527-72-0

Basic information

• Product Name: 2-Thiophenecarboxylic acid
• Synonyms: Thiophene-2-carboxylicacid,99%;2-Thiophenecarboxylic;2-thiophenezoic acid;Thiophene-2-carboxylic acid 97%;2 - Thiophene Carboxilic Acid;Thiophene-2-carboxylic acid ,98%;2-Thiophenecarboxylic acid,99%;2-Thiophenecarboxyli
• CAS NO: 527-72-0
• Molecular Formula: C₅H₄O₂S
• Molecular Weight: 128.15
• EINECS: 208-423-4
• Product Categories: Thiophenes;Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Thiophene&Benzothiophene;Organic acids;Heterocyclic Compounds;Miscellaneous;Building Blocks;Heterocyclic Building Blocks;Building Blocks;C4 to C6;Chemical Synthesis;Heterocyclic Building Blocks
• Mol File: 527-72-0.mol
• Article Data: 204

Chemical Properties

• Melting Point: 125-127 °C(lit.)
• Boiling Point: 260 °C(lit.)
• Flash Point: 259-261°C
• Appearance: /solid
• Density: 1.42
• Vapor Pressure: 0.00639mmHg at 25°C
• Refractive Index: 1.5160 (estimate)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: Acetone (Slightly), Chloroform (Slightly)
• PKA: 3.49(at 25℃)
• Water Solubility: 80 g/L (20 ºC)
• Merck: 14,9354
• BRN: 110150
• CAS DataBase Reference: 2-Thiophenecarboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Thiophenecarboxylic acid(527-72-0)
• EPA Substance Registry System: 2-Thiophenecarboxylic acid(527-72-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• RTECS: XM8330200
• TSCA: Yes
• Hazardous Substances Data: 527-72-0(Hazardous Substances Data)

Usage

Uses

2-Thenoic Acid, is a sulfur-containing heterocyclic compound, used in the synthesis of pharmaceutical and biologically active compounds. It is also shown to be utilized by presumptive Rhodococcus bacterium in soil, as a sole source of carbon.

Chemical Properties

white to light yellow crystal powder

Definition

ChEBI: A thiophenecarboxylic acid in which the carboxy group is located at position 2.

Synthesis Reference(s)

The Journal of Organic Chemistry, 30, p. 3520, 1965 DOI: 10.1021/jo01021a055

Purification Methods

Crystallise the acid from water and dry it in a vacuum. The amide has m 181o(from H2O) and pK2 5 10.54(50% aqueous dioxane). [Beilstein 18 H 289, 18 I 438, 18 II 269, 18 III/IV 4011, 18/6 V 158.]

InChI:InChI=1/C5H4O2S/c6-5(7)4-2-1-3-8-4/h1-3H,(H,6,7)/p-1

Synthetic route

thiophene-2-carboxylic acid methyl ester (5380-42-7) → 2-thiophenylcarboxylic acid (527-72-0)

Conditions	Yield
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) + acetic anhydride (108-24-7) → 2-thiophenylcarboxylic acid (527-72-0)

Conditions	Yield
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) → 2-thiophenylcarboxylic acid (527-72-0)

Conditions	Yield
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 + toluene (108-88-3) → 2-thiophenylcarboxylic acid (527-72-0) + 1-methyl-3-(phenylmethyl)-benzene (620-47-3) + 1-methyl-4-(phenylmethyl)benzene (620-83-7) + 2-benzyltoluene (713-36-0)

Conditions	Yield
With boron trifluoride diethyl etherate; water at 80℃; for 2h; regioselective reaction;	A 99% B n/a C n/a D n/a

1,1,1-trifluoro-4-(2-thienyl)butane-2,4-dione (326-91-0) → 2-thiophenylcarboxylic acid (527-72-0)

Conditions	Yield
With oxygen; sodium hydrogencarbonate In acetonitrile for 4h; Molecular sieve; Irradiation;	99%

thiophene-2-carbaldehyde (98-03-3) → 2-thiophenylcarboxylic acid (527-72-0) + 2-thiophenemethanol (636-72-6)

Conditions	Yield
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) → 2-thiophenylcarboxylic acid (527-72-0)

Conditions	Yield
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) + carbon monoxide (201230-82-2) → 2-thiophenylcarboxylic acid (527-72-0)

Conditions	Yield
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) → thiophene-2-carbaldehyde (98-03-3) + 2-thiophenylcarboxylic acid (527-72-0)

Conditions	Yield
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) + 2-thienylmagnesium chloride (52770-33-9) → 2-thiophenylcarboxylic acid (527-72-0)

