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2,3-Dihydrothieno[3,4-b][1,4]dioxine-5,7-dicarbaldehyde
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Name

2,3-Dihydrothieno[3,4-b][1,4]dioxine-5,7-dicarbaldehyde

 EINECS N/A
CAS No. 211235-87-9 Density 1.511 g/cm3
PSA 80.84000 LogP 1.14430
Solubility N/A Melting Point 155 °C
Formula C8H6O4S Boiling Point 403.4 °C at 760 mmHg
Molecular Weight 198.199 Flash Point 197.8 °C
Transport Information N/A Appearance N/A
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 211235-87-9 (2,3-Dihydrothieno[3,4-b][1,4]dioxine-5,7-dicarbaldehyde) Hazard Symbols N/A
Synonyms

2,3-DIHYDROTHIENO[3,4-B][1,4]DIOXINE-5,7-DICARBALDEHYDE

Article Data 10

2,3-Dihydrothieno[3,4-b][1,4]dioxine-5,7-dicarbaldehyde Synthetic route

1269767-35-2

3,4-ethylenedioxythiophene-2,5-dicarbonitrile

211235-87-9

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

Conditions
ConditionsYield
With diisobutylaluminium hydride In toluene at 0℃;80%
68-12-2, 33513-42-7

N,N-dimethyl-formamide

126213-50-1

3,4-(ethylenedioxy)thiophene

211235-87-9

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

Conditions
ConditionsYield
Stage #1: 3,4-(ethylenedioxy)thiophene With n-butyllithium In tetrahydrofuran at -78 - 0℃; Inert atmosphere;
Stage #2: N,N-dimethyl-formamide In tetrahydrofuran at -78 - 20℃; for 2h; Inert atmosphere;		75%
With n-butyllithium In tetrahydrofuran at -78 - 20℃; Formylation;72%
With n-butyllithium In tetrahydrofuran at -78 - 20℃;62%
With n-butyllithium
Stage #1: 3,4-(ethylenedioxy)thiophene With n-butyllithium In tetrahydrofuran at -78 - 0℃; for 0.333333h; Inert atmosphere;
Stage #2: N,N-dimethyl-formamide In tetrahydrofuran at -78 - 0℃; for 2h; Inert atmosphere;
350474-52-1

2,5-di(hydroxymethyl)-3,4-ethylenedioxythiophene

211235-87-9

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

Conditions
ConditionsYield
With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In dimethyl sulfoxide at 20℃; for 96h;66%
75-27-4

bromodichloromethane

126213-50-1

3,4-(ethylenedioxy)thiophene

A

211235-87-9

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

B

204905-77-1

3,4-ethylenedioxythiophene-2-carboxaldehyde

Conditions
ConditionsYield
Stage #1: bromodichloromethane; 3,4-(ethylenedioxy)thiophene With 1,1'-bis-(diphenylphosphino)ferrocene; potassium phosphate; palladium diacetate; acetic anhydride; silver carbonate In acetonitrile at 60℃; for 48h; Schlenk technique; Inert atmosphere;
Stage #2: With hydrogenchloride In dichloromethane at 30℃; Overall yield = 66 %;		A 43%
B 22%
68-12-2, 33513-42-7

N,N-dimethyl-formamide

204905-77-1

3,4-ethylenedioxythiophene-2-carboxaldehyde

211235-87-9

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

Conditions
ConditionsYield
Stage #1: N,N-dimethyl-formamide; 3,4-ethylenedioxythiophene-2-carboxaldehyde With trichlorophosphate In 1,2-dichloro-ethane at 20℃; for 0.5h; Vilsmeier-Haack Formylation;
Stage #2: In 1,2-dichloro-ethane at 80℃; for 5h; Vilsmeier-Haack Formylation;
Stage #3: With hydrogenchloride In water at 20℃; Vilsmeier-Haack Formylation;		21%
68-12-2, 33513-42-7

N,N-dimethyl-formamide

126213-50-1

3,4-(ethylenedioxy)thiophene

A

211235-87-9

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

B

204905-77-1

3,4-ethylenedioxythiophene-2-carboxaldehyde

Conditions
ConditionsYield
With n-butyllithium; potassium tert-butylate; lithium bromide 1.) THF, hexane, -90 deg C, 30 min, 2.) -90 deg c to room temperature; Yield given; Multistep reaction. Yields of byproduct given;

potassium 2,5-dicyanothiophene-3,4-bis(olate)

211235-87-9

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

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: potassium carbonate; tetrabutylammomium bromide / N,N-dimethyl-formamide / 135 °C / Inert atmosphere
2: diisobutylaluminium hydride / toluene / 0 °C
View Scheme
126213-50-1

3,4-(ethylenedioxy)thiophene

211235-87-9

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

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: trichlorophosphate / 1,2-dichloro-ethane / 5 h / 80 °C
2.1: trichlorophosphate / 1,2-dichloro-ethane / 0.5 h / 20 °C
2.2: 5 h / 80 °C
2.3: 20 °C
View Scheme
618-40-6

1-Methyl-1-phenylhydrazine

211235-87-9

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

1141893-87-9

3,4-ethylenedioxythiophene-2,5-dicarbaldehyde di(N-methyl-N-phenylhydrazone)

Conditions
ConditionsYield
In ethanol Reflux;85%
530-47-2

N,N-diphenylhydrazine hydrochloride

211235-87-9

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

1141893-88-0

3,4-ethylenedioxythiophene-2,5-dicarbaldehyde di(N,N-diphenylhydrazone)

Conditions
ConditionsYield
In ethanol Reflux;79%

2,3-Dihydrothieno[3,4-b][1,4]dioxine-5,7-dicarbaldehyde Specification

The 2,3-Dihydrothieno[3,4-b][1,4]dioxine-5,7-dicarbaldehyde, with CAS registry number 211235-87-9, has the systematic name of 2,3-dihydrothieno[3,4-b][1,4]dioxine-5,7-dicarbaldehyde. Besides this, it is also called thieno[3,4-b]-1,4-dioxin-5,7-dicarboxaldehyde, 2,3-dihydro-. And the chemical formula of this chemical is C8H6O4S.

Physical properties of 2,3-Dihydrothieno[3,4-b][1,4]dioxine-5,7-dicarbaldehyde: (1)ACD/LogP: 0.59; (2)# of Rule of 5 Violations: 0; (3)#H bond acceptors: 4; (4)#H bond donors: 0; (5)#Freely Rotating Bonds: 2; (6)Polar Surface Area: 80.84 Å2; (7)Index of Refraction: 1.668; (8)Molar Refractivity: 48.91 cm3; (9)Molar Volume: 131.1 cm3; (10)Polarizability: 19.39×10-24cm3; (11)Surface Tension: 67.4 dyne/cm; (12)Density: 1.511 g/cm3; (13)Flash Point: 197.8 °C; (14)Enthalpy of Vaporization: 65.47 kJ/mol; (15)Boiling Point: 403.4 °C at 760 mmHg; (16)Vapour Pressure: 1.02E-06 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: O=Cc1sc(c2OCCOc12)C=O
(2)InChI: InChI=1/C8H6O4S/c9-3-5-7-8(6(4-10)13-5)12-2-1-11-7/h3-4H,1-2H2
(3)InChIKey: OYWUVHMKKSZDJH-UHFFFAOYAF
(4)Std. InChI: InChI=1S/C8H6O4S/c9-3-5-7-8(6(4-10)13-5)12-2-1-11-7/h3-4H,1-2H2
(5)Std. InChIKey: OYWUVHMKKSZDJH-UHFFFAOYSA-N

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