Product Name

  • Name

    2-Thiophenecarboxylic acid

  • EINECS 208-423-4
  • CAS No. 527-72-0
  • Article Data279
  • CAS DataBase
  • Density 1.401 g/cm3
  • Solubility water: 80 g/L (20 °C)
  • Melting Point 125-127 °C(lit.)
  • Formula C5H4O2S
  • Boiling Point 260 °C at 760 mmHg
  • Molecular Weight 128.152
  • Flash Point 117.8 °C
  • Transport Information
  • Appearance white to light yellow crystal powder
  • Safety 26-36-37/39
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 527-72-0 (2-Thiophenecarboxylic acid)
  • Hazard Symbols IrritantXi
  • Synonyms 2-Carboxythiophene;2-Thenoic acid;2-Thiophenecarboxylicacid;2-Thiophenic acid;NSC 2188;a-Thiophenecarboxylic acid;
  • PSA 65.54000
  • LogP 1.44630

Synthetic route

thiophene-2-carboxylic acid methyl ester
5380-42-7

thiophene-2-carboxylic acid methyl ester

2-thiophenylcarboxylic acid
527-72-0

2-thiophenylcarboxylic acid

Conditions
ConditionsYield
With sodium; diphenyldisulfane In 1-methyl-pyrrolidin-2-one at 90℃; for 0.25h;100%
With hydrogenchloride In 1,4-dioxane for 1h; Heating;97%
With potassium carbonate; thiophenol In 1-methyl-pyrrolidin-2-one at 190℃; for 0.166667h; Substitution;75%
thiophene
188290-36-0

thiophene

acetic anhydride
108-24-7

acetic anhydride

2-thiophenylcarboxylic acid
527-72-0

2-thiophenylcarboxylic acid

Conditions
ConditionsYield
Stage #1: thiophene; acetic anhydride at 30℃; for 0.333333h;
Stage #2: With oxygen; manganese (II) acetate tetrahydrate; cobalt(II) diacetate tetrahydrate; acetic acid; sodium bromide at 90 - 125℃; under 1654.92 Torr; for 4.75h; Reagent/catalyst;		100%
thiophene-2-carbaldehyde
98-03-3

thiophene-2-carbaldehyde

2-thiophenylcarboxylic acid
527-72-0

2-thiophenylcarboxylic acid

Conditions
ConditionsYield
With copper acetylacetonate; oxygen; sodium hydroxide; 1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene In water at 50℃; under 760.051 Torr; for 12h; Sealed tube;99%
With 4H3N*4H(1+)*CuMo6O18(OH)6(4-); water; oxygen; sodium carbonate at 50℃; under 760.051 Torr; for 12h;99%
With C20H25N2(1+)*Cl(1-); water; oxygen; 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 20℃; for 3.5h; Schlenk technique;96%
thiophene-2-carboxylic acid benzyl ester

thiophene-2-carboxylic acid benzyl ester

toluene
108-88-3

toluene

A

2-thiophenylcarboxylic acid
527-72-0

2-thiophenylcarboxylic acid

B

1-methyl-3-(phenylmethyl)-benzene
620-47-3

1-methyl-3-(phenylmethyl)-benzene

C

1-methyl-4-(phenylmethyl)benzene
620-83-7

1-methyl-4-(phenylmethyl)benzene

D

2-benzyltoluene
713-36-0

2-benzyltoluene

Conditions
ConditionsYield
With boron trifluoride diethyl etherate; water at 80℃; for 2h; regioselective reaction;A 99%
B n/a
C n/a
D n/a
...Expand
1,1,1-trifluoro-4-(2-thienyl)butane-2,4-dione
326-91-0

1,1,1-trifluoro-4-(2-thienyl)butane-2,4-dione

2-thiophenylcarboxylic acid
527-72-0

2-thiophenylcarboxylic acid

Conditions
ConditionsYield
With oxygen; sodium hydrogencarbonate In acetonitrile for 4h; Molecular sieve; Irradiation;99%
thiophene-2-carbaldehyde
98-03-3

thiophene-2-carbaldehyde

A

2-thiophenylcarboxylic acid
527-72-0

2-thiophenylcarboxylic acid

B

2-thiophenemethanol
636-72-6

2-thiophenemethanol

Conditions
ConditionsYield
Stage #1: thiophene-2-carbaldehyde With potassium hydroxide for 0.0833333h; Cannizzaro Reaction; Milling; Inert atmosphere; Sealed tube; Green chemistry;
Stage #2: With hydrogenchloride In water for 0.0833333h; Green chemistry;		A 98%
B 98%
With aluminum oxide; water; sodium hydroxide at 100℃; for 0.0333333h; Cannizzaro Reaction; Microwave irradiation;A 47%
B 47%
With aluminum oxide; sodium hydroxide; water for 0.00416667h; Irradiation; Yield given; Yields of byproduct given;
4,4-dimethyl-2-(2-thienyl)oxazoline
62521-42-0

