3,4-Ethylenedioxythiophene supplier

Name
3,4-Ethylenedioxythiophene
EINECS 1806241-263-5
CAS No. 126213-50-1
Article Data25
CAS DataBase
Density 1.319 g/cm³
Solubility Immsicible with water. Miscible with alcohol and ether.
Melting Point 10 °C
Formula C₆H₆O₂S
Boiling Point 210.494 °C at 760 mmHg
Molecular Weight 142.178
Flash Point 81.104 °C
Transport Information UN 2810 6.1/PG 3
Appearance near colorless to pale yellow liquid with slightly unpleasant ordr
Safety 26-36
Risk Codes 21/22-36
Molecular Structure
Hazard Symbols Xn,Xi
Synonyms 2,3-Dihydrothieno[3,4-b]-1,4-dioxin;3,4-Ethyleneoxythiophene;EDOT;3,4-Ethylenedioxythiophene(EDOT);
PSA 46.70000
LogP 1.51930

Synthetic route

: 18361-03-0
3,4-ethylenedioxythiophene-2,5-dicarboxyllic acid

: 126213-50-1
3,4-(ethylenedioxy)thiophene

Conditions

Conditions	Yield
copper In ethylene glycol at 20 - 140℃; for 8.5h;	98%
copper (II) carbonate hydroxide In polyethylene glycol 300 for 20h; Heating / reflux;	96%
copper (II) carbonate hydroxide In sulfolane at 140℃; for 8h;	95%

: 154934-13-1
2,3-dihydro-thieno[3,4-b][1,4]dioxine-5,7-dicarboxylic acid diethyl ester

: 126213-50-1
3,4-(ethylenedioxy)thiophene

Conditions

Conditions	Yield
With copper(II) oxide; zinc(II) oxide In water; N,N-dimethyl-formamide at 115℃; for 3h; Catalytic behavior; Temperature;	97.9%
With sodium chloride In dimethyl sulfoxide at 120℃; for 6h; Time;	84%
Multi-step reaction with 2 steps 1: 95 percent / KOH / ethanol / 3 h / Heating 2: 68 percent / CuO; quinoline / 5 h / 200 °C View Scheme
Multi-step reaction with 2 steps 1: 100 percent / potassium hydroxide / ethanol / 3 h / Heating 2: 54 percent / copper bronze, quinoline / 4 h / 180 - 200 °C View Scheme
Multi-step reaction with 2 steps 1.1: sodium hydroxide; water / 0.08 h / 100 °C / Microwave irradiation 1.2: 20 °C / pH 2.0 2.1: copper chromite / N,N-dimethyl-formamide / 0.33 h / 153 °C / Microwave irradiation View Scheme

: 51792-34-8
2,3-dimethoxythiophene

: 107-21-1
ethylene glycol

: 126213-50-1
3,4-(ethylenedioxy)thiophene

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In toluene at 95℃; for 96h; Inert atmosphere;	84%
With toluene-4-sulfonic acid In toluene Heating;	65%
With toluene-4-sulfonic acid In methanol; toluene at 100℃; for 3h; Reagent/catalyst; Inert atmosphere;	46.7%

: 107-21-1
ethylene glycol

: 122721-91-9
3,4-diethoxythiophene

: 126213-50-1
3,4-(ethylenedioxy)thiophene

Conditions

Conditions	Yield
With toluene-4-sulfonic acid; hydroquinone In o-xylene at 137 - 142℃; for 4h; Reagent/catalyst; Inert atmosphere;	84%

3,4-ethylenedioxythiophene; 3,4-dimethoxythiophene: 3,4-ethylenedioxythiophene; 3,4-dimethoxythiophene

: 126213-50-1
3,4-(ethylenedioxy)thiophene

Conditions

Conditions	Yield
Purification / work up;	76%

: 195602-16-5
2,5-bis(trimethylsilyl)-3,4-ethylenedioxythiophene

: 126213-50-1
3,4-(ethylenedioxy)thiophene

Conditions

Conditions	Yield
With tetrabutyl ammonium fluoride	70%

: 101537-27-3
diethinyl glycol

: 126213-50-1
3,4-(ethylenedioxy)thiophene

Conditions

Conditions	Yield
With 2,2'-azobis(isobutyronitrile); tiolacetic acid In toluene at 80℃; for 5h; Inert atmosphere; Schlenk technique; Green chemistry;	48%

