2,5-thiophenedicarbonitrile
Thiophene-2,5-dicarboxylic acid
Conditions | Yield |
---|---|
With hydrogenchloride for 6h; Heating; | 79% |
Conditions | Yield |
---|---|
Stage #1: Adipic acid With dmap; thionyl chloride at 78 - 81℃; for 3.5h; Large scale; Stage #2: With sodium hydroxide In water at 70 - 72℃; for 2h; pH=9.3 - 10; Reagent/catalyst; Temperature; pH-value; Large scale; | 75.58% |
2,5‐diethyl thiophene‐2,5‐dicarboxylate
Thiophene-2,5-dicarboxylic acid
Conditions | Yield |
---|---|
With potassium hydroxide In ethanol for 2h; Heating; | 70% |
With potassium hydroxide |
Conditions | Yield |
---|---|
With n-butyllithium; carbon dioxide In tetrahydrofuran; water | 60% |
With diethyl ether; phenyllithium Behandeln des Reaktionsgemisches mit festem Kohlendioxid; |
methanol
2,5-dibromothiophen
carbon monoxide
A
Thiophene-2,5-dicarboxylic acid
B
Dimethyl thiophene-2,5-dicarboxylate
Conditions | Yield |
---|---|
With tert-Amyl alcohol; sodium hydride; cobalt(II) acetate In tetrahydrofuran at 40℃; under 760 Torr; for 54h; Irradiation; | A 17% B 55% |
2,5-dibromothiophen
carbon monoxide
A
Thiophene-2,5-dicarboxylic acid
B
Dimethyl thiophene-2,5-dicarboxylate
Conditions | Yield |
---|---|
With methanol; tert-Amyl alcohol; sodium hydride; cobalt(II) acetate In tetrahydrofuran at 40℃; under 760 Torr; for 54h; Irradiation; | A 17% B 55% |
2,5-dibromothiophen
carbon dioxide
A
5-bromothiophene-2-carboxylic acid
B
Thiophene-2,5-dicarboxylic acid
Conditions | Yield |
---|---|
Stage #1: 2,5-dibromothiophen; carbon dioxide With tert.-butyl lithium In pentane at -70℃; Inert atmosphere; Stage #2: With sulfuric acid; water In pentane at 20℃; Inert atmosphere; | A 34% B 5% |
thiophene
n-pentylsodium
sodium tert-pentoxide
methylammonium carbonate
Thiophene-2,5-dicarboxylic acid
Conditions | Yield |
---|---|
aufeinanderfolgender Umsetzung; |
thiophene
Thiophene-2,5-dicarboxylic acid
Conditions | Yield |
---|---|
With n-heptane; n-pentylsodium; sodium tert-pentoxide anschliessend Behandeln mit festem Kohlendioxid; |
Conditions | Yield |
---|---|
With alkaline permanganate solution |
2-Acetyl-5-methylthiophen
A
2-methylthiophene-5-carboxylic acid
B
Thiophene-2,5-dicarboxylic acid
Conditions | Yield |
---|---|
With potassium hydroxide; potassium permanganate Behandeln des Reaktionsprodukts mit wss. Wasserstoffperoxid; |
2-Acetyl-5-methylthiophen
Thiophene-2,5-dicarboxylic acid
Conditions | Yield |
---|---|
With alkaline permanganate solution | |
With sodium hydroxide; potassium permanganate Oxidation; |
2,5-bis-chloromethyl-thiophene
Thiophene-2,5-dicarboxylic acid
Conditions | Yield |
---|---|
With potassium hydroxide; potassium permanganate | |
With potassium permanganate; acetone |
Conditions | Yield |
---|---|
With sodium ethanolate Abdampfen der mit Wasser versetzten Mischung und Ansaeuern mit Salzsaeure; |
1-(5-ethyl-thiophen-2-yl)-ethanone
Thiophene-2,5-dicarboxylic acid
Conditions | Yield |
---|---|
With alkaline permanganate solution |
thiophene
carbon dioxide
A
2-thiophenylcarboxylic acid
B
Thiophene-2,5-dicarboxylic acid
Conditions | Yield |
---|---|
With n-butyllithium 1.) methylcyclohexane, THF, from 0 deg C to 25 deg C, 20 h, 2.) methylcyclohexane, THF, ether; Yield given. Multistep reaction. Yields of byproduct given; |
Conditions | Yield |
---|---|
With n-butyllithium 1. THF/-50 - -55 deg C; Yield given. Multistep reaction; | |
Stage #1: 2,5-dibromothiophen With iodine; magnesium In tetrahydrofuran; 1,4-dioxane at 60℃; for 4h; Inert atmosphere; Stage #2: carbon dioxide In tetrahydrofuran; 1,4-dioxane Solvent; Temperature; |