4,4-dimethyl-2-(2-thienyl)oxazoline

2-thiophenylcarboxylic acid
527-72-0

2-thiophenylcarboxylic acid

Conditions
ConditionsYield
With potassium hydroxide; sodium hypochlorite; tetra-tert-butylammonium hydrogen sulfate 1.) ethyl acetate, water, 20 deg C, 12 h; 2.) MeOH, water, 12 h, 20 deg C;97%
With potassium hydroxide; sodium hypochlorite; tetra-tert-butylammonium hydrogen sulfate Product distribution; multistep.: 1.) ethyl acetate-water, 20 deg C, 12 h; 2.) MeOH-water, 20 deg C, 12 h; transformation of oxazoline derivatives into carboxylic functions;97%
Multi-step reaction with 3 steps
1: 85 percent / CH2Cl2 / 0.25 h / 0 °C
2: 98 percent / diethyl ether / Ambient temperature
3: 92 percent / 2.0M KOH / dimethylsulfoxide-d6 / 4 h / 110 °C
View Scheme
2-bromothiophene
1003-09-4

2-bromothiophene

carbon monoxide
201230-82-2

carbon monoxide

2-thiophenylcarboxylic acid
527-72-0

2-thiophenylcarboxylic acid

Conditions
ConditionsYield
With sodium hydroxide; cobalt(II) acetate In ethanol at 30℃; under 1520 Torr; for 20h; Irradiation;96.9%
With sodium hydroxide; tetra-(n-butyl)ammonium iodide; bis(benzonitrile)palladium(II) dichloride; triphenylphosphine In xylene at 90℃; for 4h; Carbonylation;18%
(thiophen-2-yl)methyl acetate
13679-77-1

(thiophen-2-yl)methyl acetate

A

thiophene-2-carbaldehyde
98-03-3

thiophene-2-carbaldehyde

B

2-thiophenylcarboxylic acid
527-72-0

2-thiophenylcarboxylic acid

Conditions
ConditionsYield
With oxygen; cobalt(II) acetate; sodium bromide In acetic acid at 100℃; for 1.66667h; Product distribution; Rate constant; dependence on temperatures and concentrations of reagent and catalysts;A n/a
B 96.5%
carbon dioxide
124-38-9

carbon dioxide

2-thienylmagnesium chloride
52770-33-9

2-thienylmagnesium chloride

2-thiophenylcarboxylic acid
527-72-0

2-thiophenylcarboxylic acid

Conditions
ConditionsYield
Stage #1: carbon dioxide; 2-thienylmagnesium chloride In tetrahydrofuran at 20℃; under 3000.3 Torr; gas-liquid flow reactor assembly;
Stage #2: With polymer-supported sulfonic acid In tetrahydrofuran		95%
In tetrahydrofuran at 1℃; for 0.0833333h;82%
2-thiophenemethanol
636-72-6

2-thiophenemethanol

2-thiophenylcarboxylic acid
527-72-0

2-thiophenylcarboxylic acid

Conditions
ConditionsYield
With C32H25Cl2N6O2Rh2(1+)*Cl(1-); sodium hydroxide In water at 100℃; for 12h; Sealed tube; Green chemistry;94%
With C30H24AgBr4N8(1+)*AgBr2(1-); potassium hydroxide In 1,2-dimethoxyethane at 60℃; for 24h; Molecular sieve; Schlenk technique;92%
With tert-butyldimethylsilyl chloride In methanol; water at 20℃; for 1h; Green chemistry;92%
Thiophene-2-carboxylic acid 2-methyl-2-(methyl-trifluoromethanesulfonyl-amino)-propyl ester
139287-42-6

Thiophene-2-carboxylic acid 2-methyl-2-(methyl-trifluoromethanesulfonyl-amino)-propyl ester

2-thiophenylcarboxylic acid
527-72-0

2-thiophenylcarboxylic acid

Conditions
ConditionsYield
With potassium hydroxide In dimethylsulfoxide-d6 at 110℃; for 4h;92%
thiophene-2-carbodithioic acid methyl ester
2168-83-4

thiophene-2-carbodithioic acid methyl ester

2-thiophenylcarboxylic acid
527-72-0

2-thiophenylcarboxylic acid

Conditions
ConditionsYield
With sodium hydroxide; dihydrogen peroxide In methanol; water at 20℃; for 0.0833333h;92%
2-Iodothiophene
3437-95-4

