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Sigma-Aldrich

2,5-Dibromo-3,4-ethylenedioxythiophene

97%

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Synonym(s):
5,7-Dibromo-2,3-dihydrothieno[3,4-b][1,4]dioxine
Empirical Formula (Hill Notation):
C6H4Br2O2S
CAS Number:
174508-31-7
Molecular Weight:
299.97
MDL number:
MFCD01651770
UNSPSC Code:
12352103
PubChem Substance ID:
329766815
NACRES:
NA.23

Assay

97%

form

solid

mp

95-100 °C

storage temp.

−20°C

SMILES string

Brc1sc(Br)c2OCCOc12

InChI

1S/C6H4Br2O2S/c7-5-3-4(6(8)11-5)10-2-1-9-3/h1-2H2

InChI key

FHMRWRBNAIDRAP-UHFFFAOYSA-N

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.

Application

Used as a monomer in the synthesis of poly(3,4-ethylenedioxythiophene) (PEDOT) polymer which are used in electrochromic devices.

Features and Benefits

Polymerisation of DBEDOT can take place under very gentle conditions in the absence of external agents or catalysts.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Hazard Classifications

Acute Tox. 4 Oral

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Hong Meng et al.
Journal of the American Chemical Society, 125(49), 15151-15162 (2003-12-05)
Prolonged storage ( approximately 2 years) or gentle heating (50-80 degrees 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
Synthesis and characterization of thiophene functionalized polystyrene copolymers and their electrochemical properties
Sahin, E., Camurlu, P., Toppare, L., Mercore, V. M., Cianga, I., & Yagci, Y.
Polymer International, 54(12), 1599-1605 (2005)
Minami Kato et al.
ChemSusChem, 13(9), 2379-2385 (2020-02-11)
Many types of batteries have been proposed as next-generation energy-storage systems. One candidate is a rocking-chair-type "molecular ion battery" in which a molecular ion, instead of Li+ , works as a charge carrier. Previously, we reported a viologen-type derivative as

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