225518-49-0

Basic information

• Product Name: 5,7-dichloro-2,3-dihydrothieno3,4-b1,4dioxine
• Synonyms: 5,7-dichloro-2,3-dihydrothieno[3,4-b][1,4]dioxin;2,5-Dichloro-3,4-ethylenedioxythiophene;5,7-dichloro-2,3-dihydrothieno3,4-b1,4dioxine;5,7-DICHLORO-2,3-DIHYDROTHIENO[3,4-B][1,4]DIOXINE,95% MIN(HPLC)
• CAS NO: 225518-49-0
• Molecular Formula: C6H4Cl2O2S
• Molecular Weight: 211.07
• Product Categories: Heterocyclic Compounds;Thiophens;Thiophen
• Mol File: 225518-49-0.mol
• Article Data: 3

Chemical Properties

• Melting Point: 65.0 to 69.0 °C
• Appearance: /
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: 5,7-dichloro-2,3-dihydrothieno3,4-b1,4dioxine(CAS DataBase Reference)
• NIST Chemistry Reference: 5,7-dichloro-2,3-dihydrothieno3,4-b1,4dioxine(225518-49-0)
• EPA Substance Registry System: 5,7-dichloro-2,3-dihydrothieno3,4-b1,4dioxine(225518-49-0)

Safety Data

• Hazardous Substances Data: 225518-49-0(Hazardous Substances Data)

Usage

Uses

5,7-Dichloro-2,3-dihydrothieno[3,4-b][1,4]dioxine is used as a reactant in the synthesis of polyethylenedioxythiophene.

Upstream product

• 126213-50-1 3,4-(ethylenedioxy)thiophene 

Relevant articles and documents

Selective and general exhaustive cross-coupling of di-chloroarenes with a deficit of nucleophiles mediated by a Pd-NHC complex

We report the first example of a general, exhaustive Pd-mediated cross-coupling of polychloroarenes in the presence of a deficit of nucleophiles, mediated by the highly active PEPPSI-IPent catalyst. Our results indicate that this catalyst system may be applicable to the pseudo-living polymerisation of chloroarene monomers.

Solid-State Synthesis of a Conducting Polythiophene via an Unprecedented Heterocyclic Coupling Reaction

Prolonged storage (～2 years) or gentle heating (50-80 °C) of crystalline 2,5-dibromo-3,4-ethylenedioxythiophene (DBEDOT) affords a highly conducting, bromine-doped poly(3,4-ethylenedioxythiophene) (PEDOT), as confirmed by solid-state NMR, FTIR, CV, and vis-NIR spectroscopies. The novel solid-state polymerization (SSP) does not occur for 2,5-dichloro-3,4-ethylenedioxythiophene (DCEDOT), and requires a much higher temperature (>130 °C) for 2,5-diiodo-3,4-ethylenedioxythiophene (DIEDOT). X-ray structural analysis of the above dihalothiophenes reveals short Hal...Hal distances between adjacent molecules in DBEDOT and DIEDOT, but not in DCEDOT. The polymerization may also occur in the melt but is significantly slower and leads to poorly conductive material. Detailed studies of the reaction were performed using ESR, DSC, microscopy, and gravimetric analyses. SSP starts on crystal defect sites; it is exothermic by 14 kcal/mol and requires activation energy of ～26 kcal/mol (for DBEDOT). The temperature dependence of the conductivity of SSP-PEDOT (σrt = 20-80 S/cm) reveals a slight thermal activation. It can be further increased by a factor of 2 by doping with iodine. Using this approach, thin films of PEDOT with conductivity as high as 20 S/cm were fabricated on insulating flexible plastic surfaces.