2-Iodothiophene

diphenylmethylsilanecarboxylic acid
18414-58-9

diphenylmethylsilanecarboxylic acid

2-thiophenylcarboxylic acid
527-72-0

2-thiophenylcarboxylic acid

Conditions
ConditionsYield
With potassium trimethylsilonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; bis(dibenzylideneacetone)-palladium(0) In toluene at 40℃; for 0.333333h;92%
2-Iodothiophene
3437-95-4

2-Iodothiophene

carbon monoxide
201230-82-2

carbon monoxide

2-thiophenylcarboxylic acid
527-72-0

2-thiophenylcarboxylic acid

Conditions
ConditionsYield
With water; palladium diacetate; potassium carbonate at 20℃; under 760.051 Torr; for 6h;91%
With potassium carbonate; palladium diacetate In water; N,N-dimethyl-formamide at 25℃; under 760 Torr; for 10h;85%
2-Acetylthiophene
88-15-3

2-Acetylthiophene

2-thiophenylcarboxylic acid
527-72-0

2-thiophenylcarboxylic acid

Conditions
ConditionsYield
With copper(l) iodide; hydroxylamine hydrochloride; oxygen In dimethyl sulfoxide at 100℃; for 12h;90%
With hydroxylamine hydrochloride; iodine In dimethyl sulfoxide at 100℃; for 5h;89%
Stage #1: 2-Acetylthiophene With iodine; dimethyl sulfoxide In chlorobenzene at 110℃; for 3h;
Stage #2: With tert.-butylhydroperoxide In chlorobenzene at 20 - 110℃; for 8h;		72%
thiophene
188290-36-0

thiophene

carbon dioxide
124-38-9

carbon dioxide

2-thiophenylcarboxylic acid
527-72-0

2-thiophenylcarboxylic acid

Conditions
ConditionsYield
Stage #1: thiophene With n-chlorooctane; sodium In toluene at 20℃;
Stage #2: carbon dioxide In toluene at 20℃;		90%
Stage #1: thiophene With lithium diisopropyl amide In tetrahydrofuran at 20℃; for 0.000833333h; Flow reactor;
Stage #2: carbon dioxide In tetrahydrofuran at 20℃; for 0.000138889h; Flow reactor;
Stage #3: With water; acetic acid In tetrahydrofuran at 20℃; under 7500.75 Torr; Flow reactor;		79%
With ethylaluminum dichloride In hexane; toluene at 100℃; under 22502.3 Torr; for 3h; Autoclave; Inert atmosphere; regioselective reaction;30%
With n-butyllithium; water Multistep reaction;
(thiophen-2-yl)methyl acetate
13679-77-1

(thiophen-2-yl)methyl acetate

2-thiophenylcarboxylic acid
527-72-0

2-thiophenylcarboxylic acid

Conditions
ConditionsYield
With oxygen; cobalt(II) acetate; sodium bromide In acetic acid at 95℃; for 0.5h;90%
C15H16O2S
1309453-50-6

C15H16O2S

A

2-thiophenylcarboxylic acid
527-72-0

2-thiophenylcarboxylic acid

B

[2-(4-methoxy-phenyl)-cyclopropyl]-thiophen-2-yl-methanone
75021-56-6

[2-(4-methoxy-phenyl)-cyclopropyl]-thiophen-2-yl-methanone

C

4-methoxybenzoic acid
100-09-4

4-methoxybenzoic acid

Conditions
ConditionsYield
Stage #1: C15H16O2S With oxygen; sodium hydride In tetrahydrofuran at 0 - 20℃; for 11h;
Stage #2: With hydrogenchloride In water		A 10%
B 90%
C 10%
...Expand
2-bromothiophene
1003-09-4

2-bromothiophene

potassium formate
590-29-4

potassium formate

2-thiophenylcarboxylic acid
527-72-0

2-thiophenylcarboxylic acid

Conditions
ConditionsYield
With [PhCOPd(PtBu3)I]; dtbpf In 2-methyltetrahydrofuran at 80℃; for 18h; Inert atmosphere;89%
2-(trimethylsilyl)thiophene
18245-28-8

2-(trimethylsilyl)thiophene

carbon dioxide
124-38-9

carbon dioxide

2-thiophenylcarboxylic acid
527-72-0

2-thiophenylcarboxylic acid

Conditions
ConditionsYield
With tetrakis[tris(dimethylamino)phosphoranylideneamino]phosphonium chloride; cesium fluoride In o-xylene at 100℃; under 760.051 Torr; for 24h; Catalytic behavior; Reagent/catalyst; Solvent;89%
2-thienyl chloride
96-43-5

