3,4-Thiophenedicarboxylic acid supplier

Name
THIOPHENE-3,4-DICARBOXYLIC ACID
EINECS
CAS No. 4282-29-5
Article Data25
CAS DataBase
Density 1.655 g/cm³
Solubility
Melting Point 227-231 °C
Formula C₆H₄O₄S
Boiling Point 405.9 °C at 760 mmHg
Molecular Weight 172.161
Flash Point 199.3 °C
Transport Information
Appearance yellow to beige-pinkish or light brown crystalline
Safety 24/25
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms NSC 672208;NSC 81793;Thiophene-3,4-dicarboxylic acid;
PSA 102.84000
LogP 1.14450

Synthetic route

: 18853-32-2
3,4-dicyanothiophene

: 4282-29-5
thiophene-3,4-dicarboxylic acid

Conditions

Conditions	Yield
With potassium hydroxide In ethylene glycol for 4h; Heating;	90%
Stage #1: 3,4-dicyanothiophene With potassium hydroxide In ethylene glycol Stage #2: With hydrogenchloride; water In ethylene glycol	88%
With potassium hydroxide In water; ethylene glycol	88%

: 4282-35-3
dimethyl thiophene-3,4-dicarboxylate

: 4282-29-5
thiophene-3,4-dicarboxylic acid

Conditions

Conditions	Yield
With sodium hydroxide In water at 80℃;	80%

: C9H10O4S

: 4282-29-5
thiophene-3,4-dicarboxylic acid

Conditions

Conditions	Yield
With sodium hydroxide at 80℃;	66%

: 19259-08-6
3,4-diiodothiophene

: 4282-29-5
thiophene-3,4-dicarboxylic acid

Conditions

Conditions	Yield
With n-butyllithium; diethyl ether at -60℃; Behandeln des Reaktionsgemisches mit festem Kohlendioxid;

: 73926-95-1
diethyl 2-formyl-3-(diethoxymethyl)succinate

: 4282-29-5
thiophene-3,4-dicarboxylic acid

Conditions

Conditions	Yield
With phosphorous (V) sulfide; toluene Erwaermen des Reaktionsprodukts mit wss.-aethanol. Natronlauge;
Multi-step reaction with 2 steps 1: P2S5 / toluene / 2 h / Heating 2: aq. NaOH / ethanol / Heating View Scheme

: 4282-30-8
3,4-thiophenedicarboxylic acid monomethyl ester

: 4282-29-5
thiophene-3,4-dicarboxylic acid

Conditions

Conditions	Yield
With sodium hydroxide In methanol; water at 41.1℃; Kinetics; various solvents, various temperatures;

: 53229-47-3
diethyl thiophene-3,4-dicarboxylate

: 4282-29-5
thiophene-3,4-dicarboxylic acid

Conditions

Conditions	Yield
With sodium hydroxide In ethanol Heating; Yield given;

: 70145-29-8
diethyl 2-(diethoxymethyl)succinate

: 4282-29-5
thiophene-3,4-dicarboxylic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium ethylate; diethyl ether 2: toluene; phosphorus (V)-sulfide / Erwaermen des Reaktionsprodukts mit wss.-aethanol. Natronlauge View Scheme

: 5472-38-8
diethyl 2-formylbutanedioate

: 4282-29-5
thiophene-3,4-dicarboxylic acid

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: ethanol; sulfuric acid 2: sodium ethylate; diethyl ether 3: toluene; phosphorus (V)-sulfide / Erwaermen des Reaktionsprodukts mit wss.-aethanol. Natronlauge View Scheme

: 3141-26-2
3,4-dibromothiophene

: 124-38-9
carbon dioxide

A: 16694-17-0
4-bromo-3-thiophenecarboxylic acid

B: 4282-29-5
thiophene-3,4-dicarboxylic acid

Conditions

Conditions	Yield
With n-butyllithium In diethyl ether

...Expand

: 3141-26-2
3,4-dibromothiophene

: 124-38-9
carbon dioxide

: 4282-29-5
thiophene-3,4-dicarboxylic acid

Conditions

Conditions	Yield
Stage #1: 3,4-dibromothiophene With n-butyllithium In diethyl ether at -70.16℃; for 0.5h; Stage #2: carbon dioxide In diethyl ether for 3h; Cooling with ether-dry ice;

