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Merck

668257

Sigma-Aldrich

3,4-Dimethoxythiophene

97%

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About This Item

Fórmula empírica (notación de Hill):
C6H8O2S
Número de CAS:
Peso molecular:
144.19
MDL number:
UNSPSC Code:
12352103
PubChem Substance ID:
NACRES:
NA.23

Quality Level

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

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

signalword

Warning

hcodes

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

224.1 °F - closed cup

flash_point_c

106.7 °C - closed cup

ppe

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


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Visite la Librería de documentos

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)
Revisiting the electropolymerization of 3, 4-dimethoxythiophene in organic and micellar media.
Fall M, et al.
Synthetic Metals, 123(3), 365-372 (2001)
Simple one-step synthesis of 3,4-dimethoxythiophene and its conversion into 3, 4-ethylenedioxythiophene (EDOT).
von Kieseritzky F, et al.
Tetrahedron Letters, 45(31), 6049-6050 (2004)
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)

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