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| | 5,7-Dibromo-2,3-dihydrothieno[3,4-b][1,4]dioxine Basic information |
| Product Name: | 5,7-Dibromo-2,3-dihydrothieno[3,4-b][1,4]dioxine | | Synonyms: | 5,7-DIBROMO-2,3-DIHYDROTHIENO[3,4-B][1,4]DIOXINE;5,7-Dibromo-2,3-dihydrothieno[3,4-b][1,4]dioxine 97%;5,7-dibroMo-2H,3H-thieno[3,4-b][1,4]dioxine;2,3-Dihydro[2,5-dibroMothioeno]
[3,4-b]-1,4-dioxin;4-b][1;2,5-Dibromo-3,4-ethylenedioxythiophene 97%;5,7-Dibromo-2,3-dihydrothieno[3,4-b][1,4]dioxine97%;2,5-Dibromo-3,4-ethylenedioxythiophene> | | CAS: | 174508-31-7 | | MF: | C6H4Br2O2S | | MW: | 299.97 | | EINECS: | | | Product Categories: | Thiophen;Materials Science;New Products for Materials Research and Engineering;Organic and Printed Electronics;Synthetic Intermediates;Synthetic Tools and Reagents;Heterocyclic Compounds;Thiophens;Thiophene Monomers and Building Blocks | | Mol File: | 174508-31-7.mol | ![5,7-Dibromo-2,3-dihydrothieno[3,4-b][1,4]dioxine Structure](CAS/GIF/174508-31-7.gif) |
| | 5,7-Dibromo-2,3-dihydrothieno[3,4-b][1,4]dioxine Chemical Properties |
| 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 | | InChI | 1S/C6H4Br2O2S/c7-5-3-4(6(8)11-5)10-2-1-9-3/h1-2H2 | | InChIKey | FHMRWRBNAIDRAP-UHFFFAOYSA-N | | SMILES | Brc1sc(Br)c2OCCOc12 | | CAS DataBase Reference | 174508-31-7 |
| Hazard Codes | Xn | | Risk Statements | 20/21/22-36/37/38-22 | | Safety Statements | 22-26-36/37/39-24/25 | | WGK Germany | 3 | | Hazard Note | Irritant | | HS Code | 29349990 | | Storage Class | 13 - Non Combustible Solids | | Hazard Classifications | Acute Tox. 4 Oral |
| | 5,7-Dibromo-2,3-dihydrothieno[3,4-b][1,4]dioxine Usage And Synthesis |
| Chemical Properties | Needle-like solid | | Uses | Used as a monomer in the synthesis of poly(3,4-ethylenedioxythiophene) (PEDOT) polymer which are used in electrochromic devices. | | 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 |
| | 5,7-Dibromo-2,3-dihydrothieno[3,4-b][1,4]dioxine Preparation Products And Raw materials |
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