: 3141-26-2
3,4-dibromothiophene

: 107-21-1
ethylene glycol

A: 3-bromo-4-(1-hydroxyethyl)oxythiophene

B: 126213-50-1
3,4-(ethylenedioxy)thiophene

Conditions

Conditions	Yield
With potassium phosphate; copper(l) iodide; 8-quinolinol In N,N-dimethyl-formamide at 120℃; for 24h; Reagent/catalyst; Solvent;	A 43% B 15%

...Expand

: 2,3-dimethoxy-2,3-dimethyl-1,4-dioxane

: 126213-50-1
3,4-(ethylenedioxy)thiophene

Conditions

Conditions	Yield
With sulfur; copper(l) iodide In toluene at 180℃; for 6h; Reagent/catalyst; Temperature; Microwave irradiation; Sealed tube;	37%

: 1271145-38-0
(3S*,4R*)-tetrahydro-3,4-ethylenedioxythiophene

: 126213-50-1
3,4-(ethylenedioxy)thiophene

Conditions

Conditions	Yield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In chlorobenzene for 9h; Inert atmosphere; Reflux;	23%

: (3S*,4S*)-tetrahydro-3,4-ethylenedioxythiophene

: 126213-50-1
3,4-(ethylenedioxy)thiophene

Conditions

Conditions	Yield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In chlorobenzene at 80℃; for 6h; Inert atmosphere;	21%

: (2R*,3R*)-2,3-bis(methanesulfonyloxymethyl)-1,4-dioxane

: 126213-50-1
3,4-(ethylenedioxy)thiophene

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sodiumsulfide nonahydrate / N,N-dimethyl-formamide / 17 h / 50 °C / Inert atmosphere 2: 2,3-dicyano-5,6-dichloro-p-benzoquinone / chlorobenzene / 6 h / 80 °C / Inert atmosphere View Scheme

: (2R*,3S*)-3-(2-bromoethoxy)-1,4-bis(benzyloxy)butan-2-ol

: 126213-50-1
3,4-(ethylenedioxy)thiophene

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: potassium hydroxide / ethanol / 12 h / Inert atmosphere; Reflux 2: hydrogenchloride; palladium 10% on activated carbon; water; hydrogen / methanol / 24 h / 20 °C / 760.05 Torr 3: triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere 4: sodiumsulfide nonahydrate / ethanol / 12 h / Inert atmosphere; Reflux 5: 2,3-dicyano-5,6-dichloro-p-benzoquinone / chlorobenzene / 9 h / Inert atmosphere; Reflux View Scheme

Yield

Multi-step reaction with 5 steps
1: potassium hydroxide / ethanol / 12 h / Inert atmosphere; Reflux
2: hydrogenchloride; palladium 10% on activated carbon; water; hydrogen / methanol / 24 h / 20 °C / 760.05 Torr
3: triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere
4: sodiumsulfide nonahydrate / ethanol / 12 h / Inert atmosphere; Reflux
5: 2,3-dicyano-5,6-dichloro-p-benzoquinone / chlorobenzene / 9 h / Inert atmosphere; Reflux
View Scheme

: 1271145-22-2
(2R*,3S*)-2,3-bis(benzyloxymethyl)-1,4-dioxane

: 126213-50-1
3,4-(ethylenedioxy)thiophene

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: hydrogenchloride; palladium 10% on activated carbon; water; hydrogen / methanol / 24 h / 20 °C / 760.05 Torr 2: triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere 3: sodiumsulfide nonahydrate / ethanol / 12 h / Inert atmosphere; Reflux 4: 2,3-dicyano-5,6-dichloro-p-benzoquinone / chlorobenzene / 9 h / Inert atmosphere; Reflux View Scheme

: 876607-67-9
(2R*,3S*)-2,3-bis(hydroxymethyl)-1,4-dioxane

: 126213-50-1
3,4-(ethylenedioxy)thiophene

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere 2: sodiumsulfide nonahydrate / ethanol / 12 h / Inert atmosphere; Reflux 3: 2,3-dicyano-5,6-dichloro-p-benzoquinone / chlorobenzene / 9 h / Inert atmosphere; Reflux View Scheme

: 1271330-69-8
(2R*,3S*)-2,3-bis(methanesulfonyloxymethyl)-1,4-dioxane

: 126213-50-1
3,4-(ethylenedioxy)thiophene

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sodiumsulfide nonahydrate / ethanol / 12 h / Inert atmosphere; Reflux 2: 2,3-dicyano-5,6-dichloro-p-benzoquinone / chlorobenzene / 9 h / Inert atmosphere; Reflux View Scheme

