Product Name

  • Name

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

  • EINECS
  • CAS No. 25796-77-4
  • Article Data17
  • CAS DataBase
  • Density 1.553
  • Solubility
  • Melting Point 134.0 to 138.0 °C
  • Formula C9H4OS2
  • Boiling Point 349.6±17.0 °C(Predicted)
  • Molecular Weight 192.262
  • Flash Point
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 25796-77-4 (4H-Cyclopenta[2,1-b:3,4-b']dithiophen-4-one)
  • Hazard Symbols
  • Synonyms 4H-Cyclopenta[2,1-b:3,4-b']dithiophen-4-one
  • PSA 73.55000
  • LogP 3.02100

Synthetic route

bis(2-iodo-3-thienyl)methanone
474416-61-0

bis(2-iodo-3-thienyl)methanone

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 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
1187970-48-4

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
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%
spiro[4H-cyclopenta[2,1-b;3,4-b']-dithiophene-4,2'-[1,3]dioxolan]
156547-71-6

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
25796-77-4

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

Conditions
ConditionsYield
With hydrogenchloride Hydrolysis;91%
3,3'dibromo-2,2'-bithiophene
51751-44-1

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

N,N-Dimethylcarbamoyl chloride
79-44-7

N,N-Dimethylcarbamoyl chloride

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
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
6007-83-6

2,3-thiophenedicarboxylic acid anhydride

A

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

B

4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-dione
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
3-thiophene carboxaldehyde
498-62-4

3-thiophene carboxaldehyde

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
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
474416-59-6

bis(2-iodothiophen-3-yl)methanol

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
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
26453-81-6

di(thiophen-3-yl)methanone

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
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
19690-72-3

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

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
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
1451-95-2

thiophene-2,3-dicarboxylic acid

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
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
1,1-di(thien-3-yl)-methanol
31936-92-2

1,1-di(thien-3-yl)-methanol

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
Multi-step reaction with 3 steps
1.1: n-butyllithium / diethyl ether; hexane / 0.5 h / -78 °C
1.2: -78 - 20 °C
2.1: pyridinium chlorochromate / dichloromethane / 12 h / 20 °C
3.1: copper / N,N-dimethyl-formamide / 15 h / Reflux
View Scheme
Multi-step reaction with 3 steps
1.1: n-butyllithium / diethyl ether / -23 - 20 °C
1.2: -23 - 20 °C
2.1: pyridinium chlorochromate / 1,2-dichloro-ethane / 80 °C
3.1: copper / N,N-dimethyl-formamide / Reflux
View Scheme
3-bromo-[2,2’]bithiophenyl
19690-69-8

3-bromo-[2,2’]bithiophenyl

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
Multi-step reaction with 4 steps
1.1: acetic acid; N-Bromosuccinimide / chloroform / 20 h / 20 - 50 °C
2.1: n-butyllithium / diethyl ether / Inert atmosphere
2.2: Inert atmosphere
3.1: n-butyllithium / hexane; tetrahydrofuran / -60 - -30 °C / Inert atmosphere
3.2: -30 - 0 °C / Inert atmosphere
4.1: trifluoroacetic acid / chloroform / 1 h / 20 °C
View Scheme
3,3'-dibromo-5,5'-bis(trimethylsilyl)-2,2'-bithiophene
207742-50-5

3,3'-dibromo-5,5'-bis(trimethylsilyl)-2,2'-bithiophene

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
Multi-step reaction with 2 steps
1.1: n-butyllithium / hexane; tetrahydrofuran / -60 - -30 °C / Inert atmosphere
1.2: -30 - 0 °C / Inert atmosphere
2.1: trifluoroacetic acid / chloroform / 1 h / 20 °C
View Scheme
3,3',5,5'-tetrabromo-2,2'-bithiophene
125143-53-5