Conditions	Yield
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-thiophenylcarboxylic acid (527-72-0)

Conditions	Yield
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) → 2-thiophenylcarboxylic acid (527-72-0)

Conditions	Yield
With potassium hydroxide In dimethylsulfoxide-d6 at 110℃; for 4h;	92%

thiophene-2-carbodithioic acid methyl ester (2168-83-4) → 2-thiophenylcarboxylic acid (527-72-0)

Conditions	Yield
With sodium hydroxide; dihydrogen peroxide In methanol; water at 20℃; for 0.0833333h;	92%

2-Iodothiophene (3437-95-4) + diphenylmethylsilanecarboxylic acid (18414-58-9) → 2-thiophenylcarboxylic acid (527-72-0)

Conditions	Yield
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) + carbon monoxide (201230-82-2) → 2-thiophenylcarboxylic acid (527-72-0)

Conditions	Yield
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-thiophenylcarboxylic acid (527-72-0)

Conditions	Yield
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) + carbon dioxide (124-38-9) → 2-thiophenylcarboxylic acid (527-72-0)

Conditions	Yield
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) → 2-thiophenylcarboxylic acid (527-72-0)

Conditions	Yield
With oxygen; cobalt(II) acetate; sodium bromide In acetic acid at 95℃; for 0.5h;	90%

C15H16O2S (1309453-50-6) → 2-thiophenylcarboxylic acid (527-72-0) + [2-(4-methoxy-phenyl)-cyclopropyl]-thiophen-2-yl-methanone (75021-56-6) + 4-methoxybenzoic acid (100-09-4)

Conditions	Yield
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%

2-bromothiophene (1003-09-4) + potassium formate (590-29-4) → 2-thiophenylcarboxylic acid (527-72-0)

Conditions	Yield
With [PhCOPd(PtBu3)I]; dtbpf In 2-methyltetrahydrofuran at 80℃; for 18h; Inert atmosphere;	89%

2-(trimethylsilyl)thiophene (18245-28-8) + carbon dioxide (124-38-9) → 2-thiophenylcarboxylic acid (527-72-0)

Conditions	Yield
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) + carbon dioxide (124-38-9) → 2-thiophenylcarboxylic acid (527-72-0)

Conditions	Yield
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) + carbon dioxide (124-38-9) → 2-thiophenylcarboxylic acid (527-72-0)

Conditions	Yield
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) + thiophen-2-yl magnesium bromide (5713-61-1) → 2-thiophenylcarboxylic acid (527-72-0)

Conditions	Yield
In tetrahydrofuran at 1℃; for 0.0833333h;	87%
	3%

2-bromothiophene (1003-09-4) + carbon dioxide (124-38-9) → 2-thiophenylcarboxylic acid (527-72-0)

Conditions	Yield
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) → 2-thiophenylcarboxylic acid (527-72-0)

Conditions	Yield
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-thiophenylcarboxylic acid (527-72-0)

Conditions	Yield
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) + 5,5-dimethyl-2-(thiophen-2-yl)-1,3,2-dioxaborinane (355408-55-8) → 2-thiophenylcarboxylic acid (527-72-0)

Conditions	Yield
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) + carbon monoxide (201230-82-2) → 2-thiophenylcarboxylic acid (527-72-0)

Conditions	Yield
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) + 2-thiopheneboronic acid pinacol ester (193978-23-3) → 2-thiophenylcarboxylic acid (527-72-0)

Conditions	Yield
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) + dimethyl sulfate (77-78-1) → thiophene-2-carboxylic acid methyl ester (5380-42-7)

Conditions	Yield
With lithium hydroxide In tetrahydrofuran for 0.5h; Methylation; esterification; Heating;	100%

2-thiophenylcarboxylic acid (527-72-0) + β-naphthol (135-19-3) → 2'-naphthyl thiophene-2-carboxylate

Conditions	Yield
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-hydroxy-1-(2-hydroxy-4,6-dimethoxyphenyl)ethan-1-one (83768-75-6) → 3,5-dimethoxy-2-(2-((thiophene-2-carbonyl)oxy)acetyl)phenyl thiophene-2-carboxylate

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 8h;	100%

2-thiophenylcarboxylic acid (527-72-0) + ethyl (S)-2-{[(prop-2-yn-1-ylthio)carbonothioyl]oxy}propanoate → (R)-1-ethoxy-1-oxopropan-2-yl thiophene-2-carboxylate

Conditions	Yield
In toluene Inert atmosphere; Reflux; enantioselective reaction;	100%

