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

Name
Benzo[1,2-b:4,5-b']dithiophene-4,8-dione
EINECS 605-241-0
CAS No. 32281-36-0
Article Data32
CAS DataBase
Density 1.595 g/cm³
Solubility
Melting Point 260-262℃
Formula C₁₀H₄O₂S₂
Boiling Point 408 °C at 760 mmHg
Molecular Weight 220.273
Flash Point 200.6 °C
Transport Information
Appearance
Safety 24/25
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms Thieno[2,3-f][1]benzothiophene-4,8-dione;
PSA 90.62000
LogP 2.58500

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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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;

...Expand

: 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

Conditions	Yield
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;

...Expand

: 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

Conditions	Yield
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;

...Expand

: 267-65-2
benzo[1,2-b:4,5-b']dithiophene

: 32281-36-0
4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-dione

Conditions

Conditions	Yield
With sodium dithionite; tetrabutylammomium bromide In water for 0.166667h; Inert atmosphere;

: 32281-36-0
4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-dione

: 138519-02-5
dimethyl 4,5-bis(methylthio)-1,3-dithiole phosphonate ester

: 8-(4,5-bis(methylthio)-1,3-dithiol-2-ylidene)benzo[1,2-b:4,5-b']dithiophen-4(8H)-one

Conditions

Conditions	Yield
Stage #1: dimethyl 4,5-bis(methylthio)-1,3-dithiole phosphonate ester With n-butyllithium In tetrahydrofuran at -78℃; for 1.5h; Stage #2: 4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-dione In tetrahydrofuran at -78 - 20℃;	99%

: 32281-36-0
4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-dione

: 149-73-5
trimethyl orthoformate

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

Conditions

Conditions	Yield
With triethylamine In methanol for 18.1667h; Inert atmosphere; Reflux;	99%

: 32281-36-0
4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-dione

: 17049-49-9
octylmagnesium bromide

: 8-hydroxy-8-octylbenzo[1,2-b:4,5-b']dithiophen-4-one

Conditions

Conditions	Yield
In toluene at 0 - 20℃;	98.7%
In toluene at 0 - 20℃; Inert atmosphere;	98.7%
In toluene

: 32281-36-0
4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-dione

: 925899-21-4
2-bromo-5-(2-ethylhexyl)thiophene

: 4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4-hydroxy-4-(2-(2-ethylhexyl)thiophen)-8-one

Conditions

Conditions	Yield
Stage #1: 2-bromo-5-(2-ethylhexyl)thiophene With magnesium In tetrahydrofuran for 5h; Reflux; Stage #2: 4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-dione In toluene at 20℃; for 1h;	97.6%
Stage #1: 2-bromo-5-(2-ethylhexyl)thiophene With iodine; magnesium In tetrahydrofuran for 3h; Inert atmosphere; Reflux; Stage #2: 4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-dione In toluene at 20℃; for 30h; Inert atmosphere;	65%

: 32281-36-0
4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-dione

: 1430594-30-1
benzo[1,2-b:4,5-b']dithiophene-4,8-dione dioxime

Conditions

Conditions	Yield
With pyridine; hydroxylamine hydrochloride Reflux; Inert atmosphere;	97%

: 32281-36-0
4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-dione

: 196491-93-7
2,6-dibromobenzo[1,2-b:4,5-b']dithiophene-4,8-phenylhydrazine

Conditions

Conditions	Yield
With bromine at 20℃; for 1.5h; Reagent/catalyst; Temperature;	96%

: 32281-36-0
4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-dione

: 77-78-1
dimethyl sulfate

: 85903-02-2
4,8-Dimethoxybenzo<1,2-b:4,5-b'>dithiophene

Conditions

Conditions	Yield
Stage #1: 4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-dione With sodium tetrahydroborate In ethanol; water for 0.666667h; Inert atmosphere; Schlenk technique; Stage #2: With potassium hydroxide In ethanol; water for 0.5h; Inert atmosphere; Schlenk technique; Reflux; Stage #3: dimethyl sulfate In ethanol; water for 8h; Inert atmosphere; Schlenk technique; Reflux;	96%
Stage #1: 4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-dione With sodium tetrahydroborate In ethanol; water for 1h; Stage #2: With potassium hydroxide In ethanol; water for 0.5h; Stage #3: dimethyl sulfate In ethanol; water for 64h;	5.3 g