3,3',5,5'-tetrabromo-2,2'-bithiophene

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
Multi-step reaction with 3 steps
1.1: n-butyllithium / diethyl ether / Inert atmosphere
1.2: Inert atmosphere
2.1: n-butyllithium / hexane; tetrahydrofuran / -60 - -30 °C / Inert atmosphere
2.2: -30 - 0 °C / Inert atmosphere
3.1: trifluoroacetic acid / chloroform / 1 h / 20 °C
View Scheme
Multi-step reaction with 2 steps
1.1: zinc; acetic acid; hydrogenchloride / ethanol; water / 3 h / 70 °C / Inert atmosphere
2.1: n-butyllithium / diethyl ether; hexane / 1 h / -70 °C / Inert atmosphere
2.2: 3 h / Inert atmosphere
View Scheme
[2,2'-bithiophene]-3-carboxylic acid
19783-52-9

[2,2'-bithiophene]-3-carboxylic acid

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
Multi-step reaction with 2 steps
1: thionyl chloride; N,N-dimethyl-formamide / 12 h / 20 °C / Reflux
2: aluminum (III) chloride / dichloromethane / 4 h / 0 - 20 °C / Inert atmosphere
View Scheme
Stage #1: [2,2'-bithiophene]-3-carboxylic acid With thionyl chloride In N,N-dimethyl-formamide for 12h; Reflux;
Stage #2: With aluminum (III) chloride In dichloromethane at 0 - 20℃; for 9h;
20.7 mg
3-Thiophene carboxylic acid
88-13-1

3-Thiophene carboxylic acid

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
Multi-step reaction with 3 steps
1: dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; dipotassium hydrogenphosphate; silver(l) oxide / tert-butyl alcohol / 24 h / 130 °C / Schlenk technique; Inert atmosphere
2: thionyl chloride; N,N-dimethyl-formamide / 12 h / 20 °C / Reflux
3: aluminum (III) chloride / dichloromethane / 4 h / 0 - 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1.1: dipotassium hydrogenphosphate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver(l) oxide / tert-butyl alcohol / 24 h / 20 - 130 °C / Inert atmosphere
2.1: thionyl chloride / N,N-dimethyl-formamide / 12 h / Reflux
2.2: 9 h / 0 - 20 °C
View Scheme
C9H5ClOS2

C9H5ClOS2

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 aluminum (III) chloride In dichloromethane at 0 - 20℃; for 4h; Inert atmosphere;20.5 mg
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

dimethyl 4,5-bis(methylthio)-1,3-dithiole phosphonate ester
138519-02-5

dimethyl 4,5-bis(methylthio)-1,3-dithiole phosphonate ester

4-(4,5-Bis-methylsulfanyl-[1,3]dithiol-2-ylidene)-4H-cyclopenta[2,1-b;3,4-b']dithiophene
143736-76-9

4-(4,5-Bis-methylsulfanyl-[1,3]dithiol-2-ylidene)-4H-cyclopenta[2,1-b;3,4-b']dithiophene

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran98%
With n-butyllithium In tetrahydrofuran; hexane 1.) -78 deg C, 15 min; 2.) 20 min;98%
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

S,S'-(2-(dimethoxyphosphoryl)-1,3-dithiole-4,5-diyl)dihexanethiol

S,S'-(2-(dimethoxyphosphoryl)-1,3-dithiole-4,5-diyl)dihexanethiol

4-(4,5-Bis-hexylsulfanyl-[1,3]dithiol-2-ylidene)-4H-cyclopenta[2,1-b;3,4-b']dithiophene
143736-84-9

4-(4,5-Bis-hexylsulfanyl-[1,3]dithiol-2-ylidene)-4H-cyclopenta[2,1-b;3,4-b']dithiophene

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran96%
With n-butyllithium In tetrahydrofuran; hexane 1.) -78 deg C, 15 min; 2.) 20 min;96%
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

2,6-dibromo-4H-cyclopenta[2,1-b:3,4-b′]dithiophen-4-one

2,6-dibromo-4H-cyclopenta[2,1-b:3,4-b′]dithiophen-4-one

Conditions
ConditionsYield
With N-Bromosuccinimide; acetic acid at 20℃;96%
With N-Bromosuccinimide In N,N-dimethyl-formamide at 25℃;94%
With bromine In dichloromethane at 20℃; for 2h; Inert atmosphere;87.1%
With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃; for 0.166667h;
With N-Bromosuccinimide In tetrahydrofuran at 0℃; for 2.25h; Inert atmosphere;17.3 g
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

malononitrile
109-77-3

malononitrile

4-dicyanomethylene-4H-cyclopenta<2,1-b;3,4-b'>dithiophene
138050-21-2

4-dicyanomethylene-4H-cyclopenta<2,1-b;3,4-b'>dithiophene

Conditions
ConditionsYield
With piperidine93%
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