2-thiophenylcarboxylic acid (527-72-0) → 4-nitro-2-thiophenecarbonyl chloride (67998-17-8)

Conditions	Yield
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) + N-(2-aminoethyl)-4-methyl-N-(prop-2-yn-1-yl)benzenesulfonamide (1438397-77-3) → N-[2-(N-propargyl-N-tosylamino)ethyl]thiophene-2-carboxamide

Conditions	Yield
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) → thiophen-2-carboxylic anhydride (25569-97-5)

Conditions	Yield
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) + dichloromethane (75-09-2) → methylene bis(thiophene-2-carboxylate)

Conditions	Yield
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) + C11H11FN2O2 → C16H15FO4S

Conditions	Yield
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) + C11H11FN2O2 → C16H15FO4S

Conditions	Yield
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) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → 4,4,5,5-tetramethyl-2-(thiophen-2-ylmethoxy)-1,3,2-dioxaborolane

Conditions	Yield
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) + 2-thiophenylcarboxylic acid (527-72-0) → Dimethyl thiophene-2,5-dicarboxylate (4282-34-2)

Conditions	Yield
With cobalt(II) chloride In 1,1,2,2-tetrachloroethane at 150℃; for 2h; Temperature; Reagent/catalyst;	99%

2-thiophenylcarboxylic acid (527-72-0) + N-methylaniline (100-61-8) → N-methyl-N-(thiophen-2-ylmethyl)aniline (53119-23-6)

Conditions	Yield
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) + Diphenylmethane (101-81-5) → Thiophene-2-carboxylic acid benzhydryl ester

Conditions	Yield
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) + isopropyl chloroformate (108-23-6) → C9H10O4S

Conditions	Yield
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) + (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

Conditions	Yield
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) + (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

Conditions	Yield
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) + C11H9FN2O → C16H13FO3S

Conditions	Yield
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) + aniline (62-53-3) → N-phenyl-2-thiophenecarboxamide (6846-13-5)

Conditions	Yield
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) + 4-isopropyl-1-methylcyclohex-3-en-1-amine → N-(4-isopropyl-1-methylcyclohex-3-en-1-yl)thiophene-2-carboxamide

Conditions	Yield
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-Thiophenecarbonyl chloride (5271-67-0)

Conditions	Yield
	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) + 1,2,3-Benzotriazole (95-14-7) → (1H-benzo[d][1,2,3]triazol-1-yl)(thiophen-2-yl)methanone (301164-69-2)

Conditions	Yield
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) + 2-thiophenylcarboxylic acid (527-72-0) → thiophene-2-carboxylic acid [1,4]dioxan-2-yl ester (1284251-47-3)

Conditions	Yield
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%

Upstream product

• 13679-75-9 1-thiophen-2-yl-propan-1-one 
• 625-88-7 2,5-diiodothiophene 
• 541-41-3 chloroformic acid ethyl ester 
• 526-99-8 meso-galactaric acid 
• 89180-57-4 2-thienylmagnesium iodide 
• 15719-64-9 methylammonium carbonate 
• 188290-36-0 thiophene 
• 124-38-9 carbon dioxide 
• 201230-82-2 carbon monoxide 
• 5380-42-7 thiophene-2-carboxylic acid methyl ester 
• 59753-16-1 lithium thiophene-2-carboxylate 
• 88423-05-6 C₁₅H₁₉NO₂SSi 
• 1003-31-2 thiophene-2-carbonitrile 
• 4075-59-6 2-thiopheneglyoxylic acid 

Downstream Products

• 5380-42-7 thiophene-2-carboxylic acid methyl ester 
• 59303-19-4 propyl thiophene‐2‐carboxylate 
• 2810-04-0 Ethyl thiophene-2-carboxylate 
• 35250-80-7 thiophene-2-carboxylic acid isopentyl ester 
• 107553-61-7 4-(N-Chloroacetylamino)methyl-2-thiophene carboxylic acid 
• 857999-82-7 4-(benzoylamino-methyl)-thiophene-2-carboxylic acid 
• 56053-84-0 n-butyl thiophene-2-carboxylate 
• 19418-11-2 (+)-Tetrahydrothiophene-2-carboxylic acid 
• 3172-52-9 2,5-diclorothiophene 
• 24065-33-6 5-Chlorothiophene-2-carboxylic acid 
• 5271-67-0 2-Thiophenecarbonyl chloride 
• 5813-89-8 2-thiophenylcarboxamide 
• 7311-63-9 5-bromothiophene-2-carboxylic acid 
• 13138-70-0 4-nitro-2-thiophenecarboxylic acid 

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