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

Name
2,3-Dihydrothieno[3,4-b][1,4]dioxine-5,7-dicarbaldehyde
EINECS
CAS No. 211235-87-9
Article Data10
CAS DataBase
Density 1.511 g/cm³
Solubility
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
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 2,3-DIHYDROTHIENO[3,4-B][1,4]DIOXINE-5,7-DICARBALDEHYDE
PSA 80.84000
LogP 1.14430

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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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%

...Expand

: 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

Conditions	Yield
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

Conditions	Yield
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;

...Expand

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

: 211235-87-9
2,3-dihydrothieno[3,4-b][1,4]dioxine-5,7-dicarboxaldehyde

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
In ethanol Reflux;	79%

: 5,10,15-trihexyl-10,15-dihydro-5H-diindolo[3,2-a:3’,2’-c]carbazole-2-amine

: 211235-87-9
2,3-dihydrothieno[3,4-b][1,4]dioxine-5,7-dicarboxaldehyde

: C92H106N8O2S

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In chloroform; isopropyl alcohol for 24h; Inert atmosphere; Reflux;	77%

: 4,4’-dimethoxy-4’’-aminotriphenylamine

: 211235-87-9
2,3-dihydrothieno[3,4-b][1,4]dioxine-5,7-dicarboxaldehyde

: C48H42N4O6S

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In chloroform for 72h; Reflux; Inert atmosphere;	75%

: 23259-98-5
2-thienylmethyltriphenylphosphonium bromide

: 211235-87-9
2,3-dihydrothieno[3,4-b][1,4]dioxine-5,7-dicarboxaldehyde

: 2,2'-dithienyl-ω,ω'-2,5-(2,4-ethylenedioxy)divinyl thiophene

Conditions

Conditions	Yield
With sodium hydride In tetrahydrofuran at 20℃; for 10h; Condensation; Wittig;	74%

: 1136-86-3
methyl (3,4,5-trimethoxyphenyl) ketone

: 211235-87-9
2,3-dihydrothieno[3,4-b][1,4]dioxine-5,7-dicarboxaldehyde

: (2E,2’E)-3,3’-(2,3-dihydrothieno[3,4-b][1,4]dioxine-5,7-diyl)bis[1-(3,4,5-trimethoxyphenyl)prop-2-en-1-one]

Conditions

Conditions	Yield
With sodium hydroxide In ethanol; water for 1h; Reflux;	74%

: 80691-81-2
2,5-diamino-thiophene-3,4-dicarboxylic acid diethyl ester

: 211235-87-9
2,3-dihydrothieno[3,4-b][1,4]dioxine-5,7-dicarboxaldehyde

: 1239898-58-8
tetraethyl 5,5'-(1E,10E)-(2,3-dihydrothieno[3,4-b][1,4]dioxine-5,7-diyl)bis(methan-1-yl-1-ylidene)bis(azan-1-yl-1-ylidene)-bis(2-aminothiophene-3,4-dicarboxylate)

Conditions

Conditions	Yield
With trifluoroacetic acid In ethanol at 20℃; for 16h;	67%

: 211235-87-9
2,3-dihydrothieno[3,4-b][1,4]dioxine-5,7-dicarboxaldehyde

: 609369-55-3
diethyl (5-hexylthiophen-2-yl)methylphosphonate

: (E,E)-2,5-bis[2-(5-hexyl-2-thienyl)-1-ethenyl]-3,4-ethylenedioxythiophene

Conditions

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran at 20℃; for 1h; Wittig-Horner reaction;	53%

: 4651-91-6
3-cyano-2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene

: 211235-87-9
2,3-dihydrothieno[3,4-b][1,4]dioxine-5,7-dicarboxaldehyde

: 2,2'-(((1E,1'E)-(2,3-dihydrothieno[3,4-b][1,4]dioxine-5,7-diyl)bis(methanylylidene))bis(azanylylidene))bis(4,5,6,7-tetrahydrobenzo[b]thiophene-3-carbonitrile)

Conditions

Conditions	Yield
With trifluoroacetic acid In ethanol at 40℃; for 16h;	52%

: 148344-30-3
4-(N-isopropylamidino)-1,2-phenylene diamine

: 211235-87-9
2,3-dihydrothieno[3,4-b][1,4]dioxine-5,7-dicarboxaldehyde

: 2,5-bis[(5-(N-isopropylamidino)benzimidazo-2-yl)]-3,4-ethylenedioxythiophene dihydrochloride

Conditions

Conditions	Yield
Stage #1: 4-(N-isopropylamidino)-1,2-phenylene diamine; 2,3-dihydrothieno[3,4-b][1,4]dioxine-5,7-dicarboxaldehyde With p-benzoquinone In ethanol for 4h; Reflux; Inert atmosphere; Stage #2: With hydrogenchloride In ethanol	50.7%

: 211235-87-9
2,3-dihydrothieno[3,4-b][1,4]dioxine-5,7-dicarboxaldehyde

: C11H20O3PS2(1-)

: 2,5-bis<4,5-bis(n-propyl)-2H-1,3-dithiol-2-ylidenemethyl>-3,4-ethylenedioxythiophene

Conditions

Conditions	Yield
	50%

: 66639-63-2
2-(3,4-diaminophenyl)-imidazoline

: 211235-87-9
2,3-dihydrothieno[3,4-b][1,4]dioxine-5,7-dicarboxaldehyde

: 2,5-bis[5-(3,4-dihydroimidazol-2-yl)benzimidazol-2-yl]-3,4-ethylenedioxythiophene dihydrochloride