2-thienyl chloride

carbon dioxide
124-38-9

carbon dioxide

2-thiophenylcarboxylic acid
527-72-0

2-thiophenylcarboxylic acid

Conditions
ConditionsYield
Stage #1: 2-thienyl chloride With bis(cyclopentadienyl)titanium dichloride; butyl magnesium bromide In tetrahydrofuran at 40℃; for 6h; Inert atmosphere; Schlenk technique;
Stage #2: carbon dioxide In tetrahydrofuran at 20℃; for 2h; Inert atmosphere; Schlenk technique;		88%
Stage #1: 2-thienyl chloride With magnesium In tetrahydrofuran for 2h; Inert atmosphere; Reflux;
Stage #2: carbon dioxide In tetrahydrofuran at -78 - 20℃;		82%
In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide at 5℃; electrochemical oxidation;80%
Stage #1: 2-thienyl chloride; carbon dioxide With manganese; bis(triphenylphosphine)nickel(II) chloride; tetraethylammonium iodide; triphenylphosphine In 1,3-dimethyl-2-imidazolidinone at 35℃; under 760.051 Torr; for 30h;
Stage #2: With hydrogenchloride; water In diethyl ether at 20℃; for 0.166667h;		52%
With manganese; 2,9-dibutyl-4,7-dimethyl-1,10-phenanthroline; tetraethylammonium iodide; lithium acetate; cobalt(II) bromide In N,N-dimethyl acetamide at 100℃; under 760.051 Torr; for 12h; Inert atmosphere; Schlenk technique;35%
2-Iodothiophene
3437-95-4

2-Iodothiophene

carbon dioxide
124-38-9

carbon dioxide

2-thiophenylcarboxylic acid
527-72-0

2-thiophenylcarboxylic acid

Conditions
ConditionsYield
With 3,4-benzo-1,1,2,2-tetraethyl-1,2-disilacyclobut-3-ene; cesium fluoride In N,N-dimethyl-formamide at 0 - 20℃; under 760.051 Torr; for 2h;88%
With copper(l) iodide; N,N,N,N,-tetramethylethylenediamine; diethylzinc In dimethyl sulfoxide at 25℃; under 760.051 Torr;63%
carbon dioxide
124-38-9

carbon dioxide

thiophen-2-yl magnesium bromide
5713-61-1

thiophen-2-yl magnesium bromide

2-thiophenylcarboxylic acid
527-72-0

2-thiophenylcarboxylic acid

Conditions
ConditionsYield
In tetrahydrofuran at 1℃; for 0.0833333h;87%
3%
2-bromothiophene
1003-09-4

2-bromothiophene

carbon dioxide
124-38-9

carbon dioxide

2-thiophenylcarboxylic acid
527-72-0

2-thiophenylcarboxylic acid

Conditions
ConditionsYield
With (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; 2-(diphenylphosphino)-2’(3-(dimethylamino)-3-oxopropyl)-6’-(3-(icosyloxy)-3-oxopropyl)biphenyl; water; palladium diacetate; N-ethyl-N,N-diisopropylamine In toluene under 760.051 Torr; for 16h; Inert atmosphere; Schlenk technique; Irradiation;87%
Stage #1: 2-bromothiophene With magnesium In tetrahydrofuran for 0.75h; Inert atmosphere; Reflux;
Stage #2: carbon dioxide In tetrahydrofuran at -78 - 20℃;		86%
With diethylzinc; palladium diacetate; tert-butyl XPhos In hexanes; N,N-dimethyl acetamide at 40℃; under 7600.51 Torr; Automated synthesizer;62%
thiophene-2-carbonitrile
1003-31-2

thiophene-2-carbonitrile

2-thiophenylcarboxylic acid
527-72-0

2-thiophenylcarboxylic acid

Conditions
ConditionsYield
With phosphate buffer at 30℃; for 48h; rhodococcus rhodocrous AJ270, pH 7.0;86%
With potassium phosphate buffer at 30℃; for 48h; Rhodococcus sp. AJ270 cells;85.8%
2-thiophenylcarboxamide
5813-89-8

2-thiophenylcarboxamide

2-thiophenylcarboxylic acid
527-72-0

2-thiophenylcarboxylic acid

Conditions
ConditionsYield
With niobium(V) oxide; water In neat (no solvent) for 20h; Reflux; Inert atmosphere;85%
With potassium hydroxide; water
With sodium hydroxide; water
With hydrogenchloride In dibutyl ether at 100℃; for 7h;
carbon dioxide
124-38-9

carbon dioxide

5,5-dimethyl-2-(thiophen-2-yl)-1,3,2-dioxaborinane
355408-55-8

5,5-dimethyl-2-(thiophen-2-yl)-1,3,2-dioxaborinane

2-thiophenylcarboxylic acid
527-72-0

2-thiophenylcarboxylic acid

Conditions
ConditionsYield
Stage #1: carbon dioxide; 5,5-dimethyl-2-(thiophen-2-yl)-1,3,2-dioxaborinane With potassium tert-butylate; silver(I) acetate; triphenylphosphine In tetrahydrofuran at 70℃; under 15201 Torr; for 16h; Inert atmosphere; Autoclave;
Stage #2: With hydrogenchloride In tetrahydrofuran; water Inert atmosphere;		84%
With potassium tert-butylate; copper(l) chloride; 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride In tetrahydrofuran at 70℃; under 760.051 Torr; for 24h;83%
2-thienyl chloride
96-43-5