2-thiophenylcarboxylic acid
carbon dioxide
A
Thiophene-2,5-dicarboxylic acid
B
thiophene-2,3-dicarboxylic acid
Conditions | Yield |
---|---|
With n-butyllithium 1.) THF/hexane, -78 deg C, 30 min, 2.) THF/hexane, -78 -> -10 deg C; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts; |
Thiophene-2,5-dicarboxylic acid
Conditions | Yield |
---|---|
With nitric acid |
Thiophene-2,5-dicarboxylic acid
Conditions | Yield |
---|---|
With alkaline permanganate solution |
Thiophene-2,5-dicarboxylic acid
Conditions | Yield |
---|---|
With alkaline permanganate solution |
Thiophene-2,5-dicarboxylic acid
Conditions | Yield |
---|---|
With potassium cyanide Verseifen durch Kochen mit alkoh. Kali; |
Conditions | Yield |
---|---|
With cadmium catalyst unter Kohlendioxid; |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: petroleum ether; aluminium chloride 2: alkaline permanganate solution View Scheme |
Conditions | Yield |
---|---|
With sulfuric acid In water at 60℃; for 2h; Large scale; | 1679 g |
Thiophene-2,5-dicarboxylic acid
ethanol
2,5‐diethyl thiophene‐2,5‐dicarboxylate
Conditions | Yield |
---|---|
With sulfuric acid Reflux; | 100% |
With sulfuric acid for 120h; Reflux; | 90% |
With graphene oxide at 100℃; for 24h; | 67% |
With sulfuric acid at 85℃; for 72h; Inert atmosphere; | 3.2 g |
for 6h; Reflux; |
methanol
Thiophene-2,5-dicarboxylic acid
Dimethyl thiophene-2,5-dicarboxylate
Conditions | Yield |
---|---|
With thionyl chloride at 0 - 20℃; for 3h; Heating / reflux; | 99.9% |
With thionyl chloride Reflux; | 99% |
With thionyl chloride Reflux; | 99% |
1,4-diaza-bicyclo[2.2.2]octane
Thiophene-2,5-dicarboxylic acid
1,2-dihydroxybutane
Conditions | Yield |
---|---|
Stage #1: 1,4-diaza-bicyclo[2.2.2]octane; Thiophene-2,5-dicarboxylic acid; zinc(II) nitrate hexahydrate In N,N-dimethyl-formamide for 1h; Stage #2: 1,2-dihydroxybutane In N,N-dimethyl-formamide at 130℃; for 48h; Sealed tube; | 99% |
Conditions | Yield |
---|---|
With boric acid In toluene at 170 - 240℃; Solvent; Temperature; Inert atmosphere; | 98.7% |
1,4-diaza-bicyclo[2.2.2]octane
Thiophene-2,5-dicarboxylic acid
ethylene glycol
Conditions | Yield |
---|---|
Stage #1: 1,4-diaza-bicyclo[2.2.2]octane; Thiophene-2,5-dicarboxylic acid; zinc(II) nitrate hexahydrate In N,N-dimethyl-formamide for 1h; Stage #2: ethylene glycol In N,N-dimethyl-formamide at 130℃; for 48h; Sealed tube; | 98% |
Conditions | Yield |
---|---|
In ethanol for 2h; Reflux; | 97.9% |
Conditions | Yield |
---|---|
In toluene for 24h; Reflux; water segregator; | 96% |
1,4-diaza-bicyclo[2.2.2]octane
propylene glycol
Thiophene-2,5-dicarboxylic acid
Conditions | Yield |
---|---|
Stage #1: 1,4-diaza-bicyclo[2.2.2]octane; Thiophene-2,5-dicarboxylic acid; zinc(II) nitrate hexahydrate In N,N-dimethyl-formamide for 1h; Stage #2: propylene glycol In N,N-dimethyl-formamide at 130℃; for 48h; Sealed tube; | 96% |
1,4-diaza-bicyclo[2.2.2]octane
Thiophene-2,5-dicarboxylic acid
1,2-pentanediol
Conditions | Yield |
---|---|
Stage #1: 1,4-diaza-bicyclo[2.2.2]octane; Thiophene-2,5-dicarboxylic acid; zinc(II) nitrate hexahydrate In N,N-dimethyl-formamide for 1h; Stage #2: 1,2-pentanediol In N,N-dimethyl-formamide at 130℃; for 48h; Sealed tube; | 96% |
N,N’,N’’,N’’’-tetrakis(2-pyridylmethyl)-1,6-diaminohexane
Thiophene-2,5-dicarboxylic acid
cobalt(II) diacetate tetrahydrate
Conditions | Yield |
---|---|