: 32281-36-0
4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-dione

: 59965-20-7, 72746-96-4, 79434-89-2, 3383-83-3
1-bromo-3,7-dimethyloctane

: 2,6-bis(trimethyltin)-4,8-di(3,7-dimethyl)octyloxybenzo[1,2-b;3,4-b′]dithiophene

Conditions

Conditions	Yield
Stage #1: 4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-dione With sodium hydroxide; zinc In water for 1h; Inert atmosphere; Reflux; Stage #2: 1-bromo-3,7-dimethyloctane With tetrabutylammomium bromide In water for 2h; Inert atmosphere; Reflux;	95.5%

: 32281-36-0
4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-dione

: 17049-50-2
n-decyl magnesium bromide

: C20H26O2S2

Conditions

Conditions	Yield
In toluene at 0 - 20℃; Inert atmosphere;	93.6%

: 32281-36-0
4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-dione

: 1357156-35-4
4,8-dihydroxybenzo[1,2-b:4,5-b']dithiophene

Conditions

Conditions	Yield
With sodium tetrahydroborate In ethanol at 90℃; for 12h; Cooling with ice; Inert atmosphere;	92.6%
With sodium tetrahydroborate; ethanol at 0 - 85℃; Inert atmosphere;	91%
With sodium tetrahydroborate; ethanol at 0 - 85℃; Inert atmosphere;	91%

: 32281-36-0
4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-dione

: 629-05-0
n-octyne

: 4,8-bis(oct-1-ynyl)benzo[1,2-b:4,5-b']dithiophene

Conditions

Conditions	Yield
Stage #1: n-octyne With isopropylmagnesium chloride at 20 - 60℃; Stage #2: 4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-dione With hydrogenchloride; tin(ll) chloride In water at 20 - 65℃;	90%
Stage #1: 4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-dione; n-octyne With isopropylmagnesium bromide Stage #2: With tin(ll) chloride
Stage #1: n-octyne With isopropylmagnesium chloride In tetrahydrofuran at 0 - 60℃; for 1.66667h; Stage #2: 4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-dione In tetrahydrofuran at 20 - 60℃; for 2h; Stage #3: With hydrogenchloride; tin(ll) chloride In tetrahydrofuran at 20 - 65℃; for 1h;

: 32281-36-0
4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-dione

: 17135-74-9
1,8-dibromonaphthalene

: C30H12O2S2

Conditions

Conditions	Yield
With di-tert-butyl(methyl)phosphonium tetrafluoroborate salt; palladium diacetate; potassium carbonate In N,N-dimethyl acetamide at 100℃; for 20h; Inert atmosphere;	90%

: 32281-36-0
4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-dione

: 111-83-1
1-bromo-octane

: 1098102-94-3
4,8-bis(octyloxy)benzo[1,2-b:4,5-b']dithiophene

Conditions

Conditions	Yield
Stage #1: 4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-dione With sodium hydroxide; zinc In water for 1h; Reflux; Stage #2: 1-bromo-octane With tetrabutylammomium bromide In water for 8h; Reflux;	89.7%
Stage #1: 4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-dione With sodium hydroxide; zinc In water for 2h; Inert atmosphere; Reflux; Stage #2: 1-bromo-octane With tetrabutylammomium bromide In water Inert atmosphere; Reflux;	86%
Stage #1: 4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-dione With sodium hydroxide; zinc In water for 1h; Reflux; Stage #2: 1-bromo-octane With tetrabutylammomium bromide In water for 12h; Reflux;	74.3%

: 32281-36-0
4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-dione

: 75-16-1
methylmagnesium bromide

: 8-hydroxy-8-methylbenzo[1,2-b:4,5-b']dithiophen-4-one

Conditions

Conditions	Yield
In toluene at 0 - 20℃;	87.5%
In toluene at 0 - 20℃; Inert atmosphere;	87.5%

: 18908-66-2
2-ethylhexyl bromide

: 32281-36-0
4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-dione

: 1160823-77-7
4,8-di(2-ethylhexyloxy)benzo[1,2-b:4,5-b']dithiophene

Conditions

Conditions	Yield
Stage #1: 4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-dione With potassium hydroxide; zinc In N,N-dimethyl-formamide at 80℃; for 48h; Stage #2: 3-bromomethylheptane In N,N-dimethyl-formamide at 80℃; for 24h; Inert atmosphere;	87%
Stage #1: 4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-dione With sodium hydroxide; zinc In water at 120℃; for 13h; Stage #2: 3-bromomethylheptane With tetrabutylammomium bromide In water Time;	87%
Stage #1: 4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-dione With sodium hydroxide; zinc In water at 120℃; for 13h; Stage #2: 3-bromomethylheptane With tetrabutylammomium bromide In water	87%

