| Identification | Back Directory | [Name]
5,7-Dibromo-2,3-dihydrothieno[3,4-b][1,4]dioxine | [CAS]
174508-31-7 | [Synonyms]
4-b][1
2,5-Dibromo-3,4-ethylenedioxythiophene>
2,5-Dibromo-3,4-ethylenedioxythiophene 97%
5,7-dibroMo-2H,3H-thieno[3,4-b][1,4]dioxine
5,7-DIBROMO-2,3-DIHYDROTHIENO[3,4-B][1,4]DIOXINE
2,3-Dihydro[2,5-dibroMothioeno]
[3,4-b]-1,4-dioxin
Thieno[3,4-b]-1,4-dioxin, 5,7-dibromo-2,3-dihydro-
5,7-Dibromo-2,3-dihydrothieno[3,4-b][1,4]dioxine97%
5,7-Dibromo-2,3-dihydrothieno[3,4-b][1,4]dioxine 97%
5,7-Dibromo-2,3-dihydrothieno[3,4-b][1,4]dioxine ISO 9001：2015 REACH | [Molecular Formula]
C6H4Br2O2S | [MDL Number]
MFCD01651770 | [MOL File]
174508-31-7.mol | [Molecular Weight]
299.97 |
| Chemical Properties | Back Directory | [Melting point ]
98 °C | [Boiling point ]
306.5±42.0 °C(Predicted) | [density ]
2.139±0.06 g/cm3(Predicted) | [storage temp. ]
?20°C | [solubility ]
Chloroform (Slightly), Methanol (Slightly) | [form ]
Solid | [color ]
Grey to Dark Blue | [CAS DataBase Reference]
174508-31-7 |
| Hazard Information | Back Directory | [Chemical Properties]
Needle-like solid | [Uses]
5,7-Dibromo-2,3-dihydrothieno[3,4-b]-1,4-dioxine is used in the preparation of 3,4-ethylenedioxythiophene oligomers with optical and redox properties. | [General Description]
2,5-Dibromo-3,4-ethylenedioxythiophene (DBEDOT) is a monomer which is used in the synthesis of highly conducting poly(3,4-ethylenedioxythiophene) (PEDOT) polymer. This polymer is formed by solid-state polymerisation of DBEDOT and is used widely in organic-light emitting diodes and polymer field effect transistors. DBEDOT is a well-ordered crystalline monomer and produces PEDOT polymer which has a high degree of order. | [Synthesis]
The general procedure for the synthesis of 2,5-dibromo-3,4-ethenyldioxythiophene from 3,4-ethenyldioxythiophene was as follows: a solution of tetrahydrofuran (THF, 20 mL) with 3,4-ethenyldioxythiophene (1.42 g, 10.60 mmol), N-bromosuccinimide (3.74 g, 12.80 mmol), and acetic acid (20 mL) was added sequentially to a round bottomed flask. The reaction mixture was stirred at room temperature for 2 hours. Upon completion of the reaction, the mixture was poured into distilled water and stirred with a glass rod to promote the formation of the precipitate. Subsequently, the precipitate was collected by filtration to afford the target product 2,5-dibromo-3,4-vinyl dioxythiophene (A4) as a white solid (2.50 g, 8.30 mmol, 83% yield). The product was characterized by 1H NMR (400 MHz, CDCl3) with chemical shift δ = 4.27 (s, 4H). | [References]
[1] Journal of the American Chemical Society, 2000, vol. 122, # 28, p. 6746 - 6753
[2] Journal of Organic Chemistry, 2003, vol. 68, # 13, p. 5357 - 5360
[3] Organic Letters, 2018, vol. 20, # 16, p. 4728 - 4731
[4] Journal of the American Chemical Society, 2000, vol. 122, # 41, p. 10121 - 10125
[5] Macromolecules, 2004, vol. 37, # 11, p. 4087 - 4098 |
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