Stage #1: N,N’,N’’,N’’’-tetrakis(2-pyridylmethyl)-1,6-diaminohexane; cobalt(II) diacetate tetrahydrate In methanol at 20℃; Stage #2: Thiophene-2,5-dicarboxylic acid In methanol at 20℃; | 96% |
Thiophene-2,5-dicarboxylic acid
Conditions | Yield |
---|---|
In toluene C4H2S(COOH)2 added to soln. of W2((CH3)3CCOO)4 in toluene; soln. stirredfor 7-10 d at rt; precipitate filtered off; detd. by elem. anal.; | 95% |
In toluene under Ar atm. to soln. (W2(O2C(t)Bu)4) in toluene 2,5-Th(COOH)2 was added and stirred at room temp. for 5-10 days; ppt. was filtered, washed with toluene and hexane, and dried in vacuo; elem. anal.; | 95% |
Conditions | Yield |
---|---|
With acetic acid In ethanol at 20℃; for 120 - 168h; pH=4 - 5; | 94% |
Conditions | Yield |
---|---|
Stage #1: 1,4-diaza-bicyclo[2.2.2]octane; Thiophene-2,5-dicarboxylic acid; zinc(II) nitrate hexahydrate In N,N-dimethyl-formamide for 1h; Stage #2: glycerol In N,N-dimethyl-formamide at 130℃; for 48h; Sealed tube; | 94% |
Thiophene-2,5-dicarboxylic acid
3-amino-4-hydroxytoluene
5,5'-dimethyl-2,2'-thiophene-2,5-diyl-bis-benzooxazole
Conditions | Yield |
---|---|
With boric acid; tin(ll) chloride In 1,2-dichloro-benzene at 220℃; for 24h; Inert atmosphere; Dean-Stark; | 94% |
Conditions | Yield |
---|---|
In toluene for 24h; Reflux; water segregator; | 93% |
Thiophene-2,5-dicarboxylic acid
(2S)-2-phenylglycinol
(+)-2,5-bis[4'-(S)-phenyloxazolin-2'-yl]thiophene
Conditions | Yield |
---|---|
In toluene for 24h; Reflux; water segregator; | 93% |
Thiophene-2,5-dicarboxylic acid
N,0-dimethylhydroxylamine
N2,N5-dimethoxy-N2,N5-dimethylthiophene-2,5-dicarboxamide
Conditions | Yield |
---|---|
Stage #1: Thiophene-2,5-dicarboxylic acid; N,0-dimethylhydroxylamine In toluene at 0℃; for 0.166667h; Stage #2: With phosphorus trichloride In toluene at 20 - 60℃; for 0.5h; | 92% |
Thiophene-2,5-dicarboxylic acid
2-(5-{6-[5-(pyrazin-2-yl)-1H-1,2,4-triazol-3-yl]-pyridin-2-yl}-1H-1,2,4-triazol-3-yl)pyrazine
water
Conditions | Yield |
---|---|
With 3-ethyl-1-methyl-1H-imidazol-3-ium bromide In acetonitrile at 160℃; for 72h; Reagent/catalyst; Autoclave; | 92% |
Conditions | Yield |
---|---|
In toluene for 24h; Reflux; water segregator; | 91% |
Thiophene-2,5-dicarboxylic acid
Conditions | Yield |
---|---|
In toluene C4H2S(COOH)2 added to soln. of Mo2((CH3)3CCOO)4 in toluene; soln. stirred for 7-10 d at rt; precipitate filtered off; detd. by elem. anal., MALDI; | 90% |
In toluene under Ar atm. to soln. (Mo2(O2C(t)Bu)4) in toluene 2,5-Th(COOH)2 was added and stirred at room temp. for 5-10 days; ppt. was filtered; elem. anal.; | 90% |
Conditions | Yield |
---|---|
With NH3*H2O In water High Pressure; mixt. of MnCl2*4H2O, thiohene-2,5-dicarboxylic acid, H2O adjusted to pH 7.4 by aq. soln. of NH3*H2O, placed in autoclave, heated at 110°Cfor 3 d, slow cooled to room temp.; ppt. filtered, washed with H2O; elem. anal.; | 90% |
Conditions | Yield |
---|---|
With NH3*H2O In water High Pressure; mixt. of CoCl2*6H2O, thiohene-2,5-dicarboxylic acid, H2O adjusted to pH 7.4 by aq. soln. of NH3*H2O, placed in autoclave, heated at 110°Cfor 3 d, slow cooled to room temp.; ppt. filtered, washed with H2O; elem. anal.; | 90% |
Thiophene-2,5-dicarboxylic acid
N,N-dimethyl-formamide
Conditions | Yield |
---|---|
at 120℃; for 72h; | 90% |
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 135℃; for 24h; | 90% |
Thiophene-2,5-dicarboxylic acid
cobalt(II) diacetate tetrahydrate
N,N’-(1,4-phenylenebis(methylene))bis(1-(pyridin-2-yl)-N-(pyridin-2-ylmethyl)methanamine)