: (2R*,3R*)-3-(2-bromoethoxy)-1,4-bis(benzyloxy)butan-2-ol

: 126213-50-1
3,4-(ethylenedioxy)thiophene

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: potassium hydroxide / ethanol / 6 h / Inert atmosphere; Reflux 2: hydrogenchloride; palladium 10% on activated carbon; water; hydrogen / methanol / 4 h / 20 °C / 760.05 Torr 3: triethylamine / dichloromethane / 5.5 h / 0 °C / Inert atmosphere 4: sodiumsulfide nonahydrate / N,N-dimethyl-formamide / 17 h / 50 °C / Inert atmosphere 5: 2,3-dicyano-5,6-dichloro-p-benzoquinone / chlorobenzene / 6 h / 80 °C / Inert atmosphere View Scheme

Yield

Multi-step reaction with 5 steps
1: potassium hydroxide / ethanol / 6 h / Inert atmosphere; Reflux
2: hydrogenchloride; palladium 10% on activated carbon; water; hydrogen / methanol / 4 h / 20 °C / 760.05 Torr
3: triethylamine / dichloromethane / 5.5 h / 0 °C / Inert atmosphere
4: sodiumsulfide nonahydrate / N,N-dimethyl-formamide / 17 h / 50 °C / Inert atmosphere
5: 2,3-dicyano-5,6-dichloro-p-benzoquinone / chlorobenzene / 6 h / 80 °C / Inert atmosphere
View Scheme

: (2R*,3R*)-2,3-bis(benzyloxymethyl)-1,4-dioxane

: 126213-50-1
3,4-(ethylenedioxy)thiophene

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: hydrogenchloride; palladium 10% on activated carbon; water; hydrogen / methanol / 4 h / 20 °C / 760.05 Torr 2: triethylamine / dichloromethane / 5.5 h / 0 °C / Inert atmosphere 3: sodiumsulfide nonahydrate / N,N-dimethyl-formamide / 17 h / 50 °C / Inert atmosphere 4: 2,3-dicyano-5,6-dichloro-p-benzoquinone / chlorobenzene / 6 h / 80 °C / Inert atmosphere View Scheme

Yield

Multi-step reaction with 4 steps
1: hydrogenchloride; palladium 10% on activated carbon; water; hydrogen / methanol / 4 h / 20 °C / 760.05 Torr
2: triethylamine / dichloromethane / 5.5 h / 0 °C / Inert atmosphere
3: sodiumsulfide nonahydrate / N,N-dimethyl-formamide / 17 h / 50 °C / Inert atmosphere
4: 2,3-dicyano-5,6-dichloro-p-benzoquinone / chlorobenzene / 6 h / 80 °C / Inert atmosphere
View Scheme

: (2R*,3R*)-2,3-bis(hydroxymethyl)-1,4-dioxane

: 126213-50-1
3,4-(ethylenedioxy)thiophene

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: triethylamine / dichloromethane / 5.5 h / 0 °C / Inert atmosphere 2: sodiumsulfide nonahydrate / N,N-dimethyl-formamide / 17 h / 50 °C / Inert atmosphere 3: 2,3-dicyano-5,6-dichloro-p-benzoquinone / chlorobenzene / 6 h / 80 °C / Inert atmosphere View Scheme

: 51792-34-8
2,3-dimethoxythiophene

: 107-21-1
ethylene glycol

A: C7H10O3S

B: C8H12O4S

C: 126213-50-1
3,4-(ethylenedioxy)thiophene

Conditions

Conditions	Yield
With [(1S)-7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl]methanesulfonic acid In methanol; toluene at 100℃; for 1h; Reagent/catalyst; Inert atmosphere;	A 19.3 %Chromat. B 12.84 %Chromat. C 56.29 %Chromat.
With 2-aminonaphthalenesulfonic acid In methanol; toluene at 100℃; for 3h; Reagent/catalyst; Inert atmosphere;	A 7.3 %Chromat. B 11.78 %Chromat. C 70.74 %Chromat.