: (S)-2-ethylhexyl p-toluenesulfonate

: 32281-36-0
4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-dione

: 4,8-bis((S)-2-ethylhexyloxy)benzo[1,2-b:4,5-b']dithiophene

Conditions

Conditions	Yield
Stage #1: 4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-dione With sodium hydroxide; zinc In water for 1h; Reflux; Stage #2: (S)-2-ethylhexyl p-toluenesulfonate With tetrabutylammomium bromide In water for 12h; Reflux;	87%

: 32281-36-0
4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-dione

: 143-15-7
1-dodecylbromide

: 1044795-04-1
4,8-didodecyloxybenzo[1,2-b:4,5-b’]dithiophene

Conditions

Conditions	Yield
With tetrabutylammomium bromide; sodium hydroxide; zinc In water at 90℃; for 14h; Temperature;	86%
Stage #1: 4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-dione With sodium hydroxide; zinc In water at 90℃; Stage #2: 1-dodecylbromide With tetrabutylammomium bromide In water Temperature;	86%
Stage #1: 4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-dione With sodium hydroxide; zinc In water for 1h; Reflux; Stage #2: 1-dodecylbromide With tetrabutylammomium bromide In water for 10h; Reflux;	80%

: 32281-36-0
4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-dione

: 55944-43-9
3-ethyl-1-heptyne

: 1353720-52-1
4,8-bis-(3-ethyl-hept-1-ynyl)-benzo[1,2-b;4,5-b']dithiophene

Conditions

Conditions	Yield
Stage #1: 3-ethyl-1-heptyne With n-butyllithium In tetrahydrofuran; hexane at 23℃; for 0.5h; Stage #2: 4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-dione In tetrahydrofuran; hexane at 60℃; for 1h; Stage #3: With hydrogenchloride; tin(ll) chloride In tetrahydrofuran; hexane; water at 23 - 60℃; for 1h;	86%
With n-butyllithium; stannous chloride In tetrahydrofuran; hydrogenchloride; water	35%

: 32281-36-0
4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-dione

: 291753-67-8
4-bromine-1,2-bis(octyloxy)benzene

: 4,8-bis(1,2-bis(octyloxy)-4-phenyl)benzo[1,2-b:4,5-b']dithiophene

Conditions

Conditions	Yield
Stage #1: 4-bromo-1,2-bis(n-octyloxy)benzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere; Stage #2: 4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-dione In tetrahydrofuran; hexane at 20℃; Inert atmosphere; Stage #3: With hydrogenchloride; tin(II) chloride dihdyrate In tetrahydrofuran; hexane; water at 20℃; for 5h; Inert atmosphere;	85%

: 32281-36-0
4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-dione

: 111360-16-8
2-hexyldecyl methanesulfonate

: 1254985-73-3
4,8-bis((2-hexyldecyl)oxy)benzo[1,2-b:4,5-b’]dithiophene

Conditions

Conditions	Yield
Stage #1: 4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-dione With tetrabutylammomium bromide; sodium hydroxide; zinc In water for 1h; Inert atmosphere; Reflux; Stage #2: 2-hexyldecyl methanesulfonate With zinc In water Inert atmosphere; Reflux;	84%
Stage #1: 4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-dione With tetrabutylammomium bromide; sodium hydroxide; zinc In water for 1h; Reflux; Inert atmosphere; Stage #2: 2-hexyldecyl methanesulfonate In water for 2h; Reflux; Inert atmosphere;	72%