: 766-39-2
2,3-Dimethylmaleic anhydride

: 4282-29-5
thiophene-3,4-dicarboxylic acid

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: toluene-4-sulfonic acid / methanol / Reflux; Inert atmosphere 2: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 6 h / Inert atmosphere; Reflux 3: sodiumsulfide nonahydrate / tetrahydrofuran / 1 h / 20 °C 4: 3-chloro-benzenecarboperoxoic acid / 6 h / 20 °C 5: acetic anhydride / Inert atmosphere; Reflux 6: sodium hydroxide / water / 80 °C View Scheme

Yield

Multi-step reaction with 6 steps
1: toluene-4-sulfonic acid / methanol / Reflux; Inert atmosphere
2: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 6 h / Inert atmosphere; Reflux
3: sodiumsulfide nonahydrate / tetrahydrofuran / 1 h / 20 °C
4: 3-chloro-benzenecarboperoxoic acid / 6 h / 20 °C
5: acetic anhydride / Inert atmosphere; Reflux
6: sodium hydroxide / water / 80 °C
View Scheme

: 13314-92-6
dimethyl (Z)-2,3-dimethyl-2-butenedioate

: 4282-29-5
thiophene-3,4-dicarboxylic acid

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 6 h / Inert atmosphere; Reflux 2: sodiumsulfide nonahydrate / tetrahydrofuran / 1 h / 20 °C 3: 3-chloro-benzenecarboperoxoic acid / 6 h / 20 °C 4: acetic anhydride / Inert atmosphere; Reflux 5: sodium hydroxide / water / 80 °C View Scheme

: 80356-26-9, 80356-27-0
(E/Z)-Dimethyl 2,3-bis-butenedioate

: 4282-29-5
thiophene-3,4-dicarboxylic acid

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: sodiumsulfide nonahydrate / tetrahydrofuran / 1 h / 20 °C 2: 3-chloro-benzenecarboperoxoic acid / 6 h / 20 °C 3: acetic anhydride / Inert atmosphere; Reflux 4: sodium hydroxide / water / 80 °C View Scheme

: 20946-32-1
3,4-dimethyl 2,5-dihydrothiophene-3,4-dicarboxylate

: 4282-29-5
thiophene-3,4-dicarboxylic acid

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 3-chloro-benzenecarboperoxoic acid / 6 h / 20 °C 2: acetic anhydride / Inert atmosphere; Reflux 3: sodium hydroxide / water / 80 °C View Scheme

: C8H10O5S

: 4282-29-5
thiophene-3,4-dicarboxylic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: acetic anhydride / Inert atmosphere; Reflux 2: sodium hydroxide / water / 80 °C View Scheme

: 4282-29-5
thiophene-3,4-dicarboxylic acid

: 6007-85-8
1H,3H-thieno[3,4-c]furan-1,3-dione

Conditions

Conditions	Yield
With acetic anhydride at 110℃;	100%
With acetic anhydride at 140℃; for 12h;	95%
With acetic anhydride	93%

: 4282-29-5
thiophene-3,4-dicarboxylic acid

: 33527-26-3
thiophene-3,4-dicarboxylic acid chloride

Conditions

Conditions	Yield
With oxalyl dichloride In N,N-dimethyl-formamide; toluene at 111℃; for 2h; Schlenk technique; Inert atmosphere;	96%
With thionyl chloride for 1h; Heating;
With oxalyl dichloride; N,N-dimethyl-formamide In 1,2-dichloro-ethane at 20 - 60℃; for 1.33333h; Inert atmosphere;

: 4282-29-5
thiophene-3,4-dicarboxylic acid

: 111-87-5
octanol

: 1392422-45-5
dioctyl thiophene-3,4-dicarboxylate

Conditions

Conditions	Yield
With chloro-trimethyl-silane at 65℃; for 24h; Inert atmosphere;	90%

: 4282-29-5
thiophene-3,4-dicarboxylic acid

: 2-butyloctan-1-amine

: 5-(2-butyloctyl)-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione

Conditions

Conditions	Yield
Stage #1: thiophene-3,4-dicarboxylic acid With acetic anhydride at 75℃; for 2h; Stage #2: 2-butyloctan-1-amine With dmap In 1,4-dioxane at 55 - 80℃;	88.41%

: 4282-29-5
thiophene-3,4-dicarboxylic acid

: 190723-12-7
2,5-dibromo-3,4-dicarboxylic acid thiophene

Conditions

Conditions	Yield
Stage #1: thiophene-3,4-dicarboxylic acid With acetic acid for 0.5h; Cooling with ice; Stage #2: With bromine at 85℃; Cooling with ice;	87.2%
With bromine; acetic acid at 20℃; for 12h;	85.6%
With bromine In acetic acid	80%

