Product Name

  • Name

    5-Acetylthiophene-2-carboxylic acid

  • EINECS 609-857-0
  • CAS No. 4066-41-5
  • Article Data14
  • CAS DataBase
  • Density 1.383 g/cm3
  • Solubility
  • Melting Point 210-212 °C
  • Formula C7H6O3S
  • Boiling Point 385.2 °C at 760 mmHg
  • Molecular Weight 170.189
  • Flash Point 186.8 °C
  • Transport Information
  • Appearance
  • Safety 26-36/37/39
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 4066-41-5 (5-Acetylthiophene-2-carboxylic acid)
  • Hazard Symbols IrritantXi
  • Synonyms 5-Acetyl-2-thiophenecarboxylicacid;5-Carboxy-2-acetylthiophene;Labotest-bb lt00454683;Buttpark 121\06-15;Akos msc-0226;Rarechem al bo 0535;
  • PSA 82.61000
  • LogP 1.64890

Synthetic route

5-bromothiophene-2-carboxylic acid
7311-63-9

5-bromothiophene-2-carboxylic acid

acetyl chloride
75-36-5

acetyl chloride

5-acetylthiophene-2-carboxylic acid
4066-41-5

5-acetylthiophene-2-carboxylic acid

Conditions
ConditionsYield
Stage #1: 5-bromothiophene-2-carboxylic acid; acetyl chloride With isopropylmagnesium bromide In tetrahydrofuran at -40 - -10℃; for 12h; Solid phase reaction;
Stage #2: In dichloromethane at 20℃; for 0.25h; Hydrolysis; Further stages.;		90%
2-Acetyl-5-methylthiophen
13679-74-8

2-Acetyl-5-methylthiophen

5-acetylthiophene-2-carboxylic acid
4066-41-5

5-acetylthiophene-2-carboxylic acid

Conditions
ConditionsYield
With cerium(III) chloride; 1,1,1-trichloroethanol; oxygen In acetonitrile at 60℃; Irradiation;81%
With oxygen; cobalt(II) acetate; sodium bromide In acetic acid at 95℃; for 1.5h; Kinetics; Rate constant;
With oxygen; cobalt(II) acetate; sodium bromide In acetic acid at 100℃; for 1.5h;
2-Acetylthiophene
88-15-3

2-Acetylthiophene

carbon dioxide
124-38-9

carbon dioxide

5-acetylthiophene-2-carboxylic acid
4066-41-5

5-acetylthiophene-2-carboxylic acid

Conditions
ConditionsYield
With 2,3,6,7-tetramethoxy-9(10H)-anthracenone; caesium carbonate In dimethyl sulfoxide at 25℃; under 2280.15 Torr; for 18h; Irradiation; Sealed tube; regioselective reaction;39%
2-thiophenylcarboxylic acid
527-72-0

2-thiophenylcarboxylic acid

malonic acid
141-82-2

malonic acid

5-acetylthiophene-2-carboxylic acid
4066-41-5

5-acetylthiophene-2-carboxylic acid

Conditions
ConditionsYield
With PPA at 60 - 80℃; for 2h; Acylation; Friedel-Crafts acylation;10%
1-(5-ethanesulfonylmethyl-[2]thienyl)-ethanone
98954-61-1

1-(5-ethanesulfonylmethyl-[2]thienyl)-ethanone

5-acetylthiophene-2-carboxylic acid
4066-41-5

5-acetylthiophene-2-carboxylic acid

Conditions
ConditionsYield
With potassium permanganate
N'-tetramethylethylenediamine

N'-tetramethylethylenediamine

2-methyl-2-(thiophen-2-yl)-[1,3]dioxolane
5916-12-1

2-methyl-2-(thiophen-2-yl)-[1,3]dioxolane

5-acetylthiophene-2-carboxylic acid
4066-41-5

5-acetylthiophene-2-carboxylic acid

Conditions
ConditionsYield
With hydrogenchloride; n-butyllithium; carbon dioxide In tetrahydrofuran; hexane
2-Acetylthiophene
88-15-3

