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4,8-Dihydrobenzo[1,2-b:4,5-b']dithiophen-4,8-dione
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Name

4,8-Dihydrobenzo[1,2-b:4,5-b']dithiophen-4,8-dione

 EINECS 605-241-0
CAS No. 32281-36-0 Density 1.595 g/cm3
PSA 90.62000 LogP 2.58500
Solubility N/A Melting Point 260-262℃
Formula C10H4O2S2 Boiling Point 408 °C at 760 mmHg
Molecular Weight 220.273 Flash Point 200.6 °C
Transport Information N/A Appearance N/A
Safety 24/25 Risk Codes N/A
Molecular Structure Molecular Structure of 32281-36-0 (Benzo[1,2-b:4,5-b']dithiophene-4,8-dione) Hazard Symbols N/A
Synonyms

Thieno[2,3-f][1]benzothiophene-4,8-dione;

Article Data 32

4,8-Dihydrobenzo[1,2-b:4,5-b']dithiophen-4,8-dione Synthetic route

73540-75-7

3-thiophenecarboxylic acid,N,N-diethylamide

32281-36-0

4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-dione

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran at 0 - 20℃; Temperature; Inert atmosphere;86.1%
With n-butyllithium In tetrahydrofuran at 20℃; for 1h; Inert atmosphere; Cooling with ice;80%
With n-butyllithium In tetrahydrofuran at 0℃;80%
498-62-4

3-thiophene carboxaldehyde

73540-75-7

3-thiophenecarboxylic acid,N,N-diethylamide

32281-36-0

4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-dione

Conditions
ConditionsYield
With N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium In diethyl ether 1.) -78 deg C, 1 h, 2.) -78 deg C -> RT, 12 h;77%
41507-35-1

3-thiophene carboxylic acid chloride

73540-75-7

3-thiophenecarboxylic acid,N,N-diethylamide

32281-36-0

4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-dione

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran at -30 - 20℃; Inert atmosphere;77%
59906-37-5

N,N-dimethyl-3-thiophene carboxamide

32281-36-0

4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-dione

Conditions
ConditionsYield
With n-butyllithium In diethyl ether; hexane for 12h;56%
With n-butyllithium In hexane; water; benzene
6007-83-6

2,3-thiophenedicarboxylic acid anhydride

32281-36-0

4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-dione

Conditions
ConditionsYield
In neat (no solvent) at 270℃; for 2.5h;24%
6007-83-6

2,3-thiophenedicarboxylic acid anhydride

A

25796-77-4

4H-cyclopenta[2,1-b:3,4-b']dithiophen-4-one

B

32281-36-0

4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-dione

Conditions
ConditionsYield
at 500℃; under 1 - 5 Torr;A 1.2%
B n/a
6007-85-8

1H,3H-thieno[3,4-c]furan-1,3-dione

A

32281-36-0

4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-dione

B

33527-22-9

4,8-Dihydrobenzo<1,2-b:4,5-c'>dithiophen-4,8-dion

Conditions
ConditionsYield
at 470℃; for 0.00833333h;A 0.12%
B 0.36%
109-72-8, 29786-93-4

n-butyllithium

73540-75-7

3-thiophenecarboxylic acid,N,N-diethylamide

A

90534-16-0

1-(3-thienyl)-1-pentanone

B

32281-36-0

4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-dione

C

148527-59-7

N,N-diethyl-2-(1,1,1,3,3-pentafluoro-2-hydroxypropan-2-yl)thiophene-3-carboxamide

Conditions
ConditionsYield
With N,N,N,N,-tetramethylethylenediamine; foscarnet 1.) hexane, ether, -78 deg C, 1.5 h, 2.) hexane, ether, a) -78 deg C, 7 h, b) RT, 12 h; Yield given. Multistep reaction. Yields of byproduct given;
431-71-0

1,1,1,3,3-pentafluoro-2-propanone

73540-75-7

3-thiophenecarboxylic acid,N,N-diethylamide

A

90534-16-0

1-(3-thienyl)-1-pentanone

B

32281-36-0

4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-dione

C

148527-59-7

N,N-diethyl-2-(1,1,1,3,3-pentafluoro-2-hydroxypropan-2-yl)thiophene-3-carboxamide

Conditions
ConditionsYield
With n-butyllithium; N,N,N,N,-tetramethylethylenediamine 1.) hexane, ether, -78 deg C, 1.5 h, 2.) hexane, ether, a) -78 deg C, 7 h, b) RT, 12 h; Yield given. Multistep reaction. Yields of byproduct given;
73540-75-7

3-thiophenecarboxylic acid,N,N-diethylamide

A

90534-16-0

1-(3-thienyl)-1-pentanone

B

32281-36-0

4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-dione

C

148527-59-7

N,N-diethyl-2-(1,1,1,3,3-pentafluoro-2-hydroxypropan-2-yl)thiophene-3-carboxamide

Conditions
ConditionsYield
With n-butyllithium; N,N,N,N,-tetramethylethylenediamine; foscarnet 1.) hexane, ether, -78 deg C, 1.5 h, 2.) hexane, ether, a) -78 deg C, 7 h, b) RT, 12 h; Yield given. Multistep reaction. Yields of byproduct given;

4,8-Dihydrobenzo[1,2-b:4,5-b']dithiophen-4,8-dione Specification

The Benzo[1,2-b:4,5-b']dithiophene-4,8-dione, with the CAS registry number 32281-36-0, is also known as Thieno[2,3-f][1]benzothiophene-4,8-dione. This chemical's molecular formula is C10H4O2S2 and molecular weight is 220.2676. What's more, its systematic name is called Benzo[1,2-b:4,5-b']bisthiophene-4,8-dione.

Physical properties about Benzo[1,2-b:4,5-b']dithiophene-4,8-dione are: (1)ACD/LogP: 2.74; (2)#of Rule of 5 Violations: 0; (3)#H bond acceptors: 2; (4)#H bond donors: 0; (5)#Freely Rotating Bonds: 0; (6)Polar Surface Area: 90.62 Å2; (7)Index of Refraction: 1.736; (8)Molar Refractivity: 55.43 cm3; (9)Molar Volume: 138 cm3; (10)Polarizability: 21.97×10-24 cm3; (11)Surface Tension: 73.8 dyne/cm; (12)Density: 1.595 g/cm3; (13)Flash Point: 200.6 °C; (14)Enthalpy of Vaporization: 66 kJ/mol; (15)Boiling Point: 408 °C at 760 mmHg; (16)Vapour Pressure: 7.23E-07 mmHg at 25 °C.

You can still convert the following datas into molecular structure:
(1) SMILES: O=C2c3sccc3C(=O)c1sccc12
(2) InChI: InChI=1/C10H4O2S2/c11-7-5-1-3-13-9(5)8(12)6-2-4-14-10(6)7/h1-4H
(3) InChIKey: SIUXRPJYVQQBAF-UHFFFAOYAI

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