25796-77-4

Basic information

• Product Name: 4H-Cyclopenta[2,1-b:3,4-b']dithiophen-4-one
• Synonyms: 4H-Cyclopenta[2,1-b:3,4-b']dithiophen-4-one;3,4-b']dithiophen-4-one;Cyclopenta[2,1-b;4H-Cyclopenta-[2,1-b:3,4-b']dithiophene-4-one;4H-Cyclopenta[1,2-b:5,4-b']dithiophen-4-one;Cyclopenta[2,1-b:3,4-b']dithiophen-4-one;4H-Cyclopenta[1,2-b:5,4-b']dithiophen-4-one;4H-Δ4,4'-dicyclopenta[2,1 -b:3,4-b']dithiophen-4-one
• CAS NO: 25796-77-4
• Molecular Formula: C₉H₄OS₂
• Molecular Weight: 192.25746
• Product Categories: DTC
• Mol File: 25796-77-4.mol
• Article Data: 17

Chemical Properties

• Melting Point: 134.0 to 138.0 °C
• Boiling Point: 349.6±17.0 °C(Predicted)
• Appearance: /
• Density: 1.553
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• CAS DataBase Reference: 4H-Cyclopenta[2,1-b:3,4-b']dithiophen-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: 4H-Cyclopenta[2,1-b:3,4-b']dithiophen-4-one(25796-77-4)
• EPA Substance Registry System: 4H-Cyclopenta[2,1-b:3,4-b']dithiophen-4-one(25796-77-4)

Safety Data

• Hazardous Substances Data: 25796-77-4(Hazardous Substances Data)

Usage

Uses

suzuki reaction

Synthetic route

bis(2-iodo-3-thienyl)methanone (474416-61-0) → 4H-cyclopenta[2,1-b:3,4-b']dithiophen-4-one (25796-77-4)

Conditions	Yield
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) → 4H-cyclopenta[2,1-b:3,4-b']dithiophen-4-one (25796-77-4)

Conditions	Yield
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) → 4H-cyclopenta[2,1-b:3,4-b']dithiophen-4-one (25796-77-4)

Conditions	Yield
With hydrogenchloride Hydrolysis;	91%

3,3'dibromo-2,2'-bithiophene (51751-44-1) + N,N-Dimethylcarbamoyl chloride (79-44-7) → 4H-cyclopenta[2,1-b:3,4-b']dithiophen-4-one (25796-77-4)

Conditions	Yield
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) → 4H-cyclopenta[2,1-b:3,4-b']dithiophen-4-one (25796-77-4) + 4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-dione (32281-36-0)

Conditions	Yield
at 500℃; under 1 - 5 Torr;	A 1.2% B n/a

3-thiophene carboxaldehyde (498-62-4) → 4H-cyclopenta[2,1-b:3,4-b']dithiophen-4-one (25796-77-4)

Conditions	Yield
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) → 4H-cyclopenta[2,1-b:3,4-b']dithiophen-4-one (25796-77-4)

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 (26453-81-6) → 4H-cyclopenta[2,1-b:3,4-b']dithiophen-4-one (25796-77-4)

Conditions	Yield
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) → 4H-cyclopenta[2,1-b:3,4-b']dithiophen-4-one (25796-77-4)

Conditions	Yield
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) → 4H-cyclopenta[2,1-b:3,4-b']dithiophen-4-one (25796-77-4)

Conditions	Yield
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) → 4H-cyclopenta[2,1-b:3,4-b']dithiophen-4-one (25796-77-4)

Conditions	Yield
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) → 4H-cyclopenta[2,1-b:3,4-b']dithiophen-4-one (25796-77-4)

Conditions	Yield
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) → 4H-cyclopenta[2,1-b:3,4-b']dithiophen-4-one (25796-77-4)

Conditions	Yield
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) → 4H-cyclopenta[2,1-b:3,4-b']dithiophen-4-one (25796-77-4)

Conditions	Yield
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) → 4H-cyclopenta[2,1-b:3,4-b']dithiophen-4-one (25796-77-4)

Conditions	Yield
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) → 4H-cyclopenta[2,1-b:3,4-b']dithiophen-4-one (25796-77-4)

Conditions	Yield
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 → 4H-cyclopenta[2,1-b:3,4-b']dithiophen-4-one (25796-77-4)

Conditions	Yield
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) + dimethyl 4,5-bis(methylthio)-1,3-dithiole phosphonate ester (138519-02-5) → 4-(4,5-Bis-methylsulfanyl-[1,3]dithiol-2-ylidene)-4H-cyclopenta[2,1-b;3,4-b']dithiophene (143736-76-9)

Conditions	Yield
With n-butyllithium In tetrahydrofuran	98%
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) + 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)