2-Acetylthiophene

5-(α-methoxyimino)ethyl-2-thiophenecarboxylic acid
1379398-60-3

5-(α-methoxyimino)ethyl-2-thiophenecarboxylic acid

5-acetylthiophene-2-carboxylic acid
4066-41-5

5-acetylthiophene-2-carboxylic acid

2-Acetylthiophene
88-15-3

2-Acetylthiophene

5-acetylthiophene-2-carboxylic acid
4066-41-5

5-acetylthiophene-2-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: sodium carbonate; acetic acid / methanol; water / 86 °C / pH 4 - 5
2: polyphosphoric acid / 100 °C
3: sodium hypochlorite / methanol / 10 - 70 °C
4: hydrogenchloride / water / 55 - 60 °C
View Scheme
Multi-step reaction with 4 steps
1: acetic acid; sodium carbonate / water; methanol / 3 h / pH 5 / Heating
2: zinc(II) chloride; hydrogenchloride / water; chloroform / 12 h / 100 °C
3: sodium hypochlorite; hydrogenchloride / water; methanol / 4 h / 70 °C
4: hydrogenchloride / water / 12 h / 65 °C
View Scheme
2-(α-methoxyimino)ethylthiophene
114773-97-6

2-(α-methoxyimino)ethylthiophene

5-acetylthiophene-2-carboxylic acid
4066-41-5

5-acetylthiophene-2-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: polyphosphoric acid / 100 °C
2: sodium hypochlorite / methanol / 10 - 70 °C
3: hydrogenchloride / water / 55 - 60 °C
View Scheme
Multi-step reaction with 3 steps
1: zinc(II) chloride; hydrogenchloride / water; chloroform / 12 h / 100 °C
2: sodium hypochlorite; hydrogenchloride / water; methanol / 4 h / 70 °C
3: hydrogenchloride / water / 12 h / 65 °C
View Scheme
2-acetyl-5-(α-methoxyimino)ethylthiophene
114774-08-2

2-acetyl-5-(α-methoxyimino)ethylthiophene

5-acetylthiophene-2-carboxylic acid
4066-41-5

5-acetylthiophene-2-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium hypochlorite / methanol / 10 - 70 °C
2: hydrogenchloride / water / 55 - 60 °C
View Scheme
Multi-step reaction with 2 steps
1: sodium hypochlorite; hydrogenchloride / water; methanol / 4 h / 70 °C
2: hydrogenchloride / water / 12 h / 65 °C
View Scheme
5-(α-methoxyimino)ethyl-2-thiophenecarboxylic acid

5-(α-methoxyimino)ethyl-2-thiophenecarboxylic acid

5-acetylthiophene-2-carboxylic acid
4066-41-5

5-acetylthiophene-2-carboxylic acid

Conditions
ConditionsYield
With hydrogenchloride In water at 55 - 60℃;
With hydrogenchloride In water at 65℃; for 12h;
5-acetylthiophene-2-carboxylic acid
4066-41-5

5-acetylthiophene-2-carboxylic acid

diazomethyl-trimethyl-silane
18107-18-1

diazomethyl-trimethyl-silane

methyl 5-acetyl-2-thiophenecarboxylate
4101-81-9

methyl 5-acetyl-2-thiophenecarboxylate

Conditions
ConditionsYield
In methanol; toluene at 0 - 20℃;100%
With tetrafluoroboric acid In dichloromethane; water at 0℃; for 2h;11%
methanol
67-56-1

methanol

5-acetylthiophene-2-carboxylic acid
4066-41-5

5-acetylthiophene-2-carboxylic acid

methyl 5-acetyl-2-thiophenecarboxylate
4101-81-9

methyl 5-acetyl-2-thiophenecarboxylate

Conditions
ConditionsYield
With sulfuric acid Reflux;92.81%
With thionyl chloride In N,N-dimethyl-formamide for 5h; Reflux;
5-acetylthiophene-2-carboxylic acid
4066-41-5

