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365547-20-2

365547-20-2 Structure

365547-20-2 Structure
IdentificationBack Directory
[Name]

4,4-di(2-ethylhexyl)-4H-cyclopenta[2,1-b:3,4-b]dithiophene
[CAS]

365547-20-2
[Synonyms]

DTC26
S1372
4,4-Di-2-ethylhexyl
4,4-di(2-ethylhexyl)-4H-cyclopenta[2,1-b
4,4-Di-2-ethylhexyl-cyclopenta[2,1-b:3,4-b']dithiophene
4,4-di(2-ethylhexyl)-4H-cyclopenta[2,1-b:3,4-b]dithiophene
4,4-Bis(2-ethylhexyl)-4H-cyclopenta[2,1-b:3,4-b']dithiophene
4H-Cyclopenta[2,1-b:3,4-b']dithiophene, 4,4-bis(2-ethylhexyl)-
4,4-Bis(2-ethylhexyl)-4H-cyclopenta[2,1-b:3,4-b']dithiophene >
4,4-Bis(2-ethylhexyl)-4H-cyclopenta[2,1-b:3,4-b']dithiophene
[Molecular Formula]

C25H38S2
[MDL Number]

MFCD28291964
[MOL File]

365547-20-2.mol
[Molecular Weight]

402.7
Chemical PropertiesBack Directory
[Boiling point ]

490.0±25.0 °C(Predicted)
[density ]

1.007±0.06 g/cm3(Predicted)
[refractive index ]

1.5430 to 1.5470
[Fp ]

189.00°C
[storage temp. ]

Inert atmosphere,2-8°C
[form ]

clear liquid
[color ]

Colorless to Red to Green
[InChI]

InChI=1S/C25H38S2/c1-5-9-11-19(7-3)17-25(18-20(8-4)12-10-6-2)21-13-15-26-23(21)24-22(25)14-16-27-24/h13-16,19-20H,5-12,17-18H2,1-4H3
[InChIKey]

NUCIQEWGTLOQTR-UHFFFAOYSA-N
[SMILES]

C12C3SC=CC=3C(CC(CC)CCCC)(CC(CC)CCCC)C=1C=CS2
Safety DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Warning
[Hazard statements ]

H302-H315-H319-H335
[Precautionary statements ]

P261-P305+P351+P338
[HS Code ]

2934.99.4400
Spectrum DetailBack Directory
[Spectrum Detail]

4,4-di(2-ethylhexyl)-4H-cyclopenta[2,1-b:3,4-b]dithiophene(365547-20-2)1HNMR
Hazard InformationBack Directory
[Synthesis]

2-Ethylhexyl bromide

18908-66-2

3,4-Dithia-7H-cyclopenta[a]pentalene

389-58-2

4,4-di(2-ethylhexyl)-4H-cyclopenta[2,1-b:3,4-b]dithiophene

365547-20-2

Example 5 Synthesis of 4,4-bis-(2-ethylhexyl)-4H-cyclopenta[2,1-b;3,4-b']dithiophene: Cyclopentylbithiophene (1.5 g, 0.00843 mol) was dissolved in DMSO (50 mL). KOH (1.89 g, 0.0337 mol), sodium iodide (50 mg) and 2-ethylhexyl bromide (3.25 g, 0.0169 mol) were sequentially added to the solution under nitrogen protection. The reaction mixture was stirred under nitrogen atmosphere for 16 hours. After completion of the reaction, water was added and the reaction mixture was extracted with tert-butyl methyl ether. The organic layer was separated, dried with magnesium sulfate and concentrated. The residue was purified by column chromatography using hexane as eluent. The grades containing pure 4,4-bis-(2-ethylhexyl)-4H-cyclopenta[2,1-b;3,4-b']dithiophene were combined and concentrated. After vacuum drying, a colorless oily product was obtained in a yield of 2.68 g (79%).1H NMR (CDCl3, 250 MHz): δ 7.13 (m, 2H), 6.94 (m, 2H), 1.88 (m, 4H), 0.94 (m, 16H), 0.78 (t, J=6.4 Hz, 6H), 0.61 (t, J=7.3 Hz, 6H).

[References]

[1] Journal of Polymer Science, Part A: Polymer Chemistry, 2012, vol. 50, # 8, p. 1622 - 1635
[2] RSC Advances, 2014, vol. 4, # 71, p. 37738 - 37745
[3] RSC Advances, 2014, vol. 40, # 71, p. 37738 - 37745
[4] Macromolecules, 2010, vol. 43, # 2, p. 697 - 708
[5] Patent: US7772485, 2010, B2. Location in patent: Page/Page column 11-12
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