: 67-56-1
methanol

: 4282-29-5
thiophene-3,4-dicarboxylic acid

: 4282-35-3
dimethyl thiophene-3,4-dicarboxylate

Conditions

Conditions	Yield
With sulfuric acid Reflux;	84%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride at 20℃;	23%
With sulfuric acid

: 4282-29-5
thiophene-3,4-dicarboxylic acid

: 501-65-5
diphenyl acetylene

: 4-oxo-6,7-diphenyl-4H-thieno[3,2-c]pyran-3-carboxylic acid

Conditions

Conditions	Yield
With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; tetrabutylammomium bromide In N,N-dimethyl-formamide at 100℃; for 16h; Sealed tube;	82%

: 4282-29-5
thiophene-3,4-dicarboxylic acid

: 18354-73-9
[4-(hydroxymethyl)-3-thienyl]methanol

Conditions

Conditions	Yield
With diisobutylaluminium hydride In tetrahydrofuran; hexane at 0 - 20℃; for 16h;	77%
With diisobutylaluminium hydride
Multi-step reaction with 2 steps 1: oxalyl dichloride; N,N-dimethyl-formamide / 1,2-dichloro-ethane / 1.33 h / 20 - 60 °C / Inert atmosphere 2: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / 20 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / 20 °C 2: diisobutylaluminium hydride / dichloromethane; toluene / 0.08 h / 0 °C View Scheme
With borane-THF In tetrahydrofuran at 0 - 26℃; for 24h; Inert atmosphere;

: 4282-29-5
thiophene-3,4-dicarboxylic acid

: 109-73-9
N-butylamine

: 1428567-53-6
5-butyl-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione

Conditions

Conditions	Yield
Stage #1: thiophene-3,4-dicarboxylic acid With acetic anhydride at 140℃; for 24h; Inert atmosphere; Schlenk technique; Molecular sieve; Stage #2: N-butylamine In toluene for 24h; Inert atmosphere; Schlenk technique; Reflux; Stage #3: With thionyl chloride at 88℃; Inert atmosphere; Schlenk technique;	77%

: 4282-29-5
thiophene-3,4-dicarboxylic acid

: 6007-82-5
thieno[3,4-c]pyrrole-4,6-dione

Conditions

Conditions	Yield
Stage #1: thiophene-3,4-dicarboxylic acid With ammonium hydroxide In water Heating; Stage #2: at 260 - 280℃;	76%

: 553-26-4
4,4'-bipyridine

: 4282-29-5
thiophene-3,4-dicarboxylic acid

: 5743-04-4
cadmium(II) acetate dihydrate

: 2C6H3O4S(1-)*Cd(2+)*C10H8N2

Conditions

Conditions	Yield
In water at 140℃; for 120h; Sealed tube;	76%

...Expand

: 4282-29-5
thiophene-3,4-dicarboxylic acid

: 62281-05-4
2-n-hexyldecan-1-amine

: 1355961-59-9
5-(2-hexyldecyl)-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione

Conditions

Conditions	Yield
at 220 - 250℃; Inert atmosphere; Dean-Stark;	74%
Stage #1: thiophene-3,4-dicarboxylic acid With acetic anhydride at 75℃; for 2h; Stage #2: 2-n-hexyldecan-1-amine With dmap In 1,4-dioxane at 55℃; for 20h; Stage #3: With acetic anhydride In 1,4-dioxane at 80℃; for 4h;	66%

: 104-75-6
2-Ethylhexylamine

: 4282-29-5
thiophene-3,4-dicarboxylic acid

: 1231160-82-9
5-(2-ethylhexyl)-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione

Conditions

Conditions	Yield
Stage #1: thiophene-3,4-dicarboxylic acid With acetic anhydride at 140℃; Stage #2: 2-Ethylhexylamine In toluene for 24h; Reflux; Stage #3: With thionyl chloride for 4h; Reflux;	73.6%
Stage #1: thiophene-3,4-dicarboxylic acid With acetic anhydride at 140℃; Stage #2: 2-Ethylhexylamine In toluene for 24h; Reflux; Stage #3: With thionyl chloride In toluene Reflux;	65%
Stage #1: thiophene-3,4-dicarboxylic acid With acetic anhydride at 140℃; Stage #2: 2-Ethylhexylamine In toluene for 24h; Reflux; Stage #3: With thionyl chloride for 4h; Reflux;	48%
Stage #1: thiophene-3,4-dicarboxylic acid With acetic anhydride at 140℃; Stage #2: 2-Ethylhexylamine In toluene for 24h; Reflux; Stage #3: With thionyl chloride for 12h; Reflux;
Stage #1: thiophene-3,4-dicarboxylic acid With acetic anhydride at 140℃; Stage #2: 2-Ethylhexylamine In toluene for 24h; Reflux; Stage #3: With thionyl chloride for 12h; Reflux;