5-acetylthiophene-2-carboxylic acid

N,N-dimethyl-formamide dimethyl acetal
4637-24-5

N,N-dimethyl-formamide dimethyl acetal

5-(3-dimethylaminoacryloyl)thiophene-2-carboxylic acid methyl ester
866523-73-1

5-(3-dimethylaminoacryloyl)thiophene-2-carboxylic acid methyl ester

Conditions
ConditionsYield
In toluene at 110℃; for 16h;91%
In N,N-dimethyl-formamide Reflux;80%
In toluene for 15h; Heating / reflux;
In toluene Reflux;
5-acetylthiophene-2-carboxylic acid
4066-41-5

5-acetylthiophene-2-carboxylic acid

ethanol
64-17-5

ethanol

5-acetyl-thiophene-2-carboxylic acid ethyl ester
33148-82-2

5-acetyl-thiophene-2-carboxylic acid ethyl ester

Conditions
ConditionsYield
With toluene-4-sulfonic acid In toluene for 3h; Reflux; Dean-Stark;91%
With sulfuric acid for 72h; Heating / reflux;84%
5-acetylthiophene-2-carboxylic acid
4066-41-5

5-acetylthiophene-2-carboxylic acid

N-[2-amino-1-(3-amino-3-oxopropyl)-1H-benzimidazol-5-yl]-N-methylbenzamide
658700-12-0

N-[2-amino-1-(3-amino-3-oxopropyl)-1H-benzimidazol-5-yl]-N-methylbenzamide

C25H23N5O4S
1092486-13-9

C25H23N5O4S

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;90%
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 24h;
5-acetylthiophene-2-carboxylic acid
4066-41-5

5-acetylthiophene-2-carboxylic acid

N,O-dimethylhydroxylamine*hydrochloride
6638-79-5

N,O-dimethylhydroxylamine*hydrochloride

5-Acetyl-N-methoxy-N-methylthiophene-2-carboxamide
844502-57-4

5-Acetyl-N-methoxy-N-methylthiophene-2-carboxamide

Conditions
ConditionsYield
With 4-methyl-morpholine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dimethyl amine at 25℃; for 16h;86%
5-acetylthiophene-2-carboxylic acid
4066-41-5

5-acetylthiophene-2-carboxylic acid

methyl iodide
74-88-4

methyl iodide

methyl 5-acetyl-2-thiophenecarboxylate
4101-81-9

methyl 5-acetyl-2-thiophenecarboxylate

Conditions
ConditionsYield
With sodium carbonate In DMF (N,N-dimethyl-formamide) at 20℃;80%
With potassium carbonate In N,N-dimethyl-formamide at 23℃; for 72h;72%
With potassium carbonate In N,N-dimethyl-formamide at 23℃;72%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 60h;
With sodium carbonate In N,N-dimethyl-formamide at 20℃;
5-acetylthiophene-2-carboxylic acid
4066-41-5

5-acetylthiophene-2-carboxylic acid

tert-butyl alcohol
75-65-0

tert-butyl alcohol

tert-butyl-5-acetylthiophene-2-carboxylate
844502-29-0

tert-butyl-5-acetylthiophene-2-carboxylate

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dimethyl amine at 25℃; for 16h;72%
5-acetylthiophene-2-carboxylic acid
4066-41-5

5-acetylthiophene-2-carboxylic acid

N-(2-(pyridin-2-yl)propan-2-yl)benzamide

N-(2-(pyridin-2-yl)propan-2-yl)benzamide

2-(5-acetylthiophen-2-yl)-N-(2-(pyridin-2-yl)propan-2-yl)benzamide

2-(5-acetylthiophen-2-yl)-N-(2-(pyridin-2-yl)propan-2-yl)benzamide

Conditions
ConditionsYield
With copper (I) acetate; lithium carbonate; silver nitrate In N,N-dimethyl-formamide at 100℃; for 24h; Inert atmosphere; Sealed tube;45%
5-acetylthiophene-2-carboxylic acid
4066-41-5

