3,4-Ethylenedioxythiophene Chemical Properties

Melting point:

10 °C

Boiling point:

193 °C (lit.)

Density 

1.331 g/mL at 25 °C (lit.)

vapor pressure 

11.9Pa at 25℃

refractive index 

n20/D 1.5765(lit.)

Flash point:

230 °F

storage temp. 

2-8°C

form 

clear liquid

color 

Colorless to Yellow

Water Solubility 

Immsicible with water. Miscible with alcohol and ether.

InChI

InChI=1S/C6H6O2S/c1-2-8-6-4-9-3-5(6)7-1/h3-4H,1-2H2

InChIKey

GKWLILHTTGWKLQ-UHFFFAOYSA-N

SMILES

O1CCOC2=CSC=C12

LogP

1.976 at 25℃ and pH7.1

CAS DataBase Reference

126213-50-1(CAS DataBase Reference)

EPA Substance Registry System

Thieno[3,4-b]-1,4-dioxin, 2,3-dihydro- (126213-50-1)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

21/22-36

Safety Statements 

26-36

RIDADR 

UN 2810 6.1/PG 3

WGK Germany 

2

TSCA 

Yes

HazardClass 

6.1

PackingGroup 

III

HS Code 

29349990

MSDS

• Language:English Provider:SigmaAldrich

3,4-Ethylenedioxythiophene Usage And Synthesis

Chemical Properties

Light yellow liquid

Uses

3,4-Ethylenedioxythiophene is used as a monomer to synthesize the conductive polymers and used as a reductant in the one-pot synthesis of gold nanoparticles from chloroauric acid, as starting material used in palladium-catalyzed mono and bis-arylation reactions and in the synthesis of conjugated polymers and copolymers, with potential optical applications. It is also used in redox activity, electroactivity and conductivity.

General Description

3,4-Ethylenedioxythiophene (EDOT) is an electro-active conductive monomer with a thiol group that combines an electron donor and electron acceptor in a donor-acceptor-donor arrangement.

Synthesis

The general procedure for the synthesis of 3,4-ethylenedioxythiophene (EDOT) from diethyl 2,3-dihydrothieno[3,4-b][1,4]dioxane-5,7-dicarboxylate was as follows: thiophene 3,4-ethylenedioxy-2,5-dicarboxylic acid (209g, 0.73mol) was dissolved in a solvent mixture of dimethylsulfoxide and water (4:1 v/v) in a total volume of 1.5 L) and sodium chloride (128 g, 2.19 mol) was added. The reaction mixture was heated to 120 °C and kept at this temperature for 4 hours. Upon completion of the reaction, dimethyl sulfoxide, the by-product methyl acetate and the target product 3,4-ethylenedioxythiophene (EDOT) were separated by distillation. EDOT was finally obtained as a colorless liquid with a yield of 86 g in 83% yield.

References

[1] Patent: CN102775423, 2017, B. Location in patent: Paragraph 0021; 0087-0088
[2] Journal of Materials Chemistry, 2005, vol. 15, # 45, p. 4783 - 4792
[3] Synthetic Communications, 1996, vol. 26, # 11, p. 2205 - 2212
[4] Patent: EP2548875, 2013, A1

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