: 4282-29-5
thiophene-3,4-dicarboxylic acid

: 55946-68-4
Mo2(O2C(t)Bu)4

: 108-88-3
toluene

: Mo8(O2C(t)Bu)4(μ-SC4H2-3,4-(CO2)2)6*1.9toluene

Conditions

Conditions	Yield
In toluene under inert atm. suspn. Mo2(O2C-t-Bu)4 and SC4H2-3,4-(COOH)2 in toluene was stirred for 21 days; ppt. was centrifuged, washed with toluene and hexane and dried in vacuo;elem. anal.;	70%

...Expand

: 4282-29-5
thiophene-3,4-dicarboxylic acid

: 86728-84-9
W2(O2C(t)Bu)4

: 872603-00-4
W8(O2C(t)Bu)4(μ-SC4H2-3,4-(CO2)2)6

Conditions

Conditions	Yield
In toluene under inert atm. suspn. W2(O2C-t-Bu)4 and SC4H2-3,4-(COOH)2 in toluene was stirred for 28 days; ppt. was centrifuged, washed with toluene and hexane and dried in vacuo;	68%

: 4282-29-5
thiophene-3,4-dicarboxylic acid

: 64-17-5
ethanol

: 53229-47-3
diethyl thiophene-3,4-dicarboxylate

Conditions

Conditions	Yield
With sulfuric acid Fischer-Speier Esterification; Reflux;	61%
With sulfuric acid
With sulfuric acid In water Inert atmosphere;

: 4282-29-5
thiophene-3,4-dicarboxylic acid

: 111-86-4
n-Octylamine

: 773881-43-9
5-octyl-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione

Conditions

Conditions	Yield
Stage #1: thiophene-3,4-dicarboxylic acid With acetic anhydride at 140℃; Stage #2: n-Octylamine In toluene for 24h; Reflux; Stage #3: With thionyl chloride for 4h; Reflux;	57%
Stage #1: thiophene-3,4-dicarboxylic acid With acetic anhydride at 140℃; Stage #2: n-Octylamine In toluene for 24h; Reflux; Stage #3: With thionyl chloride In toluene for 12h; Reflux;
Stage #1: thiophene-3,4-dicarboxylic acid With acetic anhydride at 140℃; Stage #2: n-Octylamine In toluene for 24h; Reflux; Stage #3: With thionyl chloride for 12h; Reflux;
Stage #1: thiophene-3,4-dicarboxylic acid With acetic anhydride at 140℃; Stage #2: n-Octylamine In toluene for 24h; Reflux; Stage #3: With thionyl chloride for 12h; Reflux;
In neat (no solvent) at 200 - 280℃; for 0.166667h;

: 4282-29-5
thiophene-3,4-dicarboxylic acid

: 124-22-1
n-Dodecylamine

: 773881-44-0
5-dodecyl-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione

Conditions

Conditions	Yield
Stage #1: thiophene-3,4-dicarboxylic acid With acetic anhydride at 140℃; Stage #2: n-Dodecylamine In toluene for 24h; Reflux; Stage #3: With thionyl chloride In toluene Reflux;	55%

: 4282-29-5
thiophene-3,4-dicarboxylic acid

: 5743-04-4
cadmium(II) acetate dihydrate

: 1135-32-6
trans-1,2-bis(4-pyridyl)ethylene

: C6H2O4S(2-)*C12H10N2*Cd(2+)*3H2O

Conditions

Conditions	Yield
In water at 140℃; for 120h; Sealed tube;	53%

...Expand

: 4282-29-5
thiophene-3,4-dicarboxylic acid

: 17252-51-6
1,3-di(4-pyridyl)propane

: 5743-04-4
cadmium(II) acetate dihydrate

: 2C6H2O4S(2-)*3C13H14N2*2Cd(2+)

Conditions

Conditions	Yield
In water at 140℃; for 120h; Sealed tube;	53%

...Expand

: 108-89-4
picoline

: 4282-29-5
thiophene-3,4-dicarboxylic acid

: N3,N4-bis(pyridin-4-ylmethyl)thiophene-3,4-dicarboxamide

Conditions

Conditions	Yield
Stage #1: picoline; thiophene-3,4-dicarboxylic acid With pyridine; ammonia at 20℃; under 750.075 Torr; for 0.5h; Stage #2: With phosphoric acid triphenyl ester for 6h; Reflux;	46%