...Expand

: 51792-34-8
2,3-dimethoxythiophene

: 107-21-1
ethylene glycol

A: C7H10O3S

B: 126213-50-1
3,4-(ethylenedioxy)thiophene

Conditions

Conditions	Yield
With para-dodecylbenzenesulfonic acid In methanol; toluene at 100℃; for 1h; Reagent/catalyst; Inert atmosphere;	A 13.67 %Chromat. B 79.08 %Chromat.

...Expand

: 51792-34-8
2,3-dimethoxythiophene

: 107-21-1
ethylene glycol

A: C8H12O4S

B: 126213-50-1
3,4-(ethylenedioxy)thiophene

Conditions

Conditions	Yield
With naphthalene-2-sulfonate In methanol; toluene at 100℃; for 3h; Inert atmosphere;	A 14.42 %Chromat. B 78.58 %Chromat.

...Expand

: thieno[3,4-b]-1,4-dioxine-5,7-dicarboxylic acid

: 126213-50-1
3,4-(ethylenedioxy)thiophene

Conditions

Conditions	Yield
With copper oxide nanoparticles coated on Ni-Cr alloy In N,N-dimethyl-formamide at 110℃; for 2.25h; Temperature;

: 68-12-2, 33513-42-7
N,N-dimethyl-formamide

: 126213-50-1
3,4-(ethylenedioxy)thiophene

: 204905-77-1
3,4-ethylenedioxythiophene-2-carboxaldehyde

Conditions

Conditions	Yield
With trichlorophosphate at -10 - 20℃; for 1.25h;	100%
With n-butyllithium In tetrahydrofuran at -78 - 20℃; Formylation;	95%
With trichlorophosphate at 20℃; Vilsmeier-Haack Formylation; Cooling with ice;	95%

: 126213-50-1
3,4-(ethylenedioxy)thiophene

: 174508-31-7
5,7-dibromo-2,3-dihydrothieno[3,4-b][1,4]dioxine

Conditions

Conditions	Yield
With N-Bromosuccinimide; acetic acid In tetrahydrofuran at 20℃; for 2h;	100%
With N-Bromosuccinimide In N,N-dimethyl-formamide at 0 - 20℃; for 2h;	95%
With N-Bromosuccinimide In N,N-dimethyl-formamide at -15℃; for 1h;	91%

: 126213-50-1
3,4-(ethylenedioxy)thiophene

: 204905-77-1
3,4-ethylenedioxythiophene-2-carboxaldehyde

Conditions

Conditions	Yield
With N,N-dimethyl-formamide; trichlorophosphate at -10 - 20℃; Vilsmeier formylation;	100%

: 126213-50-1
3,4-(ethylenedioxy)thiophene

: 195602-17-6
2,2'-bis(3,4-ethylenedioxythiophene)

Conditions

Conditions	Yield
Stage #1: 3,4-(ethylenedioxy)thiophene With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran at -10℃; for 0.5h; Metallation; Stage #2: With iron(III)-acetylacetonate In tetrahydrofuran for 6h; Oxidation; Heating;	99%
With n-butyllithium; copper dichloride In tetrahydrofuran; hexane at -78 - 0℃; for 12h; Dimerization;	84%
With n-butyllithium; copper dichloride In tetrahydrofuran at -80 - -40℃;	76%

: 126213-50-1
3,4-(ethylenedioxy)thiophene

: 74-88-4
methyl iodide

: 5-methyl-2,3-dihydrothieno[3,4-b][1,4]dioxine

Conditions

Conditions	Yield
Stage #1: 3,4-(ethylenedioxy)thiophene In tetrahydrofuran; hexane at -78℃; for 1h; Stage #2: methyl iodide In tetrahydrofuran; hexane at -78 - 20℃;	99%
Stage #1: 3,4-(ethylenedioxy)thiophene With 2,2,6,6-tetramethyl-piperidine; tert.-butyl lithium In tetrahydrofuran; pentane for 1.5h; Sealed tube; Inert atmosphere; Cooling with acetone-dry ice; Stage #2: methyl iodide In tetrahydrofuran; pentane	97%

: 617-86-7
triethylsilane

: 126213-50-1
3,4-(ethylenedioxy)thiophene

: 2,5-bis(triethylsilyl)-3,4-ethylenedioxythiophene

Conditions

Conditions	Yield
With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 3,4,7,8-Tetramethyl-o-phenanthrolin; norbornene In di-isopropyl ether at 80℃; for 22h; Inert atmosphere;	99%