Conditions | Yield |
---|---|
Stage #1: cobalt(II) diacetate tetrahydrate; N,N’-(1,4-phenylenebis(methylene))bis(1-(pyridin-2-yl)-N-(pyridin-2-ylmethyl)methanamine) In methanol at 20℃; Stage #2: Thiophene-2,5-dicarboxylic acid In methanol at 20℃; | 90% |
Thiophene-2,5-dicarboxylic acid
2-amino-phenol
2,2'-thiophene-2,5-diylbis(benzoxazole)
Conditions | Yield |
---|---|
With boric acid; tin(ll) chloride In 1,2-dichloro-benzene at 220℃; for 24h; Inert atmosphere; Dean-Stark; | 89.23% |
Stage #1: Thiophene-2,5-dicarboxylic acid; 2-amino-phenol at 150℃; for 2h; Inert atmosphere; Stage #2: With ammonia In water at 20℃; pH=~ 10 - 11; Cooling with cold water; | 5.5% |
With boric acid In 1-methyl-pyrrolidin-2-one; toluene at 20 - 185℃; for 13h; |
Thiophene-2,5-dicarboxylic acid
(S)-tert-leucinol
Conditions | Yield |
---|---|
In toluene for 24h; Reflux; water segregator; | 89% |
Conditions | Yield |
---|---|
at 120℃; for 120h; High pressure; | A 89% B n/a |
formic acid
Thiophene-2,5-dicarboxylic acid
zirconium(IV) chloride
N,N-dimethyl-formamide
Conditions | Yield |
---|---|
In 1-methyl-pyrrolidin-2-one at 120℃; for 48h; Sonication; | 89% |
formic acid
Thiophene-2,5-dicarboxylic acid
zirconium(IV) chloride
N,N-dimethyl-formamide
Conditions | Yield |
---|---|
In 1-methyl-pyrrolidin-2-one at 80℃; for 48h; | 89% |
Empirical Formula: C6H4O4S
Molecular Weight: 172.1586
Index of Refraction: 1.662
Molar Refractivity: 38.49 cm3
Molar Volume: 103.9 cm3
Surface Tension: 83.9 dyne/cm
Density: 1.655 g/cm3
Flash Point: 222.7 °C
Enthalpy of Vaporization: 74.03 kJ/mol
Boiling Point: 444.6 °C at 760 mmHg
Vapour Pressure: 1.1E-08 mmHg at 25 °C
Melting point: >300 °C(lit.)
Appearance: White to light yellow crystal powder
Structure of 2,5-Thiophenedicarboxylic acid (CAS NO.4282-31-9):
Product Category of 2,5-Thiophenedicarboxylic acid (CAS NO.4282-31-9): Thiophenes;Thiophens;Functional Materials;Reagents for Conducting Polymer Research;Thiophene Derivatives (for Conduting Polymer Research);Thiophen;Heterocyclic Building Blocks
Hazard Codes: Xi
Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36-37/39
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36:Wear suitable protective clothing.
S37/39:Wear suitable gloves and eye/face protection.
2,5-Thiophenedicarboxylic acid , its cas register number is 4282-31-9. It also can be called Thiophene-2,5-dicarboxylic acid ; and NSC 81789 . It is hazardous, so the first aid measures and others should be known. Such as: When on the skin: first, should flush skin with plenty of water immediately for at least 15 minutes while removing contaminated clothing. Secondly, get medical aid. Or in the eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Then get medical aid soon. While, it's inhaled: Remove from exposure and move to fresh air immediately. Give artificial respiration while not breathing. When breathing is difficult, give oxygen. And as soon as to get medical aid. Then you have the ingesting of the product: Wash mouth out with water, and get medical aid immediately. Notes to physician: Treat supportively and symptomatically.
In addition, 2,5-Thiophenedicarboxylic acid (CAS NO.4282-31-9) is not compatible with strong oxidizing agents, and you must not take it with incompatible materials. And also prevent it to broken down into hazardous decomposition products: Carbon monoxide, carbon dioxide, sulfur oxides (SOx), including sulfur oxide and sulfur dioxide.
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