2-thienyl chloride

carbon monoxide
201230-82-2

carbon monoxide

2-thiophenylcarboxylic acid
527-72-0

2-thiophenylcarboxylic acid

Conditions
ConditionsYield
With 1,3-bis(dicyclohexylphosphino)propane bis(tetrafluoroborate) salt; water; palladium diacetate; potassium carbonate In dimethyl sulfoxide at 100℃; under 760.051 Torr; for 15h;84%
carbon dioxide
124-38-9

carbon dioxide

2-thiopheneboronic acid pinacol ester
193978-23-3

2-thiopheneboronic acid pinacol ester

2-thiophenylcarboxylic acid
527-72-0

2-thiophenylcarboxylic acid

Conditions
ConditionsYield
With copper(l) iodide; cesium fluoride; sodium t-butanolate; 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride In 2-methyltetrahydrofuran at 120℃; for 24h; Solvent; Sealed tube;84%
2-thiophenylcarboxylic acid
527-72-0

2-thiophenylcarboxylic acid

dimethyl sulfate
77-78-1

dimethyl sulfate

thiophene-2-carboxylic acid methyl ester
5380-42-7

thiophene-2-carboxylic acid methyl ester

Conditions
ConditionsYield
With lithium hydroxide In tetrahydrofuran for 0.5h; Methylation; esterification; Heating;100%
2-thiophenylcarboxylic acid
527-72-0

2-thiophenylcarboxylic acid

β-naphthol
135-19-3

β-naphthol

2'-naphthyl thiophene-2-carboxylate

2'-naphthyl thiophene-2-carboxylate

Conditions
ConditionsYield
Stage #1: 2-thiophenylcarboxylic acid With trifluoroacetic anhydride; indium(III) chloride at 20℃; for 0.5h;
Stage #2: β-naphthol at 20℃; for 0.166667h;		100%
2-thiophenylcarboxylic acid
527-72-0

2-thiophenylcarboxylic acid

2-hydroxy-1-(2-hydroxy-4,6-dimethoxyphenyl)ethan-1-one
83768-75-6

2-hydroxy-1-(2-hydroxy-4,6-dimethoxyphenyl)ethan-1-one

3,5-dimethoxy-2-(2-((thiophene-2-carbonyl)oxy)acetyl)phenyl thiophene-2-carboxylate

3,5-dimethoxy-2-(2-((thiophene-2-carbonyl)oxy)acetyl)phenyl thiophene-2-carboxylate

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 8h;100%
2-thiophenylcarboxylic acid
527-72-0

2-thiophenylcarboxylic acid

ethyl (S)-2-{[(prop-2-yn-1-ylthio)carbonothioyl]oxy}propanoate

ethyl (S)-2-{[(prop-2-yn-1-ylthio)carbonothioyl]oxy}propanoate

(R)-1-ethoxy-1-oxopropan-2-yl thiophene-2-carboxylate

(R)-1-ethoxy-1-oxopropan-2-yl thiophene-2-carboxylate

Conditions
ConditionsYield
In toluene Inert atmosphere; Reflux; enantioselective reaction;100%
2-thiophenylcarboxylic acid
527-72-0

2-thiophenylcarboxylic acid

4-nitro-2-thiophenecarbonyl chloride
67998-17-8

4-nitro-2-thiophenecarbonyl chloride

Conditions
ConditionsYield
Stage #1: 2-thiophenylcarboxylic acid With sulfuric acid; nitric acid at 10 - 20℃;
Stage #2: With thionyl chloride Reagent/catalyst; Reflux;		100%
Stage #1: 2-thiophenylcarboxylic acid With sulfuric acid; nitric acid at 10 - 20℃;
Stage #2: With thionyl chloride Reflux;
2-thiophenylcarboxylic acid
527-72-0

2-thiophenylcarboxylic acid

N-(2-aminoethyl)-4-methyl-N-(prop-2-yn-1-yl)benzenesulfonamide
1438397-77-3

N-(2-aminoethyl)-4-methyl-N-(prop-2-yn-1-yl)benzenesulfonamide

N-[2-(N-propargyl-N-tosylamino)ethyl]thiophene-2-carboxamide

N-[2-(N-propargyl-N-tosylamino)ethyl]thiophene-2-carboxamide

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 0.5h;100%
2-thiophenylcarboxylic acid
527-72-0

