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5 G
$186.48
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5 G
$186.48
About This Item
Empirical Formula (Hill Notation):
C6H8O2S
CAS Number:
Molecular Weight:
144.19
MDL number:
UNSPSC Code:
12352103
PubChem Substance ID:
NACRES:
NA.23
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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.[1][2]
Application
Building block in the synthesis of an N2S2-N4 porphyrin dyad used to study photoinduced energy transfer.[3]
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.[4][5] It can be polymerized to form poly(dimethoxythiphenes) which can potentially be used in the fabrication energy storage devices on electrochemical doping.[6]
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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Revisiting the electropolymerization of 3, 4-dimethoxythiophene in organic and micellar media.
Fall M, et al.
Synthetic Metals, 123(3), 365-372 (2001)
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)
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)
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)
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)
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