2-(dimethoxyphosphoryl)-[1,3]dithiole-4,5-dicarboxylic acid dimethyl ester
148192-05-6

2-(dimethoxyphosphoryl)-[1,3]dithiole-4,5-dicarboxylic acid dimethyl ester

2-Cyclopenta[2,1-b;3,4-b']dithiophen-4-ylidene-[1,3]dithiole-4,5-dicarboxylic acid dimethyl ester
143736-80-5

2-Cyclopenta[2,1-b;3,4-b']dithiophen-4-ylidene-[1,3]dithiole-4,5-dicarboxylic acid dimethyl ester

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran; hexane 1.) -78 deg C, 15 min; 2.) 20 min;91%
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

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

4H-cyclopenta[2,1-b:3,4-b']dithiophen-4-one-2-carbaldehyde
1376711-77-1

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

Conditions
ConditionsYield
With trichlorophosphate In 1,2-dichloro-ethane at 0 - 80℃; for 6h;91%
With trichlorophosphate In dichloromethane at 0 - 80℃; for 6h;91%
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

dimethyl 1,3-benzodithiol-2-ylphosphonate
62217-35-0

dimethyl 1,3-benzodithiol-2-ylphosphonate

4-Benzo[1,3]dithiol-2-ylidene-4H-cyclopenta[2,1-b;3,4-b']dithiophene
143736-74-7

4-Benzo[1,3]dithiol-2-ylidene-4H-cyclopenta[2,1-b;3,4-b']dithiophene

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran89%
With n-butyllithium In tetrahydrofuran; hexane 1.) -78 deg C, 15 min; 2.) 20 min;89%
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

4H-cyclopenta[2,1-b;3,4-b']dithiophene
389-58-2

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

Conditions
ConditionsYield
With hydrazine hydrate; potassium hydroxide In ethylene glycol at 180℃;89%
With hydrazine hydrate; potassium hydroxide In ethylene glycol at 200℃; for 2h; Inert atmosphere;67%
With potassium hydroxide; hydrazine In ethylene glycol at 190℃; for 13h;66%
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

ethane-1,2-dithiol
540-63-6

ethane-1,2-dithiol

C11H8S4
164727-17-7

C11H8S4

Conditions
ConditionsYield
With aluminium trichloride In 1,2-dichloro-ethane at 20℃; for 1h;89%
With aluminum (III) chloride In 1,2-dichloro-ethane at 20℃;
With aluminum (III) chloride In chloroform at 25℃; Inert atmosphere;
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

3-bromo-[2,2’]bithiophenyl
19690-69-8

3-bromo-[2,2’]bithiophenyl

4-(2,2’-bithiophen-3-yl)-4-hydroxycyclopenta[2,1-b;3,4-b’]dithiophene
1500083-89-5

4-(2,2’-bithiophen-3-yl)-4-hydroxycyclopenta[2,1-b;3,4-b’]dithiophene

Conditions
ConditionsYield
Stage #1: 3-bromo-[2,2’]bithiophenyl With n-butyllithium In diethyl ether; hexane at -78℃; for 1h; Inert atmosphere;
Stage #2: 4H-cyclopenta[2,1-b:3,4-b']dithiophen-4-one In diethyl ether; hexane at -78 - 20℃; for 6h; Inert atmosphere;
88%
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

2,6-di-iodo-cyclopenta[1,t2-b:5,4-b’]dithiophen-4-one
1222450-34-1

2,6-di-iodo-cyclopenta[1,t2-b:5,4-b’]dithiophen-4-one

Conditions
ConditionsYield
With N-iodo-succinimide; trifluoroacetic acid In acetonitrile at 20℃;88%
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