2-thiophenylcarboxylic acid

thiophen-2-carboxylic anhydride
25569-97-5

thiophen-2-carboxylic anhydride

Conditions
ConditionsYield
Stage #1: 2-thiophenylcarboxylic acid With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 0℃;
Stage #2: With bis(trichloromethyl) carbonate In tetrahydrofuran at 0 - 20℃;		99%
With methanesulfonyl chloride; triethylamine In tetrahydrofuran at 0℃; for 1h; Inert atmosphere;99%
With triethylamine; trichloroacetonitrile; triphenylphosphine In dichloromethane at 20℃; for 2h;82%
2-thiophenylcarboxylic acid
527-72-0

2-thiophenylcarboxylic acid

dichloromethane
75-09-2

dichloromethane

methylene bis(thiophene-2-carboxylate)

methylene bis(thiophene-2-carboxylate)

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In neat (no solvent) at 80℃; Microwave irradiation;99%
With potassium carbonate In dimethyl sulfoxide at 130℃; for 5h;99%
2-thiophenylcarboxylic acid
527-72-0

2-thiophenylcarboxylic acid

C11H11FN2O2

C11H11FN2O2

C16H15FO4S

C16H15FO4S

Conditions
ConditionsYield
Stage #1: 2-thiophenylcarboxylic acid With dirhodium tetraacetate In tetrahydrofuran at 30℃; for 0.5h;
Stage #2: C11H11FN2O2 In diethyl ether at -10℃; for 1h; enantioselective reaction;		99%
2-thiophenylcarboxylic acid
527-72-0

2-thiophenylcarboxylic acid

C11H11FN2O2

C11H11FN2O2

C16H15FO4S

C16H15FO4S

Conditions
ConditionsYield
Stage #1: 2-thiophenylcarboxylic acid With dirhodium tetraacetate; C28H44N4O In tetrahydrofuran at 30℃; for 0.5h;
Stage #2: C11H11FN2O2 In diethyl ether at -10℃; for 1h; Temperature; Reagent/catalyst; enantioselective reaction;		99%
2-thiophenylcarboxylic acid
527-72-0

2-thiophenylcarboxylic acid

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
25015-63-8

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane

4,4,5,5-tetramethyl-2-(thiophen-2-ylmethoxy)-1,3,2-dioxaborolane

4,4,5,5-tetramethyl-2-(thiophen-2-ylmethoxy)-1,3,2-dioxaborolane

Conditions
ConditionsYield
In neat (no solvent) at 30℃; Inert atmosphere; Schlenk technique; Glovebox; chemoselective reaction;99%
With (4-Me)Triaz(NHPiPr2)2Mn(CO)2Br In toluene at 25℃; for 6h; Catalytic behavior; Inert atmosphere; chemoselective reaction;> 99 %Spectr.
methanol
67-56-1

methanol

2-thiophenylcarboxylic acid
527-72-0

2-thiophenylcarboxylic acid

Dimethyl thiophene-2,5-dicarboxylate
4282-34-2

Dimethyl thiophene-2,5-dicarboxylate

Conditions
ConditionsYield
With cobalt(II) chloride In 1,1,2,2-tetrachloroethane at 150℃; for 2h; Temperature; Reagent/catalyst;99%
2-thiophenylcarboxylic acid
527-72-0

2-thiophenylcarboxylic acid

N-methylaniline
100-61-8

N-methylaniline

N-methyl-N-(thiophen-2-ylmethyl)aniline
53119-23-6

N-methyl-N-(thiophen-2-ylmethyl)aniline

Conditions
ConditionsYield
With potassium phosphate; 18-crown-6 ether; phenylsilane In tetrahydrofuran at 80℃; for 12h; Glovebox; Molecular sieve; Schlenk technique;99%
2-thiophenylcarboxylic acid
527-72-0

2-thiophenylcarboxylic acid

Diphenylmethane
101-81-5

Diphenylmethane

Thiophene-2-carboxylic acid benzhydryl ester

Thiophene-2-carboxylic acid benzhydryl ester

Conditions
ConditionsYield
With trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone In 1,2-dichloro-ethane at 100℃; for 24h; Schlenk technique; Inert atmosphere;98%
2-thiophenylcarboxylic acid
527-72-0

2-thiophenylcarboxylic acid

isopropyl chloroformate
108-23-6

isopropyl chloroformate

C9H10O4S

C9H10O4S

Conditions
ConditionsYield
Stage #1: 2-thiophenylcarboxylic acid With trimethylamine In tetrahydrofuran at 20℃; for 0.166667h; Inert atmosphere; Sealed tube;
Stage #2: isopropyl chloroformate With triethylamine In tetrahydrofuran; toluene at 0 - 20℃; for 1.66667h; Inert atmosphere; Sealed tube;		98%
2-thiophenylcarboxylic acid
527-72-0