5-acetylthiophene-2-carboxylic acid

(R)-1-phenyl-ethyl-amine
3886-69-9

(R)-1-phenyl-ethyl-amine

sodium ethyltrithiocarbonate
67715-76-8

sodium ethyltrithiocarbonate

ethyl 2-oxo-2-[5-((R)-1-phenylethylcarbamoyl)thiophen-2-yl]ethyl trithiocarbonate
1039454-46-0

ethyl 2-oxo-2-[5-((R)-1-phenylethylcarbamoyl)thiophen-2-yl]ethyl trithiocarbonate

Conditions
ConditionsYield
Stage #1: 5-acetylthiophene-2-carboxylic acid With 4-methyl-morpholine; isobutyl chloroformate In tetrahydrofuran at 0℃; for 0.75h;
Stage #2: (R)-1-phenyl-ethyl-amine In tetrahydrofuran at 20℃; for 18h;
Stage #3: sodium ethyltrithiocarbonate Further stages;		44%
...Expand
5-acetylthiophene-2-carboxylic acid
4066-41-5

5-acetylthiophene-2-carboxylic acid

sodium ethyltrithiocarbonate
67715-76-8

sodium ethyltrithiocarbonate

aniline
62-53-3

aniline

ethyl 2-oxo-2-(5-phenylcarbamoylthiophen-2-yl)ethyl trithiocarbonate
1039454-48-2

ethyl 2-oxo-2-(5-phenylcarbamoylthiophen-2-yl)ethyl trithiocarbonate

Conditions
ConditionsYield
Stage #1: 5-acetylthiophene-2-carboxylic acid With 4-methyl-morpholine; isobutyl chloroformate In tetrahydrofuran at 0℃; for 0.75h;
Stage #2: aniline In tetrahydrofuran at 20℃; for 18h;
Stage #3: sodium ethyltrithiocarbonate Further stages;		22%
...Expand
5-acetylthiophene-2-carboxylic acid
4066-41-5

5-acetylthiophene-2-carboxylic acid

3,5-dimethylbenzyl amine
78710-55-1

3,5-dimethylbenzyl amine

sodium ethyltrithiocarbonate
67715-76-8

sodium ethyltrithiocarbonate

2-[5-(3,5-dimethylbenzylcarbamoyl)thiophen-2-yl]-2-oxoethyl ethyl trithiocarbonate
1039454-47-1

2-[5-(3,5-dimethylbenzylcarbamoyl)thiophen-2-yl]-2-oxoethyl ethyl trithiocarbonate

Conditions
ConditionsYield
Stage #1: 5-acetylthiophene-2-carboxylic acid With 4-methyl-morpholine; isobutyl chloroformate In tetrahydrofuran at 0℃; for 0.75h;
Stage #2: 3,5-dimethylbenzyl amine In tetrahydrofuran at 20℃; for 18h;
Stage #3: sodium ethyltrithiocarbonate Further stages;		21%
...Expand
5-acetylthiophene-2-carboxylic acid
4066-41-5

5-acetylthiophene-2-carboxylic acid

2-hydrazino-1,3-thiazole
30216-51-4

2-hydrazino-1,3-thiazole

5-[1-(Thiazol-2-yl-hydrazono)-ethyl]-thiophene-2-carboxylic acid
109793-48-8

5-[1-(Thiazol-2-yl-hydrazono)-ethyl]-thiophene-2-carboxylic acid

Conditions
ConditionsYield
In ethanol at 95℃; for 0.166667h;20%
5-acetylthiophene-2-carboxylic acid
4066-41-5

