| Identification | Back Directory | [Name]
4H-Cyclopenta[2,1-b:3,4-b']dithiophen-4-one | [CAS]
25796-77-4 | [Synonyms]
DTCO
S1370
Cyclopenta[2,1-b
]dithiophen-4-one
3,4-b']dithiophen-4-one
Cyclopenta[2,1-b:3,4-b']d
Cyclopentadithiophene ketone
4H-Cyclopenta[2,1-b:3,4-b'
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-Cyclopenta[2,1-b:3,4-b']dithiophen-4-one
4H-Cyclopenta-[2,1-b:3,4-b']dithiophene-4-one
4H-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
4H-Δ4,4'-dicyclopenta[2,1 -b:3,4-b']dithiophen-4-one
4H-Cyclopenta[1,2-b:5,4-b']dithiophen-4-one | [Molecular Formula]
C9H4OS2 | [MDL Number]
MFCD16619150 | [MOL File]
25796-77-4.mol | [Molecular Weight]
192.257 |
| Chemical Properties | Back Directory | [Melting point ]
134.0 to 138.0 °C | [Boiling point ]
349.6±17.0 °C(Predicted) | [density ]
1.553 | [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [form ]
powder to crystal | [color ]
Orange to Amber to Dark red | [InChI]
InChI=1S/C9H4OS2/c10-7-5-1-3-11-8(5)9-6(7)2-4-12-9/h1-4H | [InChIKey]
HFIUHKXJUKKOIZ-UHFFFAOYSA-N | [SMILES]
C12C3SC=CC=3C(=O)C=1C=CS2 |
| Hazard Information | Back Directory | [Uses]
suzuki reaction | [Synthesis]
The general procedure for the synthesis of 4H-cyclopenta[2,1-B:3,4-B']dithiophen-4-one from 3,3'-dibromo-2,2'-bithiophene and dimethylcarbamoyl chloride was carried out as follows: 30 g of diethyl ether was added to a 250 mL three-necked flask under nitrogen protection and cooled to -70 °C by a cryogenic bath with stirring. Subsequently, 20 mL (0.05 mol, 2.5 mol/L) of hexane solution was slowly added, followed by the dropwise addition of 6.28 g (0.02 mol) of diethyl ether solution of Intermediate 1. After addition, the reaction was continued with stirring for 1 hour. Then, 2.58 g (0.024 mol) of N,N-dimethylcarbonyl chloride was added slowly and the reaction was continued with stirring for 3 hours. Upon completion of the reaction, the temperature of the reaction system was raised to 0°C and 20 g of water was added to terminate the reaction. The reaction mixture was partitioned and the organic phase was extracted with ethyl acetate. The organic phases were combined and concentrated under reduced pressure to remove the solvent to give a yellow oil. Finally, 2.88 g of light yellow liquid product was obtained in 75.1% yield by column chromatography separation and purification using petroleum ether: ethyl acetate = 20:1 (v/v) as eluent. | [References]
[1] Journal of Materials Chemistry A, 2017, vol. 5, # 17, p. 7811 - 7815
[2] Journal of Materials Chemistry C, 2018, vol. 6, # 3, p. 500 - 511
[3] Patent: CN108148074, 2018, A. Location in patent: Paragraph 0058; 0059; 0060
[4] Inorganic Chemistry, 2016, vol. 55, # 13, p. 6653 - 6659 |
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