2-thiophenylcarboxylic acid

(4S,10S,12R,E)-4-hydroxy-10-(methoxymethoxy)-12-methyloxacyclododec-5-ene-2,8-dione

(4S,10S,12R,E)-4-hydroxy-10-(methoxymethoxy)-12-methyloxacyclododec-5-ene-2,8-dione

(4S,10S,12R,E)-10-(methoxymethoxy)-12-methyl-2,8-dioxooxacyclododec-5-en-4-yl thiophene-2-carboxylate

(4S,10S,12R,E)-10-(methoxymethoxy)-12-methyl-2,8-dioxooxacyclododec-5-en-4-yl thiophene-2-carboxylate

Conditions
ConditionsYield
Stage #1: 2-thiophenylcarboxylic acid With 2,4,6-trichlorobenzoyl chloride; triethylamine In tetrahydrofuran at 0 - 20℃; for 2h; Yamaguchi Lactonization;
Stage #2: (4S,10S,12R,E)-4-hydroxy-10-(methoxymethoxy)-12-methyloxacyclododec-5-ene-2,8-dione With dmap In toluene at 0℃; Yamaguchi Lactonization;		98%
2-thiophenylcarboxylic acid
527-72-0

2-thiophenylcarboxylic acid

(4S,10R,12R,E)-4-hydroxy-10-(methoxymethoxy)-12-methyloxacyclododec-5-ene-2,8-dione

(4S,10R,12R,E)-4-hydroxy-10-(methoxymethoxy)-12-methyloxacyclododec-5-ene-2,8-dione

(4S,10R,12R,E)-10-(methoxymethoxy)-12-methyl-2,8-dioxooxacyclododec-5-en-4-yl thiophene-2-carboxylate

(4S,10R,12R,E)-10-(methoxymethoxy)-12-methyl-2,8-dioxooxacyclododec-5-en-4-yl thiophene-2-carboxylate

Conditions
ConditionsYield
Stage #1: 2-thiophenylcarboxylic acid With 2,4,6-trichlorobenzoyl chloride; triethylamine In tetrahydrofuran at 0 - 20℃; for 2h; Yamaguchi Lactonization;
Stage #2: (4S,10R,12R,E)-4-hydroxy-10-(methoxymethoxy)-12-methyloxacyclododec-5-ene-2,8-dione With dmap In toluene at 0℃; Yamaguchi Lactonization;		98%
2-thiophenylcarboxylic acid
527-72-0

2-thiophenylcarboxylic acid

C11H9FN2O

C11H9FN2O

C16H13FO3S

C16H13FO3S

Conditions
ConditionsYield
Stage #1: 2-thiophenylcarboxylic acid With dirhodium tetraacetate; C28H44N4O In tetrahydrofuran at 30℃; for 0.5h;
Stage #2: C11H9FN2O In diethyl ether at -30℃; for 3h; enantioselective reaction;		98%
2-thiophenylcarboxylic acid
527-72-0

2-thiophenylcarboxylic acid

aniline
62-53-3

aniline

N-phenyl-2-thiophenecarboxamide
6846-13-5

N-phenyl-2-thiophenecarboxamide

Conditions
ConditionsYield
With fluorosulfonyl fluoride; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 5h;98%
Stage #1: 2-thiophenylcarboxylic acid With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 0 - 20℃; for 0.5h;
Stage #2: aniline In N,N-dimethyl-formamide at 20℃; for 24h;
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 20℃; for 12h; Schlenk technique;
2-thiophenylcarboxylic acid
527-72-0

2-thiophenylcarboxylic acid

4-isopropyl-1-methylcyclohex-3-en-1-amine

4-isopropyl-1-methylcyclohex-3-en-1-amine

N-(4-isopropyl-1-methylcyclohex-3-en-1-yl)thiophene-2-carboxamide

N-(4-isopropyl-1-methylcyclohex-3-en-1-yl)thiophene-2-carboxamide

Conditions
ConditionsYield
Stage #1: 2-thiophenylcarboxylic acid With thionyl chloride; N,N-dimethyl-formamide In dichloromethane Reflux;
Stage #2: 4-isopropyl-1-methylcyclohex-3-en-1-amine With triethylamine In dichloromethane; N,N-dimethyl-formamide Reflux;		97.27%
2-thiophenylcarboxylic acid
527-72-0