: 4282-29-5
thiophene-3,4-dicarboxylic acid

: lanthanum(III) nitrate hexahydrate

: 7732-18-5
water

: 3C6H2O4S(2-)*2La(3+)*3H2O

Conditions

Conditions	Yield
With piperazine at 180℃; for 73h; Autoclave;	43.2%

...Expand

: 4282-29-5
thiophene-3,4-dicarboxylic acid

: 1374155-84-6
3,5‐bis(1‐imidazolyl)pyridine

: 5743-04-4
cadmium(II) acetate dihydrate

: 1603817-94-2
{[Cd(3,4-thiophenedicarboxylate)(3,5-bis(imidazol-1’-yl)pyridine)](H2O)}n

Conditions

Conditions	Yield
In water at 140℃; for 120h; Autoclave;	43%

...Expand

: 4282-29-5
thiophene-3,4-dicarboxylic acid

: 74-88-4
methyl iodide

: 4282-35-3
dimethyl thiophene-3,4-dicarboxylate

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 40℃; for 18h;	40%

: 4282-29-5
thiophene-3,4-dicarboxylic acid

: 4916-57-8
1,2-bis(4'-pyridyl)ethane

: 5743-04-4
cadmium(II) acetate dihydrate

: C6H2O4S(2-)*C12H12N2*Cd(2+)*3H2O

Conditions

Conditions	Yield
In water at 140℃; for 120h; Autoclave;	39%

...Expand

: 4282-29-5
thiophene-3,4-dicarboxylic acid

: cerium(III) nitrate hexahydrate

: 7732-18-5
water

: 3C6H2O4S(2-)*3H2O*2Ce(3+)

Conditions

Conditions	Yield
With piperazine at 180℃; for 73h; Autoclave;	28.6%

...Expand

: 4282-29-5
thiophene-3,4-dicarboxylic acid

: 75-65-0
tert-butyl alcohol

A: 108180-68-3
1-t-Butoxycarbonylthieno<3,4-d>imidazolone

B: 108180-69-4
5,10-Dihydroxydithieno<3,4-b:3',4'-f><1,5>diazocine

C: 108180-66-1
tert-butyl {4-[(tert-butoxycarbonyl)amino]thien-3-yl}carbamate

Conditions

Conditions	Yield
With diphenyl phosphoryl azide; triethylamine for 20h; Heating;	A 17% B 28% C 5%

...Expand

3,4-Thiophenedicarboxylic acid Specification

The 3,4-Thiophenedicarboxylicacid, with the CAS registry number 4282-29-5, is also known as 3,4-Dicarboxythiophene. It belongs to the product categories of Acids and Derivatives; Heterocycles; API Intermediates; Building Blocks; Carboxy; Thiophene. This chemical's molecular formula is C₆H₄O₄S and molecular weight is 172.16. What's more, both its IUPAC name and systematic name are the same which is called Thiophene-3,4-dicarboxylic acid. It is yellow to beige-pinkish or light brown crystalline.

Physical properties about 3,4-Thiophenedicarboxylicacid are: (1)ACD/LogP: 0.35; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -2.74; (4)ACD/LogD (pH 7.4): -3.8; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 4; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 80.84 Å²; (13)Index of Refraction: 1.662; (14)Molar Refractivity: 38.49 cm³; (15)Molar Volume: 103.9 cm³; (16)Surface Tension: 83.9 dyne/cm; (17)Density: 1.655 g/cm³; (18)Flash Point: 199.3 °C; (19)Enthalpy of Vaporization: 69.34 kJ/mol; (20)Boiling Point: 405.9 °C at 760 mmHg; (21)Vapour Pressure: 2.57E-07 mmHg at 25 °C; (22)Melting Point: 227-231 °C.

When you are dealing with this chemical, you should be very careful. This chemical is irritating to eyes, respiratory system and skin. Therefore, you should wear suitable protective clothing, gloves and eye/face protection. You should avoid contacting with skin and eyes. In case of contacting with eyes, you should rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1) SMILES: O=C(O)c1cscc1C(=O)O
(2) InChI: InChI=1/C6H4O4S/c7-5(8)3-1-11-2-4(3)6(9)10/h1-2H,(H,7,8)(H,9,10)
(3) InChIKey: ZWWLLYJRPKYTDF-UHFFFAOYAU

Product Name

THIOPHENE-3,4-DICARBOXYLIC ACID

Synthetic route

3,4-Thiophenedicarboxylic acid Specification

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