Conditions

Conditions	Yield
Stage #1: 2-(3,4-diaminophenyl)-imidazoline; 2,3-dihydrothieno[3,4-b][1,4]dioxine-5,7-dicarboxaldehyde With p-benzoquinone In ethanol for 4h; Reflux; Inert atmosphere; Stage #2: With hydrogenchloride In ethanol	47.9%

: 68827-43-0
4-amidino-1,2-phenylenediamine

: 211235-87-9
2,3-dihydrothieno[3,4-b][1,4]dioxine-5,7-dicarboxaldehyde

: 2,5-bis[(5-amidinobenzimidazo-2-yl)]-3,4-ethylenedioxythiophene dihydrochloride

Conditions

Conditions	Yield
Stage #1: 4-amidino-1,2-phenylenediamine; 2,3-dihydrothieno[3,4-b][1,4]dioxine-5,7-dicarboxaldehyde With p-benzoquinone In ethanol for 4h; Reflux; Inert atmosphere; Stage #2: With hydrogenchloride In ethanol	42.6%

: 88430-82-4
2-(Triphenyl-λ5-phosphanylidene)-[1,3]dithiole-4,5-dicarboxylic acid dimethyl ester

: 211235-87-9
2,3-dihydrothieno[3,4-b][1,4]dioxine-5,7-dicarboxaldehyde

: 2,5-bis<4,5-bis(methoxycarbonyl)-2H-1,3-dithiol-2-ylidenemethyl>-3,4-ethylenedioxythiophene

Conditions

Conditions	Yield
	40%

: diethyl (3-hexylthiophen-2-yl)-methylphosphonate

: 211235-87-9
2,3-dihydrothieno[3,4-b][1,4]dioxine-5,7-dicarboxaldehyde

: C30H38O2S3

Conditions

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran at -78℃; for 2h; Inert atmosphere;	36%

: 1-(4-(2,3-dihydrothieno[3,4-b][1,4]dioxin-7-yl)phenyl)ethanone

: 211235-87-9
2,3-dihydrothieno[3,4-b][1,4]dioxine-5,7-dicarboxaldehyde

: C36H26O8S3

Conditions

Conditions	Yield
With potassium hydroxide In ethanol for 12h; Claisen-Schmidt Condensation;	34%

: C7H12O3PS4(1-)

: 211235-87-9
2,3-dihydrothieno[3,4-b][1,4]dioxine-5,7-dicarboxaldehyde

: 2,5-bis<4,5-bis(methylsulfanyl)-2H-1,3-dithiol-2-ylidenemethyl>-3,4-ethylenedioxythiophene

Conditions

Conditions	Yield
	27%

: diethyl (3,4-ethylenedioxy-5-hexyl-2-thienyl)methylphosphonate

: 211235-87-9
2,3-dihydrothieno[3,4-b][1,4]dioxine-5,7-dicarboxaldehyde

: C34H42O6S3

Conditions

Conditions	Yield
Stage #1: diethyl (3,4-ethylenedioxy-5-hexyl-2-thienyl)methylphosphonate With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.25h; Inert atmosphere; Stage #2: 2,3-dihydrothieno[3,4-b][1,4]dioxine-5,7-dicarboxaldehyde In N,N-dimethyl-formamide at 20℃; for 18h; Horner-Wadsworth-Emmons Olefination; Inert atmosphere;	26%

: 38172-19-9
1,3-bis(dicyanomethylidene)-indane

: 211235-87-9
2,3-dihydrothieno[3,4-b][1,4]dioxine-5,7-dicarboxaldehyde

: 2-{2-[7-(1,3-Bis-dicyanomethylene-indan-2-ylidenemethyl)-2,3-dihydro-thieno[3,4-b][1,4]dioxin-5-ylmethylene]-3-dicyanomethylene-indan-1-ylidene}-malononitrile

: 80691-81-2
2,5-diamino-thiophene-3,4-dicarboxylic acid diethyl ester

: 211235-87-9
2,3-dihydrothieno[3,4-b][1,4]dioxine-5,7-dicarboxaldehyde

: 1245748-31-5
C28H30N4O10S3

Conditions

Conditions	Yield
In ethanol Acidic conditions;

: 1586816-08-1
diethyl 2-amino-5-benzamidothiophene-3,4-dicarboxylate

: 211235-87-9
2,3-dihydrothieno[3,4-b][1,4]dioxine-5,7-dicarboxaldehyde

: 1586816-06-9
tetraethyl-5,5'-((1E,1'E)-((2,3-dihydrothieno[3,4-b][1,4]dioxine-5,7-diyl)bis(methanylylidene))bis(azanylylidene))bis(2-benzamidothiophene-3,4-dicarboxylate)

Conditions

Conditions	Yield
With trifluoroacetic acid In ethanol at 20℃; Inert atmosphere;

: 347895-10-7
C17H19NO3

: 211235-87-9
2,3-dihydrothieno[3,4-b][1,4]dioxine-5,7-dicarboxaldehyde

: C42H40N2O8S

Conditions

Conditions	Yield
With acetic acid In ethanol for 4h; Reflux; Inert atmosphere;

: 65388-44-5
4-aminophenyl 4-(hexyloxy)benzoate

: 211235-87-9
2,3-dihydrothieno[3,4-b][1,4]dioxine-5,7-dicarboxaldehyde

: C46H48N2O8S

Conditions

Conditions	Yield
With acetic acid In ethanol for 4h; Reflux; Inert atmosphere;

: 163856-08-4
4-aminophenyl 4-octyloxybenzoate

: 211235-87-9
2,3-dihydrothieno[3,4-b][1,4]dioxine-5,7-dicarboxaldehyde

: C50H56N2O8S

Conditions

Conditions	Yield
With acetic acid In ethanol for 4h; Reflux; Inert atmosphere;

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

Product Name

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

Synthetic route

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

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