Conditions	Yield
With n-butyllithium In tetrahydrofuran	96%
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) → 2,6-dibromo-4H-cyclopenta[2,1-b:3,4-b′]dithiophen-4-one

Conditions	Yield
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) + malononitrile (109-77-3) → 4-dicyanomethylene-4H-cyclopenta<2,1-b;3,4-b'>dithiophene (138050-21-2)

Conditions	Yield
With piperidine	93%

4H-cyclopenta[2,1-b:3,4-b']dithiophen-4-one (25796-77-4) + 2-(dimethoxyphosphoryl)-[1,3]dithiole-4,5-dicarboxylic acid dimethyl ester (148192-05-6) → 2-Cyclopenta[2,1-b;3,4-b']dithiophen-4-ylidene-[1,3]dithiole-4,5-dicarboxylic acid dimethyl ester (143736-80-5)

Conditions	Yield
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) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → 4H-cyclopenta[2,1-b:3,4-b']dithiophen-4-one-2-carbaldehyde (1376711-77-1)

Conditions	Yield
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) + dimethyl 1,3-benzodithiol-2-ylphosphonate (62217-35-0) → 4-Benzo[1,3]dithiol-2-ylidene-4H-cyclopenta[2,1-b;3,4-b']dithiophene (143736-74-7)

Conditions	Yield
With n-butyllithium In tetrahydrofuran	89%
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']dithiophene (389-58-2)

Conditions	Yield
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) + ethane-1,2-dithiol (540-63-6) → C11H8S4 (164727-17-7)

Conditions	Yield
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) + 3-bromo-[2,2’]bithiophenyl (19690-69-8) → 4-(2,2’-bithiophen-3-yl)-4-hydroxycyclopenta[2,1-b;3,4-b’]dithiophene (1500083-89-5)

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

Conditions	Yield
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) + 1-bromo-4-octyloxybenzene (96693-05-9) → 4-(4-(octyloxy)phenyl)-4H-cyclopenta[1,2-B:5,4-B']dithiophen-4-ol

Conditions	Yield
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) + 2-Bromobiphenyl (2052-07-5) → 4-(Biphenyl-2-yl)-4-hydroxy-4H-cyclopenta[2,1-b:3,4-b']dithiophene (350031-83-3)

Conditions	Yield
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) → C9H3BrOS2

Conditions	Yield
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) + 10-(dicyanomethylidene)-9(10H)-anthrone hydrazone (156755-16-7) → 2-[10-(cyclopenta[2,1-b;3,4-b']dithiophen-4-ylidene-hydrazono)-10H-anthracen-9-ylidene]-malononitrile

Conditions	Yield
With pyridinium p-toluenesulfonate acidic;	80%

4H-cyclopenta[2,1-b:3,4-b']dithiophen-4-one (25796-77-4) + (2-ethylhexyl)triphenylphosphonium bromide → 4-(2′-ethylhexylidene)-4H-cyclopenta[2,1-b:3,4-b′]-dithiophene (1523510-31-7)

Conditions	Yield
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) + 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)

Conditions	Yield
With n-butyllithium In tetrahydrofuran	78%
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) + 10-hydrazono-9,10-dihydroanthracen-9-one (3166-13-0) → 10-(cyclopenta[2,1-b;3,4-b']dithiophen-4-ylidene-hydrazono)-10H-anthracen-9-one

Conditions	Yield
With pyridinium p-toluenesulfonate	76%

4H-cyclopenta[2,1-b:3,4-b']dithiophen-4-one (25796-77-4) + benzyl bromide (100-39-0) → C16H10S2

Conditions	Yield
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) + n-octyltriphenylphosphoniumbromide (42036-78-2) → 4-(octylidene)-4H-cyclopenta[2,1-b:3,4-b′]dithiophene (1523510-28-2)

Conditions	Yield
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) + 2-dimethoxyphosphinyl-4,5-dimethyl-1,3-dithiole (69212-98-2) → 4-(4,5-Dimethyl-[1,3]dithiol-2-ylidene)-4H-cyclopenta[2,1-b;3,4-b']dithiophene (143736-78-1)

Conditions	Yield
With n-butyllithium In tetrahydrofuran	71%
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) + 1-bromo-4-octylbenzene (51554-93-9) → 4-(4-octylphenyl)-4H-cyclopenta[1,2-B:5,4-B']dithiophen-4-ol

Conditions	Yield
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) → cyclopenta[2,1-b;3,4-b']dithiophen-4-ylidene-hydrazine

Conditions	Yield
With pyridinium p-toluenesulfonate; hydrazine	68%

4H-cyclopenta[2,1-b:3,4-b']dithiophen-4-one (25796-77-4) + dimethyl (1,3-dithiol-2-yl)phosphonate (133113-76-5) → 4-(1,3-Dithiol-2-ylidene)-4H-cyclopenta<2,1-b;3,4-b'>dithiophene (143693-14-5)