5-acetylthiophene-2-carboxylic acid

sodium ethyltrithiocarbonate
67715-76-8

sodium ethyltrithiocarbonate

benzylamine
100-46-9

benzylamine

2-(5-benzylcarbamoylthiophen-2-yl)-2-oxoethyl ethyl trithiocarbonate
1039454-42-6

2-(5-benzylcarbamoylthiophen-2-yl)-2-oxoethyl ethyl trithiocarbonate

Conditions
ConditionsYield
Stage #1: 5-acetylthiophene-2-carboxylic acid With 4-methyl-morpholine; isobutyl chloroformate In tetrahydrofuran at 0℃; for 0.75h;
Stage #2: benzylamine In tetrahydrofuran at 20℃; for 18h;
Stage #3: sodium ethyltrithiocarbonate Further stages;		12%
...Expand
5-acetylthiophene-2-carboxylic acid
4066-41-5

5-acetylthiophene-2-carboxylic acid

(S)-1-phenyl-ethylamine
2627-86-3

(S)-1-phenyl-ethylamine

sodium ethyltrithiocarbonate
67715-76-8

sodium ethyltrithiocarbonate

ethyl 2-oxo-2-[5-((S)-1-phenylethylcarbamoyl)thiophen-2-yl]ethyl trithiocarbonate
1039454-44-8

ethyl 2-oxo-2-[5-((S)-1-phenylethylcarbamoyl)thiophen-2-yl]ethyl trithiocarbonate

Conditions
ConditionsYield
Stage #1: 5-acetylthiophene-2-carboxylic acid With 4-methyl-morpholine; isobutyl chloroformate In tetrahydrofuran at 0℃; for 0.75h;
Stage #2: (S)-1-phenyl-ethylamine In tetrahydrofuran at 20℃; for 18h;
Stage #3: sodium ethyltrithiocarbonate Further stages;		6%
...Expand
5-acetylthiophene-2-carboxylic acid
4066-41-5

5-acetylthiophene-2-carboxylic acid

5-ethyl-2-thiophenecarboxylic acid
23229-72-3

5-ethyl-2-thiophenecarboxylic acid

Conditions
ConditionsYield
With hydrazine hydrate; ethylene glycol at 145℃; Erhitzen des Reaktionsgemisches mit Kaliumhydroxid bis auf 193grad;
5-acetylthiophene-2-carboxylic acid
4066-41-5

5-acetylthiophene-2-carboxylic acid

5-(1-hydroxyimino-ethyl)-thiophene-2-carboxylic acid
98279-55-1

5-(1-hydroxyimino-ethyl)-thiophene-2-carboxylic acid

Conditions
ConditionsYield
With potassium hydroxide; ethanol; hydroxylamine hydrochloride
5-acetylthiophene-2-carboxylic acid
4066-41-5

5-acetylthiophene-2-carboxylic acid

diazodiphenylmethane
908093-98-1

diazodiphenylmethane

5-Acetyl-thiophene-2-carboxylic acid benzhydryl ester

5-Acetyl-thiophene-2-carboxylic acid benzhydryl ester

Conditions
ConditionsYield
In methanol at 25℃; Rate constant;
5-acetylthiophene-2-carboxylic acid
4066-41-5

5-acetylthiophene-2-carboxylic acid

5-(2-Bromo-acetyl)-thiophene-2-carboxylic acid
96543-76-9

5-(2-Bromo-acetyl)-thiophene-2-carboxylic acid

Conditions
ConditionsYield
With bromine In acetic acid at 110℃; for 0.166667h;
5-acetylthiophene-2-carboxylic acid
4066-41-5

5-acetylthiophene-2-carboxylic acid

[4-(5-amino-thiophen-2-yl)-pyrimidin-2-yl]-methyl-amine
866523-80-0

[4-(5-amino-thiophen-2-yl)-pyrimidin-2-yl]-methyl-amine

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 91 percent / toluene / 16 h / 110 °C
2: NaOEt / 40 h / 70 °C
3: 87 percent / hydrazine / methanol / 16 h / 70 °C
4: 91 percent / aq. HCl; NaNO2 / acetic acid / 0.5 h / 0 °C
5: 30 percent / aq. HCl / 16 h / 100 °C
View Scheme
5-acetylthiophene-2-carboxylic acid
4066-41-5