: 109-72-8, 29786-93-4
n-butyllithium

: 1461-22-9
tributyltin chloride

: 126213-50-1
3,4-(ethylenedioxy)thiophene

: 175922-79-9
tributyl(2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)-stannane

Conditions

Conditions	Yield
In tetrahydrofuran; hexane	98%

...Expand

: 108-86-1
bromobenzene

: 126213-50-1
3,4-(ethylenedioxy)thiophene

: 5,7-diphenyl-2,3-dihydrothieno[3,4-b][1,4]-dioxine

Conditions

Conditions	Yield
With palladium diacetate; caesium carbonate; tri(m-tolyl)phosphine In toluene at 110℃; for 24h; Inert atmosphere;	98%
With palladium diacetate; caesium carbonate; triphenylphosphine In toluene at 110℃; for 24h; Inert atmosphere;	75%

: 853955-58-5
dimethyl(2-(((tetrahydro-2H-pyran-2-yl)oxy)methyl)phenyl)silane

: 126213-50-1
3,4-(ethylenedioxy)thiophene

: 2,5-bis[2-{(2-tetrahydropyranyloxy)methyl}phenyldimethylsilyl]-3,4-ethylenedioxythiophene

Conditions

Conditions	Yield
With norborn-2-ene; (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 3,4,7,8-Tetramethyl-o-phenanthrolin In di-isopropyl ether at 80℃; for 5h; Inert atmosphere; Sealed tube;	98%

: 626-55-1
3-Bromopyridine

: 126213-50-1
3,4-(ethylenedioxy)thiophene

: 5,7-di(pyridin-3-yl)-2,3-dihydrothieno[3,4-b][1,4]dioxine

Conditions

Conditions	Yield
With {N,N-(1,2-diphenylethane-1,2-diylidene)bis(2-benzhydryl-4,6-dimthylaniline)}dichloropalladium; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 130℃; for 12h; Catalytic behavior;	98%

: 1532-97-4
4-bromoisoquinoline

: 126213-50-1
3,4-(ethylenedioxy)thiophene

: 5,7-di(isoquinolin-4-yl)-2,3-dihydrothieno[3,4-b][1,4]dioxine

Conditions

Conditions	Yield
With {N,N-(1,2-diphenylethane-1,2-diylidene)bis(2-benzhydryl-4,6-dimthylaniline)}dichloropalladium; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 130℃; for 12h; Catalytic behavior;	97%

: 126213-50-1
3,4-(ethylenedioxy)thiophene

: C6H4(2)H2O2S

Conditions

Conditions	Yield
With potassium carbonate; silver carbonate; johnphos In dimethyl sulfoxide at 25℃; for 12h;	97%
With deuteromethanol; silver carbonate; johnphos at 50 - 80℃;	91%

: 126213-50-1
3,4-(ethylenedioxy)thiophene

: 25015-63-8
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane

: 250726-93-3
2-(2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)-4,4,5,5-tetramethyl-2-thiophen-2-yl-1,3,2-dioxaborolane

Conditions

Conditions	Yield
With 1-(difluoromethoxyborato)-2-TMP-benzene In chloroform at 80℃; for 16h; Inert atmosphere;	96%
With 1-(2-borylphenyl)-2,2,6,6-tetramethylpiperidine dimer In chloroform at 80℃; for 16h;	87%
With 1-(trifluoroborato)-2-TMP-benzene In neat (no solvent) at 80℃; for 6h; Reagent/catalyst; Inert atmosphere;	85%
With 1-(trifluoroborato)-2-TMP-benzene In neat (no solvent) at 80℃; for 6h; Inert atmosphere; regioselective reaction;	85%
With poly((2-(piperidin-1-ium-1-yl)-5-vinylphenyl)trifluoroborate) In neat (no solvent) at 90℃; for 16h; Reagent/catalyst; Inert atmosphere; Glovebox; Sealed tube;

: 61676-62-8
2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

: 126213-50-1
3,4-(ethylenedioxy)thiophene

: 250726-93-3
2-(2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)-4,4,5,5-tetramethyl-2-thiophen-2-yl-1,3,2-dioxaborolane

Conditions

Conditions	Yield
Stage #1: 3,4-(ethylenedioxy)thiophene With n-butyllithium Stage #2: 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane	95%
Stage #1: 3,4-(ethylenedioxy)thiophene With n-butyllithium In tetrahydrofuran at -78 - 0℃; for 0.333333h; Inert atmosphere; Stage #2: 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In tetrahydrofuran at -78 - 20℃; for 17h; Irradiation;	78%
With n-butyllithium In tetrahydrofuran at -78 - 20℃; for 6h; Substitution;	71%