: 32281-36-0
4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-dione

: 1271438-65-3
2-(2'-butyl-1'-octyl)thiophene

: 4,8-bis(5-(2-butyloctyl)thiophene-2-yl)benzo[1,2-b;4,5-b']-dithiophene

Conditions

Conditions	Yield
Stage #1: 2-(2'-butyl-1'-octyl)thiophene With n-butyllithium In tetrahydrofuran; hexane at -78 - 50℃; for 2h; Stage #2: 4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-dione In tetrahydrofuran; hexane at 50℃; for 2h; Stage #3: With hydrogenchloride; tin(II) chloride hydrate In tetrahydrofuran; hexane; water at 20℃; for 2h;	84%
Stage #1: 2-(2'-butyl-1'-octyl)thiophene With n-butyllithium In tetrahydrofuran at 0 - 50℃; for 1.25h; Inert atmosphere; Stage #2: 4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-dione In tetrahydrofuran at 50℃; for 1h; Inert atmosphere; Stage #3: With hydrogenchloride; tin(II) chloride dihdyrate In tetrahydrofuran; water for 1.5h; Inert atmosphere;	69%
Stage #1: 2-(2'-butyl-1'-octyl)thiophene With n-butyllithium In tetrahydrofuran at 0 - 50℃; for 0.666667h; Inert atmosphere; Stage #2: 4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-dione In tetrahydrofuran at 50℃; for 1h; Inert atmosphere; Stage #3: With hydrogenchloride; tin(II) chloride dihdyrate In tetrahydrofuran; water at 20℃; Inert atmosphere;	63%
Stage #1: 2-(2'-butyl-1'-octyl)thiophene With n-butyllithium In tetrahydrofuran at 0 - 50℃; for 1h; Inert atmosphere; Stage #2: 4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-dione In tetrahydrofuran at 50℃; for 1h; Inert atmosphere; Stage #3: With hydrogenchloride; tin(II) chloride dihdyrate In tetrahydrofuran; water at 20℃; for 4h; Inert atmosphere;	61%

: 32281-36-0
4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-dione

: 110-53-2
1-Bromopentane

: 4,8-bis(pentyloxy)benzo[1,2-b:4,5-b’]dithiophene

Conditions

Conditions	Yield
Stage #1: 4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-dione With sodium hydroxide; zinc In water for 3h; Reflux; Stage #2: 1-Bromopentane In water at 80℃; for 12h; Reflux; Alkaline conditions;	84%

: 4861-61-4
2-dodecylthiophene

: 32281-36-0
4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-dione

: 1351130-14-7
4,8-bis(2-dodecylthiophene-5-yl)benzo[1,2-b:4,5-b’]dithiophene

Conditions

Conditions	Yield
Stage #1: 2-dodecylthiophene With n-butyllithium In tetrahydrofuran at -30 - 50℃; for 2h; Inert atmosphere; Stage #2: 4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-dione In tetrahydrofuran at 50℃; for 2h; Inert atmosphere; Stage #3: With hydrogenchloride; tin(II) chloride dihdyrate In tetrahydrofuran; water at 20℃; Inert atmosphere;	83%
Stage #1: 2-dodecylthiophene With n-butyllithium In tetrahydrofuran; hexane at -20℃; for 2h; Inert atmosphere; Schlenk technique; Stage #2: 4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-dione In tetrahydrofuran; hexane for 1h; Reflux; Inert atmosphere; Schlenk technique; Stage #3: With tin(ll) chloride In tetrahydrofuran; hexane; water at 20℃; for 1h; Reflux; Inert atmosphere; Schlenk technique;	59%
Stage #1: 2-dodecylthiophene; 4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-dione With n-butyllithium In tetrahydrofuran Stage #2: With hydrogenchloride; tin(ll) chloride In water	48%
Stage #1: 2-dodecylthiophene With n-butyllithium In tetrahydrofuran at 0℃; Inert atmosphere; Stage #2: 4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-dione Inert atmosphere; Stage #3: With tin(II) chloride dihdyrate Reflux; Inert atmosphere;
Stage #1: 2-dodecylthiophene With n-butyllithium In tetrahydrofuran at 0℃; Inert atmosphere; Stage #2: 4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-dione Inert atmosphere; Stage #3: With tin(II) chloride dihdyrate Inert atmosphere;

: 32281-36-0
4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-dione

: 4891-44-5
2-(2-ethylhexyl)thiophen

: 1352642-35-3
4-(5-(2-ethylhexyl)thiophen-2-yl)-8-(5-(2-ethylhexyl)thiophene-2-yl)benzo[1,2-b:4,5-b']dithiophene

