inert atmosphere View Scheme |
di(thiophen-3-yl)methanone
4H-cyclopenta[2,1-b:3,4-b']dithiophen-4-one
Conditions | Yield |
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Multi-step reaction with 3 steps 1.1: 66 percent / TMSOTf / CH2Cl2 / 3 h / 20 °C 2.1: n-BuLi; I2 2.2: 90 percent / Cu / dimethylformamide / 15 h / Heating 3.1: 91 percent / aq. HCl View Scheme |
2,2-Di(3-thienyl)-1,3-dioxolane
4H-cyclopenta[2,1-b:3,4-b']dithiophen-4-one
Conditions | Yield |
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Multi-step reaction with 2 steps 1.1: n-BuLi; I2 1.2: 90 percent / Cu / dimethylformamide / 15 h / Heating 2.1: 91 percent / aq. HCl View Scheme |
thiophene-2,3-dicarboxylic acid
4H-cyclopenta[2,1-b:3,4-b']dithiophen-4-one
Conditions | Yield |
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Multi-step reaction with 2 steps 1: 99.7 percent / acetic anhydride / 2 h / Heating 2: 1.2 percent / 500 °C / 1 - 5 Torr View Scheme |