: 1600-27-7
mercury(II) diacetate

: 126213-50-1
3,4-(ethylenedioxy)thiophene

: 640737-73-1
2,5-diacetoxymercuro-3,4-ethylenedioxythiophene

Conditions

Conditions	Yield
In acetic acid to soln. 3,4-ethylenedioxythiophene in acetic acid soln. Hg(OAc)2 in acetic acid was added dropwise and stirred overnight; ppt. was filtered, washed with MeOH and et2O and dried in vacuo; elem. anal.;	95%

: 27126-76-7
[hydroxy(tosyloxy)iodo]benzene

: 126213-50-1
3,4-(ethylenedioxy)thiophene

: 1222887-22-0
(2,3-dihydro-thieno[3,4-b][1,4]dioxin-5-yl)(phenyl)iodonium tosylate

Conditions

Conditions	Yield
In 2,2,2-trifluoroethanol at 20℃; for 3h;	94%

: C10H18BrClSi

: 126213-50-1
3,4-(ethylenedioxy)thiophene

: C16H23ClO2SSi

Conditions

Conditions	Yield
Stage #1: 3,4-(ethylenedioxy)thiophene With n-butyllithium In 1,2-dimethoxyethane Stage #2: With copper(l) cyanide Stage #3: C10H18BrClSi at -78 - -30℃;	94%

: 126213-50-1
3,4-(ethylenedioxy)thiophene

: 640737-72-0
5,7-diiodo-2,3-dihydrothieno[3,4-b][1,4]dioxine

Conditions

Conditions	Yield
With iodine monochloride-pyridine In dichloromethane at 20℃; for 1h;	93%
With N-iodo-succinimide; acetic acid In tetrahydrofuran at 20℃;	88%
With N-iodo-succinimide; toluene-4-sulfonic acid In ethanol at 25℃; for 0.166667h; Green chemistry; regioselective reaction;	87%

: 106-38-7
para-bromotoluene

: 126213-50-1
3,4-(ethylenedioxy)thiophene

A: 925674-57-3
5-(p-tolyl)-2,3-dihydrothieno[3,4-b][1,4]dioxine

B: 1579939-66-4
2,3-dihydro-5,7-bis(4-methylphenyl)thieno[3,4-b][1,4]dioxine

Conditions

Conditions	Yield
With C40H36N2O2Pd(2+)*2C2H4O2; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 100℃; for 24h; Inert atmosphere; Schlenk technique; regioselective reaction;	A 7% B 93%

...Expand

: 126213-50-1
3,4-(ethylenedioxy)thiophene

: 5-bromo-2,3-dihydrothieno[3,4-b][1,4]dioxine

Conditions

Conditions	Yield
With N-Bromosuccinimide; acetic acid In tetrahydrofuran at 0 - 20℃; for 2h; Schlenk technique;	92%
With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃; for 1h; Inert atmosphere; Darkness;	52%
With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃; for 1h; Bromination;

: 5798-75-4
Ethyl 4-bromobenzoate

: 126213-50-1
3,4-(ethylenedioxy)thiophene

: 2,5-di(4-ethoxycarbonylphenyl)-3,4-ethylenedioxythiophene

Conditions

Conditions	Yield
With potassium acetate; tetra(n-tert-butyl)ammonium bromide; palladium diacetate In N,N-dimethyl-formamide at 80℃; for 1h;	92%

: 126213-50-1
3,4-(ethylenedioxy)thiophene

: 5,7-ditributyltin-2,3-dihydrothieno[3,4-b][1,4]dioxin

Conditions

Conditions	Yield
With lithium diisopropyl amide In tetrahydrofuran at 0 - 20℃;	92%

: 126213-50-1
3,4-(ethylenedioxy)thiophene

: 25015-63-8
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane

: 2,5-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-ethylenedioxythiophene

Conditions

Conditions	Yield
With 1-(2-borylphenyl)-2,2,6,6-tetramethylpiperidine dimer In chloroform at 80℃; for 16h;	92%
With 1-(2-borylphenyl)-2,2,6,6-tetramethylpiperidine dimer In chloroform at 80℃; for 16h; Sealed tube; Microwave irradiation; Glovebox; Inert atmosphere;	92%
With 1-(trifluoroborato)-2-TMP-benzene In neat (no solvent) at 80℃; for 24h; Inert atmosphere; regioselective reaction;	91%