Conditions

Conditions	Yield
Stage #1: 2-(2-ethylhexyl)thiophen With n-butyllithium In tetrahydrofuran; hexane at 0 - 50℃; for 1h; Inert atmosphere; Stage #2: 4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-dione In tetrahydrofuran; hexane at 50℃; for 1h; Inert atmosphere; Stage #3: With hydrogenchloride; tin(ll) chloride In tetrahydrofuran; hexane; water at 20℃; for 2h; Inert atmosphere;	82%
Stage #1: 2-(2-ethylhexyl)thiophen With n-butyllithium In tetrahydrofuran at -30 - 50℃; for 2h; Inert atmosphere; Stage #2: 4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-dione In tetrahydrofuran at 50℃; for 2h; Inert atmosphere;	76%
Stage #1: 2-(2-ethylhexyl)thiophen With n-butyllithium In tetrahydrofuran; hexane at -78 - 50℃; for 2h; Stage #2: 4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-dione In tetrahydrofuran; hexane at 50℃; for 2h; Stage #3: With hydrogenchloride; tin(II) chloride hydrate In tetrahydrofuran; hexane; water at 20℃; for 2h;	76%

: 74-96-4
ethyl bromide

: 32281-36-0
4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-dione

: 4,8-diethoxybenzo[1,2-b:4,5-b′]dithiophene

Conditions

Conditions	Yield
Stage #1: 4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-dione With sodium hydroxide; zinc In water at 130℃; Stage #2: ethyl bromide With tetrabutylammomium bromide In water	82%
Stage #1: 4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-dione With sodium hydroxide; zinc In water for 3h; Inert atmosphere; Schlenk technique; Reflux; Stage #2: ethyl bromide With tetrabutylammomium bromide In water for 6h; Inert atmosphere; Schlenk technique; Reflux;	67%

: 32281-36-0
4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-dione

: 772-38-3
4-tert-Butylphenylacetylene

: C34H30S2

Conditions

Conditions	Yield
Stage #1: 4-tert-Butylphenylacetylene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere; Stage #2: 4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-dione In tetrahydrofuran; hexane at 20℃; for 6h; Inert atmosphere; Stage #3: With hydrogenchloride; tin(ll) chloride In tetrahydrofuran; hexane; water Inert atmosphere;	82%
Stage #1: 4-tert-Butylphenylacetylene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere; Stage #2: 4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-dione In tetrahydrofuran; hexane at 20℃; for 1h; Stage #3: With hydrogenchloride; tin(ll) chloride In tetrahydrofuran; hexane; water

: 32281-36-0
4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-dione

: 74-88-4
methyl iodide

: 85903-02-2
4,8-Dimethoxybenzo<1,2-b:4,5-b'>dithiophene

Conditions

Conditions	Yield
Stage #1: 4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-dione With sodium hydroxide; zinc In water for 2h; Inert atmosphere; Schlenk technique; Reflux; Stage #2: methyl iodide With tetrabutylammomium bromide for 16h; Inert atmosphere; Schlenk technique; Reflux;	82%

: 32281-36-0
4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-dione

: 3032-92-6
4-cyanophenylacetylene

: C28H12N2S2

Conditions

Conditions	Yield
Stage #1: 4-cyanophenylacetylene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere; Stage #2: 4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-dione In tetrahydrofuran; hexane at 20℃; for 1h; Stage #3: With hydrogenchloride; tin(ll) chloride In tetrahydrofuran; hexane; water	82%

: 2,3-dihexylthiophene

: 32281-36-0
4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-dione

: 1421924-02-8
4,8-bis(4,5-dihexylthiophen-2-yl)benzo[1,2-b:4,5-b']dithiophene

Conditions

Conditions	Yield
Stage #1: 2,3-dihexylthiophene With n-butyllithium In tetrahydrofuran; hexane at 0 - 50℃; for 1h; Inert atmosphere; Stage #2: 4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-dione In tetrahydrofuran at 50℃; for 2h; Stage #3: With hydrogenchloride; tin(II) chloride dihdyrate In tetrahydrofuran; hexane; water at 20℃; for 2h;	81%
Stage #1: 2,3-dihexylthiophene With n-butyllithium In tetrahydrofuran at 50℃; for 2.75h; Cooling with ice; Inert atmosphere; Stage #2: 4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-dione In tetrahydrofuran at 50℃; for 2.5h; Inert atmosphere; Stage #3: With hydrogenchloride; tin(II) chloride dihdyrate In tetrahydrofuran; water at 20℃; Inert atmosphere;	64.6%

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

Product Name

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

Synthetic route

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

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