1-bromo-4-octyloxybenzene
96693-05-9

1-bromo-4-octyloxybenzene

4-(4-(octyloxy)phenyl)-4H-cyclopenta[1,2-B:5,4-B']dithiophen-4-ol

4-(4-(octyloxy)phenyl)-4H-cyclopenta[1,2-B:5,4-B']dithiophen-4-ol

Conditions
ConditionsYield
With magnesium In tetrahydrofuran at 50℃; for 18h; Inert atmosphere;85%
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

2-Bromobiphenyl
2052-07-5

2-Bromobiphenyl

4-(Biphenyl-2-yl)-4-hydroxy-4H-cyclopenta[2,1-b:3,4-b']dithiophene
350031-83-3

4-(Biphenyl-2-yl)-4-hydroxy-4H-cyclopenta[2,1-b:3,4-b']dithiophene

Conditions
ConditionsYield
Stage #1: 2-Bromobiphenyl With n-butyllithium In hexane for 1h; Heating;
Stage #2: 4H-cyclopenta[2,1-b:3,4-b']dithiophen-4-one In tetrahydrofuran; hexane at -70℃; for 1h; Further stages.;
83%
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

C9H3BrOS2

C9H3BrOS2

Conditions
ConditionsYield
With bromine In dichloromethane at 20℃; for 2h; Inert atmosphere;82.9%
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

10-(dicyanomethylidene)-9(10H)-anthrone hydrazone
156755-16-7

10-(dicyanomethylidene)-9(10H)-anthrone hydrazone

2-[10-(cyclopenta[2,1-b;3,4-b']dithiophen-4-ylidene-hydrazono)-10H-anthracen-9-ylidene]-malononitrile

2-[10-(cyclopenta[2,1-b;3,4-b']dithiophen-4-ylidene-hydrazono)-10H-anthracen-9-ylidene]-malononitrile

Conditions
ConditionsYield
With pyridinium p-toluenesulfonate acidic;80%
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

(2-ethylhexyl)triphenylphosphonium bromide

(2-ethylhexyl)triphenylphosphonium bromide

4-(2′-ethylhexylidene)-4H-cyclopenta[2,1-b:3,4-b′]-dithiophene
1523510-31-7

4-(2′-ethylhexylidene)-4H-cyclopenta[2,1-b:3,4-b′]-dithiophene

Conditions
ConditionsYield
Stage #1: (2-ethylhexyl)triphenylphosphonium bromide With n-butyllithium In tetrahydrofuran; hexane at -82℃; Inert atmosphere;
Stage #2: 4H-cyclopenta[2,1-b:3,4-b']dithiophen-4-one In tetrahydrofuran; hexane at -82℃; for 0.5h;
79%
Stage #1: (2-ethylhexyl)triphenylphosphonium bromide With n-butyllithium In tetrahydrofuran at -78℃; Inert atmosphere;
Stage #2: 4H-cyclopenta[2,1-b:3,4-b']dithiophen-4-one In tetrahydrofuran; diethyl ether at -78 - 20℃; Inert atmosphere;
77%
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

dimethyl [4,5-bis(butylthio)-1,3-dithiol-2-yl]phosphonate

dimethyl [4,5-bis(butylthio)-1,3-dithiol-2-yl]phosphonate

4-(4,5-Bis-butylsulfanyl-[1,3]dithiol-2-ylidene)-4H-cyclopenta[2,1-b;3,4-b']dithiophene
143736-82-7

4-(4,5-Bis-butylsulfanyl-[1,3]dithiol-2-ylidene)-4H-cyclopenta[2,1-b;3,4-b']dithiophene

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran78%
With n-butyllithium In tetrahydrofuran; hexane 1.) -78 deg C, 15 min; 2.) 20 min;78%
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