5-acetylthiophene-2-carboxylic acid

[4-(5-isocyanato-thiophen-2-yl)-pyrimidin-2-yl]-methyl-amine

[4-(5-isocyanato-thiophen-2-yl)-pyrimidin-2-yl]-methyl-amine

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 91 percent / toluene / 16 h / 110 °C
2: NaOEt / 40 h / 70 °C
3: 87 percent / hydrazine / methanol / 16 h / 70 °C
4: 91 percent / aq. HCl; NaNO2 / acetic acid / 0.5 h / 0 °C
5: xylene / 0.42 h / 120 °C
View Scheme
5-acetylthiophene-2-carboxylic acid
4066-41-5

5-acetylthiophene-2-carboxylic acid

5-(2-methylsulfanyl-pyrimidin-4-yl)-thiophene-2-carboxylic acid methyl ester
908834-77-5

5-(2-methylsulfanyl-pyrimidin-4-yl)-thiophene-2-carboxylic acid methyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 91 percent / toluene / 16 h / 110 °C
2: 69 percent / pyridine / H2O / 68 h / 100 °C
View Scheme
5-acetylthiophene-2-carboxylic acid
4066-41-5

5-acetylthiophene-2-carboxylic acid

5-(2-amino-pyrimidin-4-yl)-thiophene-2-carboxylic acid ethyl ester

5-(2-amino-pyrimidin-4-yl)-thiophene-2-carboxylic acid ethyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 91 percent / toluene / 16 h / 110 °C
2: NaOEt / 40 h / 70 °C
View Scheme
5-acetylthiophene-2-carboxylic acid
4066-41-5

5-acetylthiophene-2-carboxylic acid

5-(2-methylamino-pyrimidin-4-yl)-thiophene-2-carboxylic acid ethyl ester
866523-74-2

5-(2-methylamino-pyrimidin-4-yl)-thiophene-2-carboxylic acid ethyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 91 percent / toluene / 16 h / 110 °C
2: NaOEt / 40 h / 70 °C
View Scheme

5-Acetylthiophene-2-carboxylic acid Chemical Properties

IUPAC Name: 5-Acetylthiophene-2-carboxylate
Synonyms of 5-Acetylthiophene-2-carboxylic acid (CAS NO.5452-37-9): Labotest-bb lt00454683 ; Buttpark 121\06-15 ; Akos msc-0226 ; 5-Acetyl-2-thiophenecarboxylic acid ; Rarechem al bo 0535 ; 5-Acetylthiophene-2-CarboxylicAcid98% ; 5-Acetylthiophene-2-Carboxylic Acid 98%
CAS NO: 5452-37-9
Molecular Formula of 5-Acetylthiophene-2-carboxylic acid (CAS NO.5452-37-9): C7H6O3S
Molecular Weight: 170.1857
Molecular Structure:

Melting Point: 210-212°C 
Polar Surface Area: 71.61 Å2
Index of Refraction: 1.591
Molar Refractivity: 41.59 cm3
Molar Volume: 122.9 cm3
Surface Tension: 56.8 dyne/cm
Density of 5-Acetylthiophene-2-carboxylic acid (CAS NO.5452-37-9): 1.383 g/cm3
Flash Point: 186.8 °C
Enthalpy of Vaporization: 66.87 kJ/mol
Boiling Point: 385.2 °C at 760 mmHg
Vapour Pressure: 1.27E-06 mmHg at 25°C

5-Acetylthiophene-2-carboxylic acid Safety Profile

Hazard Codes: IrritantXi
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. 
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection.
Hazard Note: Irritant

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