2-thiophenylcarboxylic acid

2-Thiophenecarbonyl chloride
5271-67-0

2-Thiophenecarbonyl chloride

Conditions
ConditionsYield
97%
With thionyl chloride for 2h; Heating;82%
With thionyl chloride; N,N-dimethyl-formamide; sodium hydroxide In ethyl acetate at 58 - 65℃; for 2.5h; Inert atmosphere;81%
2-thiophenylcarboxylic acid
527-72-0

2-thiophenylcarboxylic acid

1,2,3-Benzotriazole
95-14-7

1,2,3-Benzotriazole

(1H-benzo[d][1,2,3]triazol-1-yl)(thiophen-2-yl)methanone
301164-69-2

(1H-benzo[d][1,2,3]triazol-1-yl)(thiophen-2-yl)methanone

Conditions
ConditionsYield
With thionyl chloride In dichloromethane at 25℃; for 2h;97%
With thionyl chloride In dichloromethane at 20℃;93%
Stage #1: 1,2,3-Benzotriazole With thionyl chloride In tetrahydrofuran at 20℃; for 0.5h;
Stage #2: 2-thiophenylcarboxylic acid In tetrahydrofuran at 20℃; for 2h;		90%
1,4-dioxane
123-91-1

1,4-dioxane

2-thiophenylcarboxylic acid
527-72-0

2-thiophenylcarboxylic acid

thiophene-2-carboxylic acid [1,4]dioxan-2-yl ester
1284251-47-3

thiophene-2-carboxylic acid [1,4]dioxan-2-yl ester

Conditions
ConditionsYield
With iron(III)-acetylacetonate; di-tert-butyl peroxide at 120℃; for 24h; Schlenk technique;97%
With tert.-butylhydroperoxide; tetra-(n-butyl)ammonium iodide In water; ethyl acetate at 80℃; for 12h;95%
With di-tert-butyl peroxide; Fe3O(1,4-benzenedicarboxylate)3 at 120℃; for 3h; High pressure;68%

2-Thiophenecarboxylic acid Consensus Reports

Reported in EPA TSCA Inventory.

2-Thiophenecarboxylic acid Standards and Recommendations

ASSAY: 98.0% min
WATER: 0.5% max

2-Thiophenecarboxylic acid Specification

The 2-Thiophenecarboxylic acid, with the cas registry number527-72-0, has the systematic name of thiophene-2-carboxylic acid. This is a kind of white to light yellow crystal powder, and is soluble in hot water, ethanol, ethyl ether, and slightly soluble in chloroform. Its product categories are various, including thiophenes; aromatic carboxylic acids, amides, anilides, anhydrides & salts; thiophene&benzothiophene; organic acids; heterocyclic compounds; miscellaneous; building blocks; heterocyclic building blocks. As to its usage, it could be used as the intermediate of analgesics anti-inflammatory and the organic synthesis reagents.

The characteristics of this chemical are as follows: (1)ACD/LogP: 1.57; (2)ACD/LogD (pH 5.5): -0.39; (3)ACD/LogD (pH 7.4): -1.5; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 1.85; (7)ACD/KOC (pH 7.4): 1; (8)#H bond acceptors: 2; (9)#H bond donors: 1; (10)#Freely Rotating Bonds: 1; (11)Polar Surface Area: 54.54; (12)Index of Refraction: 1.606; (13)Molar Refractivity: 31.56 cm3; (14)Molar Volume: 91.4 cm3; (15)Polarizability: 12.51 ×10-24 cm3; (16)Surface Tension: 58.1 dyne/cm; (17)Density: 1.401 g/cm3; (18)Flash Point: 117.8 °C; (19)Enthalpy of Vaporization: 52.58 kJ/mol; (20)Boiling Point: 260 °C at 760 mmHg; (21)Vapour Pressure: 0.00639 mmHg at 25°C.

Production method of 2-Thiophenecarboxylic acid is as below: thiophene could react to produce 2-Thiophenecarboxylic acid, with the following condition: reagent: mercury diethyl and sodium; other condition: unter Durchleiten von Kohlendioxyd.

Use of 2-Thiophenecarboxylic acid: 2-Thiophenecarboxylic acid reacts to produce thiophene-2-carbonyl chloride, with the following condition: reagent: thionyl chloride; reaction time: 3 hours; other condition: heating.

While dealing with this chemical, you should be very cautious. This is irritating to eyes, respiratory system and skin, and may cause inflammation to the skin or other mucous membranes. You should take the following instructions. Wear suitable protective clothing, gloves and eye/face protection, and ig in case of contact with eyes, rinse immediately with plenty of water and seek medical advice.

Additionally, the following datas could be converted into the molecular structure:
(1)SMILES:O=C(O)c1sccc1
(2)InChI:InChI=1/C5H4O2S/c6-5(7)4-2-1-3-8-4/h1-3H,(H,6,7)
 

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