10-hydrazono-9,10-dihydroanthracen-9-one
3166-13-0

10-hydrazono-9,10-dihydroanthracen-9-one

10-(cyclopenta[2,1-b;3,4-b']dithiophen-4-ylidene-hydrazono)-10H-anthracen-9-one

10-(cyclopenta[2,1-b;3,4-b']dithiophen-4-ylidene-hydrazono)-10H-anthracen-9-one

Conditions
ConditionsYield
With pyridinium p-toluenesulfonate76%
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

benzyl bromide
100-39-0

benzyl bromide

C16H10S2

C16H10S2

Conditions
ConditionsYield
Stage #1: benzyl bromide With triphenylphosphine
Stage #2: 4H-cyclopenta[2,1-b:3,4-b']dithiophen-4-one With sodium ethanolate Wittig Olefination;
76%
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

n-octyltriphenylphosphoniumbromide
42036-78-2

n-octyltriphenylphosphoniumbromide

4-(octylidene)-4H-cyclopenta[2,1-b:3,4-b′]dithiophene
1523510-28-2

4-(octylidene)-4H-cyclopenta[2,1-b:3,4-b′]dithiophene

Conditions
ConditionsYield
Stage #1: n-octyltriphenylphosphoniumbromide With n-butyllithium In tetrahydrofuran; hexane at -82℃; Inert atmosphere;
Stage #2: 4H-cyclopenta[2,1-b:3,4-b']dithiophen-4-one In tetrahydrofuran; hexane at -82℃; for 0.5h;
74%
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

2-dimethoxyphosphinyl-4,5-dimethyl-1,3-dithiole
69212-98-2

2-dimethoxyphosphinyl-4,5-dimethyl-1,3-dithiole

4-(4,5-Dimethyl-[1,3]dithiol-2-ylidene)-4H-cyclopenta[2,1-b;3,4-b']dithiophene
143736-78-1

4-(4,5-Dimethyl-[1,3]dithiol-2-ylidene)-4H-cyclopenta[2,1-b;3,4-b']dithiophene

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran71%
With n-butyllithium In tetrahydrofuran; hexane 1.) -78 deg C, 15 min; 2.) 20 min;71%
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

1-bromo-4-octylbenzene
51554-93-9

1-bromo-4-octylbenzene

4-(4-octylphenyl)-4H-cyclopenta[1,2-B:5,4-B']dithiophen-4-ol

4-(4-octylphenyl)-4H-cyclopenta[1,2-B:5,4-B']dithiophen-4-ol

Conditions
ConditionsYield
With magnesium In tetrahydrofuran at 50℃; for 18h; Inert atmosphere;70%
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

cyclopenta[2,1-b;3,4-b']dithiophen-4-ylidene-hydrazine

cyclopenta[2,1-b;3,4-b']dithiophen-4-ylidene-hydrazine

Conditions
ConditionsYield
With pyridinium p-toluenesulfonate; hydrazine68%
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

dimethyl (1,3-dithiol-2-yl)phosphonate
133113-76-5

dimethyl (1,3-dithiol-2-yl)phosphonate

4-(1,3-Dithiol-2-ylidene)-4H-cyclopenta<2,1-b;3,4-b'>dithiophene
143693-14-5

4-(1,3-Dithiol-2-ylidene)-4H-cyclopenta<2,1-b;3,4-b'>dithiophene

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran65%
With n-butyllithium In tetrahydrofuran; hexane 1.) -78 deg C, 15 min; 2.) 20 min;65%
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

dimethyl 4,5-bis(decylthio)-2H-1,3-dithiol-2-ylphosphonate
155442-43-6

dimethyl 4,5-bis(decylthio)-2H-1,3-dithiol-2-ylphosphonate

4-(4,5-Bis-decylsulfanyl-[1,3]dithiol-2-ylidene)-4H-cyclopenta[2,1-b;3,4-b']dithiophene
143736-86-1

4-(4,5-Bis-decylsulfanyl-[1,3]dithiol-2-ylidene)-4H-cyclopenta[2,1-b;3,4-b']dithiophene

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran64%
With n-butyllithium In tetrahydrofuran; hexane 1.) -78 deg C, 15 min; 2.) 20 min;64%
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

2,3,5,6-tetrabromo-4H-cyclopenta[2,1-b:3,4-b’]dithiophen-4-one

2,3,5,6-tetrabromo-4H-cyclopenta[2,1-b:3,4-b’]dithiophen-4-one

Conditions
ConditionsYield
With bromine In chloroform at 70℃; for 12h;63%
With bromine In chloroform for 12h; Reflux;63%
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