: 815-24-7
Di-t-butyl ketone

: 126213-50-1
3,4-(ethylenedioxy)thiophene

: 3,4-ethylenedioxy-2-[3-(2,2,4,4-tetramethylpentan-3-ol)]thiophene

Conditions

Conditions	Yield
Stage #1: 3,4-(ethylenedioxy)thiophene With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In diethyl ether; hexane at 20℃; for 0.5h; Stage #2: Di-t-butyl ketone In diethyl ether at 20℃; for 0.5h; Further stages.;	91%

: 110-91-8
morpholine

: 50-00-0
formaldehyd

: 126213-50-1
3,4-(ethylenedioxy)thiophene

: 2,5-bis(morpholin-4-ylmethyl)-2,3-dihydrothieno[3,4-b][1,4]dioxin

Conditions

Conditions	Yield
With acetic acid In water at 100℃; for 4h; Mannich reaction;	91%

...Expand

: 126213-50-1
3,4-(ethylenedioxy)thiophene

: 802919-90-0
[(difluoroiodomethyl)sulfonyl]benzene

: 1609470-37-2
C13H10F2O4S2

Conditions

Conditions	Yield
With dipotassium hydrogenphosphate; tris(bipyridine)ruthenium(II) dichloride hexahydrate In dichloromethane at 40℃; for 48h; Sealed tube; Inert atmosphere; Irradiation;	91%

: 126213-50-1
3,4-(ethylenedioxy)thiophene

: 219621-78-0
5-iodo-2,3-dihydrothieno[3,4-b][1,4]dioxine

Conditions

Conditions	Yield
Stage #1: 3,4-(ethylenedioxy)thiophene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Stage #2: With iodine In tetrahydrofuran; hexane at 20℃; for 1h; Further stages.;	90%
With potassium dichloroiodate monohydrate In water at 25℃; for 1h;	63%
With n-butyllithium; iodine In tetrahydrofuran

3,4-Ethylenedioxythiophene Specification

1. Introduction of 3,4-Ethylenedioxythiophene
3,4-Ethylenedioxythiophene, its cas register number is 126213-50-1. The IUPAC Name of 3,4-Ethylenedioxythiophene is 2,3-Dihydrothieno[3,4-b][1,4]dioxine. 3,4-Ethylenedioxythiophene can also be called 2,3-Dihydrothieno[3,4-b][1,4]dioxine and 2,3-Dihydro-thieno[3,4-b][1,4]dioxine. Its classification code are TSCA Flag P [A commenced PMN (Premanufacture Notice) substance] and TSCA Flag S [Substance is identified in a proposed or final SNUR (Significant New Use Rule) under TSCA] .

2. Properties of 3,4-Ethylenedioxythiophene
Index of Refraction: 1.57
Molar Refractivity: 35.41 cm³
Molar Volume: 107.8 cm³
Density: 1.318 g/cm³
Flash Point: 81.1 °C
Polarizability: 14.03 10^-24cm³
Surface Tension: 49.3 dyne/cm
Enthalpy of Vaporization: 42.86 kJ/mol
Boiling Point: 210.5 °C at 760 mmHg
Vapour Pressure: 0.278 mmHg at 25 °C
Product Categories of 3,4-Ethylenedioxythiophene: Thiophenes; Sulphur Derivatives; Thiophens; Thiophen

3. Structure Descriptors of 3,4-Ethylenedioxythiophene
Canonical SMILES: C1COC2=CSC=C2O1
InChI: InChI=1S/C6H6O2S/c1-2-8-6-4-9-3-5(6)7-1/h3-4H,1-2H2
InChIKey: GKWLILHTTGWKLQ-UHFFFAOYSA-N

4. Safety Information of 3,4-Ethylenedioxythiophene
Hazard Codes: Harmful Xn, Irritant Xi
Risk Statements: 21/22-36
R21/22:Harmful in contact with skin and if swallowed.
R36:Irritating to eyes.
Safety Statements: 26-36
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36:Wear suitable protective clothing.
RIDADR: UN 2810 6.1/PG 3
WGK Germany: 2

Product Name

3,4-Ethylenedioxythiophene

Synthetic route

3,4-Ethylenedioxythiophene Specification

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