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Sigma-Aldrich

3,4-Dimethoxythiophene

97%

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About This Item

Empirical Formula (Hill Notation):
C6H8O2S
CAS Number:
51792-34-8
Molecular Weight:
144.19
MDL number:
MFCD01096546
UNSPSC Code:
12352103
PubChem Substance ID:
24884971
NACRES:
NA.23

Quality Level

100

assay

97%

refractive index

n20/D 1.5409

bp

100-102 °C/10-11 mmHg

density

1.209 g/mL at 25 °C

storage temp.

−20°C

SMILES string

COc1cscc1OC

InChI

1S/C6H8O2S/c1-7-5-3-9-4-6(5)8-2/h3-4H,1-2H3

InChI key

ZUDCKLVMBAXBIF-UHFFFAOYSA-N

Related Categories

General description

3,4-Dimethoxythiophene (DMOT) is a monomer and a precursor which can be synthesized by ring closure reaction of 2,3-dimethoxy-1,3-butadiene and sulfur dichloride in hexane medium. It is an oligothiphene that is majorly used in the development of electroactive materials for organic electronics based applications.

Application

Building block in the synthesis of an N2S2-N4 porphyrin dyad used to study photoinduced energy transfer.
DMOT can be trans-esterified to form 3,4-ethylenendioxythiophene (EDOT). It can further be polymerized to produce PEDOT which can be used as a conductive polymer in π-conjugated systems. It can be polymerized to form poly(dimethoxythiphenes) which can potentially be used in the fabrication energy storage devices on electrochemical doping.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

wgk_germany

WGK 3

flash_point_f

closed cup

flash_point_c

closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

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Revisiting the electropolymerization of 3, 4-dimethoxythiophene in organic and micellar media.
Fall M, et al.
Synthetic Metals, 123(3), 365-372 (2001)
Sokkalingam Punidha et al.
The Journal of organic chemistry, 73(1), 323-326 (2007-12-12)
Click chemistry has been successfully applied in the synthesis of the first example of a triazole-bridged porphyrin dyad containing N(2)S(2) porphyrin and N(4) or ZnN(4) porphyrin subunits, and fluorescence study indicated a possibility of singlet-singlet energy transfer from the N(4)
In situ conductance studies of p-and n-doping of poly (3, 4-dialkoxythiophenes).
Skompska M, et al.
Journal of Electroanalytical Chemistry, 577(1), 9-17 (2005)
Biomimetic Synthesis of Water Soluble Conductive Polypyrrole and Poly (3, 4 ethylenedioxythiophene).
Bruno FF, et al.
MRS Online Proceedings Library, 736(4), 607-609 (2002)
Thieno [3, 4-b]-1, 4-oxathiane: An Unsymmetrical Sulfur Analogue of 3, 4-Ethylenedioxythiophene (EDOT) as a Building Block for Linear pi-Conjugated Systems.
Blanchard P, et al.
Organic Letters, 4(4), 607-609 (2002)
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Articles

Development of Organic Semiconductors from Highly Ordered Oligo and Polythiophenes

The soaring global demand for energy, coupled with the limited supply of fossil fuels, has increased the need for renewable, low-cost energy sources. Organic electronics have shown great promise for applications in lighting, power, and circuitry, with rapidly improving performance already surpassing that of amorphous silicon-based counterparts.

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