Conditions	Yield
With n-butyllithium In tetrahydrofuran	65%
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) + dimethyl 4,5-bis(decylthio)-2H-1,3-dithiol-2-ylphosphonate (155442-43-6) → 4-(4,5-Bis-decylsulfanyl-[1,3]dithiol-2-ylidene)-4H-cyclopenta[2,1-b;3,4-b']dithiophene (143736-86-1)

Conditions	Yield
With n-butyllithium In tetrahydrofuran	64%
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) → 2,3,5,6-tetrabromo-4H-cyclopenta[2,1-b:3,4-b’]dithiophen-4-one

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

Upstream product

• 51751-44-1 3,3'dibromo-2,2'-bithiophene 
• 79-44-7 N,N-Dimethylcarbamoyl chloride 
• 1187970-48-4 2,6-bis(trimethylsilyl)-4H-cyclopenta[2,1-b:3,4-b′]dithiophen-4-one 
• 125143-53-5 3,3',5,5'-tetrabromo-2,2'-bithiophene 
• 207742-50-5 3,3'-dibromo-5,5'-bis(trimethylsilyl)-2,2'-bithiophene 
• 19690-69-8 3-bromo-[2,2’]bithiophenyl 
• 31936-92-2 1,1-di(thien-3-yl)-methanol 
• 19690-72-3 2,2-Di(3-thienyl)-1,3-dioxolane 
• 26453-81-6 di(thiophen-3-yl)methanone 
• 474416-59-6 bis(2-iodothiophen-3-yl)methanol 
• 498-62-4 3-thiophene carboxaldehyde 
• 474416-61-0 bis(2-iodo-3-thienyl)methanone 
• 156547-71-6 spiro[4H-cyclopenta[2,1-b;3,4-b']-dithiophene-4,2'-[1,3]dioxolan] 
• 6007-83-6 2,3-thiophenedicarboxylic acid anhydride 

Downstream Products

• 350031-83-3 4-(Biphenyl-2-yl)-4-hydroxy-4H-cyclopenta[2,1-b:3,4-b']dithiophene 
• 365547-21-3 2,6-dibromo-4,4-bis(2-ethylhexyl)-4H-cyclopenta[2,1-b:3,4-b']dithiophene 
• 942398-52-9 C₉H₃BrOS₂ 
• 1295502-12-3 5H-dithieno[3,2-b:2',3'-d]pyran-5-one 
• 1221821-39-1 6-bromo-4,4-dihexyl-4H-cyclopenta[2,1-b:3,4-b′]dithiophene-2-carbaldehyde 
• 1315276-46-0 6-[4-(diphenylamino)phenyl]-4,4-dihexyl-4H-cyclopenta[2,1-b:3,4-b′]dithiophene-2-carbaldehyde 
• 1295502-20-3 5-(3,7-dimethyloctyl)-5-(3-methyloctyl)-5Hdithieno[3,2-b:2',3'-d]pyran 
• 1416261-35-2 C₂₁H₂₀F₅NS₂Sn₂ 
• 1422042-01-0 C₂₁H₂₄FNS₂Sn₂ 

Relevant articles and documents

A new, improved and convenient synthesis of 4H-cyclopenta[2,1-b:3,4-b′]-dithiophen-4-one

A new and efficient three-step synthesis of 4H-cyclopenta[2,1-b:3,4-b′]dithiophen-4-one (CDT) (1) is described. This was achieved by a one-pot, regiospecific synthesis of bis(2-iodo-3-thienyl)methanol (13), its subsequent oxidation to the bls(2-iodo-3-thienyl) ketone (14) which after Ullmann coupling yielded the title compound 1.

COMPOUND AND ORGANIC LIGHT EMITTING DEVICE COMPRISING THE SAME

The present specification relates to a compound and an organic light emitting device comprising the same. The compound is represented by chemical formula 1. The abovementioned compound can be used as a material for an organic material layer of an organic light emitting device. The compound according to at least one embodiment of the present invention can improve the efficiency, the low driving voltage and/or the lifetime characteristics in the organic light emitting device.COPYRIGHT KIPO 2018

A two-thieno cyclopentanone compound and its preparation method and application (by machine translation)

The present invention discloses a two-thieno cyclopentanone compound and its preparation method and application, which belongs to the technical field of solar cell. Said two thiophene and cyclopentanone compound, the structure of the formula I as shown: Wherein L1 , L2 Respectively and independently represent a hydrogen atom or R, and L1 , L2 At least one is a R. The invention also discloses the above-mentioned two thiophene and cyclopentanone compound of preparation method and application. The compounds of this invention introduced two fragrant amines group is branched, can make the molecule has space three-dimensional structure, to avoid material crystallization; introduced two thiophene and cyclopentanone can greatly improve the thermal stability of the material. (by machine translation)