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4H-Cyclopenta[2,1-b:3,4-b']dithiophen-4-one
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Name

4H-Cyclopenta[2,1-b:3,4-b']dithiophen-4-one

 EINECS N/A
CAS No. 25796-77-4 Density 1.553
PSA 73.55000 LogP 3.02100
Solubility N/A Melting Point 134.0 to 138.0 °C
Formula C9H4OS2 Boiling Point 349.6±17.0 °C(Predicted)
Molecular Weight 192.262 Flash Point N/A
Transport Information N/A Appearance N/A
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 25796-77-4 (4H-Cyclopenta[2,1-b:3,4-b']dithiophen-4-one) Hazard Symbols N/A
Synonyms

4H-Cyclopenta[2,1-b:3,4-b']dithiophen-4-one

Article Data 17

4H-Cyclopenta[2,1-b:3,4-b']dithiophen-4-one Synthetic route

474416-61-0

bis(2-iodo-3-thienyl)methanone

25796-77-4

4H-cyclopenta[2,1-b:3,4-b']dithiophen-4-one

Conditions
ConditionsYield
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%
1187970-48-4

2,6-bis(trimethylsilyl)-4H-cyclopenta[2,1-b:3,4-b′]dithiophen-4-one

25796-77-4

4H-cyclopenta[2,1-b:3,4-b']dithiophen-4-one

Conditions
ConditionsYield
With trifluoroacetic acid In chloroform at 20℃; for 1h;95%
156547-71-6

spiro[4H-cyclopenta[2,1-b;3,4-b']-dithiophene-4,2'-[1,3]dioxolan]

25796-77-4

4H-cyclopenta[2,1-b:3,4-b']dithiophen-4-one

Conditions
ConditionsYield
With hydrogenchloride Hydrolysis;91%
51751-44-1

3,3'dibromo-2,2'-bithiophene

79-44-7

N,N-Dimethylcarbamoyl chloride

25796-77-4

4H-cyclopenta[2,1-b:3,4-b']dithiophen-4-one

Conditions
ConditionsYield
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%
6007-83-6

2,3-thiophenedicarboxylic acid anhydride

A

25796-77-4

4H-cyclopenta[2,1-b:3,4-b']dithiophen-4-one

B

32281-36-0

4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-dione

Conditions
ConditionsYield
at 500℃; under 1 - 5 Torr;A 1.2%
B n/a
498-62-4

3-thiophene carboxaldehyde

25796-77-4

4H-cyclopenta[2,1-b:3,4-b']dithiophen-4-one

Conditions
ConditionsYield
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
474416-59-6

bis(2-iodothiophen-3-yl)methanol

25796-77-4

4H-cyclopenta[2,1-b:3,4-b']dithiophen-4-one

Conditions
ConditionsYield
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
26453-81-6

di(thiophen-3-yl)methanone

25796-77-4

4H-cyclopenta[2,1-b:3,4-b']dithiophen-4-one

Conditions
ConditionsYield
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
19690-72-3

2,2-Di(3-thienyl)-1,3-dioxolane

25796-77-4

4H-cyclopenta[2,1-b:3,4-b']dithiophen-4-one

Conditions
ConditionsYield
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
1451-95-2

thiophene-2,3-dicarboxylic acid

25796-77-4

4H-cyclopenta[2,1-b:3,4-b']dithiophen-4-one

Conditions
ConditionsYield
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
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